Oculatol, oculatolide, and A-nor sterols from the sponge Haliclona oculata.
Chemical investigation of the marine sponge Haliclona oculata resulted in the isolation of eight new compounds including oculatol (1) and oculatolide (2) and six unusual A-nor steroids, 2-ethoxycarbonyl-2beta-hydroxy-A-nor-ergosta-5,24(28)-dien-4-one (3), 2-ethoxycarbonyl-24-ethyl-2beta-hydroxy-A-nor-cholesta-5-en-4-one (4), 2-ethoxycarbonyl-2beta,7beta-dihydroxy-A-nor-ergosta-5,24(28)-dien-4-one (5), 2-ethoxycarbonyl-2beta,7beta-dihydroxy-A-nor-cholesta-5-en-4-one (6), 2-ethoxycarbonyl-2beta,7beta-dihydroxy-24-methyl-A-nor-cholesta-5,22(E)-dien-4-one (7), and 2-ethoxycarbonyl-2beta,7beta-dihydroxy-A-nor-cholesta-5,22(E)-dien-4-one (8), along with 16 known steroids and indole derivatives. Their structures were unambiguously determined on the basis of extensive spectroscopic analyses.
Yu
Shanjiang
S
State Key Laboratory of Natural and Biomimetic Drugs, Peking University, Beijing 100083, People's Republic of China.
Deng
Zhiwei
Z
Proksch
Peter
P
Lin
Wenhan
W
D000818:Animals; D000970:Antineoplastic Agents / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D004354:Drug Screening Assays, Antitumor; D047129:Haliclona / Q000737:chemistry*; D006801:Humans; D020128:Inhibitory Concentration 50; D015394:Molecular Structure; D013261:Sterols / Q000737:chemistry / Q000302:isolation & purification / Q000494:pharmacology; D014407:Tumor Cells, Cultured
D000970:Antineoplastic Agents; D013261:Sterols; C514399:oculatol; C514400:oculatolide