raffauf - plant alkaloids - a guide to their discovery and distribution [dp] (fpf, 1996)

In this study of about 400 samples representing 297 species, six known alkaloidal species were included: Acanthus ilicifolius 1/2, Adha!o-da vasica, Anisoles sessi/ijlorus, f-lypoestes v

FOOD PRODUCTS PRESS

H e rb s, S pi ces, and M edici nal Plams: Recent Advallces

ill BolallY Horticulture, alld Pharma cology

Volum es 1-4, edied by Lyle E Craker and James E Simon

Related lilies of interest from Food Products Press:

Opillm Popp y: BotollY, Che mi stry, and Pharm acology

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Th e HOll est H er bal: A Sensible Guide [0 the Use of H erbs

and R el at ed R e m edies, T hird E diti o n by V<lITO E Tyler

H erbs ojC/lOice: 71!e 711erapelltic Us'e oj Phytomedic i l/ a/ s

by ValTo E Tyler

Plant Alkaloids

A Guide to Their Discovery

and Distribution

Robert F Raffa u f, FLS, FMAS

F ood Pro d ltcts P ress

An l!nprinl of T h e H<lwOrlh Pr ess, Ine

New York London

Publish ed hy

ood Produels l'Tess, a~ imprint "fThe Haworth "ress, 11I 10 Alice Sired Binghamton, NY

13904·1580

t) 1996 by The Ilaworth Press, lite All righls reserved No pm! o f Ihis wurk n~ly be rC l lfoduccd

or IIli liz.:d in Any form Of b y HII)' meliUS, e!cClronic 01 me h:Ulicnl iucl utlillg phott)Cllllyilll!

micrufilm and recording, or by any illforn1aI,o'l slnragc a l l<' rc tric~a l system, witholl permission

in w ri t ing {Iu rn Ihe J)u bl i >h~r, J>ri n\ L'd in tlie Uniled SiDles uf Am errca

Ralfaur, n ober! F (Koher! I'mucis)

1916-l)l~nl alkaloids 11 uide to the i r discovery a nd dislri\)lIlion { Robert F Rll ilnu f

ABOUT HIE AUTUOI!

Robert F Raffauf, PhD, is Professor Emeritus of Phannacognosy

and Medicinal Chemistry at Northeastern University in Boston lie

current y hollis an appointment as Research Associate at the Bot

ani-cal Museum of Harvard University, where he has also t a ught Ilc

has served as Visitng P ro f esso r at the School of Pharmacy at the

University of Puerto Rico and al the School f Biological Sciences

of lhe National Polytechnic Institute of Mexico Dr Ranilllf has led

numerous expeditions in Ill a n y paris of the world in the SC:U'C ~l for

new plants of pOI enta I medicinal value and has lectured extenSIvely

on this and related matters, including the rain forests and conserva

-tion lie is the auth r of eight books, 69 journal publications, and

four patents, and he con nues to work with graduate students inter

ested in natural products research A 50-year member or the

Ameri-can Chemical Society, Dr RafTauf is <llso a Fellow of the Lin can

Society of London and of the American Association of Advan

ce-ment of Science In 1988, he was awarded an appointment as

Resi-den Scholar at the Rockefeller Study Center in Be agio, Italy

Foreword

During scveral years of fi ld work in the Northwcst A I~lazon i ~, I

lived and worked with members of many of the AmaZOnian Indian

tribes Il was an extraordinary opp0l1unity 10 obsclve, apprcciate,

and record their local customs, rituals, and particularly, as a botanist,

their inte igent uses of the plants of the forests in which they lived

The imp0l1ance oflhis information beyond simply creating an inte

r-esting ethno otanieal record, was n t entirely o violLs at the time

Aficr my return to more academic pursui s, I met the auth r·of

the following pages, then a chemist for II major North American pharmaceutical compn y, with an interest primarily in that portion

of my n tes denling with the treatment of disease as it WHS under

stood by the Indian peoples Some p illiS, it was th u ht, could be

sources of new chemical compounds lor cventual use in our own

system of medicine Furthermore, in (In u t~Clllpl to reach that g?(lI,

the addition of chemical and p annacologlc(li data to thc botalllcal

record would expand our knowledge of the rain forest and its plant

ami <lIlimal inhabitants A collaboration seemed a natural and lical consequence

og-As a result of the work described in this book many plants have been the su jects of further botanical, chemical, and phalmncologi-

cal research This integrated, interdisciplinary approach has been of

great advantage to our students, thosc in my cO ~l rses at Harvard

University as well as those of Professor Raffaul at t:'!011heastern

University A number of our students have even carncd out field

work in variolls parts of tropical A1I1erica With them we have been

able to co-author a number of technical papers on aspects of the wealth of natural resources in the Western Amawll and to su ply

them with cha enging problems in the numerous disciplines bear

-ing on rain forest science Together we have published two books

(Th e H ea lillg For est, Ville 0/ tl i"e SO IlI) extending our k owledge of

the bio iversity of this vast area of So lith America

•

1'11/ PLANT ALKALOIDS

It is Ollr hope that the inFonnation which my colleague has as~

sembled here will continue to encourage academic as well as com~

mercial research on the uselulncss of plants to humans and con trib~

ute to current efforts at conservation of Amazonian resources, some

of which are on the verge of extinction as a result of continued

uncontrolled devastation in many areas of these marvelous forests

~ Richard Evans Schultes PhD FMLS

Jeffrey Professor of Biology

Emeritus Direc!OI; Botanical Museum,

H arvard University, Cambridge, Massachusetts

Preface

The senrch for plant alkaloids ofnovcl chemical structure having potential value as medicinal agents, as toxic principles, or as ap~ propriate starling materials for synthetic modification leading to other useful products, has occupied the attention of phytochemisls for over 150 years In 1950, about 2,000 of these substances were recognized; by 1970 this number had increased to about 4,000 and

20 years later 10,000 were known In recent times, they have been considered as uscthl taxonomic markers in attempts to construct more "natural" systems of plant classification through chemotax~ onomy, and as suitable substances for the study of biosynthctic pathways in plant metabolism During the laller part of the present century, emphasis on the conservation of plant resources and the

ethl1obotanical information concerning their use by many of the world's aboriginal societies has given added impetus to the imp or~ tance of the continued study of the "chemical factory," represented

by the large unexploited portion of the plant kingdom before much

or it disappear!> under the pressures incident to the mass movements

of peoples and the increase in the world's population Both lire in

large part responsible for devastation of many noms, particularly those of the rain forests Not only will a number of species be lost even before they arc known and named by botanists, but litemlly thousands of chemical compounds new to science will disappear forever

During the past 40 years I have been involved, in one way or another, with the screening of several thousand plants for the presence

of alkaloids as potential medicinal agents under the auspices of a number of governmental, industrial, and academic institutions Under~

lying this activity has been the hope thai the discovery of new eo m ~ pounds of this class would lead to substances at least as usefi.1 as tJlose which simil r studies have produced in the pasL This screening has been done on lI·esh plant material in the field, on small q antities laken

ix

PLAN1'ALKALO/VS

fmrn hcrbmium specimcns, and in thc lab ratOty using a few grams of

dricd malerialmade available by bot.anists, colk"Ctors, herb dcalers, and

my personal collections in many p<u1S of the world

Variolls methods for the screening of largc numbers of plant

samplcs for alkaloids have been lIsed by many investigators more or

less sliccessfully (Famsworth, 1966) Seveml of thcse were used,

depending on the facilities available at the time, but most of the

results reported herein were obtained by simplc methods described

some years ago (RarTauf, 1962a; RafTauf and Altschul, 1968) In the

field, these involve spoiling a droplet of plant sap on filter paper and

applying a droplet of DmgcndorfT's rcagcnt; the development of II

red·onlllge color iwJicates the presence of alkaloids In the laboralo·

ry or herbarium, simplc extracts of dried plant material may bc used

with certain limitatio s, for thc samc purpose (Balick Rivier, and

Plowman, 1982)

Methods may be adapted to needs of the investigator; tests for somc

specific ty es of nitrogen lls compounds may be included (e.g • in

doles simplc amines and amino acids) All npproximation of the

quantity of alkaloid in n sample may be made by compming the

intensity of the color produced in thc DragendorfT test with those

produced by standard alkaloid solutions of known concentratioll fiy

using the Dragcndorn' fC.lgent as a spray, it is also possible 10 conduct

thin-layer chromatographic studies in the ficld Several yt 'ars ago, in an

a empt to devise a method for the idenlification of specific compounds

in a particular alkaloid-positive collection 11 pol1able laooratOlY was

assembled for the evalua on of small extracts of fresh plant material

by chromatographic analysis using alumina-coated microscope slides

and samples of the alkaloids expected to be prescnt In the course of

the study, it was found that some of the compounds were present o ly

during a re:'itlicted portion of the plant's growth cycle We now know

that, in some cases at least, alkaloids are indeed further modi lied by the

plants thnl produce them

An advantage of these simple methods is {Iwt they allow such

studies to bc done far Irom a source of electric power and other

amenities oflhe laboratory But it is also tme thutthcre arc a Ilumber

ofullcertainties in such procedures; nol al! ni rogcl1-eontninillg sub

-stances will react with either DragendortT's or Mayer's reagent A

ballery of test reagents would give a more definitive althou h even

Pre/act!

then, not an infallible result (Abisch and Reichstein, 1960) Fal~c positivc tests arc given by many Iypes ofnoll lkal~idal plant con ht

uents with a variety of alkaluidal rcagents (Habib, ~980) Ballck

Rivier and Plowman (1982) have pointed out the Importance of methods used in field drying lind preservation of herbar!um speci· mens with respect to the reliability of the result~ obtamcd when

tcsting them A plea for such testing nnd a revt~w of the n~ore

elegant methods for its accomplishment has been givenby Plllllp~·

son (1982) Furlhennore,lIs every plant collector has (llscovered, It

is n t always practical in a given instance to collect all oftl~e parts of

a plant in which alkaloids may occur Nonetheless, an estimated 85

percent ofnlkaloid·colltaining plants can bc d~tcctcd by the methods

described here; a number of k own alkalO al plants have b~en

included in thc survcy to serve us controls '

Ilerbarium specimens representing otherwise relatively Inacces·

sible specics of several families (Apocyno~eac, Bomba~ ceac, L~ copodiaceae, Lytliraceae, Orchidaceae, Rubtaceae) wc r~ mdudc,d III

Ihis survey Small samples were selected fr~)1n sheets III the Gra~ Oakes Ames, and Arnold Arborctum herb<lna of Ilarvard Untvers~·

ty under the guidance of Professor Richard Evan~ Schul~es, Ementus Director of the Botanical Museum, whose assistance I S grateful·

Not all of this testing was done by me; some of It was done by anthropologists, ethnobotanists, ~Ild pl,allt col.lectors in the course of field work sponsored by academiC or IIldUSlrllll programs und~r my

direction some by laboratory technicians under my su p c r v l s l~n ,

somc by' fonner students as preliminary exerci~s ill phytochelnls· try, and some in collaboration with phytochemical programs sup-porled by the COlilicils of Scientific and lndustnal Resenrch of Australa and South Africa Portions of the test rcsults from these

pmgrams which had been at my disposal, I~ave been include~l he.re

for completencss in order to cOllvey some Idea of the alkal?ld diS·

tribution in plant families represented in the southern h l~lsph~re Further data 0 11 these studies,.as well as the results of the Isola on and pharmacological testng of a large number of nlkaloids, arc to be

fOllnd in a rccent excell nt publication by the Melbo rne group (Coliins et aI., \990)

ALKALOID TEST RESULTS

Alkaloids have been detected previously in a few genera In this study of about 400 samples representing 297 species, six known alkaloidal species were included: Acanthus ilicifolius (1/2), Adha!o-

da vasica, Anisoles sessi/ijlorus, f-lypoestes verticillaris (2 /4), rtmgia /ungistrobus, Rhinacont/lIls commllnis (112)

Macro-Alkaloids were also detected in the following: Angkafal1thus lrQl1SVaafeflsis (2/2), Allisacaflthus illsignis, Aphelaf/dra deppeana (1 /4), Asystasia atripficiJolia, A we/wifchii, Barfel'ia matopoellsis,

B Ivlllndi/o!ia, B sinensis, Blechllln pyramidalum (113), Blepha!'is boerhaaviJolia, B 11/argillata, B lIatalensis, Btephan's sp., Cmss(fn- dra spinescens, Dicfiptera cfinipodio, Duvemoya (= Justicia) aco- ni/iJolia, D adhatoides (1/2), Dyscho!'iste hirsutissimo ( 1 /4), Ecbo- lium sp., Elylraria acaulis, E squamosa (3/3), Hellligmphis hirta

(whole plant), I-1emigmphis spp (2/2 ), Hypoesfes aristata (113),

Ja cobinia (= Jlls/icia) .~picigera (112), Justicia america no, J liana, J elegantllla, J jlava (112), J montalla, J orchioides,

allsel-J protracta (2/2), J salviae/olia, J thymi/olio, 1 lrinervia, J lricosa, Mirandea grisea, Monechma atherstol1ei, M australis,

ven-M ineal/uIII, Monechmo sp ( 1 /3 ), Net/racanth"s aji'iclllltls ( 1 /2), OrthO{aClus lI/onlallus (1 1 , leaves and flowers), Peris/raphe cer-

Ill/a, Ph/ogacanthus thyrsiflorus (1 /2, root), Rultya ova/a (1/2), Sallchezia lhinophila (bark), Siphonoglossa ramosa

-'

PLANTALIVILOIDS

The alkaloids of AdlUltoda vasica have been reviewed (Jain,

1984) Acallthlls iJiCijiJ/iIiS contains bcnzoxazolinc¥2-one; the alka¥

loids of Acallthl/s mollis have been reporled (Wolf ct al., 1985) and

new spennine-type alkaloids have becn isolated from Aphe/alldm

piJosa (Tawil el aI., 1989) I n vie}v of the native use of at least one

species of Justicia as a hallucinogcn jn South Amcrica (Schultes and

Holmstcdt, 1 968), the report of its presumed conte nt of I l yp t am ine

needs corroboration In this cOIUleetion, the several listed

alkaloid-positive species from other pariS of the world should be of interest

Negative tests were obtained from the following species:

AcolI-tllOpsis ca rdlli/olia , A canth ll s ebracteatu.~·, A 1II0/lis, AdelloslI/a g/u¥

tinosum, Adhatoda sp., Allcy/acallilms baillesii, Allisacalltlms

gOIl-zalezii, A qlladrifolills, A ochole r e na e, A lllllrheri, A lulellsis,

A wrightii, Anisolesji)/'II/osissiI1lIIS, Aphe/alldm auriontiaca, A

blal/-cherial/a, A clWlllissol1ialla, A deppeana, A ifl( :erta, A pilosa,

Alplle/antll'll ::'1)., ASleracalltha (== Hygrophila) spinosa, Asystasia

gallgelica, A schimperi, A varia, Bad eria a/bostellala, 8 cristata,

B cros.w lIIdr ijormis, 8 discolor, 8 e/egans, 8 guemii, B

herero-triclm, B kirkii, B lwu: ijulill , B /ugal'dii, B mical/s, B vbtllsa,

B pl'elorieflsl:5 B priol/Uoides, B pUllgell.l', IJ pyramidata, IJ

rall-dii, B rigida, B 'scandens, Barleria sp., Beloperol/e (== Jilsticia)

ca/i/ornica, B comasa, B./ragilis, B gllt/ata, B e/operolle \p.,

Ble-chum nipPolI/CIIIII, B plagiogy/'ijIorus, BlechuIII ::.p., B/epIUl/'is

Cll-pellsis, B diw:/'sispilla, B gllllllacea, B maderaspatellsis, B/epharis

sp., 8 squarrosa, Bravaisia illlegerrillla, Cal'iowrightia g/abrata,

C glandu/osa, C selpyJ/i/olia, Cal'iowrig hli a spp (2),

C"aetacan-,hus seliger, Chae/ollly/ax hatschbachii, ChilenwthemulI/ vio/a

-ce lllll , Codol/acant/llIs pal/eijloms, Crabbell allgLlstifolia, C hirsula,

Crossal/d ra g r eellsfockii, C ulldululae/olia, Cy r tal/lhera pohlialla,

Daedalacallihus (= Erallihemum) I1lOlIfallu.\·, D lIerVOSlIS, D

pur-purescens, Dialllhera (= J/I:)·ticia) ovala, Diapedilllll (= Diclipfera)

assurgel1s, D chillellsis, D lIIicral/lhllS, D I/obilis, D

pedullcula-ris, D pringlel, D resupil/ata, D rigidissima, Disperma (==

Duos-penna) crena/lilli, Dysc/lOriste declIlIlbells, D fischeri, D ovala,

D microphylla, D quadrangularis, D rogersii, DyscilOriste sp.,

D verticil/aris, Ebermaiera (= Staltrogylle) cOl'1liclilata, Echo/ill//!

