HALICHONADINS M-Q, SESQUITERPENES FROM AN OKINAWAN MARINE SPONGE HALICHONDRIA SP.

被引:11
作者
Tanaka, Naonobu [1 ]
Suto, Shohei [1 ]
Asai, Miki [1 ]
Kusama, Taishi [1 ]
Takahashi-Nakaguchi, Azusa [2 ]
Gonoi, Tohru [2 ]
Fromont, Jane [3 ]
Kobayashi, Jun'ichi [1 ]
机构
[1] Hokkaido Univ, Grad Sch Pharmaceut Sci, Sapporo, Hokkaido 0600812, Japan
[2] Chiba Univ, Med Mycol Res Ctr, Chiba 2608673, Japan
[3] Western Australian Museum, Welshpool Dc, WA 6986, Australia
关键词
Marine Sponge; Helichondria sp; Sesquiterpene; Halichonadins M-Q; NATURAL-PRODUCTS;
D O I
10.3987/COM-14-S(K)2
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Four new dimeric sesquiterpenes, halichonadins M-P (1-4), and one new sesquiterpene, halichonadin Q (5), were isolated from an Okinawan marine sponge Halichondria sp. The sesquiterpenes have eudesmane skeleton in common Halichonadin M (1) is a symmetrical dimer linked to a nitrilotriacetic acid fragment through amide bonds. Halichonadin N (2) is a structurally unique dimeric sesquiterpene connected via a pyrrolidine unit, while halichonadins 0 (3) and P (4) have linker moieties consisting of a piperidine unit. Halichonadin Q (5) is a sesquiterpene possessing a pyrrolidine unit. The structures of 1-5 were elucidated by spectroscopic analysis. Halichonadin 0 (3) showed antimicrobial activity against Staphylococcus aureus, Micrococcus luteus, and Trichophyton mentagrophytes.
引用
收藏
页码:173 / 185
页数:13
相关论文
共 50 条
  • [41] Cytotoxic linear acetylenes from a marine sponge Pleroma sp.
    Takanashi, Emi
    Takada, Kentaro
    Hashimoto, Masahiro
    Itoh, Yoshiyuki
    Ise, Yuji
    Ohtsuka, Susumu
    Okada, Shigeru
    Matsunaga, Shigeki
    TETRAHEDRON, 2015, 71 (51) : 9564 - 9570
  • [42] New Bioactive Polyacetylenes from the Marine Sponge Petrosia sp.
    Liu, Xin-Lian
    Ding, Ya-Fang
    Wang, Shu-Ping
    Liu, Li
    Wang, Jie
    Yang, Fan
    CHEMISTRY & BIODIVERSITY, 2022, 19 (06)
  • [43] New Sterol Derivatives from the Marine Sponge Xestospongia sp.
    Cheng, Zhongbin
    Liu, Dong
    de Voogd, Nicole J.
    Proksch, Peter
    Lin, Wenhan
    HELVETICA CHIMICA ACTA, 2016, 99 (08) : 588 - 596
  • [44] New Nitrogenous Bisabolene-Type Sesquiterpenes from a Formosan Sponge Axinyssa sp.
    Liu, Wangta
    Liang, Kai-Ju
    Chiang, Ching-Ying
    Lu, Mei-Chin
    Su, Jui-Hsin
    CHEMICAL & PHARMACEUTICAL BULLETIN, 2014, 62 (04) : 392 - 394
  • [45] Bisabolane type sesquiterpenes from a marine Didiscus sponge
    Tasdemir, D
    Bugni, TS
    Mangalindan, GC
    Concepción, GP
    Harper, MK
    Ireland, DM
    TURKISH JOURNAL OF CHEMISTRY, 2003, 27 (02): : 273 - 279
  • [46] Brevibacterium spongiae sp. nov., isolated from marine sponge Hymeniacidon sp
    Zhang, Mimi
    Song, Qianqian
    Sang, Jin
    Li, Zhiyong
    INTERNATIONAL JOURNAL OF SYSTEMATIC AND EVOLUTIONARY MICROBIOLOGY, 2023, 73 (05)
  • [47] Sesquiterpenes from the Vietnamese Marine Sponge Dysidea fragilis
    Nguyen Thi Cue
    Hoang Le Tuan Anh
    Dan Thi Thuy Hang
    Nguyen Xuan Nhiem
    Nguyen Hai Dang
    Nguyen Hoai Nam
    Pham Hai Yen
    Do Cong Thung
    Vu Kim Thu
    Chau Van Minh
    Phan Van Kiem
    NATURAL PRODUCT COMMUNICATIONS, 2015, 10 (08) : 1341 - 1342
  • [48] Clionaterpene, a New Cadinene Sesquiterpene from the Marine Sponge Cliona sp.
    Zhou, Ying
    Liang, Huixian
    Wang, Zhaocong
    Liao, Xiaojian
    Xu, Shihai
    Zhao, Bingxin
    JOURNAL OF MARINE SCIENCE AND ENGINEERING, 2023, 11 (01)
  • [49] Diversity of culturable actinobacteria isolated from marine sponge Haliclona sp.
    Shumei Jiang
    Wei Sun
    Minjie Chen
    Shikun Dai
    Long Zhang
    Yonghong Liu
    Kyung Jin Lee
    Xiang Li
    Antonie van Leeuwenhoek, 2007, 92 : 405 - 416
  • [50] Antimalarial Activity of Pyrroloiminoquinones from the Australian Marine Sponge Zyzzya sp.
    Davis, Rohan A.
    Buchanan, Malcolm S.
    Duffy, Sandra
    Avery, Vicky M.
    Charman, Susan A.
    Charman, William N.
    White, Karen L.
    Shackleford, David M.
    Edstein, Michael D.
    Andrews, Katherine T.
    Camp, David
    Quinn, Ronald J.
    JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (12) : 5851 - 5858