MEDICINAL PLANTS OF ASIA AND THE PACIFIC - PART 4 pptx

[From: Greek diospyros = persimmon fruit and from Latin multiflora = numerous flowers.] 11.4.1 Botany Diospyros multiflora Blco.. [From: Greek diospyros = persimmon fruit and from Latin p

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tion: F S P Ng, July 20, 1991 Geographical localization: East summit of Mountain Bongsu,

Bongsu Forest Reserve South Kedah, steep hillside on previously logged forest.]

vary in number between 26 and 47, mostly in antero posterior pairs The female ﬂowers are solitary, 4-merous, with four styles, and an 8-celled ovary The fruits are globose, up to 3.5cm in diameter, and seated on a persistent calyx The fruit is green, tinted red (Figure 11.3)

11.3.2 Ethnopharmacology

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In China, the plant is known as pei shih (Chinese) The fruits are used to treat diarrhea and dysentery

The medicinal properties ascribed to it by the Chinese are somewhat remarkable It is said to break fever, to be an antidote for snake poisoning, and to be demulcent An extract of the fruit has been used

as a vaginal injection in gonorrhea A dark oil prepared from the fruit makes an excellent varnish for paper umbrellas and fans In Cambodia, Laos, and Vietnam, the juice of the fruit is used to heal sores and wounds The medicinal properties are most likely owed to tannins Note that Choudhary et al (1990)5 made the observation that ethanolic leaf extracts of Diospyros embryopteris completely

inhibited the libido of male rats when an oral dose of 100mg/Kg was given daily for 21 days

11.4 DIOSPYROS MULTIFLORA BLCO

[From: Greek diospyros = persimmon fruit and from Latin multiﬂora = numerous ﬂowers.]

11.4.1 Botany

Diospyros multiﬂora Blco is a timber tree that grows to a height of 12m in the rain forests of the

Philippines Leaves are simple, their base acute to acuminate, the apex is pointed The petiole is grooved, woody, and up to 1cm long The blade is lanceolate to elliptic, 5cm – 12cm × 2.5cm – 6.5cm and shows 9–12 pairs of secondary nerves The midrib is sunken above There are no tertiary nerves The fruits are up to 2cm in diameter on a cup-shaped persistent calyx (Figure 11.4)

In the Philippines, the bark and leaves are used to treat herpetic eruptions The antiviral property of the plant is unexplored as of yet Some evidence has already been presented that indicates that naphthoquinones have antiherpes properties In a recent study, Tandon et al.6 synthesized and evaluated a series of naphthoquinone derivatives for antifungal, antibacterial, antiviral, and anticancer

activities by using the standard assay and showed in vitro antiviral activity with the herpes simplex virus The antiviral property of naphthoquinones of the Diospyros species could be mediated by the

inhibition of protease as reported by Matsumoto et al (2001).7

11.5 DIOSPYROS PILOSANTHERA BLCO

[From: Greek diospyros = persimmon fruit and from Latin pilosanthera = pilose anthers.]

11.5.1 Botany

Diospyros pilosanthera Blco is a tree that grows to a height of 27m in the rain forests of Burma,

Cambodia, Laos, Vietnam, Malaysia, and Indonesia The bark is blackish, cracked, and fissured The leaves are elliptical, 6cm – 14cm × 2.5cm – 6cm The apex is acuminate, the base is pointed, and the midrib is sunken above There are 8–16 pairs of secondary nerves The male flowers are 5-merous, in 3–5 flowered cymes with 17 anthers The female flowers are solitary, on 2mm peduncles The fruits are depressed and ovoid, 2cm × 3cm, with a large woody calyx (Figure 11.5)

In the Philippines, Indonesia, and Malaysia, the plant is known as kumu Filipinos drink a decoction of

the bark to treat a cough The pharmacological potential of this plant is unexplored

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Gardens, Singapore Botanical identiﬁcation: F S P Ng, March 17, 2000 Geographical localiza tion: Mandai Road, Singapore Field collector: M S Kiah, Aug 1, 1940.]

as of yet The bechic property might be due to saponins, which are known to abound in members of the Ebenaceae family.8

11.6 DIOSPYROS SUMATRANA MIQ

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[From: Greek diospyros = persimmon fruit and from Latin sumatrana = from Sumatra.]

