Modified peptides from a water bloom of the cyanobacterium Nostoc sp.

被引:53
作者
Ploutno, A [1 ]
Carmeli, S [1 ]
机构
[1] Tel Aviv Univ, Sch Chem, Raymond & Beverly Sackler Fac Exact Sci, IL-69978 Tel Aviv, Israel
关键词
cyanobacteria; Nostoc; protease inhibitors; cyclichexapeptides;
D O I
10.1016/S0040-4020(02)01326-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Six new metabilites, nostopeptin BN920 (1), nostoginin BN741 (2), nostoginin BN578 (3), banyascyclamide A (4) banyascyclamide B (5) and banyascyclamide C (6), were isolated from the hydrophilic extract of a Nostoc sp. The planar structure of compounds 1-6 was determined by homonuclear and inverse-heteronuclear 2D NMR techniques as well as high-resolution mass spectrometry. The absolute configuration of the asymmetric centers was studied using Marfey's method for HPLC. Compound 1 inhibits the serine-protease chymotrypsin while compound 2 inhibits amino-proteases. (C) 2002 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:9949 / 9957
页数:9
相关论文
共 27 条
  • [11] A novel extracellular diterpenoid with antibacterial activity from the cyanobacterium Nostoc commune
    Jaki, B
    Orjala, J
    Sticher, O
    [J]. JOURNAL OF NATURAL PRODUCTS, 1999, 62 (03): : 502 - 503
  • [12] Novel extracellular diterpenoids with biological activity from the cyanobacterium Nostoc commune
    Jaki, B
    Orjala, J
    Heilmann, J
    Linden, A
    Vogler, B
    Sticher, O
    [J]. JOURNAL OF NATURAL PRODUCTS, 2000, 63 (03): : 339 - 343
  • [13] Nostocyclamide M:: a cyanobacterial cyclic peptide with allelopathic activity from Nostoc 31
    Jüttner, F
    Todorova, AK
    Walch, N
    von Philipsborn, W
    [J]. PHYTOCHEMISTRY, 2001, 57 (04) : 613 - 619
  • [14] KNUBEL G, 1990, J ANTIBIOT, V43, P1236
  • [15] 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
  • [16] TOTAL SYNTHESIS OF MICROGININ, AN ANGIOTENSIN-CONVERTING ENZYME-INHIBITORY PENTAPEPTIDE FROM THE BLUE-GREEN-ALGA MICROCYSTIS-AERUGINOSA
    MATSUURA, F
    HAMADA, Y
    SHIOIRI, T
    [J]. TETRAHEDRON, 1994, 50 (38) : 11303 - 11314
  • [17] Microviridins, elastase inhibitors from the cyanobacterium Nostoc minutum (NIES-26)
    Murakami, M
    Sun, Q
    Ishida, K
    Matsuda, H
    Okino, T
    Yamaguchi, K
    [J]. PHYTOCHEMISTRY, 1997, 45 (06) : 1197 - 1202
  • [18] MUSCORIDE-A - A NEW OXAZOLE PEPTIDE ALKALOID FROM FRESH-WATER CYANOBACTERIUM NOSTOC-MUSCORUM
    NAGATSU, A
    KAJITANI, H
    SAKAKIBARA, J
    [J]. TETRAHEDRON LETTERS, 1995, 36 (23) : 4097 - 4100
  • [19] STRUCTURES OF 3 NEW CYCLIC HEPTAPEPTIDE HEPATOTOXINS PRODUCED BY THE CYANOBACTERIUM (BLUE-GREEN-ALGA) NOSTOC SP STRAIN 152
    NAMIKOSHI, M
    RINEHART, KL
    SAKAI, R
    SIVONEN, K
    CARMICHAEL, WW
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (25) : 6135 - 6139
  • [20] Nostopeptins A and B, elastase inhibitors from the cyanobacterium Nostoc minutum
    Okino, T
    Qi, S
    Matsuda, H
    Murakami, M
    Yamaguchi, K
    [J]. JOURNAL OF NATURAL PRODUCTS, 1997, 60 (02): : 158 - 161