Cytotoxic triterpenoids and steroids from the bark of Melia azedarach

Planta Medica

Volumn 77, Issue 9, 2011, Pages 922-928

  Wu, Shi Biao ^a   Bao, Qiu Ying ^a   Wang, Wen Xuan ^a   Zhao, Yun ^a   Xia, Gang ^a   Zhao, Zheng ^a   Zeng, Huaqiang ^b   Hu, Jin Feng ^a  

^a EAST CHINA NORMAL UNIVERSITY   (China)

^b NATIONAL UNIVERSITY OF SINGAPORE   (Singapore)

Author keywords

cytotoxicity; Melia azedarach; Meliaceae; steroids; triterpenoids

Indexed keywords

2 ALPHA,3 ALPHA,20 TRIHYDROXY 5 ALPHA PREGNANE 16BETA METHACRYLATE; 21,24 CYCLOEUPHA 7 ENE 3 BETA,16 BETA,21 ALPHA,25 TETROL; 24 EPSILON HYDROPEROXY 24 VINYL CHOLESTEROL; 24 EPSILON HYDROPEROXY 24 VINYL LATHOSTEROL; 29 HYDROPEROXY STIGMASTA 7,24(28) DIEN 3 BETA OL; 3 BETA ACETOXY 12 BETA HYDROXY EUPHA 7,24 DIEN 21,16 BETA OLIDE; 7 ALPHA HYDROXYSITOSTEROL 3 BETA GLUCOSIDE; 7 BETA HYDROXYSITOSTEROL 3 BETA GLUCOSIDE; [11], 3 OXO OLEAN 12 EN 28 OIC ACID; [12], (24) 24 ETHYL 5 ALPHA CHOLESTANE 3 BETA,5,6 BETA TRIOL; [13], (22,24) 5 ALPHA,8 ALPHA EPIDIOXY 24 METHYLCHOLESTA 6,22 DIEN 3 BETA OL; [14, 15], BETA SITOSTEROL; [9, 10], MELIASTATIN 3; CABRALENOE; DAUCOSTERINE; KULINONE; STEROID; TRITERPENOID; UNCLASSIFIED DRUG;

ARTICLE; BARK; CANCER CELL CULTURE; CELL ASSAY; CELL VIABILITY; CONTROLLED STUDY; CYTOTOXICITY; DRUG ISOLATION; DRUG STRUCTURE; HUMAN; HUMAN CELL; HUMAN CELL CULTURE; IC 50; LUMINESCENCE; MELIA AZEDARACH; MOLECULAR MODEL; SPECTROSCOPY;

ANTINEOPLASTIC AGENTS, PHYTOGENIC; CELL LINE, TUMOR; CELL SURVIVAL; CRYSTALLOGRAPHY, X-RAY; HUMANS; INHIBITORY CONCENTRATION 50; MAGNETIC RESONANCE SPECTROSCOPY; MEDICINE, CHINESE TRADITIONAL; MELIA AZEDARACH; MOLECULAR STRUCTURE; PLANT BARK; PLANT EXTRACTS; STEROIDS; TRITERPENES;

MELIA AZEDARACH; MELIACEAE;

EID: 79958865895     PISSN: 00320943     EISSN: 14390221     Source Type: Journal    
DOI: 10.1055/s-0030-1250673     Document Type: Article

References (41)