11.6.1 Botany

Diospyros sumatrana Miq (Diospyros ﬂavicans [Wall.] Hiern, Diospyros dumosa King & Gamble, Diospyros decipiens King & Gamble, Diospyros tubicalyx Ridl., Diospyros vestita Bakh., Diospyros velutinosa Bakh., and Diospyros hendersoni) is a tree that grows to a height of 30m with a girth of

100cm in Indonesia, Thailand, and Malaysia (Borneo) in lowland rain forests to an altitude of 1500m above sea level The trunks are hairy when young The leaves are simple, elliptic, ovate, oblong, 3.5cm – 20cm × 1.2cm – 6.5cm, the apex is acuminate, the base is pointed, and the midrib sunken above There are 3–11 pairs of secondary nerves The male flowers are 5-merous, in 3–10 flowered subsessile cymes with 16 anthers The female flowers are 4-merous, salver-shaped, with a 4-locular ovary The fruits are globose, 1.2cm × 2.4cm, with a 2.5cm-diameter calyx (Figure 11.6)

T D Pennington, Sept 11, 1963 No: 7807 From FRIM Kepong No: 94504.]

In Malaysia, the plant is known as arang or kayu arang The seeds are poisonous and used to catch

ﬁsh The plant has not been studied for its pharmacological potential The ichthyotoxic property could involve some naphthoquinones and/or saponins.8

11.7 DIOSPYROS RUFA KING & GAMBLE

[From: Greek diospyros = persimmon fruit and from Latin rufa = wrinkled.]

11.7.1 Botany

Diospyros rufa King & Gamble is a timber tree that grows to a height of 27m and a girth of 130cm in

the lowland rain forest of Malaysia up to an altitude of 1300m The bark is black to brown and smooth The leaves are simple, oblong, oblong–obovate, 12–22cm × 4.5–8cm, the apex is acuminate, the base is pointed, and the midrib is sunken above There are 13 pairs of secondary nerves The petiole is 1–2.5cm long

The male flowers are 4-merous, in 16 flowered subsessile clusters and show 16 anthers The female flowers are 4-merous and show an 8-locular ovary The fruits are round, brown with red hairs, and

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ﬂattened; the apex is 3.5cm wide, in a 4-lobed, saucer-shaped, with a 2.5cm-diameter calyx (Figure 11.7 )

In Malaysia, the seeds are poisonous and used to catch ﬁsh The plant has not been studied for its pharmacological potential The ichthyotoxic mechanism could involve some naphthoquinones or saponins.7

Figure 11.7 Diospyros rufa King & Gamble [From: Flora of

Malaya FRI No: 35981 Geographical localization: River Durian Forest Reserve Foot of hill near a stream.]

11.8 DIOSPYROS TOPOSIOIDES KING & GAMBLE

[From: Greek diospyros = persimmon fruit and from Indian toposi = Diospyros toposia.]

11.8.1 Botany

Diospyros toposioides King & Gamble is a timber tree that grows to a height of 13m and with a girth

of 60cm in the lowland rain forests of Malaysia and Indonesia The leaves are simple, oblong, oblong–ovate, 16cm – 33cm × 4cm – 14cm, the apex is acuminate, the base is rounded, and the midrib is sunken above The secondary nerves are inconspicuous and loping at the margin The male flowers are arranged in three flowered axillary cymes and show 35–96 anthers The female flowers are 4-merous and show an 8-locular hairy ovary The fruits are globose, up to 5cm in diameter, and are seated on a 3cm-wide calyx (Figure 11.8)

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In Malaysia, the plant is known as arang, or kayu arang The seeds are poisonous and used to catch

ﬁsh The plant has not been studied for its pharmacological potential The ichthyotoxic property could involve some naphthoquinones or saponins.8

REFERENCES

1 Kuo, Y H., Chang, C I., Li, S Y., Chou, C J., Chen, C F., Kuo, Y H., and Lee, K H 1997

Cytotoxic constituents from the stems of Diospyros maritima Planta Med., 63, 363

2 Ting, C Y., Hsu, C T., Hsu, H T., Su, J S., Chen, T Y., Tarn, W Y., Kuo, Y H., Peng, J., Liu, L F., and Hwang, J 2003 Isodiospyrin as a novel human DNA topoisomerase I

