The oxidation profile at C-18 of furanocembranolides may provide a taxonomical marker for several genera of octocorals
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- 作者：Enrique Dorta ; Ana R. Dí ; az-Marrero ; Inmaculada Brito ; Mercedes Cueto ; Luis D'Croz ; José ; Darias
- 关键词：Terpenes and terpenoids ; Biogenesis ; Autoxidation ; NMR
- 刊名：Tetrahedron
- 出版年：2007
- 出版时间：10 September 2007
- 年：2007
- 卷：63
- 期：37
- 页码：9057-9062
- 全文大小：248 K
文摘
The furanocembranolides 1–3 along with the known compounds pukalide, pukalidealdehyde, epoxypukalide, and leptolide were isolated from Leptogorgia spp. and their structures were determined by spectroscopic evidences. An NMR-based method using Pirkle's reagent at low temperature allowed us to determine the absolute configuration at C-10 of a γ-butenolide unit embedded in a flexible furanocembranolide network. The C-18 of furanocembranolides undergoes an oxidation cascade leading from a methyl group to a carboxylic acid/ester that appears to be genus specific. We introduce the concept genus-specific oxidation, a feature that provides a chemotaxonomical marker for several genera of octocorals. This concept also allowed us to propose a biogenetic pathway for these compounds.