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

被引:27
作者
GUERRIERO, A [1 ]
DAMBROSIO, M [1 ]
PIETRA, F [1 ]
机构
[1] UNIV TRENTO,IST CHIM,I-38050 TRENT,ITALY
关键词
D O I
10.1002/hlca.19900730815
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A mixture of the red calcareous algae Lithothamnion corallioides CROUAN and Lithothamnion calcareum (PALLAS) ARESCHOUGH, from Brittany waters, gives, on ethanolic extraction, the novel icosanoids ethyl 13‐hydroxy‐arachidonate (=(+)‐all‐Z‐ethyl 13‐hydroxyicosa‐5,8, 11,14,‐tetraenoate; (+)‐1)), ethyl 13‐hydroxytimnodonate (=(+)‐(all‐Z)‐ethyl 13‐hydroxyicosa‐5,8,11,14,17‐pentaenoate ((+)‐2), and (5Z,9E,11E,14E)‐ethyl 8‐hydroxy‐13‐oxoicosa‐5,9,11,14‐tetraenoate (3). Moreover, the ethyl esters of four known icosatetraenoic acids are contained in the above algae. Structural elucidations of these metabolites are based mainly on NMR data. Copyright © 1990 Verlag GmbH & Co. KGaA, Weinheim
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页码:2183 / 2189
页数:7
相关论文
共 25 条
[1]   FORMATION OF A CYCLOPROPYL EICOSANOID VIA AN ALLENE OXIDE IN THE CORAL PLEXAURA-HOMOMALLA - IMPLICATIONS FOR THE BIOSYNTHESIS OF 5,6-TRANS-PROSTAGLANDIN-A2 [J].
BAERTSCHI, SW ;
BRASH, AR ;
HARRIS, TM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (13) :5003-5005
[2]   SYNTHESIS FROM ARACHIDONIC-ACID OF POTENTIAL PROSTAGLANDIN PRECURSORS [J].
BALDWIN, JE ;
DAVIES, DI ;
HUGHES, L ;
GUTTERIDGE, NJA .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1979, (01) :115-121
[3]   ISOLATION OF 12-(S)-HEPE FROM THE RED MARINE ALGA MURRAYELLA-PERICLADOS AND REVISION OF STRUCTURE OF AN ACYCLIC ICOSANOID FROM LAURENCIA-HYBRIDA - IMPLICATIONS TO THE BIOSYNTHESIS OF THE MARINE PROSTANOID HYBRIDALACTONE [J].
BERNART, M ;
GERWICK, WH .
TETRAHEDRON LETTERS, 1988, 29 (17) :2015-2018
[4]   STEREOCHEMISTRY AND MECHANISM OF THE BIOSYNTHESIS OF LEUKOTRIENE-A4 FROM 5(S)-HYDROPEROXY-6(E),8,11,14(Z)-EICOSATETRAENOIC ACID - EVIDENCE FOR AN ORGANOIRON INTERMEDIATE [J].
COREY, EJ ;
WRIGHT, SW ;
MATSUDA, SPT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (04) :1452-1455
[5]   DISPARATE PATHWAYS OF PROSTAGLANDIN BIOSYNTHESIS IN CORAL AND MAMMALIAN SYSTEMS [J].
COREY, EJ ;
ENSLEY, HE ;
HAMBERG, M ;
SAMUELSSON, B .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1975, (08) :277-278
[6]   BIOSYNTHESIS OF 8-R-HPETE AND PRECLAVULONE-A FROM ARACHIDONATE IN SEVERAL SPECIES OF CARIBBEAN CORAL - A WIDESPREAD ROUTE TO MARINE PROSTANOIDS [J].
COREY, EJ ;
MATSUDA, SPT ;
NAGATA, R ;
CLEAVER, MB .
TETRAHEDRON LETTERS, 1988, 29 (21) :2555-2558
[7]   NUCLEAR MAGNETIC-RESONANCE ENANTIOMER REAGENTS - CONFIGURATIONAL CORRELATIONS VIA NUCLEAR MAGNETIC-RESONANCE CHEMICAL-SHIFTS OF DIASTEREOMERIC MANDELATE, O-METHYLMANDELATE, AND ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETATE (MTPA) ESTERS [J].
DALE, JA ;
MOSHER, HS .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1973, 95 (02) :512-519
[8]   5-HETE AND 8-HETE PRODUCTION BY RAT HEPATIC-MICROSOMAL CYTOCHROME-P-450 [J].
FALCK, JR ;
SIDDHANTA, AK ;
ESTABROOK, RW ;
CAPDEVILA, J ;
MIOSKOWSKI, C .
TETRAHEDRON LETTERS, 1984, 25 (14) :1457-1458
[9]  
FUSETANI N, 1984, B JPN SOC SCI FISH, V50, P465
[10]  
GREGSON RP, 1979, TETRAHEDRON LETT, P4505