Chemical composition of the leaf oil of Litsea glutinosa (Lour.) C. B.Rob. from Ha Tinh province

sesquiterpenes and other components of the leaf oil of Litsea glutinosa fiom Ha Tinh province. have been investigated[r]

VNU Joumal of Science, Natural Sciences and Technolo gy 26 (2070) 161-7(/.

Chemical composition of the leaf oil of Litsea glutinosa

Nguyen Thi Hienr, Tran Dinh rhang2,Do Ngoc Dai3,*, Tran Huy Thai3

' tFaculty of Biolog, Yinh University, lB2 Le Duan, Vinh, Nghe An, vietnam

2Faculty

of chemistry, vinh (Jniversity, 182 Le Duan, vinh, Nghe An, yietnam

3lnstitute

of Ecolog and Biological Resources, Vietnamese Academy of Science and Technologt,

18 Hoang Quoc Viet, Hanoi, Vietnam

Nh{n ngdy I th6ng 3 ndm 2010

Abstract Fresh leaves of Litsea glutinosa (Lour.) C B Rob from Ha Tinh were steam distilled to produce an oil in 0'15% yield The essential oil was analysis by a combination of capillary GC and

GCA4S Seventy eight compowrds were detected in the oil, of which more than 95.18% were terpenoids The major components were (E)-p-ocimene (13.35%), p-caryophyllene (27.20%) and bicyclogermacrene ( I 8 I 6%).

fyry : Litsea glutinosa, Lauraceae, essential oil composition, (E)-p-ocimene, p-caryophyllene, bicyclogermacrene.

1 Introduction

The genus Litsea is a member of the

Lauraceae and comprises more than 400 species

which are distributed widely throughout

hopical and subtropical Asia, Ausfialia, North

America to subtropical South America; 73

species have been recorded in China, most of

them located in south and southwest warm

regions []; a5 species have been found in

Vietnam, until now [2]

Litsea glutinosa is an evergreen

medium-sized tree Its barks and leaves are used as a

demulcent and mild astringent for diarrhea and

dysentery, the roots are used for poulticing

;Co*rp*alng

author Tel.: 84-38-3855697.

E-mail: daidn23@gmail.com

sprains and bruises, and the oil extracted from

the seeds is used in the treatrnent of rheumatism [3] Some psychopharmacological actions of

the essential oil of Litsea glutinosa (Lour.) C.

B Rob have been studies by Menon K M et

al [a] Effect of essential oil of Litsea glutinosa

(Lour.) C B Rob on cardiovascular system

and isolated tissues have been investigated by same authors [5] Flavonoids and aporphine

alkaloids were isolated from Litsea glutinosa

[6, 71 A water-soluble arabinoxylan (D-xylose

and L-arabinose in the molar ratio 1.0:3.4) was

isolated from the mucilaginous bark of Litsea glutinosa l8l.

Recently, research disclosetl that the MeOH

extract of Litsea glutinosa bark effectively

inhibited both Gram-positive and

Gram-l6l

162 N.T Hien et al I WU lournal of Science, Natural Sciences and Technology 26 (20L0) 1.61.-1.64

negative bacteria The results justiff the

reported uses in diarrhea and dysentery [9]

The BuOH extract of the leaves and twigs

of Litsea glutinosa were shown to exhibit

significant cytotoxic activity against human

Hela cell lines.in vitro Chemical examination

of the BuOH extract of the leaves and tvrigs of

Litsea glutinosa collected from Xishuangbanna

resulted in the isolation of two new aporphine

alkaloids, namely litseglutine A and B, along

with two known aporphine alkaloids, boldine

and laurolitsine [10]

