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

页码：9564 / 9570

页数：7

共 50 条

[31] The haliclonacyclamines, cytotoxic tertiary alkaloids from the tropical marine sponge Haliclona sp.
Clark, RJ
Field, KL
Charan, RD
Garson, MJ
Brereton, IM
Willis, AC
TETRAHEDRON, 1998, 54 (30) : 8811 - 8826
[32] Yaku'amides A and B, Cytotoxic Linear Peptides Rich in Dehydroamino Acids from the Marine Sponge Ceratopsion sp.
Ueoka, Reiko
Ise, Yuji
Ohtsuka, Susumu
Okada, Shigeru
Yamori, Takao
Matsunaga, Shigeki
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (50) : 17692 - 17694
[33] Cytotoxic Sesterterpenoids from a Sponge Hippospongia sp.
Chang, Yu-Chia
Tseng, Shang-Wei
Liu, Li-Lian
Chou, Yalan
Ho, Yuan-Shing
Lu, Mei-Chin
Su, Jui-Hsin
MARINE DRUGS, 2012, 10 (05) : 987 - 997
[34] Three new acetylenes from the Palauan sponge Haliclona sp.
Williams, DH
Faulkner, DJ
JOURNAL OF NATURAL PRODUCTS, 1996, 59 (11): : 1099 - 1101
[35] Cytotoxic polyacetylenes related to petroformyne-1 from the marine sponge Petrosia sp.
Ueoka, Reiko
Ise, Yuji
Matsunaga, Shigeki
TETRAHEDRON, 2009, 65 (27) : 5204 - 5208
[36] 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
[37] Cytotoxic Psammaplysin Analogues from a Suberea sp. Marine Sponge and the Role of the Spirooxepinisoxazoline in Their Activity
Lee, Yeon-Ju
Han, Saem
Lee, Hyi-Seung
Kang, Jong Soon
Yun, Jieun
Sim, Chung J.
Shin, Hee Jae
Lee, Jong Seok
JOURNAL OF NATURAL PRODUCTS, 2013, 76 (09): : 1731 - 1736
[38] Anti-leishmanial and cytotoxic compounds isolated from marine sponge Hemimycale sp.
Said, Asmaa Abo Elgoud
Attia, Eman Zekry
Wanas, Amira S.
Samy, Mamdouh Nabil
Abdelmohsen, Usama Ramadan
Matsunami, Katsuyoshi
Fouad, Mostafa A.
NATURAL PRODUCT RESEARCH, 2024, 38 (20) : 3581 - 3587
[39] Renieramycin J, a highly cytotoxic tetrahydroisoquinoline alkaloid, from a marine sponge Neopetrosia sp.
Oku, N
Matsunaga, S
van Soest, RWM
Fusetani, N
JOURNAL OF NATURAL PRODUCTS, 2003, 66 (08): : 1136 - 1139
[40] Structure Elucidation and Cytotoxic Evaluation of New Polyacetylenes from a Marine Sponge Petrosia sp.
Juan, Yung-Shun
Lee, Chien-Chih
Tsao, Chia-Wei
Lu, Mei-Chin
El-Shazly, Mohamed
Shih, Huei-Chuan
Chen, Yu-Cheng
Wu, Yang-Chang
Su, Jui-Hsin
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES, 2014, 15 (09): : 16511 - 16521

← 1 2 3 4 5 →