Chemical constituents from fruits of Harrisonia perforata

Phytochemistry

Volumn 72, Issue 6, 2011, Pages 508-513

  Yan, Xiao Hui ^a,b   Di, Ying Tong ^a   Fang, Xin ^a   Yang, Shi Ying ^c   He, Hong Ping ^a   Li, Shun Lin ^a   Lu, Yang ^c   Hao, Xiao Jiang ^a  

^a KUNMING INSTITUTE OF BOTANY   (China)

^b UNIVERSITY OF CHINESE ACADEMY OF SCIENCES   (China)

^c INSTITUTE OF GEOLOGY AND GEOPHYSICS   (China)

Author keywords

Epimer; Harrisonia perforata; Limonoids; Simaroubeaceae; Single crystal X ray diffraction

Indexed keywords

ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; LIMONOID;

ARTICLE; CELL PROLIFERATION; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DOSE RESPONSE; DRUG EFFECT; DRUG SCREENING; FRUIT; HUMAN; ISOLATION AND PURIFICATION; MEDICINAL PLANT; SIMAROUBACEAE; STEREOISOMERISM; TOBACCO MOSAIC VIRUS; TUMOR CELL LINE; X RAY CRYSTALLOGRAPHY;

ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CELL LINE, TUMOR; CELL PROLIFERATION; CRYSTALLOGRAPHY, X-RAY; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG SCREENING ASSAYS, ANTITUMOR; FRUIT; HUMANS; LIMONINS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; PLANTS, MEDICINAL; SIMAROUBACEAE; STEREOISOMERISM; TOBACCO MOSAIC VIRUS;

HARRISONIA PERFORATA; TOBACCO MOSAIC VIRUS;

EID: 79952901042     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2011.01.010     Document Type: Article

References (36)

