Aplysiols C–E, brominated triterpene polyethers from the marine alga Chondria armata and a revision of the structure of aplysiol B

Ola, Antonius R.B., Babey, Anna-Marie, Motti, Cherie, and Bowden, Bruce (2010) Aplysiols C–E, brominated triterpene polyethers from the marine alga Chondria armata and a revision of the structure of aplysiol B. Australian Journal of Chemistry, 63 (6). pp. 907-914.

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Abstract

Three new brominated triterpene polyethers, aplysiols C–E (1–3), were isolated from extracts of the red alga Chondria armata. Structures were determined by comparison with the closely related metabolite, aplysiol B, which was previously reported from the anaspidean mollusc Aplysia dactylomela. The relative stereochemistry of the tetracyclic ring system was determined from 1D gradient selective NOESY experiments and from biogenetic considerations that support a revision of the stereochemistry proposed for aplysiol B. In addition, three known brominated C15 acetogenin acetylenic ethers: (−)-pinnatifidenyne, (+)-laurenyne, and (+)-obtusenyne, two brominated diterpenes: (−)-ent-angasiol and (−)-ent-angasiol acetate, and the symmetrical halogenated triterpene polyether intricatetraol were isolated.

Item ID: 11778
Item Type: Article (Refereed Research - C1)
ISSN: 1445-0038
Date Deposited: 17 Aug 2010 00:26
FoR Codes: 03 CHEMICAL SCIENCES > 0305 Organic Chemistry > 030502 Natural Products Chemistry @ 100%
SEO Codes: 97 EXPANDING KNOWLEDGE > 970103 Expanding Knowledge in the Chemical Sciences @ 100%
Citation Count from Web of Science Web of Science 9
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