Isolation and absolute configuration of ent-halimane diterpenoids from Hymenaea courbaril from the suriname rain forest

被引:37
作者
Abdel-Kader, M
Berger, JM
Slebodnick, C
Hoch, J
Malone, S
Wisse, JH
Werkhoven, MCM
Mamber, S
Kingston, DGI
机构
[1] Virginia Polytech Inst & State Univ, Dept Chem, Blacksburg, VA 24061 USA
[2] Conservat Int Suriname, Paramaribo, Suriname
[3] Natl Herbarium Suriname, Paramaribo, Suriname
[4] Commissaris Roblesweg, Bedrijf Geneesmiddelen Voorziening Suriname, Geyersvlijt, Suriname
[5] Bristol Myers Squibb Co, Pharmaceut Res Inst, Wallingford, CT 06492 USA
来源
JOURNAL OF NATURAL PRODUCTS | 2002年 / 65卷 / 01期
关键词
D O I
10.1021/np0103261
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Bioactivity-directed fractionation of a methanol extract of Hymenaea courbaril afforded the three new diterpenoids (13R)-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (1), (2S,13R)-2,13-dihydroxy-1(10),14-ent-halimadien-18-oic acid (2), and (13R)-2-oxo-13-hydroxy-1(10),14-ent-halimadien-18-oic acid (3). The configurations of these compounds were determined from X-ray crystallography of 1, circular dichroism of 2 and 3, and spectral studies of prepared derivatives. Compound 1 exhibited weak cytotoxicity toward the 1138 mutant yeast strain and the A2780 human ovarian cancer cell line.
引用
收藏
页码:11 / 15
页数:5
相关论文
共 22 条
[1]   Two bioactive saponins from Albizia subdimidiata from the Suriname rainforest [J].
Abdel-Kader, M ;
Hoch, J ;
Berger, JM ;
Evans, R ;
Miller, JS ;
Wisse, JH ;
Mamber, SW ;
Dalton, JM ;
Kingston, DGI .
JOURNAL OF NATURAL PRODUCTS, 2001, 64 (04) :536-539
[2]   DNA-damaging steroidal alkaloids from Eclipta alba from the Suriname rainforest [J].
Abdel-Kader, MS ;
Bahler, BD ;
Malone, S ;
Werkhoven, MCM ;
van Troon, F ;
Wisse, DJH ;
Bursuker, I ;
Neddermann, KM ;
Mamber, SW ;
Kingston, DGI .
JOURNAL OF NATURAL PRODUCTS, 1998, 61 (10) :1202-1208
[3]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[4]   GENERAL-METHOD FOR DETERMINING ABSOLUTE-CONFIGURATIONS OF ACYCLIC ALLYLIC ALCOHOLS [J].
GONNELLA, NC ;
NAKANISHI, K ;
MARTIN, VS ;
SHARPLESS, KB .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (13) :3775-3776
[5]   A CHIROPTICAL METHOD FOR DETERMINING THE ABSOLUTE-CONFIGURATION OF ALLYLIC ALCOHOLS [J].
HARADA, N ;
IWABUCHI, J ;
YOKOTA, Y ;
UDA, H ;
NAKANISHI, K .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1981, 103 (18) :5590-5591
[6]   DITERPENES FROM EUPATORIUM-TURBINATUM [J].
JAKUPOVIC, J ;
ELLMAUERER, E ;
BOHLMANN, F ;
WHITTEMORI, A ;
GAGE, D .
PHYTOCHEMISTRY, 1986, 25 (11) :2677-2678
[7]   STRUCTURE AND STEREOCHEMISTRY OF DITERPENES OF HYMENAEA-COURBARIL (CAESALPINIOIDEAE) SEED POD RESIN [J].
KHOO, SF ;
OEHLSCHLAGER, AC ;
OURISSON, G .
TETRAHEDRON, 1973, 29 (21) :3379-3388
[8]  
Kingston DGI, 1999, PHARM BIOL, V37, P22, DOI 10.1076/1388-0209(200010)37:SUP
[9]  
1-W
[10]  
FT022