Seco[D-Asp3]microcystin-RR and [D-Asp3,D-Glu(OMe)6]microcystin-RR, two new microcystins from a toxic water bloom of the cyanobacterium Planktothrix rubescens

被引:28
作者
Grach-Pogrebinsky, O
Sedmak, B
Carmeli, S [1 ]
机构
[1] Tel Aviv Univ, Sch Chem, Raymond & Beverly Sackler Fac Exact Sci, IL-69978 Tel Aviv, Israel
[2] Natl Inst Biol, Ljubljana 1001, Slovenia
来源
JOURNAL OF NATURAL PRODUCTS | 2004年 / 67卷 / 03期
关键词
D O I
10.1021/np034036r
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
Two novel microcystins, seco[D-Asp(3)]microcystin-RR (1) and [D-Asp(3),D-Glu(OMe)(6)]-microcystin-RR (2), along with the known [D-Asp(3)]microcystin-RR (3), were isolated from a Planktothrix rubescens toxic bloom collected in Lake Bled, Slovenia. The structures were deduced using one- and two-dimensional NMR techniques, ESIMS/CID/MS analysis, and Marfey's method for determining the amino acids' absolute stereochemistry. Compounds I and 3 exhibit weak PP1 inhibitory activity. The NMR data of compound 3 are reported here for the first time.
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收藏
页码:337 / 342
页数:6
相关论文
共 19 条
  • [11] ISOLATION AND IDENTIFICATION OF 8 MICROCYSTINS FROM 13 OSCILLATORIA-AGARDHII STRAINS AND STRUCTURE OF A NEW MICROCYSTIN
    LUUKKAINEN, R
    SIVONEN, K
    NAMIKOSHI, M
    FARDIG, M
    RINEHART, KL
    NIEMELA, SI
    [J]. APPLIED AND ENVIRONMENTAL MICROBIOLOGY, 1993, 59 (07) : 2204 - 2209
  • [12] DETERMINATION OF D-AMINO ACIDS .2. USE OF A BIFUNCTIONAL REAGENT, 1,5-DIFLUORO-2,4-DINITROBENZENE
    MARFEY, P
    [J]. CARLSBERG RESEARCH COMMUNICATIONS, 1984, 49 (06) : 591 - 596
  • [13] STRUCTURE AND TOXICITY OF A PEPTIDE HEPATOTOXIN FROM THE CYANOBACTERIUM OSCILLATORIA-AGARDHII
    MERILUOTO, JAO
    SANDSTROM, A
    ERIKSSON, JE
    REMAUD, G
    CRAIG, AG
    CHATTOPADHYAYA, J
    [J]. TOXICON, 1989, 27 (09) : 1021 - 1034
  • [14] 2 NEW L-SERINE VARIANTS OF MICROCYSTINS-LR AND MICROCYSTINS-RR FROM ANABAENA SP STRAINS 202-A1 AND 202-A2
    NAMIKOSHI, M
    SIVONEN, K
    EVANS, WR
    CARMICHAEL, WW
    SUN, F
    ROUHIAINEN, L
    LUUKKAINEN, R
    RINEHART, KL
    [J]. TOXICON, 1992, 30 (11) : 1457 - 1464
  • [15] [D-Leu1] microcystin-LR, a new microcystin isolated from waterbloom in a Canadian prairie lake
    Park, H
    Namikoshi, M
    Brittain, SM
    Carmichael, WW
    Murphy, T
    [J]. TOXICON, 2001, 39 (06) : 855 - 862
  • [16] Two (Z)-dehydrobutyrine-containing microcystins from a hepatotoxic bloom of Oscillatoria agardhii from Soulseat Loch, Scotland
    Sano, T
    Beattie, KA
    Codd, GA
    Kaya, K
    [J]. JOURNAL OF NATURAL PRODUCTS, 1998, 61 (06): : 851 - 853
  • [17] A 2-AMINO-2-BUTENOIC ACID(DHB)-CONTAINING MICROCYSTIN ISOLATED FROM OSCILLATORIA-AGARDHII
    SANO, T
    KAYA, K
    [J]. TETRAHEDRON LETTERS, 1995, 36 (47) : 8603 - 8606
  • [18] Sedmak Bojan, 2002, Acta Biologica Slovenica, V45, P17
  • [19] 1892, ANN SCI NAT 7 BOT, V16, P204