Sesterterpenoids Isolated from a Northeastern Pacific Phorbas sp

Four new sesterterpenoids, ansellone B (4), phorbadione (5), secoepoxyansellone A (6), and alotaketal C (7), have been isolated from specimens of the sponge Phorbas sp. collected in British Columbia. Ansellone B (4) has an unprecedented heterocyclic skeleton featuring an oxocane ring, and secoepoxya...

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Bibliographic Details
Published in:Journal of organic chemistry 2013-09, Vol.78 (17), p.8267-8273
Main Authors: Daoust, Julie, Chen, Min, Wang, Meng, Williams, David E, Chavez, Miguel Angel Garcia, Wang, Yan Alexander, Merchant, Catherine E, Fontana, Angelo, Kieffer, Timothy J, Andersen, Raymond J
Format: Article
Language:English
Subjects:
Animals
Cyclic AMP - metabolism
Dose-Response Relationship, Drug
HEK293 Cells
Humans
Molecular Conformation
Porifera - chemistry
Sesterterpenes - chemistry
Sesterterpenes - isolation & purification
Sesterterpenes - pharmacology
Signal Transduction - drug effects
Stereoisomerism
Structure-Activity Relationship
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Summary:Four new sesterterpenoids, ansellone B (4), phorbadione (5), secoepoxyansellone A (6), and alotaketal C (7), have been isolated from specimens of the sponge Phorbas sp. collected in British Columbia. Ansellone B (4) has an unprecedented heterocyclic skeleton featuring an oxocane ring, and secoepoxyansellone A (6) is the first example of the degraded “secoansellane” sesterterpenoid carbon skeleton. Alotaketal C (7) is an activator of cAMP signaling in HEK cells.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo4014589