The Pharma Research (T. Pharm. Res.), (2009), 2; 70-78 Copyright © 2009 by Sudarshan Publication Received: 11 Sep 2009 Sudarshan Institute of Technical Education Pvt. Ltd.
Review Article MEDICINAL USES OF EURYCOMA-LONGIFOLIA: A REVIEW
Mohd Rashid 1, Sachin kumar1; Dr. Bahar Ahmad2
Affiliated to: 1: NKBR College of Pharmacy and Research Centre, Meerut, 2: Jamia Hamdard University-New delhi.
ABSTRACT
Eurycoma longifolia Jack (also known as Tongkat Ali or Pasak Bumi) is a flowering plant in the family Simaroubaceae native to Indonesia and Malaysia.. Eurycoma longifolia is a small ever green tree growing to 15 meters (49 feets) tall with spirally arranged pinnate leaves 20-40 meters (8-16 inches)long with 13-41 leaflets.The flowers are diacious with male and female flowers or different trees; they are produced in large panicles each flower with 5-6 very small petals. The fruit is green ripening dark red, 1-2 cm long and 0.5-1 cm broad. The plant’s pharmacological activity as such Potential Antimalarial, Aphrodisiac activity, Antitumour promoting and Antiparacytic activity, Antibacterial activity, Anti hyperglycaemic Activity, Anxiolytic Activity, and Plant growth inhibitor is attributed to various quassinoids, squalene derivatives, biphenylneolignans, tirucallane –type triterpenes, canthine-6-1, and beta – carboline alkoloids.
Keywords: Eurycoma londifolia, Antimalrial, Aphrodisiac apoptosis, Quassinoids, Biphenylneolignans. Antitumour, Antibactrial, Anti-hypirglycaermic, Anxiolytic.
*Corresponding Author: Mohd Rashid, NKBR College of Pharmacy and Research Centre, Meerut. [email protected]
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1.0 INTRODUCTION: plant in the family Simaroubaceae native to It is a popular herb and mainly used as Indonesia and Malaysia The author abbreviation aphrodiasiac anti-pyretic and anti- malarial Jack in the scientific name of the plant refers to remedy. Not surprisingly village people often use the Scottish botanist. William Jack. it as anaphrodisiac remedy. This observation agrees with various pharmacological studies in Eurycoma longifolia is a small ever green tree which anti-hypirglycaemic, antimalarial, anti- growing to 15 meters (49 feets) tall with spirally proliferative, anti-schistosomal, anxiolytic and arranged pinnate leaves 20-40 meters (8-16 aphrodisiac activities are found in both in vivo inches)long with 13-41 leaflets.The flowers are and in vitro studies.[1] Fractions of Eury -coma diacious with male and female flowers or longifolia Jack extracts have been shown to different trees; they are produced in large induce apoptosis in breast cancer cells[2] and to be panicles each flower with 5-6 very small petals. cytotoxic to lung cancer cells[3] A decoction of The fruit is green ripening dark red ,1-2 cm long the roots, root barks and bark is consumed by and 0.5-1 cm broad. mouths to treat numerous conditions including diarrhoea, fever, glandular fever swelling, Chemistry bleeding. dropsy,persistantcough, hypertension, The plant’s pharmacological activity is relief of pain in the bone, and tertian malaria. The attributed to various quassinoids, squalene bark also has been used topically to treat wounds derivatives, biphenylneolignans, tirucallane – , ulcers, syphilitic sores, and headach . The plant type triterpenes, canthine-6-1, and beta – is primarily known in commerce for its carboline alkoloids.[9,10] [4,5] aphrodisiac properties, Long jack (Eurycoma Quassinoids longifolia ) is believed to stimulate the production Including eurycomanol ; eury comanol –2-o- of endogenous testosterone and to reduce the beta-D-glycopyranoside; 13 beta -18- levels of bound and metabolically inactive dihydroeurycomanol; 14,15 p-dihydroxy [6] testosterone in the body . In vitro, ethanolic klaineanone; and 6 alpha- extracts of Eurycoma longifolia increase RCG- hydroxyeurycomalactone have been isolated induced production of testosterone by rat laydiag from the roots[11,12,13,14,15]. cells [7] . The interest in the chemistry of Squalene quassinoids has accelerated rapidly with the Squalene derivatives including eurylene ; 14- American National Cancer Institute findings in deacetyleurylene; early 1970, showing that these compounds longilene peroxide and teurilene.[16,17] display marked antiluckemic activity (e.g Biphenylneolignans bruceantin )[8] including the following: 2 isomeric 2,2- SOURCE: Eurycoma longifolia Jack (also known dimethoxy-4-(3-hydroxy-1-propenyl)-4-(1,2,3- as Tongkat Ali or Pasak Bumi) is a flowering trihydroxy propyl) diphenyl esters; and 2
