Articles

Tongkat Ali

Plant Part Used

Roots

Active Constituents

Eurycomanone, 13,21-dihydroeurycomanone, 12-acetyl-13,21-dihydroeurycomanone, 13beta,21-dihydroeurycomanone, 13(21)-epoxyeurycomanone, 15-acetyl-13alpha (21)-epoxyeurycomanone, 12,15-diacetyl-13alpha(21)-epoxyeurycomanone, eurycomanol, 13beta,18-dihydroeurycomanol, eurycomanol-2-O-beta-D-glucopy-ranoside, eurycomalactone, 6alpha-hydroxyeurycomalactone, 7alpha-hydroxyeurycomalactone, 5,6-dehydroeurycomalactone, eurylactone A and B, eurycolactone A to C, eurycolactone D to F, laurycolactone A and B, longilactone, 6-dehydroxylongilactone, 6-dehydrolongilactone, 11-dehydro-klaineanone, 12-epi-11-dehydroklaineanone, 15beta-hydroxyklaineanone, 6alpha-acetoxy-15beta-hydroxyklaineanone, 14,15beta-dihydroxyklaineanone, 15beta-acetyl-14-hydroxyklaineanone, 6alpha-acetoxy-14,15beta-dihydroxyklaineanone and 6alpha-acetoxy-15beta-hydroxyklaineanone, canthin-6-one, canthin-6-one-3N-oxide, 9-hydroxycanthin-6-one, 9-hydroxycanthin-6-one-3N-oxide, 11-hydroxycanthin-6-one, 9-methoxycanthin-6-one, 9-methoxycanthin-6-one-3N-oxide, 3-methylcanthine-5,6-dione, 9,10-dimethoxycanthine-6-one, 10-hydroxy-9-methoxycanthine-6-one, 11-hydroxy-10-methoxycanthine-6-one, 5,9-dimethoxycanthine-6-one, 9-methoxy-3-methyl-canthine-5,6-dione, beta-carboline-1-propionic acid, 7-methoxy-beta-carboline-1-propionic acid, 1-methoxymethyl-carboline, squalene, longilene peroxide, eurylene, 14-deacetyl eurylene, teurilene, tirucallane-type triterpenes, niloticin, dihydroniloticin, piscidinol A, bourjotinolone A, 3-episapeline A, melianone, hispidone, biphenylneolignans, isomeric 2,2’-dimethoxy-4-(3-hydroxy-1-propenyl)-4’-(1,2,3-trihydroxypropyl)diphenyl ethers, 2-hydroxy-3,2’,6’-trimethoxy-4’-(2,3-epoxy-1-hydroxypropyl)-5-(3-hydroxy-1-propenyl)biphenyl and 2-hydroxy-3,2’-di-methoxy-4’-(2,3-epoxy-1-hydroxypropyl)-5-(3-hydroxy-1-propenyl)biphenyl, glycoproteins, acetophenone, benzaldehyde, 3-methoxybenzaldehyde, benzoic acid benzyl ether, benzoic acid ethyl ether, benzoic acid methyl ether, benzoic acid propyl ether, cardinene, gamma-cardinene, -cadinol, calamenene, alpha-copaene, alpha-cubebene, cubebene, cuminaldehyde, gamma-decalactone, fenchone, furaldehyde, 5-methylfuraldehyde, geranial, 6-methyl-hep-5-en-2-one, heptan-2-one, hexanal, linoleic acid methyl ester, alpha-muurolene, beta-muurolene, gamma-muurolene, nonan-2-one and palmitic acid. (1) , (2) , (3) , (4) , (5) , (6) , (7) , (8) , (9) , (10) , (11) , (12) , (13) , (14) , (15) , (16) , (17) , (18) , (19) , (20)

Introduction

Eurycoma longifolia, a small tree belonging to the family Simaroubaceae, is found in the jungles of Malaysia, Indochina, Sumatra, and Borneo. The tree grows as a medium size slender shrub reaching 10 meters in height, often unbranched with reddish brown petioles. It has compound leaves of even pinnates reaching 1 meter in length. Each compound leaf consists of 30-40 leaflets and each leaflet is about 5-20 cm long, 1.5-6 cm wide. The flowers are hermaphrodite and the petals are small with very fine pubescent. The fruits are hard, oblong, about 1-2 cm long, yellowish brown when young and brownish red when ripe. (21) Every part of the tree is bitter and its root is popularly sought as medicine by the natives to ease fever; as a medication after birth; for healing of boils, wounds, ulcers, syphilis, and bleeding gums. (22)

In Malaysia, Eurycoma Longifolia has been long known as a super energizer, a febrifuge, a remedy for fever (malaria), mouth ulcers, intestinal worms, and as an aphrodisiac for men. It is also believed to be effective for treating hypertension, body aches, and improve vitality and as a tonic after childbirth. It is also reported that the paste of the plant is able to relieve headaches, stomachaches, pain caused by syphilis, and many other general pains.

