Cytotoxic linear acetylenes from a marine sponge Pleroma sp.

被引：5
|
作者：
Takanashi, Emi [1 ]
Takada, Kentaro [1 ]
Hashimoto, Masahiro [2 ]
Itoh, Yoshiyuki [2 ]
Ise, Yuji [3 ]
Ohtsuka, Susumu [4 ]
Okada, Shigeru [1 ]
Matsunaga, Shigeki [1 ]
机构：
[1] Univ Tokyo, Grad Sch Agr & Life Sci, Lab Aquat Nat Prod Chem, Bunkyo Ku, Tokyo 1138657, Japan
[2] Japan JEOL Ltd, Akishima, Tokyo 1968558, Japan
[3] Nagoya Univ, Sugashima Marine Biol Lab, Toba, Mie 5170004, Japan
[4] Hiroshima Univ, Takehara Marine Sci Stn, Takehara, Hiroshima 7250024, Japan
来源：
TETRAHEDRON | 2015年 / 71卷 / 51期
关键词：
Sponge; Cytotoxic; Linear acetylene; Structure elucidation; ABSOLUTE-CONFIGURATION; NATURAL-PRODUCTS; A-F; POLYACETYLENES; MIYAKOSYNE;
D O I：
10.1016/j.tet.2015.10.062
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Bioassay-guided fractionation of the extract of the rare deep-sea marine sponge Pleroma sp. afforded seven new linear acetylenes, yakushynols A-F (1-6) and neopetroformyne E (7). The structures of 1-7 were determined by a combination of the analysis of spectroscopic data and chemical derivatization. Compounds 1-6 are the first examples of the sponge-derived acetylenes of the size of duryne with oxidation at the sixth carbon from the terminus. Compounds 1-5 and 7 exhibited moderate cytotoxic activity. A biosynthetic route of neopetroformyne A was inferred from the structural transition among sponge-derived linear acetylenes. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9564 / 9570
页数：7
相关论文
共 50 条
  • [1] (-)-Duryne and Its Homologues, Cytotoxic Acetylenes from a Marine Sponge Petrosia sp.
    Hitora, Yuki
    Takada, Kentaro
    Okada, Shigeru
    Ise, Yuji
    Matsunaga, Shigeki
    JOURNAL OF NATURAL PRODUCTS, 2011, 74 (05): : 1262 - 1267
  • [2] Miyakosynes A-F, cytotoxic methyl branched acetylenes from a marine sponge Petrosia sp.
    Hitora, Yuki
    Takada, Kentaro
    Okada, Shigeru
    Matsunaga, Shigeki
    TETRAHEDRON, 2011, 67 (25) : 4530 - 4534
  • [3] Cytotoxic alkaloids from the marine sponge Thorectandra sp.
    Charan, RD
    Mckee, TC
    Boyd, MR
    NATURAL PRODUCT RESEARCH, 2004, 18 (03) : 225 - 229
  • [4] Cytotoxic polyacetylenes from the marine sponge Petrosia sp.
    Kim, JS
    Lim, YJ
    Im, KS
    Jung, JH
    Shim, CJ
    Lee, CO
    Hong, J
    Lee, H
    JOURNAL OF NATURAL PRODUCTS, 1999, 62 (04): : 554 - 559
  • [5] Cytotoxic oxylipins from a marine sponge Topsentia sp.
    Luo, X
    Li, FM
    Hong, JK
    Lee, CO
    Sim, CJ
    Im, KS
    Jung, JH
    JOURNAL OF NATURAL PRODUCTS, 2006, 69 (04): : 567 - 571
  • [6] Cytotoxic Petrosiacetylenes from the Marine Sponge Petrosia sp.
    Lee, Yeon-Ju
    Yoo, Su-Jung
    Kang, Jong Soon
    Yun, Jieun
    Shin, Hee Jae
    Lee, Jong Seok
    Lee, Hyi-Seung
    LIPIDS, 2013, 48 (01) : 87 - 91
  • [7] Cytotoxic furanosesterterpenes from a marine sponge Psammocinia sp.
    Choi, K
    Hong, JK
    Lee, CO
    Kim, DK
    Sim, CJ
    Im, KS
    Jung, JH
    JOURNAL OF NATURAL PRODUCTS, 2004, 67 (07): : 1186 - 1189
  • [8] Callyspongiolide, a Cytotoxic Macrolide from the Marine Sponge Callyspongia sp.
    Cong-Dat Pham
    Hartmann, Rudolf
    Boehler, Philip
    Stork, Bjoern
    Wesselborg, Sebastian
    Lin, Wenhan
    Lai, Daowan
    Proksch, Peter
    ORGANIC LETTERS, 2014, 16 (01) : 266 - 269
  • [9] Cytotoxic Sesterterpenoids Isolated from the Marine Sponge Scalarispongia sp.
    Lee, Yeon-Ju
    Lee, Jeong-Woo
    Lee, Dong-Geun
    Lee, Hyi-Seung
    Kang, Jong Soon
    Yun, Jieun
    INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2014, 15 (11): : 20045 - 20053
  • [10] New cytotoxic metabolites from a marine sponge Homaxinella sp.
    Mansoor, TA
    Hong, J
    Lee, CO
    Sim, CJ
    Im, KS
    Lee, DS
    Jung, JH
    JOURNAL OF NATURAL PRODUCTS, 2004, 67 (04): : 721 - 724
12345