Whang-inhibitor Biochem Pharmacol., 66, 1981

3 Okuyama, E., Homma, M., Satoh, Y., Fujimoto, H., Ishibashi, M., Yamazaki, M., Satake, M., and Ghazali, A B 1999 Monoamine oxidase inhibitory naphthoquinone and/or naphthalene

dimers from Lemuni hitam (Diospyros sp.), a Malaysian herbal(Buy now from

http://www.drugswell.com) medicine(Buy now from http://www.drugswell.com) Chem

Pharm Bull (Tokyo), 47, 1473

4 Higa, M., Noha, N., Yokaryo, H., Ogihara, K., and Yogi, S 2002 Three new naphthoquinone

derivatives from Diospyros maritima Blume Chem Pharm Bull (Tokyo), 590

5 Choudhary, D N., Singh, J N., Verma, S K., and Singh, B P 1990 Antifertility effects of

leaf extracts of some plants in male rats Indian J Exp Biol., 28, 714

6 Tandon, V K., Singh, R V., and Yadav, D B 2004 Synthesis and evaluation of novel

1,4-naphthoquinone derivatives as antiviral, antifungal and anticancer agents Bioorg Med Chem Lett., 14, 2901

7 Matsumoto, M., Misawa, S., Chiba, N., Takaku, N., and Hayashi, N 2001 Selective nonpeptidic inhibitors of herpes simplex virus type 1 and human cytomegalovirus proteases

Biol Pharm Bull., 24, 36

8 Mallavadhani, U V., Panda, A K., and Rao, Y R 1998 Pharmacology and chemotaxonomy

of Diospyros Phytochemistry, 49, 901

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soft-To date there is not much evidence to suggest whether Bombacaceae hold any pharmaceutical potential, but one should investigate this family thoroughly for pharmacology The medicinal ﬂora of

Asia and the Paciﬁc include a few species of Bombacaceae: Bombax ceiba L., Bombax malabaricum DC., Gossampinus heptaphylla (Houtt.) Bakh., Gossampinus malabarica (DC.) Merr., Ceiba

pentandra (L.) Gaertn., Eriodendron anfractuosum DC., Gossampinus rumphii Schott, Durio zibethinus Murr., Durio oxleyanus Griff., and Neesa altisima Bl These are often used for the

treatment of inﬂammatory conditions and as diuretics

Figure 12.1 Botanical hallmarks of Bombacaceae (See color insert following page 168.)

12.2 CEIBA PENTANDRA (L.) GAERTN

[From: Latin pentandra = 5 anthers.]

12.2.1 Botany

Ceiba pentandra (L.) Gaertn (Eriodendron anfractuosum

DC., and Gossampinus rumphii Schott) is a tree that

grows to a height of 40m with a girth of 3m The plant is

native to Central America and has been introduced in

tropical Africa and Asia The wood is whitish and soft

The bark is smooth and greenish, and produces a few

thorns, which are conical The leaves are palmate and up

to 40cm in diameter and consist of 7–8 folioles, which are

5cm × 1.5cm The ﬂowers are tubular, whitish to pink, in

axillary fascicles The fruits are green, ﬂeshy, fusiform

capsules 8cm – 14cm × 4.5cm – 7cm, containing up to 175

seeds 4–8mm long, which are minute and comose (Figure

12.2)

The Kapok tree is also known as fromager (French), ceibo

(Mexican), and kapok (Malay) In Burma, the roots(Buy now from http://www.drugswell.com) are

used to invigorate and the leaves are used to treat gonorrhea In Cambodia, the root is used to reduce fever The bark is used to promote urination, to treat gonorrhea, to reduce fever, and to treat diarrhea

In Malaysia, the bark is used to treat asthma In Indonesia, a decoction is used as a drink to treat gravels (small kidney calculi), and a decoction of leaves is used to treat syphilis The juice squeezed from the leaves is used to treat asthma and coughs In the Philippines, it is used to reduce fever and to

