Three new oxylipins from an Okinawan marine sponge Plakortis sp.

被引:5
作者
Tanaka, Naonobu [1 ,2 ]
Asai, Miki [1 ]
Kusama, Taishi [1 ]
Fromont, Jane [3 ]
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
[3] Western Australian Museum, Welshpool Dc, WA 6986, Australia
关键词
Marine sponge; Plakortis sp; Oxylipin; Manzamenone P; FATTY-ACID DERIVATIVES; MANZAMENONES;
D O I
10.1016/j.tetlet.2015.01.137
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Three new oxylipins, manzamenone P (1), 6'-O-methylmanzamenone K (2), and 6'-O-ethylmanzamenone K (3), were isolated from an Okinawan marine sponge Plakortis sp. Manzamenone P (1) is a unique oxylipin possessing two long acyl chains and a novel core unit consisting of spiro-bonded cyclohexanone and beta-keto-gamma-lactone rings. The structures of 1-3 were elucidated on the basis of spectroscopic evidences including 2D NMR and FABMS/MS spectra as well as a comparison of DFT calculated NMR data with those experimental data. (C) 2015 Elsevier Ltd. All rights reserved.
引用
收藏
页码:1388 / 1391
页数:4
相关论文
共 15 条
[1]  
Blunt JW, 2014, NAT PROD REP, V31, P160, DOI [10.1039/c7np00052a, 10.1039/c3np70117d]
[2]  
Frisch M. J., 2010, GAUSSIAN 09 REVISION
[3]   UNTENONE-A, A NEW CYCLOPENTENONE FROM THE OKINAWAN MARINE SPONGE PLAKORTIS SP CORRESPONDING TO THE DIENOPHILE IN THE BIOSYNTHESIS OF MANZAMENONES [J].
ISHIBASHI, M ;
TAKEUCHI, S ;
KOBAYASHI, J .
TETRAHEDRON LETTERS, 1993, 34 (23) :3749-3750
[4]   Untenolide A, a new polyketide from an Okinawan marine sponge Plakortis sp. [J].
Ishiguro, Yuichiro ;
Kubota, Takaaki ;
Fromont, Jane ;
Shiro, Motoo ;
Kobayashi, Jun'ichi .
TETRAHEDRON LETTERS, 2010, 51 (31) :4023-4026
[5]   Plakoridine C, a novel piperidine alkaloid from an Okinawan marine sponge Plakortis sp. [J].
Ishiguro, Yuichiro ;
Kubota, Takaaki ;
Ishiuchi, Kan'ichiro ;
Fromont, Jane ;
Kobayashi, Jun'ichi .
TETRAHEDRON LETTERS, 2009, 50 (26) :3202-3204
[6]   MANZAMENONES-G AND H, NEW DIMERIC FATTY-ACID DERIVATIVES FROM THE OKINAWAN MARINE SPONGE PLAKORTIS SP [J].
KOBAYASHI, J ;
TSUKAMOTO, S ;
TAKEUCHI, S ;
ISHIBASHI, M .
TETRAHEDRON, 1993, 49 (27) :5955-5960
[7]   Manzamenones L-N, new dimeric fatty-acid derivatives from an Okinawan marine sponge Plakortis sp. [J].
Kubota, Takaaki ;
Ishiguro, Yuichiro ;
Takahashi-Nakaguchi, Azusa ;
Fromont, Jane ;
Gonoi, Tohru ;
Kobayashi, Jun'ichi .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2013, 23 (01) :244-247
[8]   PLATISIDINES A-C, N-METHYLPYRIDINIUM ALKALOIDS FROM AN OKINAWAN MARINE SPONGE OF PLAKORTIS SPECIES [J].
Kubota, Takaaki ;
Ishiguro, Yuichiro ;
Yamamoto, Sunao ;
Fromont, Jane ;
Kobayashi, Jun'ichi .
HETEROCYCLES, 2010, 80 (02) :1407-1412
[9]  
Rahm F, 2004, HETEROCYCLES, V64, P523
[10]   A Multi-standard Approach for GIAO 13C NMR Calculations [J].
Sarotti, Ariel M. ;
Pellegrinet, Silvina C. .
JOURNAL OF ORGANIC CHEMISTRY, 2009, 74 (19) :7254-7260