(Jlllplexicallle, E lilllwealfllll, E revo/Ilf11I11, mytraria bromoides,

Enm/helllfllll eidomdo, E lIel'l'OSIIIII, GrapfopllyllwlI piC/lilli,

lophylllllll sp., Haplan/hll s lIi1gherriellsis, H cm i gmphis e/egolls val'

crellala, H hirta, H latebrosa, Hemigraphis spp (2), Hellrya

(= Telramerillm) Yl1ca/(ll1el/s i s, H ygrophila taxi/olia, H salici/olia, / - /ygrophi/a \jJp (4), /1 v)illo.m, Hypoesles jlorib lllldll , H p/I(llop~

soides, I-/ pUI'plll'ea, !sag/ossa gra ll/i i, isog/o::"sa !J1)., I stipitata,

I woodi;, Jacobillia (== Justicia) aschellbomimw, J candicans,

J heterophylla, 1 iIlC(lIU1, 1 mexicalla, J pal/icil/ala, J sellow;wUl, Jacobillia spp (2), J stellata, Juslicia al1gal/oides, J belo lli ca,

J belol1icoides, J beyrichii, J bmsilialla, J campeciJialla, J ca lll py/ostemoll, J che irial/tll ijolia, J.jiII'Caia, J gel1dal'llssa, 1 kirkialla,

-J kraussi i , J m exic(lIw, J odorala, 1 ova/a, J pelio/aris, J pro

-c llmb ells, J secllnda, Jus/icia spp (5), Lepidagalltis /ormosensis,

L illclIrva, L microchilo, L persimilis, Lepidagathis sp., Ma ckaya bella, Macronmgia /ormosiss ima , Mel/dOl/cia coccine a M hoJJ~

mOllllseggitllla, M sefiow iww, Mel/dOl/cia sp (this gellus is times placed in a family of its own, Mendonciaceac), MOllee/llna debile, M divarica/lIlIl, M.jimhricatum, M lIIo/issiuIII, M pselldo- palululII, M sc abridlllll , Monechma spp (2), Odolltollema ca/ysta- chum, 0 c sp idatulll, Odolltol/ema spp (2), Pachyslaeliys cocci- Ilea, Pe"i.~·/rop"e bica/yclI/a((l, P grandibrachiat(J, P lIata/ellsis, PelalidiuIII wvmariculI1, P barlerioides, P braeleollllll, P oblongi- [oliulII, P /'ubes cells, PIU/u/ apsis belollica, P imbricato, Ph/ og a-

some-ca nlhtl s Ihyrsijlorus, Pselldel'lllltiJemulII praecox, P se ud era l1th mum spp (2), i?hillacollflius xerophi /u s, Rllel/ja alba, R a/bicoillis,

e-R a/bijlora, e-R bou r gei, R c% rat a, R cordala, R /orlllosa,

R i ll/lIld a/a, R macropilyl/a, N I/Iul ijlora, R lIudifiora val'

yuca/a-110, R palmeri, R patu/a, R pellinslI/ar i s, R pi/osa, R prostrata, Rllellia spp (4), R speciosa, R tubero.m, R tw eet/ialla, Rlmgia parvijlora, Rl/ spol ia hypocralel'ijol'lIIi.<:, Sallchezia I/obilis, Sclero- chilOl/ harveyalllls, Sel'icograp his (== JU'<:ficia) co r difolia, Sipl/ofI(}~

glossa pilosella, S Iubu/o:w, Slellalldrillm ba/'bawlII, S/1Vbi/alllhes

c s ia , S./ormosallus, T eliostocliya (= Lepidagathis) alop ecuroides, 7etramer;UIII aure/ill/, T lIi::'1);dlllll, 7: su /' elllll, Thllllbergia all/oena,

T atriplici/olia, T el'(~cl{J, T ji'agr(llls, 'J: gmlldijIora, T /anci/olia,

T lIota/ellsis, 'l1l11l1belgia sp (the genus is sometimes placed in Thunbergiaceae), Thyrsacall lllll s (= Odolttonellla) callistaL'hyu.~,

Tricallthera gigolltell

10 l'LAN'J'ALKALOJD S

Redfearn, 1 8 ) Their biosynthesis of the Scetefilllll alkaloids has

been studied (lierbert and Kallah, 1989)

REFERENCES

Ilerbert It B Knd E Kallah, Tetrahedron Lellers 30 (1989) p 141

Jeffs, P W inn/e Alkal oids 19 (1981) p 1Academic Press, New York

JefTs, P W.o T M Capps, lind R Redfearn, .l OI II'IUl f of Organic Che ll/i S / If 4 7

The one genus, Alaflgilllll of the tropics and semitropics of the

Old World, is rich in alkaloids, n t all of which have had stnlctural

assignments Considerable syn nymy exists in the family The

chemistry of A/{lll g illm lamarckii has been studied in somc detail

and positive lests for alkaloids were obtained from the single smn

-pic of Indian origin included in this stu y

ALISMATACBAB

11 gellera; 95 s peci es

This is a cosmopolitan family but it oceurs mainly in temperate

and tropical regio s of the northern hemisphere Some species arc

used as ornamentals, others are familiar aquarium plants, and the

roots of Sagittaria are used as food in China Twenty-two samples

of 16 specics were tested and positivc results were given by I:.'c" i l/ o

-dums /"(U/iCfIflS (2/2), Sagittaria engelmal/I/ i(ll/(/ , S grall/ ill ea (1/2),

and S /a l i/olia The family is not known for the presence of alka

-loids; there arc but two earlier rep rts ofthcir occurrence

Negative tests were obtained for AIi.wllI plantago, A p/alliagoll

-qllalica, A :mbcorclafllm, A trillillle, CaMes;a panwssijolia, Echi

-/lndortls cordi/alills, E grtmdijl"rlls, E Vir~(lI U S, LiIllO phytoll

vhw-Al k (f/ o;ll 'f b i Re.fI4lrs /I sifolium, LophOlo c mpli s (= Sagillaria) gtlayamell , \';, \', Sagifl{lria lanc{(olia, and S s a illarifolia

ALSTROEMBRIACEAB

4 genera; 200 , \1J ecies

This small group of Central and SOllth American plants has been

considered by some taxonomists as a family in its own right Others

have placed it as a division of the Amaryllidaccac Mabbcric"y, who follows Cronquist's system of classificatio , now lists even the

Amaryllidaccae as a subdivision of the Liliaccac The chemistry of these taxa is sufficiently <!iOcrent to argue for their separatc family

status, which will be maintained here

No alkaloids arc known n r were they detected in 15 samples

representing four species of AIsflV emeria and nine of BOfllarea: Alstroemeria il1odora A elegril/a A/slroemeria \1)P (2), BOil/area acutijolia, B edlilis, B IIirlella, B orata , D sa/i c oides, Domarea

sp p ( 4 )

ALOEACEAE

7 ge ll e ra: 400 l1Jecies

Thc family, characteristic of Arabia and Soulh Africa with some

species in other parts of Africa and Madagascar, has been separated

from the Liliaceae Species have been introduced elsewhere Several

have bcen lIsed as a source of laxative anthraquinones and as a

component ofcosmetic preparatio s Aloe is one of the oldest dmgs Ilositive alkaloid tests are apt to be due 10 Ihe fonnaton of com-plexes of nonalkaloidal cDnstituents with the Dragendorff reagent; alkaloids are not known in the liunily

Positive tests were obtained here with Aloe c(lII/IVllii, A cl eclIrlla,

A exee/sa, A lobliligemllla, A Utfora/i s, A III/III C "ii , A plio (212), and A SI!flidta

orlh%-On the other hand, 17 other species of Aloe, one of Gasteria and

three of HOlVorthia were negative: Aloe clwbmulii, A christianii,

14 PLANT /lLKALO/IJS

l lippcastrtllfl jJlllliceulfl, /-lippeaslmm Sp., Ilymelluca/Jis keyensis,

I/ ocddelllaJis, Narcissus sp.t Zephynmthes tlllllllflSCO, Z carilillta,

Z raseo

Negative results were obtained for Alllmy/lis vinolllm,

At/oigall-tl lII S (= CyrwIIIllIIs) brel'ijlorus, Brm'oa gemillijlora, Brut/faca

1'111-c h ella Cri",lm macrowflllii, C mflC rtllllherum, and an unidentified

Cr i llllm s pe cies

REFERENCE Gl1Indon, M F., N,,/umf Prodllcts Reports Ii (1989) p 79

ANA CA RI)IA CE A E

73 ge l/ era ; 850 !1 1 eci e !l '

R eprese nt atives o f I hi s m a inl y t rop i ca l fam il y ex t e n d in t o nor t h

temperate regions of Eurasia and North America Several are of

economic importance (cashew and pistachio n ts, mango fmit, J

ac-quer) and some arc known for their con l e n of substances highly

irritating 10 the skin (unlshiol and is relatives) Seven species hove

been reported 1 0 give positive tesls for olkaloids In this study, 1 0

samplcs from 111 species gave only one positive test for 0 !:lpecies

previollsly considered alkaloidal, Dra co lliome/oll lIIaglliferum

Othcrs loulld posi ive i n Ihis survey included As l rOllfllm

jlaxinijo-lililn ( 212), Bu e hallallia arbores ce ns, Lmll/ea s/ Ilhlmmlllii, L

wel-wit c hii , RlllIs (lIIgusli/olia, R ciliata, R illCisll, and R vb-ens (112)

The lollowing species were negative: A c t l/ocheitajili c i"ia,

Ana-cardiUIII gigalltellln, A micm cep h alwlI, A occ idell/ale, Astmllium

graveole ll s, A mi c rocalyx, As t m ll iu m sp., A ufei, 8leplwro c my a

invoill cr igera (in Blepharocaryaceae by some authoritic!:l),

811c11ll-nanin heteropilylla, Comoc/lldia p/atyphylla, COllloc/odin sp.,

Coli-I1I1S coggyg r ia, Dobillea \l lIl g r i s, Dracol1lomelOIl dno, D sylvestre,

Ellros c hi m ls papl/wl/ls, H arpep h yllulII caffi'Uln, Heeria argenlea,

I-/ d i spar, fI il/signis, H pal/ic ll/ osa, H r eli e llluw, lI eeria ~pp (4),

J-I s t e llopliyfla, Lalll/ea d iscolor, L edllJis L( w rophyJ/lIs

capell-sis, Ulhmea brasiliellsis, L lIIo/feoides, M{lIlgifera illdka, OdifU I

(= LWlllaea) wodier Ozoroa l-e t icufata, Pista c ia c hillell.\ ·is, /~ illteg

-e ,.,.i/l/tl , /~ mc: xicm w , Pro/Or/illS /ollgijiJ/ia, Rh odos plwera rllOdall

-A/hl/loid Test Re s lllt f 1 5 thera Rhus amerilla, R batopliyllo, R cop allillll , R delltala,

R d;;se cta, R dregealla, R dura , R ernest ; , R eros~, R g/~br~,

R giollcn, R h ypo le ll Cl l, R i1llegrifolia, R illterm~dw, R klrk.ll,

R Irmcea, R klllr;,ut, R legati , R l e llCllllllltl , R /ollglpes, R pil/a, R lucida, R IIwg(lli~'m~lItalla, R ",~c,"!,phylla, R 1II01l!s,

longls-R nataiellsis , R ovala, R pymlt l es, R ql/arllllUlIIa, R l-e"lIIat~"IO­

lUI, R rigida , R rosll/oi"ini/olia, R sill/ii, Rhlls spp (2), ~ S/~lII~s­

eem, R succedellla, R Imitel/sis, R tellllillerVlIs, R ter~b/1lt"!roflfl.'