1. China Pharmacopoeia Committee. Pharmacopoeia of the P. R. C. The first division of 2005 edition (English). Beijing: Chinese Chemical and Technologic Press; 2005: 45
2. Wu SB, Ji YP, Zhu JJ, Zhao Y, Xia G, Hu YH, Hu JF. Steroids from the leaves of Chinese Melia azedarach and their cytotoxic effects on human cancer cell lines. Steroids 2009; 74: 761-765
3. Li XW, Guo ZT, Zhao Y, Zhao Z, Hu JF. Chemical constituents from Saussurea cordifolia. Phytochemistry 2010; 71: 682-687
4. Guyot M, Davoust D, Belaud C. Hydroperoxy-24 vinyl-24 cholesterol, nouvel hydropéroxyde naturel isolé de deux tuniciers: Phallusia mamillata et Ciona intestinalis. Tetrahedron Lett 1982; 23: 1905-1906
5. 2 cell cycle arrest. Cancer Res 2004; 64: 4487-4497
6. Lövborg H, Wojciechowski J, Larsson R, Wȩsierska-Ga̧dek J. Action of a novel anticancer agent, CHS 828, on mouse fibroblasts: increased sensitivity of cells lacking poly (ADF-ribose) polymerase-1. Cancer Res 2002; 62: 4206-4211 (Pubitemid 34827273)
7. Nakatani M, Takao H, Miura I, Hase T. Azedarachol, a steroid ester antifeedant from Melia azedarach var. japonica. Phytochemistry 1985; 24: 1945-1948
8. Sheu JH, Wang GH, Sung PJ, Chiu YH, Duh CY. Cytotoxic sterols from the Formosan brown alga Turbinaria ornata. Planta Med 1997; 63: 571-572
9. Chiang CK, Chang FC. Tetracyclic triterpenoids from Melia azedarach, L.-III. Tetrahedron 1973; 29: 1911-1929
10. Pettit GR, Numata A, Iwamoto C, Morito H, Yamada T, Goswami A, Clewlow PJ, Cragg GM, Schmidt JM. Antineoplastic agents. 489. Isolation and structures of meliastatins 1-5 and related euphane triterpenes from tree Melia dubia. J Nat Prod 2002; 65: 1886-1891
11. Aalbersberg W, Singh Y. Dammarane triterpenoids from Dysoxylum richii. Phytochemistry 1991; 30: 921-926
12. Shirane N, Hashimoto Y, Ueda K, Takenaka H, Katoh K. Ring-A cleavage of 3-oxo-olean-12-en-28-oic acid by the fungus Chaetomium longirostre. Phytochemistry 1996; 43: 99-104 (Pubitemid 27065596)
13. Notaro G, Piccialli V, Sica D, Corriero G. 3β,5α,6α- Trihydroxylated sterols with a saturated nucleus from two populations of the marine sponge Cliona copiosa. J Nat Prod 1991; 54: 1570-1575
14. Ioannou E, Abdel-Razik AF, Zervou M, Christofidis D, Alexi X, Vagias C, Alexis MN, Roussis V. 5α,8α-Epidioxysterols from the gorgonian Eunicella cavolini and the ascidian Trididemnum inarmatum: isolation and evaluation of their antiproliferative activity. Steroids 2009; 74: 73-80
15. Sheikh YM, Djerassi C. Steroids from sponges. Tetrahedron 1974; 30: 4095-4103
16. Chaurasia N, Wichtl M. Sterols and steryl glycosides from Urtica dioica. J Nat Prod 1987; 50: 881-885
17. Sang YS, Zhou CY, Lu AJ, Yin XJ, Min ZD, Tan RX. Protolimonoids from Melia toosendan. J Nat Prod 2009; 72: 917-920
18. Stephens PJ, Pan JJ, Devlin FJ, Cheeseman JR. Determination of the absolute configurations of natural products using TDDFT optical rotation calculations: the iridoid oruwacin. J Nat Prod 2008; 71: 285-288 (Pubitemid 351362996)
19. Chen LX, Zhu HJ, Wang R, Zhou KL, Jing YK, Qiu F. ent-Labdane diterpenoid lactone stereoisomers from Andrographis paniculata. J Nat Prod 2008; 71: 852-855 (Pubitemid 351841435)
20. Wang B, Dossey AT,Walse SS, Edison AS, Merz Jr KM. Relative configuration of natural products using NMR chemical shifts. J Nat Prod 2009; 72: 709-713
21. Viano Y, Bonhomme D, Camps M, Briand JF, Ortalo-Magné A, Blache Y, Piovetti L, Culioli G. Diterpenoids from the Mediterranean brown alga Dictyota sp. evaluated as antifouling substances against a marine bacterial biofilm. J Nat Prod 2009; 72: 1299-1304
