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Brucea javanica (L.) Merr.

Synonyms

Ailanthus gracilis Salisb., Brucea amarissima Desv. ex Gomes, Brucea glabrata Decne., Brucea sumatrana Roxb., Brucea sumatrensis Spreng., Gonus amarissimus Lour., Rhus javanica L. [35]

Vernacular Names

Malaysia Melada Pahit, Cerek jantan, Dadih-dadih, Embalau, Hempedu Beruang, Lada burau, Lada pahit, Pedu beruang, Serajat, Sisik Manik
English Java brucea
China Ya-Danzi, A tam tsao
Indonesia Biji Makassar, Bulah Makassar, Berul kendung peucang, Ki padesa, Kualot, Malur, Sikalur, Tambir bu, Tambur sipago
Thailand Nha Dam Tur, Raat Cha Dat, Raat Dat, Ratchadat
Philippines

Balaniog, Bago-bago, Magkapayos, Manongao-bobi, Selte

Vietnam Sau dau rung [2] [3] [5] [7]

General Information

Description

Brucea javanica is a member of the Simaroubace family. It is a shrub or a small tree that could reach up to 3 m high with the younger plant parts being softly pubescent. The leaves are compound-paripinnate with leaflets numbering between 5-11. The leaflets are oval-lanceolate; apex acuminate and base broadly cuneate and often somewhat oblique; margins are serrated; both surfaces are densely pubescent, especially the underside. The leaflets measures 5-10 cm long and 2-4 cm wide. The flowers are minute, purple in colour and are in numerous small cymes or clusters collected into axillary panicles. It has 4 sepals,  connated at the base. The four petals are villous and glandular at the tips. The male flowers have 4 stamens, with pistil reduced to a stigma. The female flowers have 4 much reduced stamens and ovary with 4 free carpels. The fruits and drupe are ovoid, black when ripe. The seeds are compressed, rugose, blackish brown with 3-5 in numbers [4].

Plant Part Used

Fruits, seeds

Chemical Constituents

(20R)-3-hydroxypregn-5-en-20-yl; 3-O-(beta-D-glucopyranosyl)bruceantin; 4-ethoxycarbonyl-2-quinolone; 9+/-)-8-hydrohexadecanoic acid; 11-OH canthin-6-one; 11-OH,1-Ome canthin-6-one; a-cedrene; apiole, azelaic acid; b-sitosterol; brocicanthinoside C; bruceacanthinoside; bruceantinoside A; bruceajavanin A, B, C; bruceanols D, E, F, G & H; bruceantin; bruceantinol; bruceantinoside A; brucein A – G and Q; brucein E 2-O-b-D- glucoside; bruceine A, B, D, E, I; bruceolide, bruceoside A – C, brucicanthinoside; brusatol;  canthin-6-one; canthin-6-one-3-N-oxide; carvone; chrysophanin; chrysophanol; ehydrobruceantinol, dehydobruceins A and B, dehydrobrusatol, dihydrobruceantin; dihydrobruceajavanin A; dihydrovrucein A, dihydrobruceajavanin A; dillapiole; emodin, ethyl gallate; flazin; glycerol 1,3-bisoleate; javanicolide C – F; javanicosides B – F; luteolin; luteolin-7-O-beta-D-glucoside; quercetin, quercetin-3-O-beta-D-galactoside; thymol; vanillic acid; vanillin; yadanzigan; yadanziolide A – D, S and yadanziosides A – P [1] [2] [8] [9] [10] [11] [12] [13] [14] [15].

Traditional Uses

B. javanica is generally used in the treatment of a variety of problems especially diarrhoea and dysentery [2] [7]. The various parts of B. javanica have been advocated to use as a remedy for malaria in countries ranging from India to China and down south to the Indonesia Archipelago. Commonly, the fruits or seeds are used. [2] [16]. However, in Malaysia other parts which are leaves or roots have been used when the fruits are not available [7]

A poultice made from the crushed leaves is used in the treatment of ringworm, whipworm, roundworm, tapeworm, piles, boils, enlarged spleen, scurf, and centipede bites [4][5].

The fresh fruit is given to people suffering from stomachache. Chinese and Indonesians used the fruits as antimalarial [6].

The seeds are generally used to treat gastrointestinal motility problems and are considered a stomachic tonic. The crushed seeds are taken as remedy for piles, diarrhoea, and amoebic dysentery. A decoction of the seeds is used to kill head lice and other skin and scalp parasites as well as to treat tumour. It is drank as antiparasites and to stop bleeding in gastrointestinal tract [5]. The seed and seed oil of B. javanica are applied over warts and corns to treat this viral condition [4].