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71 Page biphenyls, 2-hydroxy-3,2,6-trimetoxy-4-(2,3- including 9,10 – dimethoxy canthin –6- one; 10- epoxy-1-hydroxypropyl)-5-(3-hydroxy-1- hydroxy – 9-methoxy canthin - 6 – one; 11- propenyl)-bi phenyl and 2-hydroxy –3,2- hydroxy –10- methoxy canthin – 6- one ; 5,9 – dimethoxy-4-(2,3- epoxy-1-hydroxy-proply ) – dimethoxy canthin –6-one; and 9 – methoxy –3- 5-(3-hydroxy-1-propenyn)- biphenyl[18]. methyl canthin –5,6- dione.[19,20] Alkoids
CHEMICAL CONSTITUENTS FROM EURYCOMA LONGIFOLIA
(A) Eurylactone A (1) [21] (D) EvryleneC-2(4) [23]; [24] C19H26O8; (M=382.410;) 14-deAc ;
Needles (MeOH) C32H56O7; M 522.790 (MP 148-150 0 C) Needles; MP 142-143 0C.
(B) Eurylactone B (2) [22] (E) Evrylactone- D (5) [25]
C19H22O9; (M=394.377) C39H22O9; M 394.377 Needles (EtoAc) Crystal (EtoAc) (MP210-212 0C) (MP 210-212 0C) (C) EvryleneC-1(3) [23]; [25] C34H58O8;(M 594.827) (F) Evrylactone- E (6) 0 Crystals; (MP 146-148 C) C39H26O7; M 394.377 Crystal (EtoAc) (MP 206-212 0C)
OH OH
HO HO
O OH OH OH OH O O O O
O O O O
Eurylactone A Eurylactone B (1) (2)
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O AcO AcO O
HO OH Eurylactone C-1 (3) O O HO OH HO HO O HO O OH OH O O O OH
O O Eurycolactone C-2 (5) Eurylactone D (4)
OH OH
HO HO HO OH OH O O OH
H O
O H H H OAc Eurycolactone E 14,15-dihydroxyklaineanone (6) (7)
A new C19-skeleton quassinoid, named inhibitor or chloroquine- resistant Gombak longilacton and three new quassinoid viz. A isolates of Plasmodium falciparum. Sevral 13,21- dihydroxyeurycomenone and 14,15 diacylated derivatives of eurycomanone: beta-dihydroxyklaineaone were isolated 1,15-di-O-(3,3- di methyl actyloyl) – from the roots of Eurycoma eurycoma-none 1,15-di-O-benzoyl longifolia[26].14,15 beta- eurycoman and 1,15- di – O-isovaleryl dihydroxyklaineanone (7). eurycomanone were syhtesized. These diarylated eury comanones exhibitted lower TRADITIONAL USES anti plasmodial activity against the Gombak Established effects: A isolate and lower toxicity in the brine Potential Antimalarial shrimp assay when compared to eury Sevral Quassinoid, eurycomanone was comanone.In contrast, the monoacylated identified as the most potent and toxic derivative displayed comprable
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73 Page antiplasmodicidal potency to eury Jack significantly increased the laevator comanone.[27] animuscle to 58.56+/-1.22,58.23+/- Aphrodisiac activity: 0.31,60.21+/-0.86 and 62.35+/- It increase male virility and sexual prowess 0.98mg/100gm body weight, respectively during sexual activity .As such the effect of when compared with the control (untreated 200,400 and 800mg /kg of butanol , in the uncaestrated intact male rats and methanol and water and chloroform fractions 49.23+/-0.82,52.23+/-0.36,50.21+/-.66and of Eurycoma longiafolia Jack were studied 52.35+/-.58 mg/100gm body weight on the laevator animuscle in both uncastrated respectively, when compared to control and testosterone –stimulated castrated intact untreated ) in the testosterone –stimulated male rats after dosing them for 12 castrated intact male rats .Hence ,the consequitive weeks.Result showed that 800 proandrogenic effect as shown by this study mg/kg of butanol , methanol ,water and further supported the traditional use of this [28] chloroform fraction of Eurycoma longifolia plant as an aphrodisiac . Comanone; 1 isovaleryl eurycomanone were Antibacterial activity:- synthesized. The Study took place in the Laboratory of These diacylated eurycomanones exhibited