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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页码：337 / 342
页数：6
相关论文
共 19 条
  • [1] ANAGNOSTIDIS K, 1988, Archiv fuer Hydrobiologie Supplement, V80, P327
  • [2] ANAGNOSTIDIS K, 1988, Archiv fuer Hydrobiologie Supplement, V80, P1
  • [3] High grazer toxicity of [D-Asp3 (E)-Dhb7]microcystin-RR of Planktothrix rubescens as compared to different microcystins
    Blom, JF
    Robinson, JA
    Jüttner, F
    [J]. TOXICON, 2001, 39 (12) : 1923 - 1932
  • [4] MICROCYSTIN-LIKE TOXINS IN DIFFERENT FRESH-WATER SPECIES OF OSCILLATORIA
    BRUNO, M
    GUCCI, PMB
    PIERDOMINICI, E
    SESTILI, P
    IOPPOLO, A
    SECHI, N
    VOLTERRA, L
    [J]. TOXICON, 1992, 30 (10) : 1307 - 1311
  • [5] Carmichael WW, 1997, ADV BOT RES, V27, P211
  • [6] ISOLATION OF LINEAR PEPTIDES RELATED TO THE HEPATOTOXINS NODULARIN AND MICROCYSTINS
    CHOI, BW
    NAMIKOSHI, M
    SUN, FR
    RINEHART, KL
    CARMICHAEL, WW
    KAUP, AM
    EVANS, WR
    BEASLEY, VR
    [J]. TETRAHEDRON LETTERS, 1993, 34 (49) : 7881 - 7884
  • [7] Falconer IR, 1999, ENVIRON TOXICOL, V14, P5, DOI 10.1002/(SICI)1522-7278(199902)14:1<5::AID-TOX3>3.3.CO
  • [8] 2-S
  • [9] Protease inhibitors from a Slovenian Lake Bled toxic waterbloom of the cyanobacterium Planktothrix rubescens
    Grach-Pogrebinsky, O
    Sedmak, B
    Carmeli, S
    [J]. TETRAHEDRON, 2003, 59 (42) : 8329 - 8336
  • [10] Comparison of protein phosphatase inhibitory activity and apparent toxicity of microcystins and related compounds
    Ito, E
    Takai, A
    Kondo, F
    Masui, H
    Imanishi, S
    Harada, K
    [J]. TOXICON, 2002, 40 (07) : 1017 - 1025
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