jf5b01931_si_001.cif (244.38 kB)
Structural Elucidation and Structure–Anti-inflammatory Activity Relationships of Cembranoids from Cultured Soft Corals Sinularia sandensis and Sinularia flexibilis
dataset
posted on 2015-08-19, 00:00 authored by Tsung-Chang Tsai, Hsueh-Yu Chen, Jyh-Horng Sheu, Michael Y. Chiang, Zhi-Hong Wen, Chang-Feng Dai, Jui-Hsin SuNew
cembranoids 4-carbomethoxyl-10-epigyrosanoldie E (1),
7-acetylsinumaximol B (2), diepoxycembrene B (6), dihydromanaarenolide I (8), and isosinulaflexiolide
K (9), along with 11 known related metabolites, were
isolated from cultured soft corals Sinularia sandensis and Sinularia flexibilis. The structures were elucidated
by means of infrared, mass spectrometry,
and nuclear magnetic resonance techniques, and the absolute configurations
of 1, 4, 9, and 15 were further confirmed by single-crystal X-ray diffraction analysis.
The absolute configurations of these coral metabolites and comparison
with known analogues showed that one hypothesis (that cembrane diterpenes
possessing an absolute configuration of an isopropyl group at C1 obtained
from Alcyonacean soft corals belong to the α series, whereas
analogues isolated from Gorgonacean corals
belong to the β series) is not applicable for a small number
of cembranoids. An in vitro anti-inflammatory study
using LPS-stimulated macrophage-like
cell line RAW 264.7 revealed that compounds 9–14 significantly suppressed the accumulation of pro-inflammatory
proteins, iNOS and COX-2. Structure–activity relationship analysis
indicated that cembrane-type compounds with
one seven-membered lactone moiety at C-1 are potential anti-inflammatory
agents. This is the first culture system in the world that has successfully
been used to farm S. sandensis.