R tomelllosa R (rilubllta, R typhilllt , R ulUlu/ala, ScllfIlllS ellglen,

S //Iolfe S C /tfIlIlS sp., S ( c rebin(hi/ulius, S weimwmii/olius, cmyll c~Jfra, Semecol'pus alra, S clU t ei/or ", is, Sl~/Odillgillm arg u - tum, Spoll t/ i a s cY ll l u : rea, S dule i s, S mOil/b ill , S I'U~Pll~-ea

Sclero-S ve Il OS( I Tclpirim gl/ai(lIIel/sis, 111JI1'Osodill lll par a ellsls, " ;'X I

At least 50 genera including some 75 specIes a.rc known to b.e alkaloidal; benzyli:roquinolincs, aporphines, berbenne!:l, and a vari-

ety of other N-containing compounds arc fo~nd throughol~t the family Rccent revicws of some of thesc constituents are aV31lable (Cave 'et a , 1989; Waterman 1985; Zhong and X~e, 1988) The

fo owing record of positive alkaloid tests was obtalllcd from 240

These plants k own to be alkaloidal, were rccoglllzed: AII "o."a 1II 01ltall(l, A m ur i c ata (2/4) , A reticu/ala, A squamosa, Asmlllw triloba (516), Gllatteria ' psi/op u s (4 / 4 ), l ' l exlilobus mO l/ opetal u s ( 1 /2), MO l/ odora m yristic a ; P opow i o piso~wp(l, .R(l l/ weflhoffla

le i e h l lmr dlii, R o llill ia ml/ cosa (8/9), Tr i vall'(lna pllllll/a (2 1 2), Xylo

Other positive lests included Alphollsea sp., A nll olla (/,.eIUlr~a

(3/3) , A clllysophyl/a, A c ras sf /lora ( 1 /2 ), A exSIlCC{/, A pail/Sins

A senegaiells i s (5/1), A1II/(ma 'iP" (2), A srellophylla, A,.tabollJIS

16 I'I ANTAtKALOIDS

1I/OlIleiro wte (112), A o(/oralissima (slcm), Asimillu /ollsi/olia,

A lIashii , A parl'ijlora, A speciosa, Bo c agegop ' i s multiflora , C a·

/lallga b/aillii (4 / 4), C adorala (5 1 6), Cleisfoc hl amys kirkii ( 1 /3),

Cleistopholis palells (1 /3 ) , Cremalmpel'lIIu fJol y phleblllll,

Cymbo-p e t aft l lll pellduliflorum (212), Des mos sp., Duguelitl afT all/ozonica,

D oc/arata, Dugueli a spp (3), D spix;Iltl, D surillamellsis ( 1 12),

Elllleastemoll schweilljimhii, Ephedra/JI/lUs omuzollicus,

Ephe-dralllhll s sl'p (2), Fusaeu Jongi/olia (3/3), Goniotfl%mus sp.,

Guolferia b1aillil' (3/3), G calva, G t!lIc emw, G dura (bark),

G dOl/ gaw, G megaphylla, G mic ll lls, G oc/ora ta (bark, Icaf),

Gllatleria \PP (7118) , MOl/adom gram/if/ora (2 /3 ) , Oxymitr(l sp ,

Paplla/,hia spp (2), Phaeal/tJlIIs I1IllClVpodllS (212), Polyatlhill

or-lII i"wlft (2 /3 ), /~ glauca, P obtollgijolia (212) , Pol yat/ hia sp.,

Popo-Will jil sca, P obO)l {ll ul1I , Popowia sp , Psellduvaria spp (212) , Rolli

-nia s p , 7e fnlmerrllll/llls dl/ckei, VI/ ol/opsis sp , V llaria c:llftlllae,

UVll ria sp , Xy/ opi a (l ma zo ll ica (4/4) , X amlllal i c a ( 2/4), X o e hmll

-tlUI , X sericea, Xy/opia sp • X tomel/losa

Negativc tcsts were obtaincd for the following: Allaxagor ea

doli-ehoe011}1I, Allluma ambo/ay, A dioica, A globiflora, A jiqllilah ",

A I Ollgijlora A f O llgipeps, A mel/tico/a , AIII/ O IUI s pp ( I)

ArlaiJo-fly bra c hyperalus, Cy at/lO c a/yx ramll/ijlO I'll S, C ridleyi,

Cymbope-falum bra ~ · i1iel/se De s mos dlllJ ' II111SclwiIlS , DlIglie fill fillfi1ra ce a ,

Gllalt e ria l lllstralis, G il/s c lIlpta, G me/iodora, Guatteria spp

( 1 0) , / so / ~lIa C ampal/II/ata Miliusa ve/llliua , Mit rel/a (= Fissi s

fig-ilia) kel/lll, OXlllulm /m/ ceo /ala, Po/yullliu ll}., Ro/lin ia do/abrip

e-Ill/lI , R eXlllbida, R exsllcca, R /llllrifolia Rollil/ia sp p (6),

Sacco-pela/llm (= Milius{l) lomenlo s um , Vvaria ajielii, X y /upia benl/wllli,

~ jhllesce n s, X gralUliflora, X Iillgll S l ijo/ill, X /Oll gs dOlj it ma,

The Apocynaceae is probably the most thoro ghly investigated

family for alkaloidal plants; about 1 ,000 of these compollnds have been isolated from its Illany Illcmbers This intensc intcrcst fol-

lowed the isolation and characterization of reserpine and ils rel

a-tves frolll the traditional Indian drug R auvolji a selpe l/ /i ll a and the

discovery of thc anticukcmic alkaloids of C lllh ara tllll s The stu y

rep rted here was donc, in part, during Ihe l mc these even Is look

place and, as a resul, a degree of emphasis was placed on screening

"u usual" rcprescnlatives of the family Some 775 samples inclu

-ing 4 3 s pe cies were exam ined

Many of the species recognized as alkaloidal by other investi

ga-tors were eonfinned as such AI/all/allda e at/Illrli c ll (417), A/slonia II/a cro phyJ/a , Alyxia olivaej(mlli.f A I'fI scifo/ ia, A s pido s perma dis-

c olor, A ma croCQ1pO II , A megalo c (IIpulI, A pyri/ofium Ihlls 1"Osell S ( 4 / 4), Dip/ o rh Y ll clllls c ondylo c mpoll (617) ErvatllllJia didlO/ollla (5 1 5), FUIlf/lmia ajri c lma ( 1 / 2), F e laslica (8 / 8), F lali - folia (3 / 5), Gabunia odomtissim{l (4 / 9) , Ge i ssospermulII vel/azii , Haplophytoll cimicidwII, f{olllrrheJla !ebrif u ga, If ItIlllfsbergii, Ma-

Clltlllll"UlI-co ubea glliallesis ( 212 ) , Ma/o u elia arbollw , M Iw/wqlwrillll (6/7) ,

NeriulII olea nder, O c hrosia ellipticll (214) , Pll gian lllll ce rifera (212),

P arsonsia siraminea , P velu timl ( 1 12), P eschierea affill is (6 / 6) P/eiocarpa mllti c a (8 / 8), Ra ullo/fia cl ifJ1'll, U c h illel/sis, R deglleri,

R hir.l'lIla , R mall iensis, R telraph y l/a, R verli ci l/alo, R viridi s,

R VO II/ ilor ill (2 / 2) , Uhazya SlriC/(l (5/5), Stem madellia d O

llllell-s mithii (212), s galeoflillllll ( 1 / 2), S obo)lata (3 / 4) , 7ldJem aemO /la tiicholoma, T e / ega ll s, T l){/IU/acqui, 7: fidelii, T rigida ,

llla-r rupicu/a (3/3 ), T ondu zi a /on Ki/ol a (212), J1,llesia g /abra (4 / 4 ), /linea ilia/or, V millar, Voacal/ga /110111'.1';;, rVrigll l ll lo/llellfosll ( lllit)

In addl o the following were positive: AI/amanda violacea ( 1 2) , Alstonia boollei (2 / 3) , A c O l/ goens i s, A cos ta/a , A glabriflo-

18 PLANT ALKALOIDS

rtl , A mOlllana, Alttonill spp (214), A vilells;s (2/2), Alyxia (mll(l/Jltm~

sis, A bllxifo/ia, A cOllcatellat a (1(2),1 Alyxia c[ markgrafia (212)

A j lallf!scens, A.fi"agnms (I12), A lancen/ala, A laurinll, A /

oesselia-IIll, A ILicida (112), A pllllClalll, /I, sinem';s (112), A s pi c aro, A

zeyltm-i e a, Ambelania ~p .• Amsonia breviflora, Apocynum ollllro memifolilllll

A ClImporum, Aspidospentl1l cruellfum (hark, fmit), A oliva ce lll/l,

Aspidmperma ~pp (4 / 5), Bai ssea wuljhorstii, Beallmon(ia gnmdiflora

(3 / 5) BealllllOlllia !l]J., Bona/usia hirlula, B swulI1ho, B lefraslachya,

/J lInt/lllafa, Carissa bispinosa (112), C gral/dijlom (112), c

tallcea/a-la (112), Ca rmlh ersia c arrulhersia, Cij/al/drops;s (= M e!adi l/lt s)

I/OVO-gllillensis, COllopharyngia eiegalls, C hol, '!ii (212), E'rvalamia erio·

ph o m (1/2), fhmferia ajric(lIl(1 (3/3), H ze ylanica (212), Kop,via

jruli c o.\'(l (212), Lmuiolphi{/ kirkii, L e pilliopsis t e mat e ll sis (212), A1(l ~

co uhea gLiianesis (212), Ma/oLielia fwfuracea (3/3), M Ilifida , Maf/(Ie ~

villa c tllleifolia , M iIIustris (whole p l anO, Mar ,w/e llia rubm/lis ca, Me ~

loilinus kmrlolphoides, M mOllogyllus (212), Oe hro sia S( lIIr1wi ce llsis

(2/2 ) , OdolllOdcnia sp , Pagiantha di c hotoma (112), P h eY lleana ,

p oligantha, P pll/meria/olia, P spil aem c mpa , i~ :mbglobosa,

P tilurst ollii, Parsonsia albiflora, P helicclllilra, P esc h ierea australis,

P bahia, P laela, Pe sc hiel'ea spp (6 n ), Plum eria rubra, Preslonia

mexj C (lIIa (212), Preslollia sp., Rauvolfia heterophylla (212), R

oxy-phy/fa, R s( lIIdwi c ellsis, R sempetjlorells (whole plant) R s uaveolenv,

Slemmailen;a ebr a c teata , S gr(lIIdij1ora , S IXI/m e ,.i , Slemmadellia spp

(4 / 4 ), Stmp hanthu s gratus, Tabemaemolluwa alba (1/3), T (Illg ul ata ,

T bllrter; (m), 1: citrifolia (313) T cras , m 7: grandi/ lora , T /il/ort/lis

(2/2 ), T lIuU"illla , T l1Iuricala (212), T ob /on gi/ol ;a , T I X l cific a,

T p \J 'c lwtr i/o!ia, T slI l/allho (3 / 3), 1flhemaemonlllll(1 spp, (619),

1 : S l l! lI%ha , T 1 ' lIbmoJ/is (212), nJell(!lia perllvi(llla , 1; ·ac: h e/o:.permll lll

jragralls (bark), 1'rachelospermumjasminoides, Un : eo la bra c hy ce pha·

la , Yinca /al/ tea (2(2), V pffsilla, Vinca spp (212), VO(fCaflgll "atal ell~

sis, Wrighlia pubescells

Negative t es t s we r e ob t ai n ed from the follow i ng: Acokmllhera

o b/ angi/o lia , A opposilifofia, A scliimperi, Adenium multi/lol'llm,

Agallosma O C Uli/illata, A aganosma, A c OIy op hyllata , A, cymostl,

A gracil e, A /1Iar gin ata , A sch!e c ht e riana, A velul;,w, AI/amanda

spp (3), Alstonia ma c rophyl/a, A/stonia spp (2), A/yxia aC I//i/olia ,

A , aff/llis, A amOelltl, A miakel/sis, A bodinieri, A brac t e%sa,

A br e vipes, A e a e l/milla, A celas /rilla , Alyxill cf de/oliala , Alyxia

cf plllle;, A cJllsiop h yJ/a, A , di s pJw e m c arpa, A {~?ratophylla,

A, ellip/i e a, A , e l y /h rosper ma , A j1oribullda , A forbesl/, A gfallco~

phylla, A Iwillall ensis, A , ili e i/olia , A int e rmedia, A lamii, A /at~I,

A , laxij1ora, A levine;, A /el/ c ogyne, A Jillearifolia, A Illz(J"en'i~s,

A microbllxus, A , m O llli e ola, A myrtillae/olia , A mUII/mlllana ,

A oroplrila, A parvifolia , A, pisiform;s, A , pseu.d~sill.ellsis, A pur~

pur-eoc/ada, A r e il/ward ii, A revo/uta, A, roma,tl1lijolta,1' sc"'e~~1,­

teri, A scabr ida, A scam/e ll s, A Se lp elllllta, A slbuyalle , m ,

A sorge ren s i s, Alyxia ' \PP (2), A s ellala, A slfbaip ;IIa, A torq u

ea-ta, A, torresialla, A yunkullialla, An c horllia sp., Allcylobothrys pet ersimw, Allgadellia berleri, A lil/denialla, Anod e ndmll , affine,

-A axillare , A bellflwmjaflllm, A, c andolleallum, A corlOcelllll,

A {aeve, A loheri, A /IIal1l1briaf U III , A oblollgijoliwlI, A pall i c u la

-(!1m, A pun c tafullt, Apocynllm cfl,,"abilllllll, A, sibriclllll, Arria o~'­

bict/laris, A s pido sper ma polyneltroll, Aspidmperma sp., Camerarw allgll sti/o lia, C belizellsis, C lull/olia, C IOl/gil, C retfls~, CariS!):~1

edufis, C haemato cll1pa, C ma cl'Ocmpa, CarrulherslO bmssfI,

C dal'OlIensis, C ma eg regorii, C pi/osa, C lati/olia, C sca lldells, Cerbera jloribwu/a, C odal/am, Ce r/ )era ,rpp (3), Cli((llldr~

orien/alis, COlldy/ocmpon rOlt'v oljiae, Cor mla m(l c rocmpa, C utl lis, E cdysa lltlr era rosea, E c Mtes Ilm~ellata, F?rste,.of/ia leptocarp~,

-F iuscJl1latltii, F riedelii, F ru/a, «()rs/emma spp (3), F tlty,:sm dea fl imatarrt1'l1s arli e lllalu s, H bracl c atu s , II obovalaus, Hlma - /all;lw s spp, (14), If subcarllosa, H st e yermmtii, icllllOCll1PUS jr~l­

lescells, Kopsia j1av;da, /"ll1ul olplt ;a bu challa/i.i, L: c ap e s s,

L owarellsis, L IIgal/dellS; S, /"(lsegllca e re c ta, /"YOIISlfJ rrm c ulara, Ma clVs;phol/;a bra c hysipllOn, M, hypo/ e uca , M fongi/lora, M I1I(1Cro ·

-s ipholl , M /1Iartii, M petraea , MaclYJsip"~lIia S {JP · (5), M ve/ame, Malldev;lla filiformis, M /oliasa, M /UI/i/Ol'mlS, M llIllllaculat~.'