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promote libido, and the gummy exudate of the plant is eaten to treat dysentery, menorrhagia, and diabetes Some evidence has already been presented, which lends support to the argument for its antidiabetic and antiinﬂammatory properties Using streptozotocin-induced diabetes mellitus in experimental rats, Ladeji et al.1 made a careful study of the antidiabetic properties of an aqueous bark extract given orally to rats for 28 days There was, they report, a statistically signiﬁcant reduction in

plasma glucose levels 5-Hydroxy-7,4′,5′-trimethoxyisoﬂavone,3′-O-β-D-glucoside,

and its aglycone, vavain, isolated from the bark of Ceiba pentandra, inhibited the enzymatic activity

of cyclooxygenase-2 with IC50 values of 381, 97, and 80µM, respectively.2

Another possible pharmacologically interesting feature of Ceiba pentandra (L.) Gaertn could be the production of sesquiterpenes and triterpenes inducing cell death or apoptosis in vitro Hibasami et al.3have recently reported the presence of 2O-methylisohemigossylic acid lactone, a sesquiterpene

lactone from the roots(Buy now from http://www.drugswell.com) of Bombax ceiba L., which induces cell death and morphological change indicative of apoptotic chromatin condensation in human

promyelotic leukemia HL-60 cells 2-O-methylisohemigossylic acid lactone affected the survival of human promyelotic leukemia HL-60 cells cultured in vitro accompanied with chromatin

condensation, fragmentation of DNA to oligonucleosomal-sized fragments, which are characteristic of apoptosis, an effect disciplined by inhibitors of caspases and proteolytic enzymes Lupeol from

Gossampinus malabarica (L.) Merr induced the formation of apoptotic bodies in HL-60 cells cultured in vitro with an increase in hypodiploid nuclei up to 70.9% after a 3-day treatment with

150µM ( Figure 12.3).4

12.3 NEESIA ALTISSIMA BL

[After Nees von Esenbeck, 1787–1837, and from Latin altissima = tallest.]

12.3.1 Botany

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Neesia altissima Bl is a large tree that grows to a height of 40m with a girth of 4m, in the primary

rain forests of Malaysia, Sumatra, Java, and Borneo The bark is dark brown The stems are glabrous, stout, and lenticelled The leaves are simple and stipulate The stipules are caducous, linear lanceolate, and 2–4 cm long The petiole is up to 10cm long, woody, and shaped like a knee The blade is obovate, thick, 30cm × 10cm, and shows 15–20 pairs of secondary nerves The ﬂowers are 1.5cm long, axillary, and show 25 stamens united at the base The fruits are massive, purple, 5-angled, and 15–20cm × 10–15cm (Figure 12.4)

The plant is used medicinally in Indonesia

Figure 12.4 Neesia altissima Bl [From: Herbarium

where the empty capsules are burned and the

Bogoriense Field collector: A J

charcoal obtained is used to make a remedy for Unesco and G H Kostermans Geo

the treatment of gonorrhea The pharmacologi-graphical localization: Southwest Java, Udjung, Kulon Reserve.]

cal potential of Neesia altissima Bl and the genus Neesia in general is as of yet unexplored

REFERENCES

1 Ladeji, O., Omekarah, I., and Solomon, M 2003 Hypoglycemic properties of aqueous bark

extract of Ceiba pentandra in streptozotocin-induced diabetic rats J Ethnopharmacol., 84,

139

2 Noreen, Y., el-Seedi, H., Perera, P., and Bohlin, L 1998 Two new isoﬂavones from Ceiba pentandra and their effect on cyclooxygenase-catalyzed prostaglandin biosynthesis J Nat Prod., 61, 8

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3 Hibasami, H., Saitoh, K., Katsuzaki, H., Imai, K., Aratanechemuge, Y., and Komiya, T 2004 2-Omethylisohemigossylic acid lactone, a sesquiterpene, isolated from roots(Buy now from http://www.drugswell.com) of mokumen (Gossampinus malabarica) induces cell death and morphological change indicative of apoptotic chromatin condensation in human promyelotic

leukemia HL-60 cells Int J Mol Med., 4, 1029

4 Aratanechemuge, Y., Hibasami, H., Sanpin, K., Katsuzaki, H., Imai, K., and Komiya, T 2004 Induction of apoptosis by lupeol isolated from mokumen in human promyelotic leukemia HL-

