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Compositacins A-K: Bioactive chamigrane-type halosesquiterpenoids from the red alga Laurencia composita Yamada.

Authors :
Yu XQ
Jiang CS
Zhang Y
Sun P
Kurtán T
Mándi A
Li XL
Yao LG
Liu AH
Wang B
Guo YW
Mao SC
Source :
Phytochemistry [Phytochemistry] 2017 Apr; Vol. 136, pp. 81-93. Date of Electronic Publication: 2017 Jan 19.
Publication Year :
2017

Abstract

Eleven highly halogenated chamigrane sesquiterpenoids, compositacins A-K, including one unusual rearranged chamigrane sesquiterpenoid, compositacin A, were isolated from the red alga Laurencia composita Yamada, along with seven known structural analogues. Compositacins B and D are the first examples of chamigranes bearing an ether bridge involving C-5/C-9 and C-3/C-5, respectively, while compositacins B and C represent the first chamigranes with a C-10 carbonyl group. Their structures were elucidated on the basis of extensive spectroscopic analysis. The absolute configuration of compositacin B was determined by ECD calculation, whereas the absolute configurations of compositacins A and C-L were proposed on biosynthetic grounds by comparison to compositacin B and the related known sesquiterpenoids johnstonol and yicterpene A. We also suggest that the structure of the previously reported sesquiterpenoid laurokamin A should be revised. Cytotoxicity and antifungal activity of these isolates were also investigated. The results showed that compositacin G exhibited good antifungal activity against Microsporum gypseum (Cmccfmza) with a MIC <subscript>80</subscript> value of 4 μg/mL relative to positive controls. Four of the chamigrane halosesquiterpenoids showed marginal cytotoxicity against the A-549 human lung adenocarcinoma cell line with IC <subscript>50</subscript> values ranging from 48.6 to 85.2 μM.<br /> (Copyright © 2017 Elsevier Ltd. All rights reserved.)

Details

Language :
English
ISSN :
1873-3700
Volume :
136
Database :
MEDLINE
Journal :
Phytochemistry
Publication Type :
Academic Journal
Accession number :
28110957
Full Text :
https://doi.org/10.1016/j.phytochem.2017.01.007