Cymatherelactone and cymatherols A-C, polycyclic oxylipins from the marine brown alga Cymathere triplicata

被引:11
作者
Choi, Hyukjae [1 ]
Proteau, Philip J. [2 ]
Byrum, Tara [1 ]
Gerwick, William H. [1 ]
机构
[1] Univ Calif San Diego, Scripps Inst Oceanog, Ctr Marine Biotechnol & Biomed, La Jolla, CA 92093 USA
[2] Oregon State Univ, Coll Pharm, Dept Pharmaceut Sci, Corvallis, OR 97331 USA
关键词
Cymathere triplicata; Brown alga; Oxylipin; Sodium channel inhibition; LAURENCIA-HYBRIDA; METABOLITES; BIOASSAY;
D O I
10.1016/j.phytochem.2011.09.014
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
An investigation of the oxylipin chemistry of the temperate brown alga Cymathere triplicata led to the isolation of several secondary metabolites, cymatherelactone (1) and cymatherols A-C (2-4), the latter as their methyl ester derivatives (5-7), which contained cyclopentyl, cyclopropyl, epoxide and lactone rings. Their structures were elucidated using a combination of spectroscopic techniques and synthetic chemistry. Cymatherelactone (1), as well as R- and S-Mosher's esters of its seco acid, exhibited moderate sodium channel blocking activity. (C) 2011 Published by Elsevier Ltd.
引用
收藏
页码:134 / 141
页数:8
相关论文
共 15 条
[11]   ISOLATION AND STRUCTURE OF CONSTANOLACTONE-A AND CONSTANOLACTONE-B, NEW CYCLOPROPYL HYDROXYEICOSANOIDS FROM THE TEMPERATE RED ALGA CONSTANTINEA-SIMPLEX [J].
NAGLE, DG ;
GERWICK, WH .
TETRAHEDRON LETTERS, 1990, 31 (21) :2995-2998
[12]   HALICHOLACTONE AND NEOHALICHOLACTONE, 2 NOVEL FATTY-ACID METABOLITES FROM THE MARINE SPONGE HALICHONDRIA-OKADAI KADOTA [J].
NIWA, H ;
WAKAMATSU, K ;
YAMADA, K .
TETRAHEDRON LETTERS, 1989, 30 (34) :4543-4546
[13]  
Proteau P.J., 1993, THESIS OREGON STATE
[14]   CYMATHERE ETHER-A AND CYMATHERE ETHER-B - BICYCLIC OXYLIPINS FROM THE MARINE BROWN ALGA CYMATHERE-TRIPLICATA [J].
PROTEAU, PJ ;
GERWICK, WH .
TETRAHEDRON LETTERS, 1992, 33 (31) :4393-4396
[15]  
TODD JS, 1993, TETRAHEDRON LETT, V34, P7689