Stelliferins J-N, isomalabaricane-type triterpenoids from Okinawan marine sponge Rhabdastrella cf. globostellata

被引:19
作者
Tanaka, Naonobu [1 ]
Momose, Rei [1 ]
Shibazaki, 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 2600856, Japan
[3] Western Australian Museum, Weishpool Dc, WA 6986, Australia
关键词
Rhabdastrella cf. globostellata; Triterpenoids; Isomalabaricane; Stelliferins J-N; ABSOLUTE-CONFIGURATIONS; JASPIS-STELLIFERA; DERIVATIVES;
D O I
10.1016/j.tet.2011.04.095
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Five new isomalabaricane-type triterpenoids, stelliferins J-N (1-5), were isolated from Okinawan marine sponge Rhabdastrella cf. globostellata. The structures of 1-5 were elucidated from the spectroscopic data and chemical means including application of a modified Mosher's method and an exciton chirality method. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:6689 / 6696
页数:8
相关论文
共 7 条
[1]   A METHOD FOR DETERMINING CHIRALITY OF 2 AROMATIC CHROMOPHORES AND ABSOLUTE CONFIGURATIONS OF CHROMOMYCIN A3 AND RELATED ANTIBIOTICS [J].
HARADA, N ;
NAKANISHI, K ;
TATSUOKA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1969, 91 (21) :5896-+
[2]   Cytotoxic Isomalabaricane Derivatives and a Monocyclic Triterpene Glycoside from the Sponge Rhabdastrella globostellata [J].
Hirashima, Miyabi ;
Tsuda, Kazuomi ;
Hamada, Toshiyuki ;
Okamura, Hiroaki ;
Furukawa, Tatsuhiko ;
Akiyama, Shin-ichi ;
Tajitsu, Yusuke ;
Ikeda, Ryuji ;
Komatsu, Masaharu ;
Doe, Matsumi ;
Morimoto, Yoshiki ;
Shiro, Motoo ;
van Soest, Rob W. M. ;
Takemura, Kaoru ;
Iwagawa, Tetsuo .
JOURNAL OF NATURAL PRODUCTS, 2010, 73 (09) :1512-1518
[3]   Jaspiferals A-G, new cytotoxic isomalabaricane-type nortriterpenoids from Okinawan marine sponge Jaspis stellifera [J].
Kobayashi, J ;
Yuasa, K ;
Kobayashi, T ;
Sasaki, T ;
Tsuda, M .
TETRAHEDRON, 1996, 52 (16) :5745-5750
[4]   Globostelletins A-I, cytotoxic isomalabaricane derivatives from the marine sponge Rhabdastrella globostellata [J].
Li, Jin ;
Xu, Bo ;
Cui, Jinrong ;
Deng, Zhiwei ;
de Voogd, Nicole J. ;
Proksch, Peter ;
Lin, Wenhan .
BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (13) :4639-4647
[5]   HIGH-FIELD FT NMR APPLICATION OF MOSHER METHOD - THE ABSOLUTE-CONFIGURATIONS OF MARINE TERPENOIDS [J].
OHTANI, I ;
KUSUMI, T ;
KASHMAN, Y ;
KAKISAWA, H .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (11) :4092-4096
[6]   Bioactive isomalabaricane triterpenes from the marine sponge Rhabdastrella globostellata [J].
Tasdemir, D ;
Mangalindan, GC ;
Concepción, GP ;
Verbitski, SM ;
Rabindran, S ;
Miranda, M ;
Greenstein, M ;
Hooper, JNA ;
Harper, MK ;
Ireland, CM .
JOURNAL OF NATURAL PRODUCTS, 2002, 65 (02) :210-214
[7]   STELLIFERINS A-F, NEW ANTINEOPLASTIC ISOMALABARICANE TRITERPENES FROM THE OKINAWAN MARINE SPONGE JASPIS-STELLIFERA [J].
TSUDA, M ;
ISHIBASHI, M ;
AGEMI, K ;
SASAKI, T ;
KOBAYASHI, J .
TETRAHEDRON, 1991, 47 (12-13) :2181-2194