A decoction of the roots is used to treat high fever, abdominal pain, after childbirth and food or other poisonings [5]

Preclinical Data

Pharmacology

Antimalarial activity

A number of screening studies of medicinal plants against malaria has shown that B. javanica contain antimalarial activity [17] [18]. A study on the activity of quassinoids isolated from B. javanica showed antimalarial activity against chloroquine resistant Plasmodium falciparum strain [19]. Bruceajavanin A, dihydrobruceajavanin A and bruceacanthinoside was found to inhibit growth of cultured P. falciparum of a chloroquine-resistant strain [11].

Hypoglycaemic Activity

Bruceines E and D extracted by bioactivity-guided fractionation had been found to significantly reduce blood glucose concentration in normoglycaemic mice and streptozotocin (STZ)-induced diabetic rats. The investigators had suggested that these two compounds might act as insulin secretagogue [20]

Anticancer activity

Few compounds had been isolated from B. javanica with anti tumour properties. Compound bruceantin is active against B16 melanoma, colon 38 and leukaemia cell lines L1210 and P388. It favoured apoptosis and exerted no toxic side effects. A study showed that bruceantin and bruceune A were found to be potentiated by (-)-hydnocarpin against the MCF-7 (human breast cancer cell line). While (20R)-O-(3)-β-D-glucopyranosyl-(1→2)-α-L-arabinopyranosyl-pregn-5-en-3β,20-diol, brusatol, bruceine B showed activity against HL-60 (human promyelocytic leukemia cells), SMMC-7721 (human hepatoma cells), A-549 (human lung adenocarcinoma epithelial cell) and MCF-7 tumours.  The brutasol activity against HL-60 cell lines was appeared to occur via activation of NK-kappaB and activation and translocation of NF-kappaB into the nucleus. In addition, a number of other quassinoids have shown potent antitumour activity including Bruceoside C against KB, A-549, RPMI, and TE-671 tumour cells while bruceanols was found to be cytotoxic against many human tumour cell lines. [2] [8] [21] [22].

Compound brucein D showed inhibitory growth activity in three pancreatic cancer cell lines (PANC-1, SW1990, CAPAN-1) but only exerted moderated cytotoxicity on non-tumourigenic Hs68 cells. The mechanism of action appears to be DNA fragmentation. Brucein D augmented caspase 3, 8, 9 and bak protein levels and attenuated bcl-2 expression. The p38-MAPK signaling pathway was involved in the apoptotic process as evidenced in the increase in phosphorylation of p38-MAPK upon exposure to the compound [26]. Another study found that bruceoside D, E and F showed selective cytotoxicity in the leukaemic and non-small lung cell, colon, CNS, melanoma and ovarian cancer cell lines with log GI50 values in the range of -4.14 to -5.72. [27]

Antimicrobial activity

Antiamoebic activity

It appeared that the quassinoid fraction of the fruit extract of B. javanica showed antiamoebic activity. The most active quassinoid was bruceantin. These compounds were also active against Plasmodium falciparum [28].

Antitrypanosomal activity

The C-20 quassinoids isolated from the fruit of B. javanica showed antitrypanosomal activities against trypanomastigotes of Trypanosoma evansi. These compounds include bruceine A, bruceantinol, bruceine C, brusatol and Bruceine B. A structural-activity relationship study done showed that the following are essential in the antitrypanosomal activity of the C20-quassinoids: (1) free hydroxyl groups at position C-3, C-11, and C-12; (2) the C-11 and C-12 hydroxyl groups are more important that the enolic hydroxyl group at C-3, and; (3) the free hydroxyl group at C-4’ of bruceine C does not have any significant effect on the activity [29] [30] [31].

Anthelmintic Activity

The dichloromethane and methanol extract of the fruits of B. javanica was found to be a potent anthelmintic against Blastocystis hominis capable of killing between 82% and 75% and inhibiting between 94%-100% of B. hominis suspension. The anthelmintic activity is attributed to the presence of bruceine A & D [32] [33] [34].

Toxicities

The methanol extract of B. amarissima  was found to exhibit a lethal toxicity to mice when screening for hypothermic effect . The toxic components isolated were identified as bruceoside A and B and yadanzioside F. [10]

Clinical Data

Clinical Trials

A clinical study showed that patient with brain metastasis secondary to lung cancer receiving a 10% B. javanica emulsion, had better quality of life and prolonged median survival rate than those not receiving the treatment [23]. This effect could be due to the ability to the emulsion to reduce intracranial pressure as evidenced in the study on rabbits [24]. There is also evidence that the emulsion could inhibit cancerous growth, arresting in G1 phase of the cell cycle [25].

