Isolation, chemotaxonomic significance and cytotoxic effects of quassinoids from Brucea javanica

Fitoterapia

Volumn 105, Issue , 2015, Pages 66-72

  Ye, Qing Mei ^a,b   Bai, Liang Liang ^a   Hu, Shu Zhi ^a   Tian, Hai Yan ^a   Ruan, Li Jun ^a   Tan, Ya Fang ^a   Hu, Li Ping ^a   Ye, Wen Cai ^a   Zhang, Dong Mei ^a,c   Jiang, Ren Wang ^a,c  

^a JINAN UNIVERSITY   (China)

^b HAINAN GENERAL HOSPITAL   (China)

^c Shenzhen Institute for Drug Control   (China)

Author keywords

Breast cancer; Brucea javanica; Bruceene A; Chemotaxonomics; Quassinoids

Indexed keywords

ANTINEOPLASTIC AGENT; BRUCEA JAVANICA EXTRACT; BRUCEINE D; BRUSATOL; CARBONYL DERIVATIVE; CASPASE 9; DOXORUBICIN; QUASSINOID; QUASSINOID DERIVATIVE;

ABSORPTION; ANTINEOPLASTIC ACTIVITY; APOPTOSIS; ARTICLE; BRUCEA; BRUCEA JAVANICA; CANCER INHIBITION; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMOTAXONOMY; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DNA DETERMINATION; DOWN REGULATION; DRUG ISOLATION; DRUG STRUCTURE; ENZYME ACTIVATION; GLYCOSIDATION; HETERONUCLEAR MULTIPLE BOND CORRELATION; HETERONUCLEAR SINGLE QUANTUM COHERENCE; HUMAN; HUMAN CELL; IC50; MCF 7 CELL LINE; MITOCHONDRIAL MEMBRANE POTENTIAL; PHYLOGENY; PRIORITY JOURNAL; STEREOCHEMISTRY; X RAY DIFFRACTION; CHEMICAL STRUCTURE; CHEMISTRY; FRUIT; ISOLATION AND PURIFICATION;

AILANTHUS; BRUCEA; BRUCEA JAVANICA;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; APOPTOSIS; BRUCEA; FRUIT; HUMANS; INHIBITORY CONCENTRATION 50; MCF-7 CELLS; MOLECULAR STRUCTURE; QUASSINS;

EID: 84931273929     PISSN: 0367326X     EISSN: 18736971     Source Type: Journal    
DOI: 10.1016/j.fitote.2015.06.004     Document Type: Article

References (30)