M kanvil/skii, M l esigna, Malldevilla spp, (17), M steycrmarkll,

M st/bcarnosa, M sllbsaggirala, M elorli f/us ba tt en·, M sual'colellS, Mesechiles trifit/a, M triJolia, NeriuIII int/icllII/, N odorul1l, 0(/011 - todenia gral1diflora, Pa e hypodiulI/ Jeolii, P sal/fldersii, P sl~cclllen­

tum, ?agi c mtlia ma c lVcmpa, P m egaca rpa, P P(~lI~~(1CqUf, Par~~

hallcomia sp" P peruvialla, Parsons;a baudoU1ff, P bms s ll ,

P brlll/ellsis, P C Wles ce llS , P ca p mlal'is, P c am ea P cOlllusa,

P crebri/ l ora , P e llmmillgimlO, P c urvi sepa la , ~ e~lIlis, P /ll.J\I~,

P hetemphyl/a, P javonica, P fa evis, Plata, P ltJaclIla , P 1II

01tssl-"

ma, P mlata I~ rubra , Parsol1sia sP't P vell/ricos", Pe/taste,\' .\ 1'.,

Peschierea australis, Plumeria (u ': lIli/iJlia, P oiJtm'a, Plumeriopsis

ahollai , POlf si a grr ll1 tiijlora, P faxijlom, P ova la , PreSIOllia (lCllti

-falia, P agglulillQ{a, P amanuensis, P balticlisis, P bra chy poda,

P cO GIi/a, P cO llcolor, P gualamalellsis, P IUlss/eri , P isrhmi c a,

p lilldleytllw, I~ lilldmmlllii , P ' margillflta , P mollis, P 0/)0\1(1((1,

P peregrina, P porlohell e llsis, P lj llill qU(mgu/aris, P riedeJii,

P so/alli/olia, Pres/onia spp (5), P IOmell l osa, P /rijida, Pteralyxia

ma c ro c(l I1)(l, /?auvo/jia lilleari.s.epala, R seJlowii, Rhabdadellin b i

-c olor, R bifiol'a, R macrostomG, Sabajlorida, Secondacia

dellsij1o-ra, SkyulI/(!ms sP't Stipecoma pe/tata, Strophanthus gerardii,

S hi.\pidus , S II/teolus, S pelel"siallll,~', S Sarll/e ll tosu.\', S specioslIs,

S weJwitchii, TabernaemolltmlO heYflealla , Tabemaemolllana spp

(4), 7(mlllad e llia sp., T stellaris, 111evetia lIeriifolia, T ovata,

1 : peruviana, T rhel Jet oides, Urceola javallica, U lucida, U pillel/sis, U IOrulosa, Urechites alldriell xii, U IUlea, Val/oris hey- /lei , V so/allocea, Wrighria saligllfl, Wrighr/a .w

philip-Several samples of the less common genera in this extensive fami!y were supplied in the form of gleanings from herbarium specimens

A QUiFOLIACEAE

4 gelleraj 420 ,~pecies Most of the species in this family are in the genus J/ex , which has three centers of distribution: South America, North America, and the SOllth Pacific The genus is important as a source of lumber and ornamentals (holly) and, in South America, as a basis for traditional cancine-containing drinks (mate and guayusa)

The chemistlY of the famity is that of the major genus (lJex)

known for its contcnt of cafTeinc and theobromine along with

cyano-glucosides of a SOlt which do not liberate HeN on usual hydrolysis

Of the 42 species of /lex tested only four were regarded as

positive: I C(lssille, I coriacea, I crell ata, and J glabra (213)

I cassille and I crellata had previously been repo'lted as alpositive The purines do not give definitive alkaloid tests with the DragendorlT reagent and are not considered true alkaloids by some investigators

kaloid-Alkaloid lesl R eMI /i s 21 The following spccics were negativc: Jlex (ll/omala, / amlremi-

ca, I asprella, I bioritellsis,l bwfordii, 1 c/talllaedIJifo/ia, J co r ~

mila , I discolor,I diuretica , I dtll1losa, I.jOl"IIIOS(1I1(1 , I IUlIl cea l/a,

I impressivella, J ;lIcana, I incanw ra, I jell1tanii, I l(levigala,

I mi crod o11fo , J mitis , I opoca, J parag/./ariellsis , l parvifolia,

l pllbescells, J rOlullda , l serrata, /lex spp (5), flex cf versfeeghii,

I verlicil/ma, l verticil/ara, I vitis-idaea , I vOlI/iroria

P/telline COlllosa SphcllosremOlI lIIiakcllsis, SphellosremOIl cf

arfilkensis, and S papllflllW1/ were also negative; they arc somtimes placed in families of their own Phellinaceae and Sphc oste-monaceae rcspectively

Alkaloids 'are known for somc 25 genera (35 species) in the

family; coniinc, hydroxytryptamine, berberines, and an assortment

of other N-conlaining compounds has been identified

Ninety-four samples representing 73 species were examined in this study C%cosia esculenla, Symplocmplis joetic/us, and Zmlle- deschia aerhiopica (1 15 ) had becn previously reported as alkaloid-positive

Several ther species were found here to give positive tests as

well: Acorlls c alamlls , A gmminell.'i, AJocasio odora, AlIfllllriulII

sp ( 1 13 ) , Cyrlospermo jolll1slolli, PeJlwuJra virgillica, pus joelidus, 1}pllOlIilllJl divaricalul1I, Urospallw saggitaefolilllll (112), Zallredeschia meltlllol e llca , Z rehmwlI1ii

SympJocar-Some of the literature reports of the presence of alkaloids ill this family may have resulted from the use of ammonium hydroxide during isolation This practice.,.has bcen shown to convert certain of the plant constihlenls to N-containing compoun s, which then react

as alkaloids in standard testing procedures

Negative tests were obtained with the following species: A ca rus

22 PLANT ALKALOIDS

graminells var p"sillus, Aglaonel/la modes/lilli , A/ocasia intiica,

AmolpilopltllJllIs glabra, Ạ mOIl/ric/lOrdia, Allt/lllriulIl mẹxicallulII,

Ạ perla/orad/alUm, AllfhuriuIII spp (2), Ạ scam/ells, Arisaemo

dra-COlli/ifill, Ạ japoniculII, Ạ tripIJylllllll, Amlll ma c ulallllll, Calla sp.,

C%casia allliquorum, Epiprelll u lIl pilllUltlllll, fle/erops;s sp., Lasio

spinosa, MOils / era perlllsa, MOIl/richart/ia (= Amorphophallus)

ar-borescens, Montridwrdia :,p., Drolltilllll aqua/lelllll, PhiloqelldrolJ

ill/be, P inaeqllilarerum, P obliquijoliulII, P rut/gemwllI, P seqlline,

P sel/OI/1Il, Philudendron spp (7), Pistia stmtioides, Pothos

see-II/atllli, Rhodospatha ÍOseospadix, Richa r dia (= Zallledeschia)

bra-siliensis, R scabra, SpathiphyllulII cochiearị\1)(lllwlII, Spathiphy l

-111111 sp., Sty/o c hitofl flata/ellsis , S p fi beru/lIs, Sty/o c lli/OII sp"

Symllltherias (= Amorphophallfls) syfl'atica, SYllgonium lIamasii,

S podophyllum, Syngonilllll sp., S lIeJ/osiwlIIlII, Urospatha sp ,

Xal/thosol1l(J mcru/ozae, X //lexical/11m, X rolmstw;, X

saggi(l!o-li ll lll , X lI iolacewlỊ

AR A Li ACE A E

57 g llent,' 800 s ecie!1 '

This is primarily a tropical family with centers of distribution in

In o-Malaysia and tropical Americạ Three genera arc found in the

United States

En lish ivy and others are cultivated as ornamentals; some are

sed <IS medicine (tbe traditional Chinese dnlg ginseng belongs in

this family)

Several unnamed alkaloids have been recorded i n some ten

gen-era of the nunilỵ Quinazolines have been chamctcrized from the

genus Mackill /aya; the known alkaloidal M schlechteri was also

found positive ill this studỵ

Positive tests were likewise obtained with the following species:

Aralia mcelllosa ( 1 /4), Clissollia pal/icll/ala, C thyrsiflora, C 11111

-bellijera ( 1 /3 ), D e ndrop(lIIax peJl/lcipllllclata (115), Didymopwwx

rremllllllll (112), Gasrol/ia pap"tllla, SeemaJmtlralitl gerrardii

The following species were negative: Acalllhopall a x I r ijoliallls,

Aralia c a li/arnica, Ạ hispida, Ạ /Iumilis, Ạ l/Iuli c allJis, Ạ

regelia-/la, Ạ spinosa, AstIVtri c ha asperijoJia, Ạ jlocosca, Bra,~·.\'{lia a

cti-llopiJylla, Cussollia kirkii, C naw/ensis, C spi c ata , Dendropmrllx

l

Alkaloir/1 est Ue:,;ult \· 2.1

arborélIIl, D CUI/eall/III, D parlliflorum , D peJl ucidopullctatus, Didymopallax Ol1gllslissillll1, D morotololli, Didymopflllax spp (3),

D vinosfl1I1, Dizygotheca (= Sc/iejJlera) coel/osa, Dizygorlteca sp., Giliberlia (l/"borea, G, clmeato, I lec/era helix , l/ep/apJeu/"uIII

(= SchejJlera) arbori co /ulII H octophyllulII, Iị velllltosulII, K~lo­

pfmax (= E/elliherococclls) pic/ llS, Kissotielldl"OlI (= Po/ys cUlS )

m istraliamll ll, Mackillftiya macrosciadia, Me lyta sp., Myodo c arpll:<; sp., Neopw/{/x a rboreulIJ, N colellsoi, N simplex, Oreopanax capl-

{(III/Ill, Ọ echillops, 0 JUIIIIIIII, 0 s a lvinia, Oreopmwx spp (2),

0 xa/apensis, Pallax gillsellg, P/emndra (= ScllẹDlera) stahltall~,

p lIifiellSis, Polyscias baljouriana, P elegal/s, P jiJicijolio, P joy/el, P sambucijoli(l, Pse/ldOp(lIIflX crassijolillm, P edgerleYi,

gll/I-p les!wllii, SchlejJ1em digitat{/, S oClophylla, S rail1'llllialla, pal/ax papyrijerus, Terrap/asfll/(/ m (= Gastollia) sp., 7ieghemopa -

Telra-1I0X (= Polyscias) elegalls

A RA UCA RI AC E AE

2 g e e rll ; 32 s p ecie s

Members of this family are ornamental southern pines familar to horticulturists In the southern hemisphere, except in Africa and southeast Asia, some are the source of lumber and resins

Therc has been but one positive tCSI for alkaloids recorded for

this small gymnospelm famiy (Agalh is allsrralis) A test of tbis species was negative as well as tests on Ạ moorei, Ạ ovẵ.'

A rob/lsla, Agot his sp., Ạ virellsis , An lllcaria bididelli i , Ạ C OOkll,

Ạ cflllllillglwm i i, A excelsạ and Ạ fltleị

A Rl S 1'OLO C flI AC E AE

7 g'e fl e ra , ' 410 s p e cie

This is essent a y a tropical famiy but some representatives occur in the temperate zonẹ

Nitrophenanthrcnes and their reduced (amino) cOllnlelparls .<lS

well as quarternary ap rp ines are characteristic Some species have been used as medicinals

24 Pi.ANTALKALOIDS

Positive tesls for alkaloids were obtained with the following

species previously known to be alkaloidal: Aris(olo chia elegalls

A gigallfea, A fagala In addition an unidentified Aris/% c /Jia sp

was found 1 0 be positive (1/3)

Negative resuits were obtained for Arisrolochia burchellii,

A dh~) I /}IlI, A jalisc( lIIa, A kallklillellsis , A macrophylla , A

pau/is-talla, ArislOJoc/lia spp (3), A 11:;mlgll!aris, Asarum c (lllad e ll se

A tell/ollii, A laitoellse

ASCLEPIADACEAE

347 genera,' 1, 850 species

Although this family is pantropical, most of its members arc

South American A few genen) extend into temperate regions; olle

of these is lhe familiar milkweed, Asclepias syriaC(l Some arc

ornamentals, some yield rubber, others are livestock p isons The

taxonomy of the family is 1I0t a matter of gencral agreement

Few alkaloids have been found in this relatively large family

Those in CJyplOlepis, CYlI(lfIcllIIlIl, Pergu/aria, 7jliophora, and

Vill-ce/oxiculIl have been characterized, some have b een synthesized

olhers have yel to be isolated in pure form

In this study, 182 species were tested with the following pr

e-viollsly known alkaloidal plants found positive: Asclepias

cums-slll' i ca (2 / 13) , A linaria (2 / 5), Ca!olropis gigalllea (l/3),

Ectadiop-s is oblol1g{ji)Jia (1 /2 ) MOl'sdellia cOlldurango

These spccies were also positive: Asclepias con/ijolia ( 1 12 )

A fil.'icicula/a, A jhlficosa A hUlI/islrala A I'OlImdifoiia A

sub-vcrlicilla/(l (21 4) , A veslira, Bleplwrodon sp , Caralluma

mammi-Jiaris, Caml/ullla sp., CJyplolepis oblollgifolia (1 /2 ) , CYIl(lllclllllll

mi(reoJa, C lIigrulII , C praecox , Gomplwcmpus physocwpus ,

Go-lIoJolJIIs gOIlUCWpIlS, G obliqlllls, Hemidesl1l1ls illdiclls ( 1 / 2) ,

He/-eros/emma ("·Ol/il/Illll, H paplJ(lIla l-Ioodill sp., Kal/(lhia JallijIora

( 1 /2), Marg(lrelta rosea, Mar.wJ el/ia dregei M ros,rrala, Mic r%m a

iI/callum, M massollii M s aggitalwlI (112), PachycQ/1JUS rigida

P sa lber Peclillaria brevi/oba, Pelliarrhillum illSipidlllll,

Pergllla-ria daemia-extensa (3/1 0), Pe l gu/aria sp., Secamolle gal'al'dii,

Sla-peJia giganlea (2/3), S oJivacea , S schillZii, Slapelia sp.,

A bidclIJata, A bmchysJep/wllia, A burchellii, A cali/ol'llic lI

A cOlltrayerba , A fililol'l/!is, A gibba, A glaberl'i1l1(1, A celiS, A in comala, A melmulta, A mexicalla A Il glecla A oello~ t/telVides, A orata, A oraloides, A ova to , A pring/ei, Asclepias J Pp· (2), A Jpeciosa, A suhulala, A syriaca, A verticil/ala, Aspidog!os - Slim bijlorum, B/epJwl'Odoll IIII1Cf'OlIatum , n sleudeliwlI/l/I Bl'achys- teflll(l pygmaell lll , C({mllul1la piC Hlllthoides C Cempegio abyss ini ca,

glal/ces-C occu/la, Ch/orocodoll (= Mondia) while;, Cosmostigmo slim Oyptofepis capensis, C clyploJepoides, Cynane/wlII aji"icOlIllIlJ,

racel/lo-C ellipticum , CjloribundwlI C /reemrllli, C klmthii, C o/JtuSijO/i lllll ,

C parvijlo/'l/III , C prillg/ei, Disc"idia raffiesifllla , Dischidia sp., Dilassa acel'Osa, D ridelii, D edlllllndoi, Ditassa !'p., Dregea abys- sil/iea, Finlaysollia obovata, Fockea /ugardii, E multiflora , Glossos- telllla carsollii, Gomphoempus (= Asclepias) aureus, G g/aucophyl- Ius, Gomphocm1Jl1s sp , GOll%bus cl l1 ),salllhus, G broadwayi,

