5-Lipoxygenase-derived oxylipins from the red alga Rhodymenia pertusa

被引:35
作者
Jiang, ZD [1 ]
Ketchum, SO [1 ]
Gerwick, WH [1 ]
机构
[1] Oregon State Univ, Coll Pharm, Corvallis, OR 97331 USA
关键词
Rhodymenia pertusa; Rhodymeniaceae; marine algae; oxylipin; 5-lipoxygenase;
D O I
10.1016/S0031-9422(99)00445-8
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
The lipid extract of the temperate red alga Rhodymenia pertusa has yielded four eicosanoid metabolites, three of which are new natural products. Using principally NMR and MS techniques, their structures were deduced as 5R,6S-dihydroxy-7(E),9(E),11(Z),14(Z)-eicosatetraenoic acid (5R,6S-diHETE), 5R*,6S*-dihydroxy-7(E),9(E),11(Z),14(Z),17(Z)-eicosapentaenoic acid (5R*,6S*-diHEPE), 5-hydroxy-6(E),8(Z),11(Z),14(Z)-eicosatetraeonic acid (5-HETE), 5-hydroxy-6(E),8(Z),11(Z),14(Z),17(Z)-eicosapentaenoic acid (5-HEPE). The co-occurrence of these metabolites strongly suggests that R. pertusa contains a unique 5R-lipoxygenase system acting on both arachidonic and eicosapentaenoic acids. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:129 / 133
页数:5
相关论文
共 18 条
[1]   EICOSANOIDS FROM THE TROPICAL RED-ALGA MURRAYELLA-PERICLADOS [J].
BERNART, MW ;
GERWICK, WH .
PHYTOCHEMISTRY, 1994, 36 (05) :1233-1240
[2]   Treatment of asthma with drugs modifying the leukotriene pathway [J].
Drazen, JM ;
Israel, E ;
O'Byrne, PM .
NEW ENGLAND JOURNAL OF MEDICINE, 1999, 340 (03) :197-206
[3]   RECENT INVESTIGATIONS INTO THE LIPOXYGENASE PATHWAY OF PLANTS [J].
GARDNER, HW .
BIOCHIMICA ET BIOPHYSICA ACTA, 1991, 1084 (03) :221-239
[4]   Epoxy allylic carbocations as conceptual intermediates in the biogenesis of diverse marine oxylipins [J].
Gerwick, WH .
LIPIDS, 1996, 31 (12) :1215-1231
[5]   STRUCTURE AND BIOSYNTHESIS OF MARINE ALGAL OXYLIPINS [J].
GERWICK, WH .
BIOCHIMICA ET BIOPHYSICA ACTA-LIPIDS AND LIPID METABOLISM, 1994, 1211 (03) :243-255
[6]  
GERWICK WH, 1993, ADV MARINE BIOTECHNO, V1, P101
[7]  
GERWICK WH, 1999, COMPREHENSIVE NATURA, P207
[8]   STEROLS OF SOME MARINE RED ALGAE [J].
GIBBONS, GF ;
GOAD, LJ ;
GOODWIN, TW .
PHYTOCHEMISTRY, 1967, 6 (05) :677-+
[9]   The isolation and characterization of agardhilactone, a novel oxylipin from the marine red alga Agardhiella subulata [J].
Graber, MA ;
Gerwick, WH ;
Cheney, DP .
TETRAHEDRON LETTERS, 1996, 37 (27) :4635-4638
[10]   NOVEL HYDROXYICOSATETRAENOIC AND HYDROXYICOSAPENTAENOIC ACIDS AND A 13-OXO ANALOG - ISOLATION FROM A MIXTURE OF THE CALCAREOUS RED ALGAE LITHOTHAMNION-CORALLIOIDES AND LITHOTHAMNION-CALCAREUM OF BRITTANY WATERS [J].
GUERRIERO, A ;
DAMBROSIO, M ;
PIETRA, F .
HELVETICA CHIMICA ACTA, 1990, 73 (08) :2183-2189