Molecular Biology of Biotechnology lower antiplasmodial activity against Engineering Department, Malaysia between Gombak the monoacylated derivative Jan 2005 and June 2006. The alcoholic and displayed comparable antiplasmodicidal acetone extract of the leaves and stem potency to eurycomanon. extracts were active on both Gram – positive and Gram – negative bacteria (Escharicha UNDER INVESTIGATION:- coli and Salmonella typhi). The root extract Antitumour promoting and Antiparacytic had no antibacterial activity against Gram- activity:- positive and Gram –negative bacteria tested. Some quassinoids isolated from the leaves Aqueous leave’s extract showed of Eurycoma longifolia Jack were subjected antibacterial activity against Staphylococcus [30] to in vitro test on antitumour promoting , aureus and Serratia marscesens. and antischistosomal activities the most active compounds for induced Epstein-Barr Anti hyperglycaemic Activity- virus activation (antitumour Promotion) was Screening of aqueous extract of Eurycoma 14,15 beta-dihydroxyklaineanvne . longifolia (TA-a andTA-b) to determine Longilactone gave significant their blood glucose lowering effects were antischistosomal effect at a concetration of conducted in normoglycaemic and 200 microg/ml. [29] streptagocin-induced hyper glycaemic rats. In the administration of TA-a and TA-b
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positive results were obtained when *Genetic diversity of eury coma longifollia 150mg/kg Body weight of the aqueous inferred from single nucleotidie [31] extract was used. polymorphism Anxiolytic Activity- Widespread harvesting of wild grown trees The anxiolytic activity of Eurycoma has led to rapid thining of natural longifolia Jack in mice was examined. population, causing a potential decrease in Fractions of Eurycoma longifolia Jack genetic diversity among extract produced a significant increase in the Eurycomalongifolia. Suitable genetic marks numbers of square crossed [control = would be very useful for propagation and 118.2+/-10.2 square], but significantly breeding programmes to support decreased both the immobility [control= conservation of this species although no 39.4+/-4.0 sec] and fecal pellets (control such marker currently exist. To meet the =12.3+/- 2.1 fecal pellets) when compared need, a genome complexity reduction with control mice in open field test. In strategy to identify a series of single addition, these results were found to be nucleotide polymorphism (SNPs) within the consistant with anxiolytic effects produced genomes of several Eurycoma longifolia by the diazepam.Hence; this study supports access has been applied. Occurance of these the medicinal use of this plant for anxiety SNPs reflects the geographic origin of therapy. [32] individual plants and can distinguish [33], [34] Plant growth inhibitor different natural population. Seven quassinoids including a new 12- epi – CONCLUSION- 11- dehydroklaineanone were isolated from The alcoholic and acetone extracts from the leaves of Eurycoma longifolia as plant leaves and stem of Eurycoma longifolia growth inhibitor. The strongest activity was containing potent antibacterial agent (s). found in 14, 15 beta- dihydroxyklaineanone. This plant can serve as a potential source of Induction of apoptosis- anti bacterial compound. The plant is The present study investigated the effects of actually native to Malysia and is widely roots extracts and their chromatographic used as an aphrodisiac than anti malarial, fraction from the root of Eurycoma although both of these activities, viz- longifolia on the growth of a human breast aphrodisiac and anti malarial have been cancer cell line MCF-7. Data indicated that established. Some other activities as Eurycoma longifolia extracts and fraction described above have some ground of small exert a direct antiproliferative activity on or occasional researches on which they MCF-7. stand. Some more activities like antipyretic, glandular swelling, bleeding dropsy and
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