G piloslls G prodllctllS, G IIIl!florus GYlllllema lalemijlo ru s,

G syiveslre, Ho ya bicarillala, Marsdenia hilarialla M macrophy lla,

M mexicalla, M pringJei, M IUbmjils cli Male/ea IIil's IiIa M.pavonii Mafa/ea sp., Melaslelllla (= CY/UlIIchum) ongllslifolium , Me l aste/ma

sp • Micl'O/oma lewlI./!f oliul1I , MOlldia whilei, Olealldm wallichii Orrh osia urceo/ala , Oxypela/llm amouial1ulIl 0 banksii, 0 1'01/- O$um 0 pedi cil/allilll, Oxypetallllll spp (9), 0 sub/allatllm, Pachy- CllI1Jl1,\' appel/dicit/allis, P va/idus Pel/talrapis cYllallchoides, Per gll- laria spp (2), Pilo sligma (= COl/stamilla) thollnil/gii Raphionllcme burkei, R elala, R jlanogllni, R hil'SIl!a, Rioel'euxia picta, R londo-

sa, Sarcoloblls clausum, Sarc%bus cf globosus, S e/eglllls, S /lal e, S mosel/sii, Sarcoslemma spp (3), SchiSlOgylle W·, Schizog!os- slim petherickalllllll, Secamolle albill;;, S j;'ulescel/s, s parvi/olill ,

vimi-S geftleffii, Stapelia variegata, Sto ma tostelllllla 1IlOlIleiroae, Stu/Jilia

(= Orbea) lapscollii, Thcazzea apicll/ala, 1i:lssadia pmpilliqua, phora grQlulijlora, Villce t oxicijlll sp

7jl/o-The following genera have been placed in a separate family,

Periplocaccac, by sor'ne taxon mists: Filliaysullia, J/emisdeslllus, Montiia , RapiJionocme , SlOmatoslellllJlll , T(lcazzea

species yield oils used in soap making; others are medicinal

One sample of an undetemlined species gave II positive test for alkaloids in this study The chemistry of the family is otherwise unknown although alkaloids are known for the Zygoph llaceae

Alkaloids have been reported for two species of Impatiens but 12

sa.mples jncl ~I i ng lhe following II species were tested in thi ~ survey without poSitive results: Im patiens btflora, I cecili, I chillensis,

I dlll/liei , / kirkii, I pallida, Impati e s 11J!) (3), I sy lvi cola, I IIl/iflora

IJ ASE LL ACEAE

4 gel/em; 15 !J1Jecies

This family is found mosty in tropical America and the West

Indies, with one species native to Asia Some are cultivated as

or.HlInentals; others are used for foo s-a leafy vegetable (Basel/a)

and a starchy roo of the Andes (UI/Ile u s)

Eight samples representing five species gave negative tests for alkaloids, Which have not yet been found in the family: Allredem vesica ria , Ba sella rllbra, BOffssi1lgallltia ( = AI/federa) basel/oides,

Indolic glucosinolates have been reported in Bat is maritima, but a

tcst of this species did not give a reaction with DragendorfT's reagent

2 ge l/ era; co 900.\pecies

The nunily has wide distribution throughout the tropics, especially

ill South America Varieties of many species have been develo ed by horticulturists and grown as familiar garden and h use plants

Alkaloids are not known in the family Twenty ~s i x samples repre~ senting 21 species were tested without positive result: Begol1ia

bafSOlllillf!.ll, B cajJi'(l, B jhltico WI, B gmcil i s, B herac/ei/o/ia,

B hi spida, B illcamala, B in ciso-serrata, B ma cdollgaJli i, B lllmbii/ olia, B palmaris, B prillceae, B ramfa i ensis, B I'icinijolia,

lIe-B sc am/ ellS, Begonia spp (4), 11 tovarellsi,fj, B u/m({o/ia

15 gel/era; 570 species

A fcw members of tile family arc found in South America but as

a group the l3erberidaceae are chiefly north temperate Many are llsed as ornamentals and some bear edible 1I'Lli!

Earlier taxonomists included 12 genera in the family, II of which

34 PLANT A L KALOIDS

A positive lest for alkaloids had been reported for the pineapple,

Allo"a.~ COIII OS U S Tests on 45 samples Including 41 species in ten

other genera failed to give a p.ositivc result These species were

negative: A ec!Jmcll hra C l eata, A dis/i e olllha, A 0/'11(//0, Anollos

.WllillliS, BiIlhetgia ma c r o/epsis, Broil/clio pinguil/, Bromelin sp.,

Dyckia croee a D sel/owa, Dy c kia -w H echti a g hres b r eg hlii ,

H glo m era /a , H po(/mllha, fl lexalla, Pil c a i rllia karwillskirllla

Qllcsllelia i llbri C llta , 7i1/anclsio a c h yrostac h ys, T olld ri eu xii, T

be1r-tlUlmifllla, T b ul bos a T Cap lIHl1 ed ll Sae, T./ascie l/fata , 1: iOllonlha,

T jU ll cea, T /tll ' ida , 7 : recurvafa, T sc hi ee/eallo, Til/alii/ sin spp (6),

r tellllijt>/ia, Vri esia ca l'inata , V !riburgellsis, v gladioliffiwa,

V plolYllelllG, Vl'iesia sp., V va ga ll s

BI IUN I ACE A E

J 1 g e n e ra ; 69 ~ 1J ecie.\'

The family is SOllth Afric n; some are cultivated for cut nower.s

No alkaloids are known Eig t samples representing seven s

pe-cies gave but one positive result, Bel'zelia im e rm edia The remain

-der were negat ve: Berzelia abmlal/ofdes, LJ /allugillosa, Bmllia

laevis, H /wdijlora , Nebeli a (= Bl"llnia) palea ce a Swavia radiata

I JU R SE RA CEAE

8 ge ll e / ' fl; 540 specie:,'

This family occurs in tropical America and in the nOl1hcastern

portions of Africa The latter region's species are most familiar as

sources of frankincense and myrrh since biblical times Some have

lise as ornamentals

Positive' lkaloid tests have been recorded for species of Comllli

-p Jw/"{/ , BoslV elli a and P rotium fn this study, a total of 149 samples

including 95 species gave positive results for Prolium macgregorii

( 1/4 ), P n eglect ll/II, <Ind one other undetermined species of tha

genus

Negative tests were oblained for the remainder of the samples:

l10 swellia ser ra la, LJllnem a t e m , I1llrsera sp all' ap t era, B ar h

rea, B arfda, B ari e s i s, lJ attenuata, B bi eo lor , IJ b ipilllwta ,

/1 cil ron ella, 13 cOIIJ u s a 11 c o pal/ifera, B cOIycemJ'i.'i, B crell{Jla,

n CII l/ eaW, Bwsera sp aff C II/leata , Bur- se ra sp aff d e l/ti c l/lala ,

B div ersija{ ia , B excelsa, 8.fagolloides, 11 g o/ eouia na , B g /ob Jolia, B g mll dtfoli a B graveo / ens, B heleresthes, B him/sial/a,

,.i-B illstabilfs, B jomllensis, 13 kerberi, B IWIC : (jo/ia, B l eptop h! o cos, B IOl/gipes, B mierophyila, 11 /// o r eJensis, B mu/tUu ga,

-B lIesopola, B oec l illa, B odoraltl, B palm er i, B penieil!ata,

B s a rco poda , B se hle chlelldalii, B s imal'll ba, Bur sera sp alT

sima ru ba, B sllbmoniliformis, 8 lerebe ll tJlIl s (l C lllllillaw, B loso, 8 Ir iJoli ll la, 8 Irim e ra , 8 veja r-v as qu ez;i, CWJ(l r ill lll a C l/l ifo-lilllll, C album, C ausimlascilllll, C Clllslmlimllllll, C malI/ elise,

lomell-C pimelllll1, C vili e n se, CV l/llllipJ w ra aji-i c( ma , C cwyaf{fu/ia,

C eel l/li s, C g lam/llio WI, C harveyi , C marl o/hi i, C m erker i ,

C mollis, C l1egl ec /(l , C pyraca llll! o ide s, C rehmmmii, C sc him ~

peri, C lellufpeliolala, Elap hriw/I si marollba , Garllga jloriblll1c/a,

f1a pla /alm s jloriblillcills, H gic mdu/ os lIs, H l eeijoli ll s, H robllS/ Il S, Protium copal, P g llian ellsis, P h ep taphylllllll , P kle i n;; , P "odulo -

S I/III , P p ara ens f s, P p o/yhrol lllll , ProtiulII spp (4), P .\j)f·lIce alllllll ,

p l e lllli/olilllll , P III1 i/oli a/llm, Telragaslris balsamifera, 1hlllillni

ck-ia rhoijolia

5 ge " e ra ; 6 0 species

The family is primarily of the tropics and subtropics or the Old

World Pa chysandra procllmbel/s of the eastern United States is a

common ground cover; S illlm oll dsia is the source of a substitute for whale oil Others are ornamentals

The "Buxus alkaloids," as the nitrogenous compounds isolated from this family arc commonly known, have been recorded rrom 33 species The genus Simmrmdsia has been placed in a family of its

own, Simll1ondsiaceac; is seeds have been reported to give a posi· tive alkaloid test but other than a cyanoglycoside, no alkoloid has

been isolated

'I\vo samples were tested Bu x s lallci/olia was positive, Sacro~

cocc a Iwokeriana was n t

This is n family of aquatics of the tropical and wann temperate

areas They arc onen lIsed in aquaria Earlier literature has the

genera in the Nymphaccac b t Cronquist gives them separate fami

-ly status

Alkaloids arc nol known; Brasel/in sc hreberi and Cabomba ca

ro-lillimw tested negative

CAC T ACEAE

.1 0 g e ll e ra j 1 , 6 0 s p ecies

The COlctaceae are indigenous to the New World They arc eco

-nomically important as omamcntals; the fruits of OPlllllilJ arc used

as food; the p eyo t e (Lophophora williams;;) is a well-known hall

u-cinogen

Several genera of the family are alkaloidal; the alkaloids are of

several types and have been the subject of reviews Samples (36)

covering 33 species were tested to give, as expected, positive lesls

for N y l oce rtl s lim/allis , / opho ee ru s seho ttii , LophopJlOrtI

william-sii, f'a ehyee r e lls peelell

Alkaloids were also detected in the following species: Ccreus .'p.,

HchillOCllctw; e llll e C (IIrlllll S, E roetleri, E sarisso ph o ru s, Opfllliia

dillcllii

Negative reslills were oblained with the rollowing: C lypto eerr!lls

:'1)., Echillocactlls a ca lltJlOde s, E horizDlrlll(llolliu ,~', 1:: ingells,

Eclri-" oee rells JOllgiseflls, E lIIojavellsis, E s lall/incll s , /-Je/io ce r cus

spe-ciu s /ls , Mammilaria dioica, Myrlillo c acllls gco lll e (ri z (lIIS , Oprllliia

atrispilll1, 0 aurimrlia c a, 0 callwbrigcIIsis, 0 CrtlllaCea, 0 hllmi

-j i/sa, 0 imbri c a(a , O Jeplocaulis, 0 occidellla/is, 0 tomeflfosa ,

P ereskia aCflleala, Perc ski a sp., Rhipsali s baccijera, R cassytlra

TexOCllCtliS me/o cac fijormis

o-Little chemical work has been d ne; alkaloids are nol known Only one species, Callilric/te s taglloli s, gave a positive lest (112);

C h elerophylla and C vem(l were ncgative

CA LY CAN TIJ ACEAE

J ge ll e m ; 9 ' ~1 1ecies

This small ramily is of imporlance as ornamentals with rragrant

nowers Alkaloids are common in the family

The known positive species, Calycmrthus.!loridus (112), C glau

-cus (2 /2 ) and C occidellla/is were also fOllnd positive in this study,

as was Chimoflalll/ws praecox

CALYCE R ACEAE

6 ge ll erll; 55 '1 1ecies

This small family is related 10 the Composilae but has none of its

economic importance Alkaloids are nol k own

Neither Aci c mpha spat/wIota nor Boopis bllpleuroidcs gave po

s-itive tesls in this study

CA Mi' ANUL A CEAE

87 ge ll er ll , ' 1 ,950 v p ec i es

The famiy is importanl chielly ror its large number of ornamen

-tals It has wide distribution throu houllhe temperate and SUbt

ropi-cal regions with somc reprc,,<;enilltives usua y confined 10 high

elevations or the tropics Some taxonomists have had Lobelia in a ramily of its own (L6bcliaeeae), but this genus is now generally

included with the other beUflowers Alkaloids are known, parlicu

-38 PLANT ALKALOIJ)S

larly in the genera Lobelia and CamplwlI/a Lobeline has medicinal

use and has served as a substitute for nicotine in attempts 10 "curc"

the nicotine habit

One hundred and twenty samples of the f.1mily were tested rcpre~

sell lng 96 species; severnl positive results were obtained /i'OIll salll ~

pies known from carlier reports to have been alkaloidal: Campwwla

c mpalhi c , C mediulII, Is%il/a /ollgijlom , I obe lia oll ce ps, L c ar

-dillalis (212), L cJiffOl'liol1(l, L.flllgem, L injlula, L tangelll/o (212)

Other alkaloid-positive species included the fOllowing: C colli

-Ilia , C g/olllerara, C Inti/olia, C mediI/III, C tolllmllsilliwUI, Ce

ll-lropOgoll W CY( l1l e a (lllgllstffolia, Cyphia assimilis, C bulbosa,

C elata, flippobromo /ongiji)/ia (2 / 2), Is%l1l(l petmea, Lobelia an:

aglllllla, L ol/ceps, L cardinalis, 1 c hinen sis, L c1iffortial/a, L e.xa l -

{(Ita , L de cipiells, 1 lulgf!lIs, L grllilla (1 /2 ), L hassle"; (3/3),

I laxij10m (6110), 1 lIicotil/ac/alia (212), L pyramidalis, L shUt

-fuae, L syphilitica, Lobelia spp (3 / 6), L splende ll s, L stellophyl/a,

Phylellma orhic u/are , Siphocampy/y/ls d/lpfoserratus, Sipho c ampy

-Ill S 'II' (112), S su(furells, S IImbellalus, S verticil/allis , lVahfe llb

er-g iaar enar ia , IV, ballksimw, IV, ca/ed()lIicll

Negative tests were obtained with the following species:

Campa/IU-10 americana , C allcheri, C barba/a, C caespifosa, C /clles/rellattl,

C jilic(lulis, C gllrgllllica, C porlellsch/agilma, C prellellfhoides,

C waldellsteillill Campmwmoea (= Codollopsis) /accin{{ofia,

Centro-PlJgolI spp (2), C sllril/ameIlSis, C/ermolltia persici/o/ia, C kakeUlUl,

Codollopsis Itlllci/olill, Cyphia /riphyJJa , Lobelia (II/gli/ala, L coem/ea,

L cOIvllopi/olia, L ehrenbergii, L era/tata, L /il/earis, L lIlu/a,

L pilli/olill, Lobelia spp (3), 1 fOmemosa, PhyJloclwris (= RI/thiel/a)

slIbcon/attl, Pratia (= Lobelia) cOllc%r, P rellijimnis, PrismalOCarplls

dijJwms, P pedlillclI/ata, P rogers;;, Siphocmllpylus I ycoides, Sip h

Q-campyllls sp., 7hodallis biflora, T pelfo/iata, Wahlellbergia

llIubvsa-ceo, W marginoto, Wahlellbergia sp , W lI/ullilaUl

CANELLACE;lE 5 genera,· 16 species

This small family occurs in the tropical regions of the Curibbcan,

Madagascar, md Africa The genus Canella is valued as an

oma-mental and hy some as a condiment (wild cinnamon)

