Structural elucidation of limonoids and steroids from Trichilia connaroides

Phytochemistry

Volumn 69, Issue 6, 2008, Pages 1319-1327

  Wang, Xiao Ning ^a   Fan, Cheng Qi ^a   Yin, Sheng ^a   Gan, Li She ^a   Yue, Jian Min ^a  

^a SHANGHAI INSTITUTE OF MATERIA MEDICA   (China)

Author keywords

Limonoids; Meliaceae; Pregnane; Trichiconnarins; Trichilia connaroides; Trijugins

Indexed keywords

LIMONOID; STEROID;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; MELIACEAE;

LIMONINS; MELIACEAE; MOLECULAR STRUCTURE; STEROIDS;

MELIACEAE; TRICHILIA;

EID: 41149167026     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.phytochem.2008.01.018     Document Type: Article

References (26)

1. Abdelgaleil S.A.M., Okamura H., Iwagawa T., Sato A., Miyahara I., Doe M., and Nakatani M. Khayanolides, rearranged phragmalin limonoid antifeedants from Khaya senegalensis. Tetrahedron 57 (2001) 119-126
2. Abdelgaleil S.A.M., Doe M., Morimoto Y., and Nakatani M. Rings B,D-seco limonoids from the leaves of Swietenia mahogany. Phytochemistry 67 (2006) 452-458
3. Champagne D.E., Koul O., Isman M.B., Scudder G.G.E., and Towers G.H.N. Biological activity of limonoids from the Rutales. Phytochemistry 31 (1992) 377-394
4. Chen S.K., Chen B.Y., and Li H. Flora of China (Zhongguo Zhiwu Zhi) vol. 433 (1997), VCH, Beijing p. 66
5. Chen Y.Y., Wang X.N., Fan C.Q., Yin S., and Yue J.M. Swiemahogins A and B, two novel limonoids from Swietenia mahogany. Tetrahedron Lett. 48 (2007) 7480-7484
6. Cui J., Deng Z., Li J., Fu H., Proksch P., and Lin W. Phragmalin-type limonoids from the mangrove plant Xylocarpus granatum. Phytochemistry 66 (2005) 2334-2339
7. D'Ambrosio M., and Guerriero A. Degraded limonoids from Melia azedarach and biogenetic implications. Phytochemistry 60 (2002) 419-424
8. Drews S.E., Grieco P.A., and Huffman J.C. A short synthesis of dl-epi-pyroangolensolide and dl-pyroanglensolide: confirmation of the structures of pyroanglensolide and calodendrolide. J. Org. Chem. 50 (1985) 1309-1311
9. Garcez F.R., Garcez W.S., Tsutsumi M.T., and Roque N.F. Limonoids from Trichilia elegans ssp. elegans. Phytochemistry 45 (1997) 141-148
10. Garcez F.R., Garcez W.S., Roque N.F., Castellano E.E., and Zukerman-Schpector J. 7β-Oxygenated limonoids from Trichilia elegans ssp. elegans. Phytochemistry 55 (2000) 733-740
11. Hay A.-E., Ioset J.-R., Ahua K.M., Diallo D., Brun R., and Hostettmann K. Limonoid orthoacetates and antiprotozoal compounds from the roots of Pseudocedrela kotschyi. J. Nat. Prod. 70 (2007) 9-13
12. Inada A., Konishi M., Murata H., and Nakanishi T. Structures of a new limonoid and a new triterpenoid derivative from pericarps of Trichilia connaroides. J. Nat. Prod. 57 (1994) 1446-1449
13. Mulholland D.A., Parel B., and Coombes P.H. The chemistry of Meliaceae and Ptaeroxylaceae of southern and eastern Africa and Madagascar. Curr. Org. Chem. 4 (2000) 1011-1054
14. Nakatani M., Huang R.C., Okamura H., Iwagawa T., and Tadera K. Degraded limonoids from Melia azedarach. Phytochemistry 49 (1998) 1773-1776
15. Purushothaman K.K., Sarada A., and Venkatanarasimhan M. Structure of heynic acid: a new triterpene acid from Heynea trijuga Roxb. Indian J. Chem. 22B (1983) 820-821
16. Purushothaman K.K., Venkatanarasimhan M., Sarada A., Connolly J.D., and Rycroft D.S. Trijugins A and B, tetranortriterpenoids with a novel rearranged carbon skeleton from Heynea trijuga (Meliaceae). Can. J. Chem. 65 (1987) 35-37
17. Roy A., and Saraf S. Limonoids: overview of significant bioactive triterpenes distributed in plants kingdom. Biol. Pharm. Bull. 29 (2006) 191-201
18. Saad M.M.G., Iwagawa T., Doe M., and Nakatani M. Swietenialides, novel ring D opened phragmalin limonoid orthoesters from Swietenia mahogani JACQ. Tetrahedron 59 (2003) 8027-8033
19. Taylor D.A.H. The chemistry of the limonoids from Meliaceae. In: Herz W., Grisebach H., and Kirby G.W. (Eds). Progress in the Chemistry of Organic Natural Products vol. 45 (1984), Springer-Verlag, New York 1-102
20. Venkatanarasimhan M., and Kundu A.B. Isolation and characterization of trijugin-B acetate from Heynea trijuga Roxb. Indian J. Chem. 29B (1990) 970
21. Wang X.N., Yin S., Fan C.Q., Wang F.D., Lin L.P., Ding J., and Yue J.M. Turrapubesins A and B, first examples of halogenated and maleimide-bearing limonoids in nature from Turraea pubescens. Org. Lett. 8 (2006) 3845-3848
22. Wang X.N., Yin S., Fan C.Q., Lin L.P., Ding J., and Yue J.M. Eight new limonoids from Turraea pubescens. Tetrahedron 63 (2007) 8234-8241
23. Yin S., Fan C.Q., Wang X.N., Lin L.P., Ding J., and Yue J.M. Xylogranatins A-D: novel tetranortriterpenoids with an unusual 9,10-seco scaffold from marine mangrove Xylocarpus granatum. Org. Lett. 8 (2006) 4935-4938
24. Yin S., Wang X.N., Fan C.Q., Liao S.G., and Yue J.M. The first limonoid peroxide in the Meliaceae family: walsuronoid A from Walsura robusta. Org. Lett. 9 (2007) 2353-2356
25. Zhang H.P., Wu S.H., Shen Y.M., Ma Y.B., Wu D.G., Qi S.H., and Luo X.D. A pentanortriterpenoid with a novel carbon skeleton and a new pregnane from Trichilia connaroides. Can. J. Chem. 81 (2003) 253-257
26. Zhang C.R., Yang S.P., Liao S.G., Fan C.Q., Wu Y., and Yue J.M. Chuktabularins A-D, four new limonoids with unprecedented carbon skeletons from the stem bark of Chukrasia tabularis. Org. Lett. 9 (2007) 3383-3386