1. M.C. Alley, D.A. Scudiero, A. Monks, M.L. Hursey, M.J. Czerwinski, D.L. Fine, B.J. Abbott, J.G. Mayo, R.H. Shoemaker, and M.R. Boyd Feasibility of drug screening with panels of human tumor cell lines using a microculture tetrazolium assay Cancer Res. 48 1988 589 601 (Pubitemid 18056527)
2. D.E. Champagne, O. Koul, M.B. Isman, G.G.E. Scudder, and G.H.N. Towers Biological activity of limonoids from the Rutales Phytochemistry 31 1992 377 394
3. S.K. Chen, B.Y. Chen, and H. Li Flora of China (Zhongguo ZhiwuZhi) vol. 433 1997 VCH Beijing p. 16
4. J. Chen, X.H. Yan, J.H. Dong, P. Sang, X. Fang, Y.T. Di, Z.K. Zhang, and X.J. Hao Tobacco mosaic virus (TMV) inhibitors from Picrasma quassioides Benn J. Agric. Food Chem. 57 2009 6590 6595
5. F.M. Dean, and M.L. Robinson Heartwood chromones of C. Grevei Phytochemistry 10 1971 3221 3227
6. Y.T. Di, H.P. He, H.Y. Liu, P. Yi, Z. Zhang, Y.L. Ren, J.S. Wang, Q.Y. Sun, F.M. Yang, X. Fang, S.L. Li, H.J. Zhu, and X.J. Hao Trijugin-type limonoids from the leaves of Cipadessa cinerascens J. Nat. Prod. 70 2007 1352 1355 (Pubitemid 47401580)
7. X. Fang, Y.T. Di, H.P. He, H.Y. Liu, Z. Zhang, Y.L. Ren, Z.L. Gao, S. Gao, and X.J. Hao Cipadonoid A, a novel limonoid with an unprecedented skeleton, from Cipadessa cinerasecns Org. Lett. 10 2008 1905 1908
8. X. Fang, Y.T. Di, C.S. Li, Z.L. Geng, Z. Zhang, Y. Zhang, Y. Lu, Q.T. Zheng, S.Y. Yang, and X.J. Hao Tetranortriterpenoids from the leaves of Cipadessa cinerascens J. Nat. Prod. 72 2009 714 718
9. X. Fang, Q. Zhang, C.J. Tan, S.Z. Mu, Y. Lu, Y.B. Lu, Q.T. Zheng, Y.T. Di, and X.J. Hao Cipadonoids B-G, six new limonoids from Cipadessa cinerascens Tetrahedron 65 2009 7408 7414
10. H.D. Flack, and G. Bernardinelli Reporting and evaluating absolute-structure and absolute-configuration determinations J. Appl. Cryst. 33 2000 1143 1148 (Pubitemid 32182502)
11. K. Kamiuchi, K. Mitsunaga, K. Koike, Y. Ouyang, T. Ohmoto, and T. Nikaido Quassinoids and limonoids from Harrisonia perforata Heterocycles 43 1996 653 664 (Pubitemid 126456345)
12. Q. Khuong-Huu, A. Chiarona, C. Riche, H. Nguyen-Ngoc, K. Nguten-Viet, and F. Khuong-Huu New rearranged limonoids from Harrisonia perforata J. Nat. Prod. 63 2000 1015 1018 (Pubitemid 30624497)
13. Q. Khuong-Huu, A. Chiaroni, C. Riche, H. Nguyen-Ngoc, K. Nguyen-Viet, and F. Khuong-Huu New rearranged limonoids from Harrisonia perforata III J. Nat. Prod. 64 2001 634 637 (Pubitemid 32488684)
14. A. Mondon, and B. Epe Bitter principles of the Cneoraceae Prog. Chem. Nat. Prod. 44 1983 101 187
15. D.A. Mulholland, and H. Mahomed Isolation of Cneorubin X, an unusual diterpenoid from Ptaeroxylon obliquum (Ptaeroxylaceae) Biochem. Syst. Ecol. 28 2000 713 716 (Pubitemid 30422294)
16. D.A. Mulholland, B. Parel, and P.H. Coombes The chemistry of Meliaceae and Ptaeroxylaceae of southern and eastern Africa and Madagascar Curr. Org. Chem. 4 2000 1011 1054
17. D.A. Mulholland, K. McFarland, M. Randrianarivelojosia, and H. Rabarison Cedkathryns A and B, pentanortriterpenoids from Cedrelopsis gracilis (Ptaeroxylaceae) Phytochemistry 65 2004 2929 2934 (Pubitemid 40292127)
18. M.-A. Ouyang, Y.-S. Wein, Z.-K. Zhang, and Y.-H. Kuo Inhibitory activity against tobacco mosaic virus (TMV) replication of pinoresinol and syringaresinol lignans and their glycosides from the root of Rhus javanica var. Roxburghiana J. Agric. Food Chem. 55 2007 6460 6465 (Pubitemid 47280017)
19. M.S. Rajab, F.R. Fronczek, D.A. Mulholland, and J.K. Rugutt 11β, 12β- Diacetoxyharrisonin, a tetranortriterpenoid from Harrisonia abyssinica Phytochemistry 52 1999 127 133
20. A. Roy, and S. Saraf Limonoids: overview of significant bioactive triterpenes distributed in plants kingdom Biol. Pharm. Bull. 29 2006 191 201 (Pubitemid 43200882)
21. J.K. Rugutt, K.J. Rugutt, and D.K. Berner Limonoids from Nigerian Harrisonia abyssinica and their stimulatory activity against Striga hermonthica seeds J. Nat. Prod. 64 2001 1434 1438 (Pubitemid 33116686)
22. P.A. Skehan, R. Storeng, A. Monks, J. McMahon, D. Vistica, J.T. Warren, H. Bokesch, S. Kenney, and M.R. Boyd New colorimetric cytotoxicity assay for anticancer-drug screening J. Nat. Can. Inst. 82 1990 1107 1112 (Pubitemid 20213250)
23. T. Sugimoto, T. Miyase, M. Kuroyanagi, and A. Ueno Limonoids and quinolone alkaloids from Evodia rutaecarpa Bentham Chem. Pharm. Bull. 36 1988 4453 4461
24. T.V. Sung, N.M. Phung, C. Kamperdick, and G. Adam Perforatinolone, a limonoid from Harrisonia perforata Phytochemistry 38 1995 213 215
25. T. Tanaka, K. Koike, K. Mitsunaga, K. Narita, S. Takano, A. Kamioka, E. Sase, Y. Ouyang, and T. Ohmoto Chromones from Harrisonia perforata Phytochemistry 40 1995 1787 1790 (Pubitemid 3009272)
26. D.A.H. Taylor The chemistry of the limonoids from Meliaceae W. Herz, H. Grisebach, G.W. Kirby, Progress in the Chemistry of Organic Natural Products vol. 45 1984 Springer-Verlag New York 1 102
27. P. Tuntiwachwuttikul, P. Phansa, Y. Pootaengon, and W.C. Taylor Chromones from the branches of Harrisonia perforata Chem. Pharm. Bull. 54 2006 44 47 (Pubitemid 43036747)
28. M.X. Wang, M.S. Zhang, and Y.L. Zhu Studies on the chemical constituents of a Chinese folk medicine Niu-Jin-Guo (Harrisonia perforata Blano Merr) Acta pharmaceutica Sinica. 18 1983 113 118
29. M.X. Wang, M.S. Zhang, W.Z. Liu, and Y.L. Zhu Isolation and structural determination of perforatic acid from Chinese folk medicine niu-jin-guo (Harrisonia perforata) Acta pharmaceutica Sinica. 19 1984 760 763
30. P.G. Waterman Phylogenetic implications of the distribution of secondary metabolites in the Rutales P.G. Waterman, M.F. Grundon, Chemistry and Chemical Taxonomy of the Rutales 1983 Academic Press London 377 400
31. P.G. Waterman The current status of chemical systematics Phytochemistry 68 2007 2896 2903 (Pubitemid 350182450)
32. X.C. Wei, Z.H. Pan, X.C. Gu, M.X. Wang, and Y.L. Zhu Chemical constituents of the Chinese medicine Niu-Jin-Guo (Harrisonia perforata Blanco Merr.). IV. Molecular and crystal structure on Niu-Jing V Jiegou Huaxue 4 1985 281 287
33. X.H. Yan, J. Chen, Y.T. Di, X. Fang, J.H. Dong, P. Sang, Y.H. Wang, H.P. He, Z.K. Zhang, and X.J. Hao Anti-tobacco mosaic virus (TMV) quassinoids from Brucea javanica (L.) Merr. J. Agric. Food Chem. 58 2010 1572 1577
34. S. Yin, X. Chen, Z.S. Su, S.P. Yang, C.Q. Fan, J. Ding, and J.M. Yue Harrisotones A-E, five novel prenylated polyketides with a rare spirocyclic skeleton from Harrisonia perforata Tetrahedron 65 2009 1147 1152
35. H.P. Zhang, J.J. Tan, D. VanDerveer, X. Wang, M.J. Wargovich, and F. Chen Khayanolides from African mahogany Khaya senegalensis (Meliaceae): a revision Phytochemistry 70 2009 294 299
36. L. Zhou, Y.C. Zhang, L.A. Gapiter, H. Ling, R. Agrwal, and K.-Y. NG Cytotoxic and anti-oxidant activities of lanostane-type triterpenes isolated from Poria cocos Chem. Pharm. Bull. 56 2008 1459 1462