Alk aloid ' J est R emlls 39

Chemical investigation of the flunily has becn scanl; dendron (= Cilllwmodelll/ron) ma(/agllscarie1lsis has yielded a quarternary base

(.apsico-Six samples representing two species were tested with a positive result obtained for Cllpsicodelldroll dillisii (1/5) lI'arbllrgia IIgal/ - densis was negative

CANNA CEA E

J gel/us; 25 .~pecies The Canna family is primarily one of the New World tropics; according to some tuxonomists, three species are indigenous to Asia and Africa A few arc lIsed as ornamentals

lillie is known of til!': chemistry ofthis family; alkaloids have not yet been detected Tests on 13 samples including nine species of

Ca nna were without posilive result: C all1la coedt/ca, C j1acddll ,

C generalis, C illdiC(l, e WlIla spp (5)

B mos sa mb icens i s, B salicijiJlill (2/3), Cadaba ap/tyJ/a ( 1 12),

C lemitaria (1/2), Cappdris angllsti/olia, C asperijolia, C brassii,

C e l ythmclllpa, C inC al/ll (416), C illdicll , C odoratissima ( 1 12),

C oleoides C verrucosa, C zcylallic ll, C zipelliaulI, COllr/Jol/ia

(= Maerua) gil/li c a (213), Crnlael'{/ bent/wlllii, C lapia (1 /4) ForchlwII/lIle ria pallidll (112), F (r{fo/iata, Ma erua allgo!ell \ · i s,

M caffra, M silgrii, M parvijo/ia, M pllhescells Thilachillm

afri-C al/1U1I ( 1 12)

42 PLANT ALKALOIDS

CA RYOCARACE AE

2 gel/em; 24 specie:, '

This is a small family of tropical America The more important

genus, CllIyvCtlr, is i l source of good lumber and its nuts yield a

bullerlike edible fixed oil

No positive alkaloid tests were obtained with samples of

Cmyo-car brasiliellse, C glahrllm, C microcmplllll, C VillOSlllll

CA RYOPflYLLACEAE

89 geltera; 1 , 0 70 ~lJede.\ · This is essentially a north temperate zone family with a few

n:prescntativcs in south temperate regions and in the tropics at high

altitudes It is known for its many ornamental flowers, inCluding the

familiar carnation

In earlier lilemlure there appear rcports of the sporadic

occur-rence of alkaloids in the family One hundred and sixteen samples

representing 78 species were tested In agreement with earlier stud·

ics, Di(lIIl1ll1s caruthisiallorllm and LYll c hflisflor c ll llli wcre round

to be alkaloid-positive as well as the rollowing species: Agro s telll

-lila walkeri, Co rrigiola lit/oratis (212), Diallthus aJ/wO()(/i, D

a{pi-1111 ', D Ilrmeria, D arventellsis, D bolusii, D deltoides , D iI/leger,

' DiwrtJws sp., D,Ylllarill cordata (1/5), Lye/Illis alpilla, PoJlichia

C lllllpestris, Silene la ci nUla, S colijomicll

Negative tests were obtained with the following samples: Arenll

-ria b,yoidej ', A clIro/in;mw, A declIsslllfl, A Imll/gil/osa, A /yco

-podioides, A l1/acrodenia, A r eplam, Cardionema ramosissimll,

Cemslium arvel/se, C brachypodill11l, C cuspidat lllll , C glowe ra

-111111 , C keys.w:ri, C ""PUfllll/lII, C rivlliare , Cerastium sp.,

Corri-giola WUl/fltI , eltc llbalu s baccijera, Ditlnrhus tlrmerill, D

ba.w-ti C II \·, D lIlooiemis, D //(IlI/tIel/j'i s, D sllperbm, Kohlrallschia

(= Pelrorhagia) profijera, LycJlIIis alba, L a/pilla, Paron ychia

bra-siliww, P mexic(lIU/, Polycmpea cO/y mb o.WI, /~ eritlll fhn , P sp i c

l/-ta, Po/ycmlJOII telraphylllllll, Sagil/fl jap(mic(l, S P(IPIl{J/W, S pro

-('/lmbells, Sapollaria ocymoides, S officiI/a lis, Silel/e lIlItirrhil/a,

S c apemi ·, S clIrolil/iww, S c cuba/lIs, S lacillialfl, S stella/a,

L

S verecullda, Siphollychia (/;ffllsa, spergttla arl'ensis, S .hOCCOII~i,

S macro/hecl/, S marilla , Stella ria aqllalica S ansallefl.\'fS,

S clIspidara, S micrantJw, S jamesiallo, S ' media, S memorum,

S neg/e c w, S ovaW, Stellaria sp (2), S u"gll/vsa

4 gelter,,; 7 0 s p ec i es

This is an Australian ramily rurnishing timber and ornamental trees Little is known of its chemistry; alkaloids have not been detected All samples tested here wcre negative: Cas ~ lfIril/~ 1 crl stat.a,

e deplanchemw, C e qllisetij olia, C glallca, C lepulophlollt, C.litroralis, C po/alllophila, Ca.wari l/(l jp., GYllllloStolll(f pOP Il(Il W

94 ge ll em; 1,100 spec i e Ii

Taxonomists have shifted the genus Hippn c ralea from this

fami-ly to one of its own and back again It ~il1 ~ t~at~d here as a

member or the Ceiastraccae, a ramily orwlde dlstnbutlOn except III the arctic regions lis only economic importance is ~s a source of

ornamentals and of khat (Callw edulis), a populur stimulant or the

It contains alkaloids among which are the maytansinoids, which

have had considerable interest as antitumor agents Samples (165)

or 92 species gave the roHowing as positives pr~viously k.no~n:

Catha edulis (213), EUOllYlIIlIS atropUlp"rells, Nippocmtea IIIdl e a,

In addition, the follOWing species wcre poSitIve: Bhesa

archob?ldta-lIa Cmsille crocea, C kmi,j'siw/ll ( 1 13), Ce /a s/rtfs le(ramert/s, EIlO ll

Y-/II~S /allceifolia, E yeddelfsis (112), Gy llllfosporia (= May t e ll li S) se lle galellS i s (212), Norto gia (= HarlOgi e l/a ) c apellsis (10), Hippocratea (lcapulc:clIs;s, !-I lIitida, we,meriel/a c r e na/(( , Loesllenel/a 11Iacralllha, Maytelllls g/llucesellS, M guian(!sis (2/4), M nell/oroSI/S, Maytemlj··W (2 / 5), Sa/acia illsiglli.\', 7Npfelygiltll/ rege/ii (3/3)

-The following were negative: ACfmtl/ollwlIIlIIlS nphyl/lIs, Cassme

44 Pl.ANTALKALO/DS

aelhioph:a, C capellsis, C maritimulII , C fJapillo:m, C pubescells

C letragolla, CeJasil'lls lIIuflospermoides , C 1I0l'oguilleellsis, C

orb-ic ularis, C pring/ei, C pUl/claiUs , C seal/delis, CroCOXY/OII

fralls-vao/ellse, ElaeodelldrOIl (= Cas~'ille) cur/ljJelldufulII, E capel/se,

E giallcLlIII, E u ollymus oCilla-rhombi/alia, E aiala, E bUlIgella,

E echillallls, E lalleum, E nikoimsis, E oxyplryllus, E

sieboldia-nus , E Il'icilocmplIs, Euonymus sp ; Goupia glabra GYlllllosporia

montana (= Maylelllls cmarginala), LopllOpela/ul1I tori cellclIse,

Mayfel/us aei/millaills , Mayfellus s p afT rigida M aloterl/aides,

M cymosus, M Wei/oLia, M aleoldes, M pedllllcular is, M

phy/-lant/wides , M scnega/ells;s, M ulldala, M IIm/ulatlls, Microlrapis

/ok iellellsis, MortOllia hidalgellsis, M 11l/iseplIla, M palmeri,

M scaberrima, Orthosphellia mexicalla, Perro(lelia alpcstris, P

ari-sal/ellsis, Perrottefia sp., P/ellckia popull/ea, Plellckia sp.,

Pseudo-cassillc Irtmsvaalcllsis, Pleroce/asll"lls echillatlls, Pterocelastrus

sp., PlItterlickia l'erI"llCO.WI, Ilhacoma sCOIpia (= Cros:mpela!wll),

Salacia elythrocarpa, S papUl1l1a, S somria, Sc/wefferia pilosa,

S sfellophylla, Sip/wl/odoll celeslrilleus, S pellalfls, Wimmeria

aca-plt/cellsis , W cO llcolor, W COli/usa, W per ci/olia, Wimme";a sp.,

ZillolVielVia illfegerrima

CENTROLEl'lDACEAE

3 ge ll era, 28 lpeciel'

This small family ranges rrom southeast Asia to Australia It is of

no known economic importance Neither alkaloids nor othcr chcmi

-cal constitucnts of the family Imve been dcscribed CellllV/cpis

philippellsis was nega ve ror alkaloids

CEl'HALOTAXACEAE

1 gelllu'" 4 species

This unigenenc Asian family is cultivated as an omamental

Alkaloids arc not known but in the present survey Cephafofax/I\ '

/orlUliei gave a positive test

"

,

Alk(ll oid Tesl U esulls

CEIIA1Vl' IIYL ACEAE

J gelllu',' 2 species

45

This is a family of cosmopolitan aquatic plants oOen used in aquaria but in nature it also serves as a she er for disease-bearing

snails and mosquitos Ceratophylfum demerslIlI1 was alkaloid-negative

CEJlC IDll'lJYLLA CEAE

1 gelll's; J species CerefdipiJyllllllljapolliclll1l is indigenolls to China and Japan and has some importance for its lumber and as an ornamental Lillie is

known of its chcmisllY; three samples were negative for alkaloids

(Che-Betacyanins and betaxanthins, along with alkaloids in somc

gen-era, arc found in the family but no one ty e is prominent or ered characteristic Or87 sp6cies tested in this survey, the following were confirmed alkaloid-positive as indicated in the cariipr work on the family: Atriplex COl/esceliS (2/8), A sell/ibaceata, A I'esfita , Beta vulgaris, Chellopodiulll albulII (117), Salso/a ka/i, Suaeda frui- licosa S linearis

consid-Additional alkaloidal species included the rollowing: Alrip/ex po/yempo (1/2), A rosae, Chenopodilllll ambrosoides (113),

C /Julla/iae (1/3), Lophiocmpus bllrc"ellii (now placed in the Ph

y-tolaccaeeae), SpilVstacliys (= Helerosfachys) africolIlls, Sllaeda

Negative tests were obtained with the following: Aflelllvlj ea cidellfalis, AIII/IIVel/eIllUIII africa/IUIII, Atriplex acallihocal]){l , A all- gulafa, A arel1Ol"ia , A cilleria, A cOlljel'lijolia, A exPOIlSlI, A "y_

oc-•

melle/ y lm , A jllbata, A lentiformis, A lim bata, A lilli/olia,

A muelleri, A fIll/ricala , A liummllJdria, A o/Jovota, A patu/a,

A pell((Uulra, A serenana, Bas:ii./a divaricata, B hirsula B obJiqlli ·

(.'1Ispis, B paradoxa , Blackiella (= A/rip/ex) inflaw, Chenopodium aClimillatum, C albulII , C arizollicllm, C hO l rys, C bushiafllllll,

C c all1l e nsis , C c ali/orni c ulIl , C filicifoli llm C foetidlllll C mOllti , C graveo/ells, C missouriellsis , C multifidI/III , C mum/e,

fre-C lIitrariaceuIII, C ruhrufll, Chenopodium spp., C strictum,

eye/a-loma fIIripli c ifolillm Ellchylaena tomentosa, EUl'Otia !mwta

Ex-omi s axyroid e \ ' , E mictVphyJllllll Ko c hia s c iclanw , MOllo/epis WJ/iww, RJwgotiia baccata, R lilli/olia, R spillescens, R matillio, Salico 1'llia australis, S bigelovii, S e llropaea, S glabrescells,

11111-S pacifica, 11111-S I'irginico, Safsold ' pesti/ er, Safsofa ~J)p (2), S s ubser

-i ce a, S ze yheri, Sacrobatus vermiculatlls, Spiflacia oleracea , SlIa e

-da c ali/omico, S di/fllSO, S m exic alla , S torr ey i(llla

C flLORA NT fl ACEAE

4 gellertli 56 .'~Jlec:ie ~ ·

With the exception of a single genus in the New World, this i s a family of the tropics and semitropics of the Old World Chlo ralltlm s glab e r is used as an ornamental in California

There has been littlc chemical investigation of the family; a lew amides have been characterized in Chloranth u s

No alkaloids were detected in Chloral/tlms elMior, C glaber,

He dyoslllum arlOcarpus, H bra s ilietlse, He(/yo s nllllll spp (2)

CISTACEAE

7 genera; J 35 , \1)ecies

The Cistaccoe ore found in the wamlcr parts of the northern hemisphere, particularly in the Mediterranean region Their only economic importance is as ornamentals

Thc family has had very little chemical investigation; alkaloids

IUlVe not been found except for a positive test in an unidentified

species of C istll s obtained in the present survey

Alk(llo id T es t R emi t s 47 The following species were negative: C i st ll s ladenif e ru s, C villo -

S II S, Halimifllll exalw tflm , l-I e lianth e mlllll c OI) l mbo s um, H tllm, H elianthe llllllll sp., I lud sollia ericoides, Lee/le a millOI', L ra ce- moso, L tr ipe/aw, L lIillosa

The seeds of Allloreux;a have been reported to give a positive test for alkaloids; a more recent report has alkaloids in Coch/ospermll lll plal/chonii In this study, nine samples representing five species gave positive results for Coch!ospemml/l gillivrae; and C vili/oli"", (1/5); Amorellxia palmatijida , Coch/oJpermum orillo c ellse, and

C religiostlm were negative

20 gel/em; 500 specie

This is a pantropical family of little present economic value

Tel'",il/alia catappa is cultivated for ils edible nuts, and a few other genera are ornamentals

48 PLANTALKALOIDS

Alkaloids (caffeine, hannans, oxazolidincs, pyridincs) are

known One hundred and cleven samples encompassing 73 species

gave posilive tests as follows: BuchclIllvia k l e ill i , 11 ser ico'1 Ja,

Bucida bllseras, B l/I(l cros/(l ch Yll (In), Com bre/11111 apiculaflllll

(2 / 3) C c affrulII, C ely rhmph yl/ um, C here/ve il s/! (113), Termillal·

These species were negative: Allo ge i ss ll s pendula, A sc himp e ri ,

Bll c h c lIll vi a afT se ri c arpa, B tomelltosa, Caco llcia (= Co m brelllm)

coed l/ c u C a/ yco pl eris jloriblmda, Clllycopteris (= Gelo/Iia) sp.,

Co mbr e tlllll c acoucia , C argelit e ulII, C e ll/ Jr um , C c(lla.~/'vides,

C cOeci l/ e mll , C ex t e llsfllll , C /arill os lIlII , C[ l'IIili COS IIIII, C goss