1. S.C. Sharma, and V.K. Agarwal Brucea javanica (Linn.) Merr.: a potent anticancer and antimalarial plant Indian J. Pharm. Sci 55 1993 77 85
2. Editorial Committee of Pharmacopoeia Pharmacopoeia of China 2010 238
3. J.H. Liu, H.Z. Jin, W.D. Zhang, S.K. Yan, and Y.H. Shen Chemical constituents of plants from the genus Brucea Chem. Biodivers. 6 2009 57 70
4. G. Fiaschetti, M.A. Grotzer, T. Shalaby, D. Castelletti, and A. Arcaro Quassinoids: from traditional drugs to new cancer therapeutics Curr. Med. Chem. 18 2011 316 328
5. D. Liu, S. Li, K.S. Bi, and X.H. Chen Capillary GC simultaneous determination of 4 fatty acids in Brucea javanica oil latex injection China Pharm. 4 2012 364 366
6. Y.L. Nie, K.X. Liu, X.Y. Mao, Y.L. Li, J. Li, and M.M. Zhang Effect of injection of Brucea javanica oil emulsion plus chemoradiotherapy for lung cancer: a review of clinical evidence J. Evid. Based Med. 5 2012 216 225
7. X.H. Yan, J. Chen, Y.T. Di, X. Fang, J.H. Dong, and P. Sang Anti-tobacco mosaic virus (TMV) quassinoids from Brucea javanica (L.) Merr. J. Agric. Food Chem. 58 2010 1572 1577
8. Y. Wang, Z.F. Wu, G.X. Wang, F. Wang, Y.T. Liu, and F.Y. Li In vivo anthelmintic activity of bruceine A and bruceine D from Brucea javanica against Dactylogyrus intermedius (Monogenea) in goldfish (Carassius auratus) Vet. Parasitol. 177 2011 127 133
9. A. NoorShahida, T.W. Wong, and C.Y. Choo Hypoglycemic effect of quassinoids from Brucea javanica (L.) Merr (Simaroubaceae) seeds J. Ethnopharmacol. 124 2009 586 591
10. L. Pan, Y.W. Chin, H.B. Chai, T.N. Ninh, D.D. Soejarto, and A.D. Kinghorn Bioactivity-guided isolation of cytotoxic constituents of Brucea javanica collected in Vietnam Bioorg. Med. Chem. 17 2009 2219 2224
11. J.H. Liu, N. Zhao, G.J. Zhang, S.S. Yu, L.J. Wu, and J. Qu Bioactive quassinoids from the seeds of Brucea javanica J. Nat. Prod. 75 2012 683 688
12. J.A. Kim, E.K. Lau, L. Pan, and E.J. De Blanco NF-kappa B inhibitors from Brucea javanica exhibiting intracellular effects on reactive oxygen species Anticancer Res. 30 2010 3295 3300
13. M. Cuendet, J.J. Gills, and J.M. Pezzuto Brusatol-induced HL-60 cell differentiation involves NF-kappa B activation Cancer Lett. 206 2004 43 50
14. D. Ren, N.F. Villeneuve, T. Jiang, T. Wu, A. Lau, and H.A. Toppin Brusatol enhances the efficacy of chemotherapy by inhibiting the Nrf2-mediated defense mechanism Proc. Natl. Acad. Sci. U. S. A. 108 2011 1433 1438
15. J.M. Shi, L.L. Bai, D.M. Zhang, A. Yiu, Z.Q. Yin, and W.L. Han Saxifragifolin D induces the interplay between apoptosis and autophagy in breast cancer cells through ROS-dependent endoplasmic reticulum stress Biochem. Pharmacol. 85 2013 913 921
16. M.H. Kang, and C. PatrickReynolds Bcl-2 inhibitors: targeting mitochondrial apoptotic pathways in cancer therapy Clin. Cancer Res. 15 2009 1126 1132
17. D.M. Zhang, J.S. Liu, L.J. Deng, M.F. Chen, A. Yiu, and H.H. Cao Arenobufagin, a natural bufadienolide from toad venom, induces apoptosis and autophagy in human hepatocellular carcinoma cells through inhibition of PI3K/Akt/mTOR pathway Carcinogenesis 34 2013 1331 1342
18. J. Zhang, R. Xu, Y. Li, and Z. Chen Chemical constituents of Brucea javanica. III. Bruceene - isolation and structure of a new quassinoid from Brucea javanica Huaxue Xuebao 42 1984 684 687
19. X. Li, L. Wu, Y. Konda, M. Iguchi, H. Takahasi, and Y. Harigaya Bruceines D, E and H J. Heterocycl. Chem. 26 1989 493 501
20. T. Sakaki, S. Yoshimura, M. Ishibashi, T. Tsuyuki, T. Takahashi, and T. Honda Structures of new quassinoid glycosides, yadanziosides A, B, C, D, E, G, H, and new quassinoids, dehydrobrusatol and dehydrobruceantinol from Brucea javanica (L.) Merr Bull. Chem. Soc. Jpn. 58 1985 2680 2686
21. Y. Harigaya, Y. Konda, M. Iguchi, M. Onda, X. Li, and L. Wu Spectroscopic studies of brusatol J. Nat. Prod. 52 1989 740 748
22. K.H. Lee, Y. Imakura, Y. Sumida, R.Y. Wu, I.H. Hall, and H.C. Huang Antitumor agents. 33. Isolation and structural elucidation of bruceoside-A and -B, novel antileukemic quassinoid glycosides, and brucein-D and -E from Brucea javanica J. Org. Chem. 44 1979 2180 2185
23. T. Sakaki, S. Yoshimura, T. Tsuyuki, T. Takahashi, T. Honda, and T. Nakanishi Structures of yadanziosides K, M, N, and O, new quassinoid glycosides from Brucea javanica (L.) Merr Bull. Chem. Soc. Jpn. 59 1986 3541 3546
24. M. Okano, N. Fukamiya, T. Toyota, K. Tagahara, and K.H. Lee Antitumor agents, 104. Isolation of yadanziosides M and P from Brucea antidysenterica and identification of bruceantinoside B as a mixture of yadanzioside P and bruceantinoside C J. Nat. Prod. 52 1989 398 401
25. F.A. Darwish, F.J. Evans, and J.D. Phillipson Cytotoxic bruceolides from Brucea javanica J. Pharm. Pharmacol. 31 1979 10
26. S. Ohnishi, N. Fukamiya, M. Okano, K. Tagahara, and K.H. Lee Bruceosides D, E, and F, three new cytotoxic quassinoid glucosides from Brucea javanica J. Nat. Prod. 58 1995 1032 1038
27. S. Yoshimura, T. Sakaki, M. Ishibashi, T. Tsuyuki, T. Takahashi, and T. Honda Constituents of seeds of Brucea javanica. Structures of new bitter principles, yadanziolides A, B, C, yadanziosides F, I, J, and L Bull. Chem. Soc. Jpn. 58 1985 2673 2679
28. Y. Wang, W.J. Wang, C. Su, D.M. Zhang, L.P. Xu, and R.R. He Cytotoxic quassinoids from Ailanthus altissima Bioorg. Med. Chem. Lett. 23 2013 654 657
29. J.W. Clayton PhD thesis Evolutionary history of Simaroubaceae (Sapindales): systematics, biogeography and diversification 132 2008 University of Florida 137
30. D.M. Zhang, J.S. Liu, M.K. Tang, A. Yiu, H.H. Cao, and L. Jiang Bufotalin from Venenum bufonis inhibits growth of multidrug resistant HepG2 cells through G2/M cell cycle arrest and apoptosis Eur. J. Pharmacol. 692 2012 19 28