Isolation and absolute configuration of ent-Halimane diterpenoids from Hymenaea courbaril from the Suriname rain forest.
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.
Abdel-Kader
Maged
M
Department of Chemistry, M/C 0212, Virginia Polytechnic Institute and State University, Blacksburg, Virginia 24061, USA.
Berger
John M
JM
Slebodnick
Carla
C
Hoch
Jeannine
J
Malone
Stan
S
Wisse
Jan H
JH
Werkhoven
Marga C M
MC
Mamber
Steven
S
Kingston
David G I
DG
D000972:Antineoplastic Agents, Phytogenic / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D018360:Crystallography, X-Ray; D004224:Diterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D007887:Fabaceae / Q000737:chemistry*; D005260:Female; D006801:Humans; D013058:Mass Spectrometry; D008968:Molecular Conformation; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D010051:Ovarian Neoplasms; D018515:Plant Leaves / Q000737:chemistry; D018520:Plant Shoots / Q000737:chemistry; D018547:Plant Stems / Q000737:chemistry; D010946:Plants, Medicinal / Q000737:chemistry*; D013237:Stereoisomerism; D013532:Suriname; D014407:Tumor Cells, Cultured / Q000187:drug effects; D015003:Yeasts / Q000187:drug effects
C449748:(13R)-13-hydroxy-1(10),14-ent-halimadien-18-oic acid; C449750:(13R)-2-oxo-13-hydroxy-1(10),14-ent-halimadien-18-oic acid; C449751:(2S,13R)-2,13-dihydroxy-1(10),14-ent-halimadien-18-oic acid; D000972:Antineoplastic Agents, Phytogenic; D004224:Diterpenes