-weileri, C sueillz;i, C imberbe , C kraussii , C la xem, C me c ho

-wimwIJI , C lIIi c rophyllulIl, C moll e , C mo ss ambi ce ll se, C ob ova

-IUIII , C ovalijl)Jiu lII , C pt/lliculalulIl , C pla/ y petalulII, Co m bre llll"

s pp (5), C sulue " se , C Jrillitense, C zey h eri, C UIIOC(/I,/ ) /I: , erecJlIs,

Laglll/ c ll/ ori a ra c emosa , LUlllllilzero t i Uorea, Pl e / eo psi.\' myrli/olia,

Quisqllolis il/di c a Romaillela ,' p., Tcmllillalia mj ll/w, r all s /mlis,

7 bal/erica, T c afllppll, T di c hofoma , T gia/)rafll, T g ll iallellsis,

7 lucida , 7: mi CI'OC tll,/)(I , 1: mollis , T /llII e ll e ra , r m yrinca/ lm ,

T ob id e n sis, 1prill/ioides, r sc/lIllllallllialla , 7: sericea, 7i.m llill alia

spp (3), r /o m en to s a , T trichopoda, 711i vll gltllI COC a/l)(l

42 ge ll era; 620 species

This family has a wide distribution through ut the tropics and

sUbtropics It has lillie economic importance except for a few mem

-bers cultivated as omamentals

Little chemistry of the family is known; alkaloids have not been

repo ed except in an obscure Korean reference to COllfllle/illa CO II/

-Ill/lI/is

In this study 10 I samples representing 77 species were tested to

give two positive results: Cy allo/i s vaga and Mlin/allllia se mit e r es

The remaindcr were negative: AlleiJ e llla aeqlliIlO'i~ia/e, A al1gll s li

-folia, A e hillalllw e llsis, A diverge l/ s, A ge l/ ic lI/aW , A Iwckii ,

· A jo llll s / rnli i , A malabariculII , A lIi ehu/solli i , A p/a gioc ap s a

A pulcheJla, Ca l/i s iajragralls , C am peiia zOIlOl , ia, C O/1/lI/eiilla

a/ri-calla , C aspel'll C be ll g lwlensis , C brac/eosa , C cec i/a e, C co e

-Al kalo itJ ' l iw U csu lt s 49

testis, C co mlllull is, C eya ll ea, C diall/hi/olio, C t1iffllsa, C lIialla, C e u si/olia, CO lllm e li"a erec lfI C e l 1!c/ a vaL all g ll s ti/olia ,

ecklo-C /o r kala e i , C gerl'(lrdi, C kirk;;, C kl1!bsilma, C lIudiflora ,

C obli qua , C pallida , C scabra, Co tl/lll elit w s pp (6), C s llbu/ata ,

C lexocalla, C lu bems (l , C umbel/ala, Cyallo fi s araclllloides

C kelVe ll sis, C lalla/a, C topid osa, C Ilodijlora , Cymbispatha com m el ill oides, IJ ic h rj sa lidra h exa ndnl , Flosc;opa glabra la ,

F g lomera la, F sc and e ll s, F or r CS fia c h illcnsis, Gi b asis 11(1, G lincar;s , G plil chella, Pollia japo lli ca, [(hoeo (= Trade sc on - lia) disc% r , 1lJyr s ailihemllill II/(lc rophy/la, 7i,utl/lin erec/ a r jil-

knnvillskya-gax, r IOll gi petlllll c ulala , T e r ee /a , 1i 'a d eseo lllia e ra ssi/o lia ,

T jlllmill e llsis, 7 : lil/eari s, r o lli e s i s, T virgill;w/(l , '/;- ipogwu/ra

a m plex, T d i sg r eg a, Zebril/O (= 1hul ese alltia) pel/dula

1 ,3 14 genera; 21,000 \1J ecie 41

The composites ean :almost compete with the orchids for the title

ofllie largest family of flowering plants They are found worldwide and in almost all habitats and have economic importance as a source

of foods (e.g., lettuce, artichokes), insecti ides (pyrcthnlln) dyes (samower), folk medicines, and many omamcntais

Alkaloids arc not uncommon in the filtnily but many are of

un-known structure They include amidcs, fOllnd in several genera,

which have becn considered alkaloids in the broadest sense Phaps most familiar of all are the illkaloids of Senecio and relatives

er-which are of importance as slock poisons

Sesquiterpene lac,ones are also found throughout the family and

some of these may be responsible for reports of positive alkaloid

tests, inasmuch as their structural features can give positive reations wilh the DragendorrT reagent

c-The ready availability ofmcmbers oflhis large family resulted in

a large numbcr of samples for testing and a tolal of over 2,000

species were examined In k~cp in g with carlicr literature reports,

the following were found positive: Aca llih osperil/ll hi s pidllm ( 1 / 4) ,

A c hillea mille jiJ /i1l1ll (312), Agera/1I1Il cO ll yzoides (1/6), Ambrosia maritima, A r c/ IIIIII minu s, Arl e m esi a I ri del/tala, 8accharis co rdifo-

50 PLAN7'ALKAtOlDS

lin (1/3),/1 Iw/mifolia (31 4 ), Bid e n s pi/osa (2 / 1 6), Caca/i afl o

ridll-11(1 (1/5), Cale ndu la officillalis (1/3), Ce ll tal/rea CYllIlIIS, C lII

acl/lo-sa ( 1 / 6) , c meli tensis, Ce " trllt/{erum IIIIl/ielil" (2/7), Coreops is

ba s ili s, C lanceo/ala, Cosmos slIlpl mr el/s, Dic:oma al/omala, Emi

-lia so n chi/o lia ( 1 / 3), Erechi t es IIteraci/olia (11 4 ) Ere ll U lIIlllII s

~phaerocephala (112), EupatoriulII oc/ora lllm , E per/o/ialllm (217)

E purpur e llm , E mtrmdifolillm (212), E sero / illulII , H e/e llium 011

-//llIIl/ale (518), /J elia llihu s Of/UtiS (213) , Liatr;s spiclll a Matr icaria

cJw lll o mil/a (2/4) OSlem'pe rmlllll spi ll escens ParthelliulII hystero

-pllOrll s, Se n ecio doug/asii ( 1/ 2), S glahe/l ll s ( 1/ 2), S gra m;nif olifls,

s ilil ege l'rilllll s (2 /2 ), s jacobaea, S j Ull ce ll s, S pt ero p" o" " s,

S vimilla/is, S vulgaris, Solidago se rrala (2 / 0), 1tm(l Ce lllm vIII·

gare (4/ 6), V erb es ina e m:el o ides (617), V s e rrala , Xallihium Plil/

-gells (112), A \· II'IIII/(lI'illlll ( 1 / 4)

I)ositive tests were also obtained lor the following: A c

mllhoce-p/m/u s c m/umba (212), Ac anlhosperum hmsililll1l , ACl ltlthosp

er-ilium sp., Ageratum cOly m hosu lII (317), A ga um eri, A slllicijolium

( 1 / 3), A s c nbl"lls c u/um (112), Ambrosia orhorescens, A ortemesi/o·

Ua (5 1 6) , A c umol/ensis , A hi sp ida (212) , A peru vi ol/ a (112),

A ph y fl os / achys, Amelliwi str i goslIs, AllisopapplI s a/ ricm lll s, A

II-themi s al"l'ellsis (112) , A co W/a ( 1 / 3), ApJopapp lI ~ ' (= /-/ap fopapp ll s)

Spi llll/ OS IIS, Archeba cc haris 11l11C rollOta (112), Ar c / otheco ca le n ula

(112), Ar ctoti s " ca llli s, A C llpr e a , A /eiocarpa, Arnica mOl/lata ,

Art e mesia afra (112), A amilia, A calijornic a (2 / 3), A c apillaris

' (1 12), A dO ll glosiOlw, A drammcllioides , A ind orici a l/u , A k /

otz-chi mw (1 / 2), A m exical/a ( 21 4 ), Ar t e mi sia s p (1/2), Aspi/ia

africa-lUI (2 / 4) , A ste r llethiopiclIS, A ec hillO/ll S, A , yssopi/olil/s, Aster \7) ,

A th a ll ru'j o ji ,scicllltlta , A pinnata, A tomellto s a (212), A trijllr C lttlt,

H acc h oris c a/l 'escells, B c l/ril ibe ll s i s, B e/ae a glloi ti es, B elioc/a

-do , B em01y i (212), B glomer l/iijlora , B megopotamica , B mille·

f lora , B pi/piaris, B p/atypotia (2/2), BaccJwri s.w ( 1 /2 4), B t rip

m e l"tl , B Irin e rvis (117), B I'll/llhieri (112), B vimillea (3/3), Bahia

ab si nthij olia (5/5 ) , B all/hell/oides (212), B s chaffn e r;, 8 xylopoda

(2 / 4) , B rl/ du l l/a r lllgll s 1{ (olia, Bal '>ll lllorhi z(l deltoid es ( 1 / 2) , BW"I"oe

-l ea se!1S ilifl o m , B e rkh eya arll/(I/(I , B Jerox, B ollOpo r;di/ o li a,

B zey heri ( 1 12), Be r/wuJiem PlllI/ita (1/2), Bidells aI/rea (3/6),

IJ /eru/ae/olia (2 1 5), /J sqll ar ro,m (In) , IJ tripli ll erv i o (2 1 2),

Blail/l'iIl ea gayww (212), Borri ch ia arbores c ens, Bm ch y/aena e

l-L

lipliCll , B trallsvaale"si.~, Brn c hymeris m Ollt all a, Br ickeJlia cal nico (213), B cord i/olio, B co u/teri (112), B diJlitsa ( 1 / 3), B / acilla-

i/or-la ( 1 / 2), B pendula (113), B thyr s iflora , B tomentella , C aca lia i(lI/ c eoiata , C sltlc ata , C al ea s e rrata , Caiea sp (1/19), Calend ula sp., Calli/epis lept o phylla , C salici/oli a Calos l eplume divaricafa ( 1 12), Cm ] Jhephorus c Ol y mbosfl s, Cmp / we/wete grahami, Cassi "ia

co mpac ta, C phylie tl e/alia, C retorttl, C r h izocephalia , Ce ll f peda

o r bicu laris , C h acllac ti s douglasii, C giab l"ll sc ula ( 1 / 3),

Chondro-ph ortl I/Iulala , C/ ll ysnpsis sp (1 / 3), C ill ysalllhe m o id es mOl/ili/ e ra ( 1 / 2) , CIIIysocol/la fermi/olia , C Jll yso ma (= So lida go) pllllCijlO ClI lo-

sa, Clu yso tJWlllllltS viscidijlorll s ( 112), c lIauseOSIi S (4/4) , C /II Yso~

tllalllll11s s p., Cillemriajhlfi ce lOl"IIIlI, C Iyrara, C irsillm r wti ers onii ,

C/ib adiuIII sp., C "i<:/I s spp ( 1 / 9) , Co n yUt ca l/ad e si s (2 /2), C c hi ·

l eI/s is, C /wchsteuerii, C ivae/olia , C so phia ejoli a ( 1 / 2), Co re

op-s i s rha y acophi/a (112), COl"Cthrogy ll c jilagillijolia (1 / 3), Cos m os ocel/atus, Co w/a /eploloiJa , Crassocep lw/um manflli, Cya llw dille

Iy rata (112), Dahlia cncci" ea (1 / 3) , D sc ap igeroides, D ico ma c a pellsis, D gerrardii, Dil11011Jlwtheca po/yptera, D ispa l' go e r ieoides, DoelJellel" gia (= Aster) reac lI/ala , Dugesia mexi clm a, Dy ssod ia a e-

-e rosa ( 1 / 3), D se l ed ( 1 / 3), E/ep/uwtopus mollis (2 / 6) Encefia/ari lIosa (112), E ca iijorlli c a (212), Ere ch ites afkillsollio (1 / 2), Er i gero n (II/n UIi S ( 1 12), K /oJios tl s, E plrilode /phi c us (1/4), E quercijolius,

-E SCllpOSUS ( 1 / 4 ), Eriop h y/lum ambigllulIl, E confe rtiflorlllll ,

E mil/tical/Ie , Er/ oll gea illya ll g allo, Espe/etia sp p (2 / 3), riu m adellopirorum ( 1 12), II ajri c llllUIII (1/2), E afT havanellsis,

Eupato-E pllzcuarellse, E a/bUill (2n), E amplijolium (213), E (ll"OlIIali

-C IlI1l, E tlSChellbomimwlII (2 / 9), E hrevipe · (2 / 3), E c a/ophylllllll (214), E capilli/o UIIIII (1/2), E comp ositifo /ill/ll ( n), E cre lllliat u lII,

E c lilleijiJlium , E tiubium ( n), E jislulosum, E gr eggii, E h pifolilllll (212), t: irra s llm , E IiIli/oIiUIII, E littorale (212), £ /in g us - trimm' (119), E lIIari e l(llllllll ( 1 /9), E mikmlOides, E "wllllllliaria,

ysso-E peli%re ( 1 /4), E pyg ll oce pJw/um (11 1 4), E reCllrlllll/S (2/2),

E mall e I/si s, E s c orolldollioldes (3/6), E serr{l/um (2 /3), E spilla cifo /illm, E t o meI/will/III , E valitherimlllll1 (1 /3 ), E wrightii (3 /4) EIllYops abrolalJijolills ( 1 / 2) , E allgo/ensis, E a sparag o id es,

-E' lalerijlortls, E la xlls, E li n earis, E IiIli/OUIlS , E mll i ifi dus (2 / 3),

E pecli llalll s, E -'"/llltlw ce lls , ElII) IO PS sp cr /ollgipes , Flaveria Iilleallls, Floreslilla pedllla (2 / 3), Fluorel1sia c el"l/ ua (2 / 6), Fn m ser -

54 PLIINTALKAI ~ OIDS

I"{I, V trachyphylla ( l /2), Wedelia mello/ri c he , I/Yethitl llngllsli/olia,

Xallihilllll iwliclIlII ( 1 /3), X pem""J1/va"ict ll1l (212), Zt ,lll Zllllia (1 1/

-gusta (m), z glo/)()sa, Z 1II(Jllissima (2/2), Z mOlllagnae/olia

(215), z robil1soll ;a (113), Z fI~i1ob(l (2 / 3) Zexmenia lalliolli/olia

( 1/3), Zifmia p e ruvi ( lI1a

Negative tests were obtained with the following: A c

anthD:ll'cr-lilt/III {lu s tra/e, Achaelogeroll ascetldens, A c hillea borealis, A c hy

-roc/ille a/ata, A Wlttlroides, A c hrocJ;IIe spp (2), Acfill omeris alte/"