Adverse Effects in Human:

No documentation

Used in Certain Conditions

Pregnancy / Breastfeeding

No documentation

Age Limitations

Neonates / Adolescents

No documentation

Geriatrics

No documentation

Chronic Disease Conditions

No documentation

Interactions

Interactions with drugs

No documentation

Interactions with Other Herbs / Herbal Constituents

No documentation

Contraindications

Contraindications

No documentation

Case Reports

No documentation

References

  1. Zhou JJ, Xie GR, Yan XJ. Encyclopedia and Traditional Chinese Medicines – Molecular Structures, Pharmacological Activities, Natural Sources and Applications. Vol .1 Springer – Verlag Berlin; 2011. p. 309.
  2. Daniel M. Medicinal Plants: Chemistry and Properties. Science Publishers New Hampshire; 2006. p. 114.
  3. Merrill: Loureiro’s “Flora Cochinchinensis” in Transactions, American Philosophical Society. (vol. 24, part 2, 1935-June) American Philosophical Soceity, Philadelphia; 1936. p. 226.
  4. World Health Organisation WHO Monograph on Selected Medicinal Plants. Volume 1. World Health Organization Geneva; 1999. p. 59–65.
  5. Ong HC. Tumbuhan Liar: Khasiat ubatan & Kegunaan Lain. Utusan Publications and Distritbutors Sdn. Bhd. Kuala Lumpur; 2008. p. 112.
  6. Philippine Medicinal Plants – Balaniog, Brucea amarissima [Cited 25th March 2012]: Available from: http://www.stuartxchange.org/Balaniog.html
  7. Ismail N, Ismail Z, Abdul Manaf M. Malaysian Medicinal Plants Index. Kuala Lumpur: Victus Semulajadi; 1999. p. 10.
  8. Yan XH, Chen J, Di YT, Fang X, Dong JH, Sang P, Wang YH, He HP, Zhang ZK, Hao XJ. Anti-tobacco mosaic virus (TMV) Quassinoids from Brucea javanica (L.) Merr. Journal of Agricultural and Food Chemistry. 2010 Feb 10;58(3):1572-7.
  9. Yu YN, Li X. Studies on the chemical constituents of Brucea javanica (L.) Merr. Yao Xue Xue Bao. 1990;25(5):382-6.
  10. Okuyama E, Gao LH, Yamazaki M. Studies on pharmacologically active principles from Indonesian crude drugs. III. Toxic components from Brucea javanica (L.) Merr]. Yakugaku Zasshi. 1990 Nov;110(11):834-8.
  11. Kitagawa I, Mahmud T, Simanjuntak P, Hori K, Uji T, Shibuya H. Indonesian medicinal plants. VIII. Chemical structures of three new triterpenoids, bruceajavanin A, dihydrobruceajavanin A, and bruceajavanin B, and  a new alkaloidal glycoside, bruceacanthinoside, from the stems of Brucea javanica (Simaroubaceae). Chemical & Pharmaceutical Bulletin (Tokyo). 1994 Jul;42(7):1416-21.
  12. Xie H, Deng H, Huang S, Wu Z, Zhang M. Studies on the chemical components of Brucea javanica. Zhong Yao Cai. 1998 Aug; 21(8):398-400.
  13. Su BN, Chang LC, Park EJ, Cuendet M, Santarsiero BD, Mesecar AD, Mehta RG, Fong HH, Pezzuto JM, Kinghorn AD. Bioactive constituents of the seeds of Brucea javanica. Planta Medica. 2002 Aug;68(8):730-3.
  14. Kim IH, Takashima S, Hitotsuyanagi Y, Hasuda T, Takeya K. New quassinoids, javanicolides C and D and javanicosides B--F, from seeds of Brucea javanica. J Nat Prod. 2004 May;67(5):863-8.
  15. Liu JH, Qin JJ, Jin HZ, Hu XJ, Chen M, Shen YH, Yan SK, Zhang WD. A new triterpenoid from Brucea javanica. Archives of Pharmacal Research. 2009 May;32(5):661-6.
  16. Md-Salleh K., Latif A. Tumbuhan Ubatan Malaysia. Pusat Pengurusan Penyelidikan Universiti Kebangsaan Malaysia Bangi; 2002. p. 485.
  17. Murnigsih T, Subeki, Matsuura H, Takahashi K, Yamasaki M, Yamato O, Maede Y, Katakura K, Suzuki M, Kobayashi S, Chairul, Yoshihara T. Evaluation of the inhibitory activities of the extracts of Indonesian traditional medicinal plants against Plasmodium falciparum and Babesia gibsoni. Journal of Veterinary Medical Science. 2005 Aug;67(8):829-31.
  18. Hout S, Chea A, Bun SS, Elias R, Gasquet M, Timon-David P, Balansard G, Azas N. Screening of selected indigenous plants of Cambodia for antiplasmodial activity. Journal of Ethnopharmacology.. 2006 Aug 11;107(1):12-8. Epub 2006 Mar 20.