22. Xu WH, Jacob MR, Agarwal AK, Clark AM, Liang ZS, Li XC. Verbesinosides A-F, 15,27-cyclooleanane saponins from the American native plant Verbesina virginica. J Nat Prod 2009; 72: 1022-1027
23. Jiao WX, Blunt JW, Cole ALJ, Munro MHG. Fumagiringillin, a new fumagillinde rivative from a strain of the fungus Aspergillus fumigatus. J Nat Prod 2004; 67: 1434-1437 (Pubitemid 39145660)
24. Taji S, Yamada T, Tanaka R. Three new lanostane triterpenoids, inonotsutriols A, B, and C, from Inonotus obliquus. Helv Chim Acta 2008; 91: 1513-1524
25. Shin Y, Tamai Y, Terazawa M. Chemical constituents of inonotus obliquus II: a new triterpene, 21,24-cyclopentalanosta-3β,21,25-triol-8-ene from sclerotium. J Wood Sci 2001; 47: 313-316
26. Achenbach H, Frey D. Cycloartanes and other terpenoids and phenylpropanoids from Monocyclanthus vignei. Phytochemistry 1992; 31: 4263-4274
27. Yoshimitsu H, Nishida M, Nohara T. Three new cycloartane glycosides from Thalictrum thunbergii D.C. Tetrahedron 2001; 57: 10247-10252 (Pubitemid 34008622)
28. Yoshimitsu H, Nishida M, Yahara S, Nohara T. Two new cycloartaneglycosides from Thalictrum thunbergii D.C. Tetrahedron Lett 1998; 39: 6919-6920 (Pubitemid 28407390)
29. Kelecom A, Cabral MMO, Garcia ES. A new euphane triterpene from the Brazilian Melia azedarach. J Braz Chem Soc 1996; 7: 39-41 (Pubitemid 126487882)
30. D'Auria MV, Riccio R, Uriarte E, Minale L, Tanaka J, Higa T. Isolation and structure elucidation of seven new polyhydroxylated sulfated sterols from the ophiuroid Ophiolepis superba. J Org Chem 1989; 54: 234-239
31. Preus MW, McMorris TC. The configuration at C-24 in oogoniol (24R-3β,11α,15β,29-tetrahydroxystigmast-5-en-7-one) and identification of 24(28)-dehydroogoniols as hormones in Achlya. J Am Chem Soc 1979; 101: 3066-3071 (Pubitemid 9229273)
32. Bates RB, Brewer AD, Knights BR, Rowe JW. Double bond configurations of 24-ethylidine sterols. Tetrahedron Lett 1968; 9: 6163-6167
33. De Marino S, Iorizzi M, Zollo F, Minale L, Amsler CD, Baker BJ, McClintock JB. Isolation, structure elucidation, and biological activity of the steroid oligoglycosides and polyhydroxysteroids from the Antarctic starfish Acodontaster conspicuus. J Nat Prod 1997; 60: 959-966 (Pubitemid 27469038)
34. Zollo F, Finamore E, Riccio R, Minale L. Starfish saponins, Part 37. Steroidal glycoside sulfates from starfishes of the genus Pisaster. J Nat Prod 1989; 52: 693-700
35. Vishnukanta ACR. Melia azedarach: A phytopharmacological review. Pharmacognosy Rev 2008; 2: 173-179
36. Tan QG, Li XN, Chen H, Feng T, Cai XH, Luo XD. Sterols and terpenoids from Melia azedarach. J Nat Prod 2010; 73: 693-697
37. Zhang Y, Tang CP, Ke CQ, Yao S, Ye Y. Limonoids and triterpenoids from the stem bark of Melia toosendan. J Nat Prod 2010; 73: 664-668
38. Kobayashi M, Krishna MM, Ishida K, Anjaneyulu V. Marine sterols. XXII. Occurrence of 3-oxo-4,6,8(14)-triunsaturated steroids in the sponge Dysidea herbacea. Chem Pharm Bull 1992; 40: 72-74
39. Sera Y, Adachi K, Shizuri Y. A new epidioxy sterol as an antifouling substance from a Palauan marine sponge, Lendenfeldia chondrodes. J Nat Prod 1999; 62: 152-154 (Pubitemid 29071400)
40. Sheu JH, Wang GH, Sung PJ, Duh CY. New cytotoxic oxygenated fucosterols from the brown alga Turbinaria conoides. J Nat Prod 1999; 62: 224-227
41. Cao SG, Brodie P, Miller JS, Birkinshaw C, Rakotondrafara A, Andriantsiferana R, Rasamison VE, Kingston DG. Antiproliferative compounds of Helmiopsis sphaerocarpa from the Madagascar rainforest. Nat Prod Res 2009; 23: 638-643