STRUCTURE AND BIOSYNTHESIS OF NOVEL CONJUGATED POLYENE FATTY-ACIDS FROM THE MARINE GREEN-ALGA ANADYOMENE STELLATA

被引:46
作者
MIKHAILOVA, MV
BEMIS, DL
WISE, ML
GERWICK, WH
NORRIS, JN
JACOBS, RS
机构
[1] UNIV CALIF SANTA BARBARA, INST MARINE SCI, SANTA BARBARA, CA 93106 USA
[2] OREGON STATE UNIV, COLL PHARM, CORVALLIS, OR 97331 USA
[3] OREGON STATE UNIV, DEPT BIOCHEM & BIOPHYS, CORVALLIS, OR 97331 USA
[4] SMITHSONIAN INST, NATL MUSEUM NAT HIST, DEPT BOT, WASHINGTON, DC 20560 USA
关键词
D O I
10.1007/BF02536993
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
Novel polyunsaturated fatty acids with four conjugated double bonds were found in extracts of the green macroalga, Anadyomene stellata. The isolation of five of these with different chain lengths and varying degrees of unsaturation-16:5, 18:4, 20:5, 20:6, and 22:7-was accomplished by organic extraction followed by a combination of vacuum and high-performance liquid chromatography. One of these that was a novel substance (22:7) was characterized as 4Z,7Z,9E,11E,13Z,16Z,19Z-docosaheptaenoic acid and assigned the trivial name stellaheptaenoic acid. The structure of this new compound, isolated as its methyl ester derivative, was deduced from detailed nuclear magnetic resonance, gas chromatography/mass spectrometry (GC/MS), and other spectroscopic methods. Incubation of a chloroplast preparation, isolated from a crude algal homogenate by differential centrifugation, with six unsaturated fatty acids (palmitoleic, 6Z,9Z,12Z,15Z-octadecatetraenoic acid, arachidonic acid, eicosapentaenoic acid, 7Z,10Z,13Z,16Z-docosatetraenoic acid, and 4Z,7Z,10Z,13Z,16Z,19Z-docosahexaenoic acid) resulted in substantially increased synthesis of unique tetraene compounds as detected by ultraviolet spectrophotometry and tentatively identified by GC/MS.
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页码:583 / 589
页数:7
相关论文
共 26 条
[1]   ANALYTICAL-SCALE HIGH-PERFORMANCE LIQUID-CHROMATOGRAPHY OF OMEGA-3 FATTY-ACID ESTERS DERIVED FROM FISH OILS [J].
BEEBE, JM ;
BROWN, PR ;
TURCOTTE, JG .
JOURNAL OF CHROMATOGRAPHY, 1989, 468 :225-233
[2]  
BORGEAT P, 1990, METHOD ENZYMOL, V187, P98
[3]  
BRADFORD MM, 1976, ANAL BIOCHEM, V72, P248, DOI 10.1016/0003-2697(76)90527-3
[4]   A NEW EICOSAPENTAENOIC ACID FORMED FROM ARACHIDONIC-ACID IN THE CORALLINE RED ALGAE BOSSIELLA-ORBIGNIANA [J].
BURGESS, JR ;
DELAROSA, RI ;
JACOBS, RS ;
BUTLER, A .
LIPIDS, 1991, 26 (02) :162-165
[5]   2-STEP INACTIVATION OF BEE VENOM PHOSPHOLIPASE-A2 BY SCALARADIAL [J].
DECARVALHO, MS ;
JACOBS, RS .
BIOCHEMICAL PHARMACOLOGY, 1991, 42 (08) :1621-1626
[6]  
DEFREITAS JC, 1984, EXPERIENTIA, V40, P864
[7]   OXYLIPIN METABOLISM IN THE RED ALGA GRACILARIOPSIS-LEMANEIFORMIS - MECHANISM OF FORMATION OF VICINAL DIHYDROXY FATTY-ACIDS [J].
GERWICK, WH ;
MOGHADDAM, M ;
HAMBERG, M .
ARCHIVES OF BIOCHEMISTRY AND BIOPHYSICS, 1991, 290 (02) :436-444
[8]   STRUCTURE AND BIOSYNTHESIS OF MARINE ALGAL OXYLIPINS [J].
GERWICK, WH .
BIOCHIMICA ET BIOPHYSICA ACTA-LIPIDS AND LIPID METABOLISM, 1994, 1211 (03) :243-255
[9]  
GERWICK WH, 1993, TOP CURR CHEM, V167, P117
[10]  
GERWICK WH, 1993, HYDROBIOLOGIA, V261, P653