In the course of the systematic study of

Litsea in Indochina, monoterpenes,

sesquiterpenes and other components of the leaf

oil of Litsea glutinosa fiom Ha Tinh province

have been investigated

2 Experimental

1 Soarce- Litsea glutinosa (Lour.) C B

Rob (Lauraceae), is a shrub tree up to 7-10'

high, growing in Vietram The leaves of Litsea

glutinosa were collected in April 2009; in Vu,

Quang National park, Ha Tinh province A'

voucher specimen (NHll0) was deposited at

the Herbarium of the Faculty of Biology, Vinh

University

Fresh leaves were shredded and their oil

were obtained by steam distillation for 3h at

normal pressure, according to the Viebramese

Pharmacopoeia [11] The yield of the fresh leaf

oil was 0.I5%

2 GC- About 15mg of oil, which was dried

with anhydrous sodium sulfate, was dissolved

in lml of n-hexane (for spectroscopy or

chromatography)

GC analysis was performed on a HP 6890

Plus Gas chromatograph equipped with a FID .

and fitted with HP-5MS column (L:30nrm,ID

: 0.25mm, film thickness : 0.25pm) The

analytical conditions were: carrier gas Hz,

injector temperature (PTV) 250oC, detector

temperature 260oC, temperature programmed

60' (2 min hold) to 220o (10 min hold) at

4"Clmin

3 GC/IWS- An Agilent Technologies HP

6890 N Plus Chromatograph was fitted with a

fused silica capillary col HP-5MS column (L:

30mm, ID : 0.25mm, film thickness :

0.25pm) The condition of use were the same as

described above with He as ca:rier gas, and

interface with a mass spectrometer HP 5973

MSD (70eV) Component identification was

carried out by comparing MS data with those

reported in Library Willey on Chemstation HP,

and in some qnes substances identified from

oils known composition and also with standard

substances lI2-171

3 Results and discussion

Of the more than 90 leaf oil components of Litsea glutinosa that were separated by capillary GC in this study, 78 were identified after GC/IMS analysis, representing 95.18% of the total (Table 1).

T4bte 1 Volatile leaf components of Litsea glutinosa (Lour.) C B Rob from Ha Tinh

FID

tricylene o-thujene a-pinene camphene sabinene p-pinene myrcene a-phellandrene 63-carene cr-terpinene p-cymene o-cymene

927 trace

931 0.37

939 3.38

953 0.41

976 0.29

980 3.26

990 1.91

1006 0.65

l0l l 0.50

l0l7 trace

1026 trace

1028 trace

N.T Hien et al / WU lournal of Science, Natural Sciences andTechnology 26 (2010) 151-754 163

limonene

(Z)-B-ocimene

(E)-B-ocimene

y-terpinene

eterpinolene

linalool

nonanal

(E)-4,8-dimethyl- 1,3,7-nonatriene

alloocimene

geijerene

mpnthone

iso-menthone

(Z)-anethol

decanal

octyl acetate

linalyl acetate

2-undecanone

(E)-anethole

bornyl acetate

undecanal

bicycloelemene

ecubebene

neryl acetate

cl-ylangene

GCOpaene

&bourbonene

$cubebene

Selemene

iso-caryopbyllene

dodecanal

$caryophyllene

y-elemene

eguaiene

aromadendrene

3,7-guaiadiene

ehumulene

(+)-epi-bicyclosesquiphellandrene

germacrene D

eamophene

Sselinene

bicyclogermacrene

(E,E)-o.farnesene

y-cadinene

6-cadinene

germacrene B

(E)-nerolidol

bourboneol

germacrene-D4-ol

spathulenol

caryophyllene oxide

cedrol

1032 r.30

1042 2.s4

1053 13.35

l06l 0.12

1090 0.14

1100 tace

ll02 tace I104 0.41

I128 0.48

ll43 tace

1153 0.66

1163 0.14

I165 1.04

1180 0.20

ll83 trace

l261 0.15

1273 tace

1285 0.24

1289 trace

1290 tace

1327 0.20

1343 0.t4

1362 tr:ace

1374 tace

1376 0.24

1386 0.15 .