Dosage Info

Dosage Range

100-400 mg powdered roots, taken orally twice daily.

Most Common Dosage

300 mg powdered roots, taken orally twice daily.

Standardization

Eurycoma longifolia is usually standardized to eurycomanone, 13alpha(21)-epoxyeurycomanone, eurycomalactone, and 14,15beta-dihydroxyklaineanone as reference markers for its organic extract whereas the more polar quassinoids and glycoproteins are used as standards for the aqueous extract.

Toxicities & Precautions

Introduction

There were no toxicities reported associated with the powdered roots at the common dosage used in humans.

Side Effects

No information available

Pregnancy/ Breast Feeding

No information available

Age Limitations

No information available

Pharmacology

Eurycoma longifolia root has been taken orally as a decoction in water and has widely gained notoriety as a male aphrodisiac since it was reported to increase male virility. (23) In this study, E. longifolia modified the orientation activities of treated male rats resulting in a significantly increase of frequent and vigorous mounting, licking and anogenital sniffing towards the receptive females. (24) The hesitation time of non-copulator male rats when treated with the chloroform, methanol, water or n-butanol extract of E. longifolia, was significantly decreased after 12 weeks post-treatment. (25) Enhancement of the sexual motivation of the animals after three days post-treatment was also observed and the effect was more prominent after eight days post-treatment. (26) The orientation activities of the middle-age (9 month old) male Sprague-Dawley rats towards the receptive female rats were also increased after 800 mg/kg of chloroform, methanol, water or n-butanol extract of E. longifolia were administered twice daily for 10 days. (27) In another study, E. longifolia produced a dose-dependent increase in sexual performance of the treated animal and promoted the growth of both ventral prostate and seminal vesicles. (28)

E. longifolia has been reported to show antimalarial activity. (29) A semi-purified extract of E. longifolia exhibited a dose-dependent antimalarial activity towards six Malaysia chloroquine-resistant parasites of P. falciparum. (30) Eurycomanone, one of its quassinoid chemical constituents was relatively more potent (152 %) than chloroquine (100%), against a multi-drug resistant Thailand K-1 strain of Plasmodium falciparum cultured in vitro. (31) In another study, 11-dehydroklaineanone and 15beta-O-acetyl-14-hydroxyklaineanone showed potent plasmodicidal activity at IC50 of 2 mg/ml.

Tumor promoter-induced Epstein-Barr virus activation was also reported to be inhibited by 14,15beta-dihydroxyklaineanone (IC50 = 5M) (32) , another quassinoid of E. longifolia. Other quassinoids, eurycomanone, 13,21-dihydroeurycomanone and 14,15beta-dihydroxyklaineanone have showed the potent cytotoxic activity against KB cells whereas only 14,15beta-dihydroxyklaineanone was potent against P388 leukaemia cells. (33) Eurycomalactone, 6alpha-hydroxyeurycomalactone, 5,6-dehydroeurycomalactone, longilactone, 11-dehydroklaineanone, 14,15beta-dihydroxyklaineanone and some tirucallane-type triterpenes such as niloticin, dihydroniloticin, piscidinol A, bourjotinolone A, 3-episapelin A, melianone, and hispidone have exhibited potent cytotoxic activity against P388 and KB cells. (34) However, eurylene, 14-deacetyl eurylene and longilene peroxide, three squalene-type triterpenes, isolated from the wood of E. longifolia gave cytotoxic activity at IC50 9.5 m10-2 mmol/l against P388 cells; 0.52 mg/ml and 5.3 mg/ml against KB cells respectively (17, 18, 6, 3). Two of the quassinoids, 6-dehydroxy-longilactone and 7alpha-hydroxyeurycomalactone were potent against P388 leukaemia cells. Recently, one of the alkaloidal constituents of E. longifolia, 9-methoxycanthine-6-one, possessing cytotoxic activity, had poor bioavailability (less than 1 % absorption) when administered orally to rats. (35)

