Two new (E)-2-amino-2-butenoic acid (Dhb)-containing microcystins isolated from Oscillatoria agardhii

被引：63

作者：

Sano, T ^{[1
]}

Kaya, K ^{[1
]}

机构：

[1] Natl Inst Environm Studies, Environm Chem Div, Tsukuba, Ibaraki 305, Japan

来源：

TETRAHEDRON | 1998年 / 54卷 / 3-4期

关键词：

D O I：

10.1016/S0040-4020(97)10291-5

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Two new 2-amino-2-butenoic acid (Dhb)-containing microcystins (Dhb-microcystins), [D-Asp(3), (E)-Dhb(7)]microcystin-LR (1) and -HtyR (2), were isolated from Oscillatoria agardhii. The structures were elucidated by the extensive NMR analyses and confirmed by mass spectral and amino acid analyses. The absolute configuration was determined by chemical degradation and chiral GC analyses. The configuration of the Dhb unit of 1 and 2 was determined as E by ROESY experiments. (C) 1997 Elsevier Science Ltd. All rights reserved.

引用

页码：463 / 470

页数：8

共 17 条

[1]

BEATTIE KA, 1997, IN PRESS PHYTOCHEMIS

[2]

BEATTY MF, 1992, J CHEM SOC PERK T 1, P1637

[3] MICROCYSTINS FROM ANABAENA-FLOS-AQUAE NRC-525-17 [J].

HARADA, K ;

OGAWA, K ;

KIMURA, Y ;

MURATA, H ;

SUZUKI, M ;

THORN, PM ;

EVANS, WR ;

CARMICHAEL, WW .

CHEMICAL RESEARCH IN TOXICOLOGY, 1991, 4 (05) :535-540

[4] ISOLATION OF 2 TOXIC HEPTAPEPTIDE MICROCYSTINS FROM AN AXENIC STRAIN OF MICROCYSTIS-AERUGINOSA, K-139 [J].

HARADA, K ;

OGAWA, K ;

MATSUURA, K ;

NAGAI, H ;

MURATA, H ;

SUZUKI, M ;

ITEZONO, Y ;

NAKAYAMA, N ;

SHIRAI, M ;

NAKANO, M .

TOXICON, 1991, 29 (4-5) :479-489

[5] ISOLATION AND CHARACTERIZATION OF THE MINOR COMPONENTS ASSOCIATED WITH MICROCYSTINS LR AND RR IN THE CYANOBACTERIUM (BLUE-GREEN-ALGAE) [J].

HARADA, K ;

MATSUURA, K ;

SUZUKI, M ;

WATANABE, MF ;

OISHI, S ;

DAHLEM, AM ;

BEASLEY, VR ;

CARMICHAEL, WW .

TOXICON, 1990, 28 (01) :55-64

[6] STRUCTURE DETERMINATION AND TOXICITY OF A NEW MICROCYSTIN FROM MICROCYSTIS-AERUGINOSA STRAIN-205 [J].

KIVIRANTA, J ;

NAMIKOSHI, M ;

SIVONEN, K ;

EVANS, WR ;

CARMICHAEL, WW ;

RINEHART, KL .

TOXICON, 1992, 30 (09) :1093-1098

[7] SEPARATION AND IDENTIFICATION OF MICROCYSTINS IN CYANOBACTERIA BY FRIT-FAST ATOM BOMBARDMENT LIQUID-CHROMATOGRAPHY MASS-SPECTROMETRY [J].

KONDO, F ;

IKAI, Y ;

OKA, H ;

ISHIKAWA, N ;

WATANABE, MF ;

WATANABE, M ;

HARADA, KI ;

SUZUKI, M .

TOXICON, 1992, 30 (03) :227-237

[8] CYANOVIRIDIN-RR, A TOXIN FROM THE CYANOBACTERIUM (BLUE-GREEN-ALGA) MICROCYSTIS-VIRIDIS [J].

KUSUMI, T ;

OOI, T ;

WATANABE, MM ;

TAKAHASHI, H ;

KAKISAWA, H .

TETRAHEDRON LETTERS, 1987, 28 (40) :4695-4698

[9] ISOLATION AND IDENTIFICATION OF 8 MICROCYSTINS FROM 13 OSCILLATORIA-AGARDHII STRAINS AND STRUCTURE OF A NEW MICROCYSTIN [J].

LUUKKAINEN, R ;

SIVONEN, K ;

NAMIKOSHI, M ;

FARDIG, M ;

RINEHART, KL ;

NIEMELA, SI .

APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1993, 59 (07) :2204-2209

[10] STRUCTURE AND TOXICITY OF A PEPTIDE HEPATOTOXIN FROM THE CYANOBACTERIUM OSCILLATORIA-AGARDHII [J].

MERILUOTO, JAO ;

SANDSTROM, A ;

ERIKSSON, JE ;

REMAUD, G ;

CRAIG, AG ;

CHATTOPADHYAYA, J .

TOXICON, 1989, 27 (09) :1021-1034

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