Lemnalemnanes A-C, Three Rare Rearranged Sesquiterpenoids from the Soft Corals Paralemnalia thyrsoides and Lemnalia sp

Org Lett. 2022 Jan 14;24(1):11-15. doi: 10.1021/acs.orglett.1c03386. Epub 2021 Dec 14.

Abstract

Three novel sesquiterpenoids, lemnalemnanes A-C (1-3), were obtained from marine soft corals Paralemnalia thyrsoides and Lemnalia sp. Their structures were determined by 1D/2D NMR spectroscopy, HRESIMS, single-crystal X-ray diffraction analysis (Cu Kα), Mosher's method, and ECD quantum chemistry calculations. Lemnalemnane A (1) possessed an intriguing basket-like structure with a spiro[bicyclo[3.3.1]nonane-furan core, while lemnalemnanes B (2) and C (3) exhibited unusual 6/6/5 and 6/5/5 carbon skeletons, respectively. In the proposed biosynthesis pathway, 1-3 were suspected to originate from the same precursor, 4-O-deacetylparalemnolin D (4), a compound coisolated from both aforementioned species. Furthermore, lemnalemnane C (3) exhibited strong in vivo promoting-angiogenesis activity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Sesquiterpenes*

Substances

  • Sesquiterpenes