Other biological studies reported have included that longilactone gave significant antischistosomal activity at a concentration of 200 mg/ml. (36) From antipyretic studies, several quassinoids including eurycomanone, eurycomalactone, and 14,15beta-dihydroxyklaineanone significantly reduced the lipopolysaccharide-induced fever of mice after 1 hour and were more potent than aspirin. (37) Eurycomanone has also been reported to show anti-ulcer properties. (38)

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  1) Botanical Info

  2) Cultivation

  3) Safety

References

  1. Suong NN, Bhatnagar S, Polonsky J. Structure of laurycolactone A and B, new C18 - quassinoids from Eurycoma longifolia and revised structure of eurycomalactone (X-ray analysis). Tetrahedron Letters. 1982;23(49):5159-5162.
  2. Morita H, Kishi E, Takeya K, Itokawa H, Tanaka O. New quassinoids from the roots of Eurycoma longifolia. Chemistry Letters. 1990;749-752.
  3. Morita H, Kishi E, Takeya K, Itokawa H, Iitaka Y. Squalene-derivatives from Eurycoma longifolia. Phytochemistry. 1993;34(3):765-771.
  4. Ang HH, Hitotsuyanagi Y, Fukaya H, Takeya K. Quassinoids from Eurycoma longifolia. Phytochemistry. 2002;59(8):833-837.
  5. Ang HH, Hitotsuyanagi Y, Takeya K. Euyrcolactones A-C, novel quassinoids from Eurycoma longifolia. Tetrahedron Letters. 2000;41:6849-6853.
  6. Morita H, Kishi E, Takeya K, Itokawa H, Iitaka Y. Highly oxygenated quassinoids from Eurycoma longifolia. Phytochemistry. 1993;33(3):691-696.
  7. Morita H, Kishi E, Takeya K, Itokawa H. Biphenylneolignans from wood of Eurycoma longifolia. Phytochemistry. 1992;31(11):3993-3995.
  8. Mitsunaga K, Koike K, Tanaka T, et al. Canthin-6-one alkaloids from Eurycoma longifolia. Phytochemistry. 1994;35(3):799-802.
  9. Malaysian Monograph Committee. Radix eurycomae eurycoma root. In Malaysian Herbal Monograph Vol 1. Malaysian Monograph Committee. Kuala Lumpur. 1999;29-32.
  10. Chan KL, Iitaka Y, Noguchi H, Sugiyama H, Saito I, Sankawa U. 6alpha-hydroxyeurycomalactone, a quassinoid from Eurycoma longifolia. Phytochemistry. 1992;31(12):4295-4298.
  11. Chan KL, Lee SP, Sam TW, Han BH. A quassinoid glycoside from the roots of Eurycoma longifolia. Phytochemistry. 1989;28(10):2857-2859.
  12. Chan KL, Lee SP, Sam TW, Tan SC, Noguchi H, Sankawa U. 13alpha,18-dihydroeurycomanol, a quassinoids from Eurycoma longifolia. Phytochemistry. 1991;30(9): 3138-3141.
  13. Kanchanapoom T, Kasai R, Chumsri P, Hiraga Y, Yamasaki K. Canthin-6-one and beta-carboline alkaloids from Eurycoma harmandiana. Phytochemistry. 2001;56:383-386.
  14. Chan KL, O’Neill MJ, Phillipson JD, Warhurst DC. Plants as sources of antimalarial drugs. Part 3. Eurycoma longifolia. Planta Medica. 1986;52:105-107.
  15. Choo CY, Chan KL. High performance liquid chromatography analysis of canthinone alkaloids from Eurycoma longifolia. Planta Medica. 2002;68:382-384.
  16. Itokawa H, Kishi E, Morita H, Takeya K. Cytotoxic quassinoids and tirucallane-type triterpene from the woods of Eurycoma longifolia. Chemical and Pharmaceutical Bulletin. 1992;40:1053-1055.
  17. Itokawa H, Kishi E, Morita H, Takeya K, Iitaka Y. A new squalene-type triterpene from the woods of Eurycoma longifolia. Chemistry Letters. 1991;2221-2222.
  18. Itokawa H, Kishi E, Morita H, Takeya K, Iitaka Y. Eurylene, a new squalene-type triterpene from Eurycoma longifolia. Tetrahedron Letters. 1991;32(15):1803-1804.
  19. Itokawa H, Qin X-R, Morita H, Takeya K. Novel quassinoids from Eurycoma longifolia. Chemical and Pharmaceutical Bulletin. 1993;41(2):403-405.
