Croissamide, a proline-rich cyclic peptide with an N-prenylated tryptophan from a marine cyanobacterium Symploca sp.

被引:16
|
作者
Iwasaki, Keitaro [1 ]
Iwasaki, Arihiro [1 ]
Sumimoto, Shimpei [1 ]
Sano, Takuya [2 ]
Hitomi, Yuki [2 ]
Ohno, Osamu [2 ]
Suenaga, Kiyotake [1 ]
机构
[1] Keio Univ, Dept Chem, Kohoku Ku, 3-14-1 Hiyoshi, Yokohama, Kanagawa 2238522, Japan
[2] Kogakuin Univ, Dept Chem & Life Sci, 2665-1 Nakano, Hachioji, Tokyo 1920015, Japan
关键词
Croissamide; Marine cyanobacteria; Cyclic peptide; Proline-rich; Symploca; DIDEMNUM-MOLLE; SPONGE; HEXAPEPTIDE; METABOLITE; TRUNKAMIDE; CARTERI;
D O I
10.1016/j.tetlet.2018.09.016
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Croissamide, a proline-rich cyclic peptide that contains an N-prenylated tryptophan, was isolated from a marine cyanobacterium Symploca sp. Its gross structure was determined by spectroscopic analyses, and the absolute configuration was established based on chiral HPLC analyses of acid hydrolysates. (C) 2018 Elsevier Ltd. All rights reserved.
引用
收藏
页码:3806 / 3809
页数:4
相关论文
共 49 条
  • [21] Largamides A-H, unusual cyclic peptides from the marine cyanobacterium Oscillatoria sp.
    Plaza, Alberto
    Bewley, Carole A.
    JOURNAL OF ORGANIC CHEMISTRY, 2006, 71 (18): : 6898 - 6907
  • [22] Axinellin C, a proline-rich cyclic octapeptide isolated from the Fijian marine sponge Stylotella aurantium
    Tabudravu, JN
    Morris, LA
    den Bosch, JJK
    Jaspars, M
    TETRAHEDRON, 2002, 58 (39) : 7863 - 7868
  • [23] Benderamide A, a Cyclic Depsipeptide from a Singapore Collection of Marine Cyanobacterium cf. Lyngbya sp.
    Ding, Chi Ying Gary
    Ong, Ji Fa Marshall
    Goh, Hui Chin
    Coffill, Cynthia R.
    Tan, Lik Tong
    MARINE DRUGS, 2018, 16 (11):
  • [24] Schizopeptin 791, a new anabeanopeptim-like cyclic peptide from the cyanobacterium Schizothrix sp.
    Reshef, V
    Carmeli, S
    JOURNAL OF NATURAL PRODUCTS, 2002, 65 (08): : 1187 - 1189
  • [25] Wainunuamide, a histidine-containing proline-rich cyclic heptapeptide isolated from the Fijian marine sponge Stylotella aurantium
    Tabudravu, J
    Morris, LA
    Kettenes-van den Bosch, JJ
    Jaspars, M
    TETRAHEDRON LETTERS, 2001, 42 (52) : 9273 - 9276
  • [26] Total synthesis and cyclization strategy of samoamide A, a cytotoxic cyclic octapeptide rich in proline and phenlalanine isolated from marine cyanobacterium
    Chang, Qi
    Li, Yu-Lei
    Zhao, Xia
    JOURNAL OF ASIAN NATURAL PRODUCTS RESEARCH, 2019, 21 (02) : 171 - 177
  • [27] Bisebromoamide, a Potent Cytotoxic Peptide from the Marine Cyanobacterium Lyngbya sp.: Isolation, Stereostructure, and Biological Activity
    Teruya, Toshiaki
    Sasaki, Hiroaki
    Fukazawa, Hidesuke
    Suenaga, Kiyotake
    ORGANIC LETTERS, 2009, 11 (21) : 5062 - 5065
  • [28] Structure and activity of largazole, a potent anti-proliferative agent from the Floridian marine cyanobacterium Symploca sp. (vol 130, pg 1806, 2008)
    Taori, Kanchan
    Paul, Valerie J.
    Luesch, Hendrik
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (40) : 13506 - 13506
  • [29] Aciculitin D, a cytotoxic heterodetic cyclic peptide from a Poecillastra sp. marine sponge
    Sugawara, Kenji
    Kanki, Daichi
    Watanabe, Ryuichi
    Matsushima, Ryoji
    Ise, Yuji
    Yokose, Hisayoshi
    Morii, Yasuhiro
    Yamawaki, Nobuhiro
    Ninomiya, Akihiro
    Okada, Shigeru
    Matsunaga, Shigeki
    TETRAHEDRON, 2022, 119
  • [30] Heptavalinamide A, an Extensively N-Methylated Linear Nonapeptide from a Cyanobacterium Symploca sp. and Development of a Highly Sensitive Analysis of N,N-Dimethylvaline by LCMS
    Suo, Rei
    Watanabe, Ryuichi
    Takada, Kentaro
    Suzuki, Toshiyuki
    Oikawa, Hiroshi
    Itoi, Shiro
    Sugita, Haruo
    Matsunaga, Shigeki
    ORGANIC LETTERS, 2020, 22 (04) : 1254 - 1258