-II i/o lia , A retrap/era, Alief/neall/oil bieolor, Adenopappus

pel:~'icaef(J/jtlm, Adellostemma brasilialllllll, A cafJnm~, A vi.~·co­

S lim, Agollippca (= Ja eger ia ) bellidiflora, A ge ratum calld ie/lflll ,

A c;/aSS()C lII]1l1l1/ , A !toll s /ol/ioIlUm , A littorale, A IOllgi/o/il/lII,

Ag-e mtlllll spp (2), /ol1lenlo.wl1I, Agiaba mpoa c Oligesta, AgrialltJllIs

empctrijoliwlI , Alberlil/ia brasiliensis, Afdall/a de iata, A/om;a

wend/amlii, Ambrosia c OIiferlijiora, A polysta c hyia, A Irijida,

Am-//I ubium a/ala, Allm :ycl lls depresslIs, Allap/w/is cO lltorta , A

lorentz-ii, A morri so llicola, A nagasawai, A mllr glirilclI, A

c all escellS, A delltatllS, A lastii, AlIlel/lwri(lllcodiui c a A plalliag

i-flifolia, A ro.~ea, Anthemis aizoon, A IUlIIsklle c hlii , Aphallostephlls

}wII/ilis, Aplopappus (= flaplopappus) Iwrlwegi, A /;>1)i1l0:ws,

A ven e ill s, Ap/osr ep hilllll (= Hap/os/ephilllll ) /asscrilloide

Ara-cium (= Cre pis) loll/cmlWII, A asperijoJitl, A /mu/Illosa A

hiera-cioitles, Archibaccharis hine//a, A mll cro naw , A sescel1ti ceps,

A am/rogyna, Ar c lill'" lappa, Arctoti s candida, A laevis, A

pctio-law, A swclwdijolia, Amica chamissonis, A co rdi/ o lia , Artemesia

mUllla A axillaris, Aspilia brachyphyllll, A caru lhii , A " bsilllhlll1l,

A fIIl s tmlis, A balcJuw dru lJI, A dra c un c lus, A dllbia, A

ludov;-C iWlfI , A Pycllocephala, A rothro c kii , Artemesia sp., A sleJ/(lrialln ,

A vlligaris, A foliac ea, A fo liosa, A h elialllhoides, A la el'issi llUl,

A lillearifolia , A kots c hy i, A mOlllevidellsis, A pro c ilmbellS,

A scll/III/ ;er i, A selosa, Aspilia .~pp (2), A verbeno/des, Asler

ageralOities, A a/p/tlIIS, A bakeriallm" , A carnlial/II ', A co

rdijo-!illS A declllll hem ', A di varica/II:", A ericaejo!ills, A exilis,

A jiliji)/ills, A gracilis, A gylllllocepllllil/s, A Jwp/opappus,

A hir mtic{ lIllis , A j llll ce lls, A lima , A Iinl!arijo!iLls, A Ju leus,

A mn crop h ylllls, A II/ olllevidensis A lIIuri c alLl s, A lIovn-ang!iae,

A paren s, A pegleme, A piloslls, A prclIltlllh oides, A pllnicells

L

Alktl/oi(/ Test Result 55

A rej1exll s, A /"OllIndi/olius, A schlechteri A sc hreberi, A :')COp lorum, A simplex, A spectabilis, Aster sp p (2), A s pmoslIs,

ll-A slIblilallls, ll-A laiwflllesi s, A tel/n ceti/o lius, A le iji,lius, A bellatus, A wallen", AlIllulIllI s ia ncerosa, A d e ll/ata, A parvij1om, Athrixia elata, A helerophylla, A phyli co lides , A rosmorinijolill, A/m c lyli s itmcea, Atri chose r;s platyphylla, Ba cc/ wridaslrllm

1111/-(= COllyza) /riplinervillill, 811 cc ha ris 1Il1gllsfijolia , B allgLlsli ce ps,

B ll omala, B arti c ulata , B (lxi/aris, B cn/vescells, B c amporum,

B cassil/ifiJlia, B c onferta, B douglas;;, B tlraclillclijo/ia, B

elm-ce mlla, B ellipli c (l, B erigeroides, B gll udicllflwu/imw, B gllliin

o-sa, B helichyso i des 8 hetefVphy lla, B ;lill ita, 8 lateralis, B /ill

-glls/rilla, 8 lIIa c ro ce phala, B III/tillella, B orgyalis, B ell1a{,lera,

B plulllm erae , B O l os/lla, B pLibertlla, B r(lmll~o'~'a, 8 ramijlora ,

8 sarl/wides, B sebaslia l1opolilmw, B serraejolll1, B serrulata ,

B sessiliflora, B soralescem, Ba c cJwris spp (22), B sub;.,pal/thu lata B tarcl101WlltllOides, 8 Illesioides, B I rimem, Ii Irillervi.,·,

-B ~a c cilloides, B varians , B I'allthieri, B vemolloides, B weirii, Baeria (= Laslhellia) clllysostoma , BoiJeya mll/timt! i ala, B IllIlr -

beri, 8a/dll illo IIlIijlOI"ll , Balsamorlliza sagittata Ba rroetea setosa,

B sllbligem , Berkheya ba r bato, 8erklreya sp alT carli"~ps!s,

B decllrrells, B echifillceae B.frllti c osa B lIeleropllylla, 8 lIis B pbll1alif o/ia, B radllla, B semillil'ea, B se /ijem , 11 ,\ peciosa, Berkheya sp., B S pillosilllllll , Berlmuliera lyra/a , BidellS ( w tlle-

IIIS/g-mo i des, B alllhris co ides, B it!ellloides, B bigelovii, B ipillllOW ,

B b ernata, B Ce l"flll a, 8 CO II/osa, B coro llala, B cyllapiijo/ia ,B discoides, B gardlleri, B ra veo/ells, 8 insecta, B mitis, B o sl lll"ll -

lioides, B p olylepis B racemosa, B rllbi c lllldu/a, B sege/lIIlI ,

B semi/aw , B sc/wjfileri, B sc himperi, 8 serrll!a[(J, BidellS spp (5), B \III/gala, Blallc/lelia heterol ;cha, BleplUlripapplIs sCllber, B IIl- meo aw·ita, B balsamif era, B lomerala , B.jacqllemoll /ii , B /a ce ra,

B lacina/a, 8 myrioce phnlll, B pufJigera , B riparia, B specta bilis,

B virells, Borric/lia /hlfescells, llmch yg lottis repam/m, Brachylaena discolor, ll lIeriijo/ia , B rofwuJata, Bmch ymeris (= Phymmper -

ilium ) bolusi/, Brasilia sieW, Bri c kel/ia caval/illesH, 8 cOllduplicara,

B cOlymbosa, B g i litil/osa, B nelsollii, B IIlltal/ticeps, /J mll( mS ,

B odontophy lla , B pacayell s is, B palmeri, B p(mi c lliala , 8 lei, B p ll/ c herrill/o, B scoparill , Brickellia '\ PP · (3), B spimtlosa,

pring-B s quarrosa, B verbellllcen, B veronicaejolia, Co c nlia (=

Anw-58 PLANT ALKALOIDS

E lIeaefl nUIII E lie/sol/ii, E oligocephalum E or/cgne, E

orgalle-sis, E ova/iflorum, E palmare , £ pazcuar e l/ se, E piiOSIIIII, E P0rl';

-ginoslIlII, E polyceplut{um, E pnmellaefolium, E PycIlocephalulII,

E pu/ c hellum E pUII/illlln, E quadrtmgulare E rJlOmboic!eulIl,

E riparium, E rligoslIm, E saggitij1orwlI F semiserratum,

ElIpa-lorilllll ~pp (40), E spinacijoliulII, E spillosarum, l!: spa/JIII/allllll,

E subpellllillervilllll, E subillfegrllm, E tashimi, E letragolliulII

It thyrosoitleulII, E treml/fum, E vemic:oslIIll, Elllyops alJulIlosillC,

e brel'ipapPlIs, 1\, oligog/osslts, E rupesfris, E lellllissimlls,

~

E virgil/eus, Elileims palmeri, Fi/ago cali/ornica, Flal/eria (lIIgu.\'·

Ii/olia, F ollo",o/a, F (l stralasica, F bidenti.\', F repolI(/a Flaveria

.\ p., F lrillervia, F/eisc/lllulIlliia argula, Flollrt!lISia re.\ ' illosa,

I'nll1-seria (= Ambmsia) acaflfhocarpa, F cO l l(erl(/lora, F malva c eae,

Gaillardia aesliva/is, C jJfI/cheJla, C iOl/kiev, GaliwlOga ciliatfl,

COlllocliaeta (= GI/oplmlium) spicala, Gall/olepis (= Sleil'Odiscus)

cllly wlfl t hemoides , C Irijllrcalfl, C brachypada, Carllieum albllm,

G piwwlijidulII, Cazal1ia lillearis, G krepsimlfl, C pygmllea,

G rigida, Geigeria schil1Zii, Cerbera gial/dlllo.m, G (lspiliflom ,

G c ro ce a, C disc%r, G nataiell s is , G piloseJ/oides, Cibbllria

iJi ciJo lia, G scabra, Cllaphalilllll aff brevicaspll, G atlelllwtul1l,

G belleolells, C bicolor, G caliJomiculII, G c harta/ellll/ , C c hi

-/e" se, G diaiclIlIJ, G iIypolellclIl1l, G imli c llm , G il/voll/ c rall/III,

G.jap(micuIII, C /ave"duli[olillm, G.leplOphyJlIlIII, G Jllleo-albllm,

G milnu : epl wllll1l , G morii, G multiceps, G oblllsiJolilllll, G

occi-delllali s, G oxyphy/l/llll, G peregrilllllll, G pWlmrescells, G plll'

-purelllll, G, ramosissimlllll, G rhodwlilllII G"aplw/ium spp (12),

C spicatum, Coc/malia hypo/ellca, Gongylolepis marlil/iwlfl ,

Gor-ce;xia sp., Gorleria cO/ymbosa, GnU/gea madera s palww,

Gri"de-lia gladulo.m, G illll/oides, Guardiola alJglI.\·liji )/i a, C mexi c( lIIa ,

Gllizolia abyssiflic:a, G sCllbra, Gulenbergia gossweileri,

Gulen-bergia sp., GI/lierrezia grandis, G lIIi c l"o ce pllllla, G sarollrrae,

Gymllosperm(/ glLllinosa, GYflura allgll/o:m, G crepioities, G tit'

-vari c ata, G jlfll1a, G formosana, G segelum, G l'ibelJilla, H alo

-cmpha IYl'flta, H scaposa, Haplopappl/s aeal/lis, H coope ri,

II divaricalll.\·, H lillearijolills, H palmeri, H s qlwrroslI \', I/ \·r%

-I/({eru ,\', Hap/osiephilllll j(llwrinoities, Hewbaell (= fielel/illlll)

scor-ZfllleriJolia, lI edyp nois crelicll, lie/enilllll (/mpltiboJIIIII, N

mexica-1111111, 1-1 mi c roc:epIIllIIlJII, 1-1 seorzo llera eJoli ul/I , II deeapelflills,

II debilis, H glVsserallls, H radula, fleJi ( lIlllllls spp (2), Ii rodes, II Iliberoslls, H elic h'yslllll aell/mlllll, H adseel/dells, H al- hoides, H appendi c u/allllll, H argyrophyllulII , H argym\'plrael'lllll,

leph-H alirrixifo/illlll, H altreonitells, H crijp uJII, H cyli"dricum, H

caes-pilillllll, H ce raslioides , I/ cOlrjerlifo liltlll , H co ria ce ulII, H pllm, If eY lllosum, H decol'lllll, H , e ri cllefo lilllll, H felimml,

crt's-H faelidlllll, H krallssli, I/ kirkii, II lallciJolilllll, H ialiJolium,

If Ilicilioid es, 1I mi co llill efoli um, H mlilldlii, H llIldij1orum,

H lIitens, H orbiculare, H pmuluralLllII, fl panicliiallllll, Ii zioides, H pelio/amm, H p/alyplel"lll1l, H rllgll/usUfII, H sesa- moides , H selOSlIlII, flelicJuysulll \ PP, (3), H splendit/lIlII, H slenop- le1'll1ll, H SWYIlI/erlOnii, H IlwpSIIS , I I IfIllbmculigel"lllll, H IlI/dalUlII,

penl-If vestitlllll, /I zeyheri, Heliops i s lIIlIllla, H helillflilwides, ll gipes, H proculllbells, Helip/(Jl'fllll gf/apJwloides, H ~peciosissi-

1011-11111111, Helminlhia (= Pieris) echioides, Hemizollia cOlymboso,

fl, kelloggii, N l1Iu/liclllllis, l1erlio (= OlhOlmo) a/ala, Helero/epis saliella, HetelVsperma pimrallll1l, Heterolhalamlls sp., Ilelemlhe c a eh'ysopsidis, H grmuliJlora, I jlll/loides, II Sllb(Ltil/aris, Hidal- goa lemMa, Hiera e il/III abseissllm, 11 eOlllaliceps, H erespidisper-

11111111, H jlagellare, II jlorelllilllllll, 1I greelle;, H grOllOvii,

/I /elicotriehiulII, H , pl'lllellSe, Hieraeil/III sp., Hippia frutescells,

fl pilosa, Hirpicillm becJwanese, If gracilis, H illlegrifo/illm, lio}

m e ; s te,.ia pluriseta, Nil/s e a w.!slila, Hym elloste phillm (= Viglliera) cordallllll, /iypericopllylllllll Oligo/elise , UypocllOeris alala, H rad-

i Cll la, Hypochoeris ~p., f c ltillyolher e laliJolia, I c ltillyolh e re sp.,

Ijlo-go llristlllllIa, I , reflexa, bill/II cappa, I glumeraill, I he/el/imll,

I pal/iclliafa, I roy/calla, lilli/a sp.,lmtiopsis (= PodocolI/a)

seapo-sa, / osteplume helerop/lyl/a, I scllllea elachoglossa, Iso e mpha pos il iJolia, lsosligmll sp., I spec;oslIlII, Iva eiliala, Ixeris japullica,

op-I microceplw/a, lxiolaella brevicompta, Jaegeria Irirla, Jaegeria sp., Jalllllea pedlln c Lllaris, Jllngiajloriblillda, Kallimia (= Mikol/ia) ohluflgijoli ll K lI i lida, Keysseria gibbsiae, K /'tIdicans, Krigill vir- gil/it'll, Klilmill (= Briekellia}rosmari l li[olia, Laehllosperllllllll eric;- foliulII, Laclllea c apel/sis, L jloridalla, L grallli"ijo!ia, L iniyha-

ce a, L canadellsis, L biellllis, L debilis, L sativa, L scariola, Lac/Ilca sp" Lagas cea allgllslijolia, L decipiells , L ghllldlilo.WI,

L "elianlliiJolia, L heleropapplIs, L ruhra, Lagel/phora slipilala, Laggera (= Bllimea) aiota, La/maea asplelli[oJia , Layia gJalldIlJo.m,