  20. Jiwajinda S, Santisopasri V, Murakami A, Hirai N, Ohigashi H. Quassinoids from Eurycoma longifolia as plant growth inhibitors. Phytochemistry. 2001;58: 959-962.
  21. Malaysian Monograph Committee. Radix eurycomae eurycoma root. In Malaysian Herbal Monograph Vol 1. Malaysian Monograph Committee. Kuala Lumpur. 1999;29-32.
  22. Malaysian Monograph Committee. Radix eurycomae eurycoma root. In Malaysian Herbal Monograph Vol 1. Malaysian Monograph Committee. Kuala Lumpur. 1999;29-32.
  23. Ang HH, Sim MK. Eurycoma longifolia Jack and orientation activities in sexually experienced male rats. Biological and Pharmaceutical Bulletin. 1998;21(2):153-155.
  24. Ang HH, Sim MK. Eurycoma longifolia Jack and orientation activities in sexually experienced male rats. Biological and Pharmaceutical Bulletin. 1998;21(2):153-155.
  25. Ang HH, Ngai TH. Aphrodisiac evaluation in non-copulator male rats after chronic administration of Eurycoma longifolia Jack. Fundamental and Clinical Pharmacology. 2001;15(4):265-268.
  26. Ang HH, Chan KL, Gan EK, Yuen KH. Enhancement of sexual motivation in sexually naïve male mice by Eurycoma longifolia. International Journal of Pharmacognosy. 1997;35(2):144-146.
  27. Ang HH, Lee KL. Effect of Eurycoma longifolia Jack on orientation activities in middle-aged male rats. Fundamental and Clinical Pharmacology. 2002;16:479-483.
  28. Ang HH, Cheang HS, Yusof AP. Effects of Eurycoma longifolia Jack (Tongkat Ali) on the initiation of sexual performance of inexperienced castrated male rats. Experimental Animal. 2000;49(1):35-38.
  29. Ang HH, Chan KL, Mak JW. In vitro antimalarial activity of quassinoids from Eurycoma longifolia against Malaysian chloroquine-resistant plasmodium falciparum isolates. Planta Medica. 1995;61(2):177-178.
  30. Ang HH, Chan KL, Mak JW. In vitro antimalarial activity of quassinoids from Eurycoma longifolia against Malaysian chloroquine-resistant plasmodium falciparum isolates. Planta Medica. 1995;61(2):177-178.
  31. Chan KL, O’Neill MJ, Phillipson JD, Warhurst DC. Plants as sources of antimalarial drugs. Part 3. Eurycoma longifolia. Planta Medica. 1986;52:105-107.
  32. Zainah A. Master Degree Thesis, School of Pharmaceutical Sciences. Universti Sains Malaysia. Penang, Malaysia. 2003.
  33. Morita H, Kishi E, Takeya K, Itokawa H, Tanaka O. New quassinoids from the roots of Eurycoma longifolia. Chemistry Letters. 1990;749-752.
  34. Itokawa H, Kishi E, Morita H, Takeya K. Cytotoxic quassinoids and tirucallane-type triterpene from the woods of Eurycoma longifolia. Chemical and Pharmaceutical Bulletin. 1992;40:1053-1055.
  35. Tan S, Yuen KH, Chan KL. HPLC analysis of plasma 9-methoxycanthin-6-one from Eurycoma longifolia and its application in a bioavailability/pharmacokinetic study. Planta Medica. 2002;68:355-358.
  36. Jiwajinda S, Santisopasri V, Murakami A, et al. In vitro anti-tumor promoting and anti-parasitic activities of the quassinoids from Eurycoma longifolia, a medicinal plant in Southeast Asia. Journal of Ethnopharmacology. 2002;82:55-58.
  37. Chan KL, Lee SP, Yuen KH. Antipyretic activity of quassinoids from Eurycoma longifolia Jack. In Ghazally, I, Murtedza M, Laily D, eds. Chemical prospecting in Malayan Forest. Selangor: Pelanduk Publications; 1995:219-224.
  38. Tada H, Yasuda F, Otani K, Doteuchi M, Ishara Y, Shiro M. New antiulcer quassinoids from Eurycoma longifolia. European Journal of Medical Chemistry. 1991;26:345-349.