A seco-laurane sesquiterpene and related laurane derivatives from the red alga Laurencia okamurai Yamada.

Abstract:

:A ring-cleaved sesquiterpene, named seco-laurokamurone, four laurane-type sesquiterpenes, laurepoxyene, 3β-hydroperoxyaplysin, 3α-hydroperoxy-3-epiaplysin, and 8,10-dibromoisoaplysin, one laurokamurane-type sesquiterpene, laurokamurene D, and one bisabolane-type sesquiterpene, (5S)-5-acetoxy-β-bisabolene, have been isolated from a re-collection of the red alga Laurencia okamurai Yamada, together with six other known sesquiterpenes. Their structures, including relative configuration, were elucidated by detailed analysis of spectroscopic data, and by comparison with data for related known compounds. In addition, on the basis of chemical conversions, degradation results, and biogenetic considerations, the absolute configurations of several of these compounds were also tentatively proposed. seco-Laurokamurone possesses an unprecedented carbon skeleton, formed from an oxidative cleavage of the laurokamurane skeleton, and laurokamurene D represents the fourth example of a laurokamurane-type sesquiterpene from a natural source. The in vitro antifungal activity of many of these compounds was evaluated against four fungi (Cryptococcus neoformans, Candida glabrata, Trichophyton rubrum, and Aspergillus fumigatus), as well as assessing cytotoxicity against HL-60 and A-549 human cancer cell lines. The compounds studied displayed moderate activities, relative to controls.

journal_name

Phytochemistry

journal_title

Phytochemistry

authors

Yu XQ,He WF,Liu DQ,Feng MT,Fang Y,Wang B,Feng LH,Guo YW,Mao SC

doi

10.1016/j.phytochem.2014.03.021

subject

Has Abstract

pub_date

2014-07-01 00:00:00

pages

162-170

eissn

0031-9422

issn

1873-3700

pii

S0031-9422(14)00140-X

journal_volume

103

pub_type

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