60 cells Oncol Rep., 11, 289

so far been found in the Cucurbitaceae and Begoniaceae Families The evidence available indicates that cucurbitacins, which abound in this family, hold some potential as a source of cytotoxic agents.1–3

A remarkable advance in the chemotherapeutic evaluation of Elaeocarpaceae has been provided by Ito

et al.3 Using a bioassay-guided investigation of the bark of Elaeocarpus mastersii, they isolated cucurbitacin D and cucurbitacin F as cytotoxic principles instead of using KB cells cultured in vitro,

together with ellagic acid derivatives

Other principles of interest in Elaeocarpaceae are indolizidine alkaloids, which have attracted a great deal of interest on account of their ability to inhibit the enzymatic activity of glucosidases because of

a structural similarity with glucose; hence there is some potential to explore it further in the treatment

of Human Immunodeﬁciency Virus (HIV), diabetes, and cancer (Figure 13.2)

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Indolizidine

Cucurbitacin

Figure 13.2 Examples of bioactive natural products in the family Elaeocarpaceae

Note that a small number of indolizidine alkaloids have emerged that have therapeutic indices favoring their introduction into clinical practice Carroll et al.4 made the interesting observation that

grandisine A, B, and (–)-isoelaeocarpiline isolated from Elaeocarpus grandis from the Australian rain

forest are able to bind to the delta type of opioid brain receptors All these pharmacological events together lend considerable support to the view that Elaeocarpaceae with its 10 genera and 400 species

of tropical trees would be worth screening thoroughly for cytotoxic agents One can reasonably expect the discovery of molecules of chemotherapeutic value in this large family An exciting approach

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would be to start with Aceratium insulare A.C., Elaeocarpus grandiflorus Smith., Elaeocarpus madopetalus Pierre, Elaeocarpus petiolatus Wall., Elaeocarpus floribundus Bl., Elaeocarpus sphaericus (Gaertn.) K Sch., and Mutingia calaruba, which are used medicinally in the Asia–Pacific

13.2 ELAEOCARPUS FLORIBUNDUS BL

[From: Greek elaion = oil and karpos = fruit, and from Latin ﬂoribundus = profuse ﬂowering.]

13.2.1 Botany

Elaeocarpus ﬂoribundus Bl is a tree that grows up to 30m high with a girth of 2.4m, and is common

in the lowland hills and mountains up to an altitude of 1500m in India, Burma, Thailand, Vietnam, Cambodia, Laos, Malaysia, Indonesia, and the Philippines The bole is columnar The bark is brown, rough, and lenticelled The inner bark is pale yellow The leaves, buds, flowers, and fruits are often dotted with small scabby or pimply pustules The blade is ovate elliptic, thinly leathery, and 6.5cm × 3cm – 19cm × 8.5 cm The apex is acuminate, the base is pointed, and the margin is toothed The blade shows 5–7 pairs of secondary nerves The petiole is 1–5.5cm long and kneed The inflorescences are axillary racemes, which are 2.5–12cm long The flowers are 5-merous, 0.5cm long, comprise 25 stamens, and have a hairy ovary The flower pedicels are 0.4–1.2cm long The fruits are smooth, glabrous, ellipsoid, narrowed at basal end, and contain a rugose of 3cm × 2.5cm stone (Figure 13.3)

In Sumatra, an infusion of bark and leaves is used as a mouthwash for inﬂamed gums The pharmacological activity of this plant is unexplored as of yet

13.3 ELAEOCARPUS OBTUSUS BL SENSU KING

[From: Greek elaion = oil, karpos = fruit, and from Latin obtusus = obtuse.]

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Figure 13.4 Elaeocarpus obtusus Bl sensu King [From: Ex

Herb Leiden Geographical localization: Taytay municipality, 15Km north Embarcadero, area near Pncol, Philippines Rain forest hill slope Alt.: 140m Field collector: A C Podzorski SMHI No: 984 April 21, 1984.]

