| Brucea javanica (L.) Merr., a evergreen shrub, is widely distributed in Southeast Asia and northern Australia. In southeast Asia, all parts of B.javanica has been employed as an antimalarial treatment, and the seeds of this plant have also been used for the alleviation of dysentery and skin conditions such as warts and corns and are known as a rich source of quassinoids with the bitter-tasting principles of many species in the family Simaroubaceae. Quassinoids have been documented from B. javanica with a wide spectrum of biological effects, such as having potential antibabesial,anti-HIV, antimalarial, antitubercular, antitumor, cancer chemopreventive,cytotoxic and antiamoebic activities.In order to find new active agents from this plant, the chemical study on the extract of Brucea javanica (L.) Merr. was carried out. By various isolation methods (silica gel column chromatography, ODS gel column chromatography and so on), sixty compounds were isolated. By means of spectroscopic analysis and physiochemical properties, the structures of fifty nine compounds were elucidated as follows: Bruceanic acid E (1), Javanic acid A (2), Bruceanic acid E methyl ester (3), Bruceanic acid F (4), Javanic acid B (5), Javanicolide H (6), Quassin A (7), Bruceine L (8), Bruceoside A (9), Bruceoside B (10),Yadanzioside C (11), Yadanzioside B (12), Bruceine E (13), Bruceine H (14),Yadanziolide C (15), Bruceantinoside A (16), Yadanzioside F (17), Bruceene(18), Bruceine D (19), Yadanziolide S (20), Bruceine B (21), Dehydrobrusatol(22), Yadanzioside A (23), Yadanzioside G (24), Bruceolide (25), Brusatol (26),Javanicolide E (27), Bruceanic acid C (28), Bruceolignan L (29), Bruceolignan G (30), Isolariciresinol (31),3-Hydroxy-1-(4-hydroxy-3-methoxyphenyl)propan-1-one (32), Vladinol D (33),(±)Lariciresinol (34), Hierochin B (35), 7-Methoxy-lariciresinol (36), Ficusal (37),3-Hydroxy-1 -(4-hydroxyphenyl)propan-1 -one (38),2-Hydroxy-1 -(4-hydroxyphenyl)propan-1 -one (39), Salicifoliol (40),3-Hydroxy-1-(4-hydroxy-3,5-dimethoxyphenyl)propan-1-one (41),1-(4-Hydroxy-3-methoxyphenyl)-2-(4-formyl-2-methoxyphenoxy)propane-1,3-diol (42), Evofolin B (43), Brucojavan acid (44), Dihydrophaseic acid (45),Blumenol B (46), Vomifoliol (47), Dehydrovomifoliol (48), Ficusic acid (49),Phaseic acid (50), Bruceajavanamic acid A (51), Bruceajavanamic acid B (52),Bruceajavanamic acid C (53), Bruceajavanamic acid D (54),3,4,5-trihydroxybenzoic acid (55), Vanillic acid (56), 4-Hydroxybenzaldehyde(57), 6-Methoxy-4-chromanone (58), and Isofraxidin (59). Among them,compounds 1, 2, 3, 4, 5, 6, 7, 29, 30, 44, 51, 52, 53, and 54 were new compounds and compound 8 was a novel natural product.With an established colorimetric MTT assay protocol, the cytotoxicity in vitro against five human cancer cell lines (HCT-8, HepG2, BGC-823, A549, SKV03),with paclitaxel as the positive control, indicated that compounds 8,14, 19, 21,and 42 exhibited cytotoxicity against all of the human cancer cell lines in which they were evaluated, whereas compounds 6, 13, 22, 27, and 53 showed selective cytotoxicity. In those cytotoxicity compounds, IC50 values of compound 8 against five human cancer cell lines were less than 0.1?M and compound 53 showed the highest selective cytotoxic activity just against human cancer cell line SKV03.All compounds isolated were subjected to an examination of their propensity to inhibit NO production in rat polymorphonuclear leukocytes (PMNS) induced by LPS. Compounds 13 and 21 displayed significant inhibitory effects on NO production, and their IC50 values were 5.0 and 1.9?M, respectively, and were compared to dexamethasone (IC50 0.0023?M). In in vitro bioasssys,compounds 31 and 44 exhibited some inhibitory activities on MDA production in the antioxidant activities; compounds 14, 21, and 26 showed inhibitory activities for PC12 cell viability in neurotoxicity; compounds 7, 14, 19, 21, 27,and 52 exhibited either same with or better than the positive control activities for fat overload rate in lipid-lowering activities. |
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