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
[21]   A new thiodiketopiperzaine from the marine sponge Tedania sp. [J].
Zhang, Hua ;
Lai, Wei ;
Guan, Zhuo-Bin ;
Liao, Xiao-Jian ;
Zhao, Bing-Xin ;
Xu, Shi-Hai .
NATURAL PRODUCT RESEARCH, 2020, 34 (08) :1113-1117
[22]   Leiodermatolide, a Potent Antimitotic Macrolide from the Marine Sponge Leiodermatium sp. [J].
Paterson, Ian ;
Dalby, Stephen M. ;
Roberts, Jill C. ;
Naylor, Guy J. ;
Guzman, Esther A. ;
Isbrucker, Richard ;
Pitts, Tara P. ;
Linley, Pat ;
Divlianska, Daniela ;
Reed, John K. ;
Wright, Amy E. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (14) :3219-3223
[23]   Discorhabdins from the Korean Marine Sponge Sceptrella sp. [J].
Jeon, Ju-eun ;
Na, Zeyei ;
Lung, Misong ;
Lee, Hyi-Seung ;
Sim, Chung J. ;
Nahm, Keepyung ;
Oh, Ki-Bong ;
Shin, Jongheon .
JOURNAL OF NATURAL PRODUCTS, 2010, 73 (02) :258-262
[24]   Bromopyrrole Alkaloids from a Marine Sponge Agelas sp. [J].
Kusama, Taishi ;
Tanaka, Naonobu ;
Takahashi-Nakaguchi, Azusa ;
Gonoi, Tohru ;
Fromont, Jane ;
Kobayashi, Jun'ichi .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2014, 62 (05) :499-503
[25]   A New Cytotoxic Polyacetylenic Alcohol from a Sponge Callyspongia sp. [J].
Balansa, Walter ;
Trianto, Agus ;
de Voogd, Nicole J. ;
Tanaka, Junichi .
NATURAL PRODUCT COMMUNICATIONS, 2017, 12 (12) :1909-1911
[26]   Cyclic peroxides and analogs: Antibacterial, antimalarial, and cytotoxic marine products from Xisha sponge Diacarnus sp. [J].
Leng, Xue ;
He, Hongying ;
Lazaro, J. Enrico H. ;
Chen, Xiaohui ;
Ouyang, Han ;
Li, Te ;
Yan, Xia ;
He, Shan .
PHYTOCHEMISTRY, 2024, 223
[27]   On the assignment of the absolute configuration at the isolated methyl branch in miyakosyne A, cytotoxic linear acetylene, from the deep-sea marine sponge Petrosia sp. [J].
Hitora, Yuki ;
Takada, Kentaro ;
Matsunaga, Shigeki .
TETRAHEDRON, 2013, 69 (52) :11070-11073
[28]   The Lipid A Structure from the Marine Sponge Symbiont Endozoicomonas sp. HEX 311 [J].
Pallach, Mateusz ;
Di Lorenzo, Flaviana ;
Duda, Katarzyna A. ;
Le Pennec, Gael ;
Molinaro, Antonio ;
Silipo, Alba .
CHEMBIOCHEM, 2019, 20 (02) :230-236
[29]   Marine natural products .37. Aragusteroketals A and C, two novel cytotoxic steroids from a marine sponge of Xestospongia sp. [J].
Kobayashi, M ;
Chen, YJ ;
Higuchi, K ;
Aoki, S ;
Kitagawa, I .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1996, 44 (10) :1840-1842
[30]   New bromopyrrole alkaloids from the marine sponge Agelas sp. [J].
Sun, Ya-Ting ;
Lin, Bin ;
Li, Sheng-Ge ;
Liu, Man ;
Zhou, Yong Jun ;
Xu, Ying ;
Hua, Hui-Ming ;
Lin, Hou-Wen .
TETRAHEDRON, 2017, 73 (19) :2786-2792
12345