1389 0.14

l39l 0.66

1409 0.10

t4t2 0.t8

t4t9 27.20

1433 0.19

1440 tace

1443 trace

1447 0.r0

1454 3.04

t474 0.10

1480 r.48

148s 0.66

1490 0.r0

1499 18.16

1506 0.81

t5t4 0.21

ts2s 0.56

1536 0.82

1558 2.73

1567 trace

1574 0.t0

1577 0.67

t58t 2.21

1598'0.16

ledol cr-cedrene

r-muurolol

$eudesmol

ecadinol

(Z)-P-asarone

minsulfide

benzylbenzoate tetadecanal 6,10,

l4-trimethyl2-pentadecanone n-eicosane n-heneicosane

phytol

n-docosane n-heptacosane

1600 0.26

1640 tace

l64l 0.91

l65l 0.13

.1653 0.13

1676 tace

1742 trace

1760 0.27

1770 e

1829 0.31

2000 tace

2100 tace

2125 0.33

2200 tace

2700 0.19 Note: trace < 0,1; KI = Kovats index

The monoterpenes represented the most abundant component with (E)-p-ocimene (l 3 3 5%), o-pinene (3 .38%), p-pinene (3 260/o),

(Z)-p-ocimene (2.54%), myrcene (I.9I%), limonene (1.30%), (E)-anethol (1.04%) and

other components with content lower than

I.00% Among the sesquitetpenes, there werd

caryophyllene (27.20Vo), bicyclogermacrene (18.16%), o-humulene (3.04o/o), nerolidol

(2.73%), caryophyllene oxide (2.21%), germacrene D (1.48%) and other constituents

with content lower than I.00%

The oxygenated compounds such its

linalool, nonanal, menthone, iso-menthon e,

(Z)-, (E)- anethol, decanal, octyl acetate, linalyl acetAte, 2-undecanone, bornyl acetzte,

undecanal, neryl acetate, dodecanal,

(E)-nerolidol, bourboneol, germacrene-D-4-ol,

spathulenol, caryophyllene oxide, cerdrol, ledol,

r-muurolol, nerolidol, p-eudesmol, o-cadinol, (Z)-p-asarone, berzyl benzoate, tetradecanal,

6,10,14-trimethyl 2-pentadecanone and phytol

have a relatively small content, but contribute to

the charactistic odor of this oil, This essential oil contains also small

amount of n-paraffin: n-eicosane,

n-heneicosane, n-docosane and n-heptacosane

N.T Hien et al I WU lournal of Scieace, Natural Sciences and Technology 25 (20L0) 161-164

r64

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Nghi6n cr?u thenh phAn h6a hgc tinh dAu ld cdy Bcri lcri nhor

(Litsea glutinosa (Lour.) C B Rob.) d Hd finh

Nguy6n Thi Hi6nt, TrAn Dinh ThEng2,D5 Nggc Dei3, Tr6n Huy Th6i3

tKhoa

Sinh hpc, Dqi hpc Vinh, 182 L6 Duiin, Vinh, Nghg An, ViQt Nam

2Khoa

H6a hpc, Dei hpc vinh, 182 L6 Duiin, Vinh, NghQ An, yist Nam

3Yipn

sinh thdi vd Tdi nguyin sinh.vgt, ItiQn Khoa hpcvd c6ng nghs vigt Nam,

18 Hodng Qu6c ViQt, Hd NAi, ViQt Nam

Hdm luqng tinh ddu fi 16 ciy Boi loi nhot h O,ll%;otheo nguyOn liQu tuoi Nghidn cuu thdnh ph6n h6a hqc cria tinh diu 15 c6y Boi ldi nhdt (Litsea glutinosa (Lour.) C B Rob.) d He Tinh bdng phuong

phdp s6c ky qi (GQ vn sic kj khi kh5i prro lccnvrs), hon 90 hqp ctr6t euqc t6ch ra tu tinn #u, tron!

t16 78 hqtp chdt ilugc xdc <linh (chiiSm gs,I8yo tdng hdm luqng tinh Thanh phdn chinh cua tinh

dAu li (E)-p-ocime n (13,35%o), p-caryophyl len (27 ,20%o) vd bicyclog ren ( I g, I 6%)