11-and 4′-Epimers of Chaetomugilin A, Novel Cytostatic Metabolites from Marine Fish-Derived Fungus Chaetomium globosum

被引：28

作者：

Muroga, Yasuhide ^{[1
]}

Yamada, Takeshi ^{[1
]}

Numata, Atsushi ^{[1
]}

Tanaka, Reiko ^{[1
]}

机构：

[1] Osaka Univ Pharmaceut Sci, Osaka 5691094, Japan

来源：

HELVETICA CHIMICA ACTA | 2010年 / 93卷 / 03期

关键词：

CELL-ADHESION INHIBITORS; ABSOLUTE STEREOSTRUCTURES; AZAPHILONES;

D O I：

10.1002/hlca.200900272

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

11- and 4'-epichaetomugilin A were isolated from a strain of Chaetomium globosum that was originally isolated from the marine fish Mugil cephalus 11-Epichaetomugilin A is the first compound to have an opposite absolute configuration at C(11) to that of other azaphilones isolated to date. Their absolute configurations were elucidated on the basis of spectroscopic analyses, including 1D- and 2D-NMR techniques, and some chemical transformations. 11-Epichaetomugilin A weakly inhibited the growth of cultured P388 cells and HL-60 cells (IC50 88.9 and 66.7 mu M resp.).

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收藏

页码：542 / 549

页数：8

相关论文

共 17 条

[1] CHEMISTRY OF FUNGI .64. STRUCTURE OF MONASCIN - RELATIVE STEREOCHEMISTRY OF AZAPHILONES [J].

CHEN, FC ;

MANCHAND, PS ;

WHALLEY, WB .

JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1971, (21) :3577-&

[2] Cytotoxic cytochalasans from a Penicillium species separated from a marine alga [J].

Iwamoto, C ;

Yamada, T ;

Ito, Y ;

Minoura, K ;

Numata, A .

TETRAHEDRON, 2001, 57 (15) :2997-3004

[3] New brominated and halogen-less derivatives and structure-activity relationship of azaphilones inhibiting gp120-CD4 binding [J].

Matsuzaki, K ;

Takara, H ;

Inokoshi, J ;

Tanaka, H ;

Masuma, R ;

Omura, S .

JOURNAL OF ANTIBIOTICS, 1998, 51 (11) :1004-1011

[4] 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

[5] Cohaerins C-F, four azaphilones from the xylariaceous fungus Annulohypoxylon cohaerens [J].

Quang, Dang Ngoc ;

Stadler, Marc ;

Fournier, Jacques ;

Tomita, Ayumi ;

Hashimoto, Toshihiro .

TETRAHEDRON, 2006, 62 (26) :6349-6354

[6] STRUCTURE OF DIHYDRODEOXY-8-EPI-AUSTDIOL AND ABSOLUTE-CONFIGURATION OF AZAPHILONES [J].

STEYN, PS ;

VLEGGAAR, R .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (02) :204-206

[7] 4 NEW AZAPHILONES FROM CHAETOMIUM-GLOBOSUM VAR FLAVO-VIRIDAE [J].

TAKAHASHI, M ;

KOYAMA, K ;

NATORI, S .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (03) :625-628

[8] RP-1551s, a family of azaphilones produced by Penicillium sp., inhibit the binding of PDGF to the extracellular domain of its receptor [J].

Toki, S ;

Tanaka, T ;

Uosaki, Y ;

Yoshida, M ;

Suzuki, Y ;

Kita, K ;

Mihara, A ;

Ando, K ;

Lokker, NA ;

Giese, NA ;

Matsuda, Y .

JOURNAL OF ANTIBIOTICS, 1999, 52 (03) :235-244

[9] Peribysins A-D, potent cell-adhesion inhibitors from a sea hare-derived culture of Periconia species [J].

Yamada, T ;

Iritani, M ;

Minoura, K ;

Kawai, K ;

Numata, A .

ORGANIC & BIOMOLECULAR CHEMISTRY, 2004, 2 (14) :2131-2135

[10] Absolute stereostructures of cell-adhesion inhibitors, macrosphelides C, E-G and I, produced by a Periconia species separated from an Aplysia sea hare [J].

Yamada, T ;

Iritani, M ;

Doi, M ;

Minoura, K ;

Ito, T ;

Numata, A .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2001, (22) :3046-3053