The Malays apply a paste of leaves to insect bites The antiinﬂammatory property of Elaeocarpus obtusus Bl sensu King is not conﬁrmed as of yet Note that the petroleum ether, benzene, chloroform, acetone, and ethanol extracts of the fruits of Elaeocarpus sphaericus stabilize the activity of mast

cells.5 The extracts at 50–200mg/Kg intraperitoneally or 200mg/Kg orally showed signiﬁcant antiinﬂammatory action against both acute and subacute models, analgesic action, barbiturate-

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hypnosis potentiation, and antiulcerogenic activities in rats, and protected guinea pigs against asphyxia induced by histamine and acetylcholine aerosols.6 Are indolizides involved here?

REFERENCES

1 Fang, X., Phoebe, Jr., C H., Pezzuto, J M., Fong, H H., Farnsworth, N R., Yellin, B., and Hecht,

S M 1984 (November–December) Plant anticancer agents, XXXIV Cucurbitacins from

Elaeocarpus dolichostylus J Nat Prod., 47, 6, 988–993

1 Rodriguez, N., Vasquez, Y., Hussein, A A., Coley, P D., Solis, P N., and Gupta, M P 2003

Cytotoxic cucurbitacin constituents from Sloanea zuliaensis J Nat Prod., 66, 1515

1 Ito, A., Chai, H B., Lee, D., Kardono, L B S., Riswan, S., Farnsworth, N R., Cordell,

G A., Pezzuto,

2 J M., and Kinghorn, A D 2002 Ellagic acid derivatives and cytotoxic cucurbitacins

from Elaeocarpus mastersii Phytochemistry, 61, 171

2 Carroll, A R., Arumugan, G., Quinn, R J., Redburn, J., Guymer, G., and Grimshaw, P 2005 Grandisine A and B, novel indolizidine alkaloids with human delta-opioid receptor binding

afﬁnity from the leaves of the Australian rain forest tree Elaeocarpus grandis J Org Chem.,

70, 1889

3 Singh, R K., Bhattacharya, S K., and Acharya, S B 2000 Studies on extracts of Elaeocarpus sphaericus fruits on in vitro rat mast cells Phytomedicine(Buy now from http://www.drugswell.com), 7, 205

4 Singh, R K., Acharya, S B., and Bhattacharya, S K 2000 Pharmacological activity of

Elaeocarpus sphaericus Phytother Res., 14, 36

CHAPTER 14

Medicinal Plants Classiﬁed in the Family Capparaceae

14.1 GENERAL CONCEPT

The family Capparaceae (A L de Jussieu, 1789 nom conserv., the Caper Family or Capparidaceae)

family consists of approximately 45 genera and about 800 species of pungent treelets, shrubs, or herbs, which have the ability to elaborate a series of isothiocyanates (mustard oils), ﬂavonoids, and

occasionally pyrrolidine alkaloids When looking for Capparaceae, search for plants with elongated

receptacles called gynophores or androgynophores, a showy protruding androecium, and by the aspect

of the corolla (Figure 14.1)

With regard to the pharmaceutical potential of Capparaceae, Shi et al.1 showed that

5,3′dihydroxy-3,6,7,8,4′-pentamethoxyﬂavone from Polanisia dodecandra inhibits a broad panel of cancer cells:

central nervous system cancer (SF-268, SF-539, SNB-75, U-251), nonsmall-cell lung cancer

(HOP-62, NCI-H266, NCI-H460, NCI-H522), small-cell lung cancer (DMS-114), ovarian cancer

(OVCAR-3, SKOV-3), colon cancer (HCT-116), renal cancer (UO-31), a melanoma cell line (SK-MEL-5), and

leukemia cell lines (HL-60, SR), cultured in vitro The cellular mechanism by which this ﬂavone is

toxic is based on inhibition of the polymerization of tubulin into the mitotic spindle (IC50 = 0.83µM) Other interesting cytotoxic natural products from Capparaceae are triterpenes of the dammarane type such as polacandrin, which inhibits the proliferation of KB (ED50: 0.6µg/mL), the P388 (ED50: 0.9µg/mL), and RPMI7951 (ED50: 0.62µg/mL) cell lines, as well as 17α-hydroxycabraleahydroxylactone (IC50 = 3.1µg/mL), 12β-acetoxycleocarpone (C50 = 8.9µg/mL), 3-O-

acetyl-12β-acetoxy-25-O-ethylcleo-

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