Agelamadin F and tauroacidin E, bromopyrrole alkaloids from an Okinawan marine sponge Agelas sp.

被引:20
作者
Kusama, Taishi [1 ,2 ]
Tanaka, Naonobu [2 ]
Kashiwada, Yoshiki [2 ]
Kobayashi, Jun'ichi [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
关键词
Marine sponge; Agelas sp; Bromopyrrole alkaloid; Agelamadin F; Tauroacidin E; OROIDIN;
D O I
10.1016/j.tetlet.2015.05.114
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new structurally unique bromopyrrole alkaloid, agelamadin F (1), comprising oroidin and 3-hydroxypyridinium was isolated from an Okinawan marine sponge Agelas sp. together with tauroacidin E (2), a new bromopyrrole alkaloid possessing a taurine moiety. Six known bromopyrrole alkaloids, oroidin, tauroacidin A, sceptrin, ageliferin, nagelamide E, and agelongine were also isolated and identified. The structures of 1 and 2 were elucidated on the basis of spectroscopic evidences, while chiral HPLC analysis suggested tauroacidin E (2) to be a racemate. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:4502 / 4504
页数:3
相关论文
共 17 条
  • [1] Aiello A., 2008, Modern alkaloids structure, isolation, synthesis and biology by, P271, DOI [10.1002/9783527621071.ch10, DOI 10.1002/9783527621071.CH10]
  • [2] Biosynthesis, asymmetric synthesis, and pharmacology, including cellular targets, of the pyrrole-2-aminoimidazole marine alkaloids
    Al-Mourabit, Ali
    Zancanella, Manuel A.
    Tilvi, Supriya
    Romo, Daniel
    [J]. NATURAL PRODUCT REPORTS, 2011, 28 (07) : 1229 - 1260
  • [3] Blunt JW, 2014, NAT PROD REP, V31, P160, DOI [10.1039/c7np00052a, 10.1039/c3np70117d]
  • [4] A NOVEL BROMOPYRROLE ALKALOID FROM THE SPONGE AGELAS-LONGISSIMA WITH ANTISEROTONERGIC ACTIVITY
    CAFIERI, F
    FATTORUSSO, E
    MANGONI, A
    TAGLIALATELASCAFATI, O
    CARNUCCIO, R
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1995, 5 (08) : 799 - 804
  • [5] Nagelamides A-H, new dimeric bromopyrrole alkaloids from marine sponge Agelas species
    Endo, T
    Tsuda, M
    Okada, T
    Mitsuhashi, S
    Shima, H
    Kikuchi, K
    Mikami, Y
    Fromont, J
    Kobayashi, J
    [J]. JOURNAL OF NATURAL PRODUCTS, 2004, 67 (08): : 1262 - 1267
  • [6] NEW BROMO-PYRROLE DERIVATIVES FROM SPONGE AGELAS-OROIDES
    FORENZA, S
    MINALE, L
    RICCIO, R
    [J]. JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1971, (18): : 1129 - &
  • [7] A Submarine Journey: The Pyrrole-Imidazole Alkaloids
    Forte, Barbara
    Malgesini, Beatrice
    Piutti, Claudia
    Quartieri, Francesca
    Scolaro, Alessandra
    Papeo, Gianluca
    [J]. MARINE DRUGS, 2009, 7 (04) : 705 - 753
  • [8] REINVESTIGATION INTO STRUCTURE OF OROIDIN, A BROMOPYRROLE DERIVATIVE FROM MARINE SPONGE
    GARCIA, EE
    BENJAMIN, LE
    FRYER, RI
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1973, (03) : 78 - 79
  • [9] Tauroacidins A and B, new bromopyrrole alkaloids possessing a taurine residue from Hymeniacidon sponge
    Kobayashi, J
    Inaba, K
    Tsuda, M
    [J]. TETRAHEDRON, 1997, 53 (49) : 16679 - 16682
  • [10] AGELIFERINS, POTENT ACTOMYOSIN ATPASE ACTIVATORS FROM THE OKINAWAN MARINE SPONGE AGELAS SP
    KOBAYASHI, J
    TSUDA, M
    MURAYAMA, T
    NAKAMURA, H
    OHIZUMI, Y
    ISHIBASHI, M
    IWAMURA, M
    OHTA, T
    NOZOE, S
    [J]. TETRAHEDRON, 1990, 46 (16) : 5579 - 5586