  19. O'Neill MJ, Bray DH, Boardman P, Chan KL, Phillipson JD, Warhurst DC, Peters W. Plants as sources of antimalarial drugs, Part 4: Activity of Brucea javanica fruits against chloroquine-resistant Plasmodium falciparum in vitro and against Plasmodium berghei in vivo. Journal of Natural Products. 1987 Jan-Feb;50(1):41-8.
  20. NoorShahida A, Wong TW, Choo CY. Hypoglycemic effect of quassinoids from Brucea javanica (L.) Merr (Simaroubaceae) seeds. Journal of Ethnopharmacology. 2009 Jul 30;124(3):586-91.
  21. Sakaki T, Yoshimura S, Tsuyuki T, Takahashi T, Honda T. Yadanzioside P, a new antileukemic quassinoid glycoside from Brucea javanica (L.) Merr with the 3-O-(beta-D-glucopyranosyl)bruceantin structure. Chemical & Pharmaceutical Bulletin (Tokyo). 1986 Oct;34(10):4447-50.
  22. Lee KH, Hayashi N, Okano M, Nozaki H, Ju-Ichi M. Antitumor agents, 65. Brusatol and cleomiscosin-A, antileukemic principles from Brucea javanica. Journal of Natural Products. 1984 May-Jun;47(3):550-1.
  23. Wang ZQ. Combined therapy of brain metastasis in lung cancer] Zhongguo Zhong Xi Yi Jie He Za Zhi. 1992 Oct;12(10):609-10, 581.
  24. Lu JB, Shu SY, Cai JQ. Experimental study on effect of Brucea javanica oil emulsion on rabbit intracranial pressure. Zhongguo Zhong Xi Yi Jie He Za Zhi. 1994 Oct;14(10):610-1.
  25. Xuan YB, Yasuda S, Shimada K, Nagai S, Ishihama H. Growth inhibition of the emulsion from to Brucea javanica cultured human carcinoma cells. Gan To Kagaku Ryoho. 1994 Oct;21(14):2421-5.
  26. Lau ST, Lin ZX, Liao Y, Zhao M, Cheng CH, Leung PS. Bruceine D induces apoptosis in pancreatic adenocarcinoma cell line PANC-1 through the activation of p38-mitogen activated protein kinase. Cancer Letters. 2009 Aug 18;281(1):42-52.
  27. Ohnishi S, Fukamiya N, Okano M, Tagahara K, Lee KH. Bruceosides D, E, and F, three new cytotoxic quassinoid glucosides from Brucea javanica. Journal of Natural Products. 1995 Jul;58(7):1032-8.
  28. Wright CW, O'Neill MJ, Phillipson JD, Warhurst DC. Use of microdilution to assess in vitro antiamoebic activities of Brucea javanica fruits, Simarouba amara stem, and a number of quassinoids. Antimicrobial Agents and Chemotherapy. 1988 Nov;32(11):1725-9.
  29. Bawm S, Matsuura H, Elkhateeb A, Nabeta K, Subeki, Nonaka N, Oku Y, Katakura K. In vitro antitrypanosomal activities of quassinoid compounds from the fruits of a medicinal plant, Brucea javanica. Veterinary Parasitology. 2008 Dec 20;158(4):288-94.
  30. Bawm S, Tiwananthagorn S, Lin KS, Hirota J, Irie T, Htun LL, Maw NN, Myaing TT, Phay N, Miyazaki S, Sakurai T, Oku Y, Matsuura H, Katakura K. Evaluation of Myanmar medicinal plant extracts for antitrypanosomal and cytotoxic activities. Journal of Veterinary Medical Science. 2010 Apr;72(4):525-8.
  31. Elkhateeb A, Tosa Y, Matsuura H, Nabeta K, Katakura K. Antitrypanosomal activities of acetylated bruceines A and C; a structure-activity relationship study. Journal of Natural Medicines. 2012 Jan;66(1):233-40.
  32. Yang LQ, Singh M, Yap EH, Ng GC, Xu HX, Sim KY. In vitro response of Blastocystis hominis against traditional Chinese medicine. Journal of Ethnopharmacology. 1996 Dec;55(1):35-42.
  33. Sawangjaroen N, Sawangjaroen K. The effects of extracts from anti-diarrheic Thai medicinal plants on the in vitro growth of the intestinal protozoa parasite: Blastocystis hominis. Journal of Ethnopharmacology. 2005 Apr 8;98(1-2):67-72.
  34. Wang Y, Wu ZF, Wang GX, Wang F, Liu YT, Li FY, Han J. In vivo anthelmintic activity of bruceine A and bruceine D from Brucea javanica against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus). Veterinary Parasitology. 2011 Apr 19;177(1-2):127-33.
  35. The Plant List. Accessed on 22nd July 2014. Available from http://www.theplantlist.org/tpl1.1/record/kew-2683970

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