Sorbicillin analogues and related dimeric compounds from Penicillium notatum

被引:75
作者
Maskey, RP
Grün-Wollny, I
Laatsch, H
机构
[1] Univ Gottingen, Dept Organ & Biomol Chem, D-37077 Gottingen, Germany
[2] Labor Grun Wollny, D-35394 Giessen, Germany
来源
JOURNAL OF NATURAL PRODUCTS | 2005年 / 68卷 / 06期
关键词
D O I
10.1021/np040137t
中图分类号
Q94 [植物学];
学科分类号
071001 ;
摘要
In our screening of microorganisms for new natural products, the fungus Penicillium notatum delivered further members of the sorbicillin family, namely, the sohirnones A [3, 1-(2,4-dihydroxy-5-methylphenyl)hex-4-en-1-one], B [4a, 1-(2,4,5-trihydroxy-3,6-dimethylphenyl)hexa-2,4-dion-1-one], and C [5, 1-(2,4,5-trihydroxy-3,6-dimethylphenyl)hex-4-en-1-one]. A stable tautomer of oxosorbicillinol (7) was characterized as 6, and the recently described 7-deacetoxyyanuthone (8) was reisolated. The additionally isolated rezishanones A-D (12-13c) are the first natural Diels-Alder products of sorbicillinol (1) with dienophiles not related with 1. The monomers and dimers showed weak antibacterial activity, but were inactive against fungi and algae. The structures were determined by spectroscopic methods and by comparison of the NMR data with those of the structurally related 2',3'-dihydrosorbicillin (2) and, in the case of 4a, by transformation into the known sorrentanone (4b).
引用
收藏
页码:865 / 870
页数:6
相关论文
共 24 条
[1]   Novel DPPH radical scavengers, bisorbicillinol and demethyltrichodimerol, from a fungus [J].
Abe, N ;
Murata, T ;
Hirota, A .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1998, 62 (04) :661-666
[2]   Novel fungal metabolites, demethylsorbicillin and oxosorbicillinol, isolated from Trichoderma sp USF-2690 [J].
Abe, N ;
Yamamoto, K ;
Hirota, A .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2000, 64 (03) :620-622
[3]   Biosynthesis of bisorbicillinoid in Trichoderma sp USF-2690;: Evidence for the biosynthetic pathway, via sorbicillinol, of sorbicillin, bisorbicillinol, bisorbibutenolide, and bisorbicillinolide [J].
Abe, N ;
Arakawa, T ;
Yamamoto, K ;
Hirota, A .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2002, 66 (10) :2090-2099
[4]   Novel oxidized sorbicillin dimers with 1,1-diphenyl-2-picrylhydrazyl-radical scavenging activity from a fungus [J].
Abe, N ;
Murata, T ;
Hirota, A .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1998, 62 (11) :2120-2126
[5]   Sorbicillinol, a key intermediate of bisorbicillinoid biosynthesis in Trichoderma sp USF-2690 [J].
Abe, N ;
Sugimoto, O ;
Arakawa, T ;
Tanji, K ;
Hirota, A .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 2001, 65 (10) :2271-2279
[6]   Structures of flagranones A, B and C, cyclohexenoxide antibiotics from the nematode-trapping fungus Duddingtonia flagrans [J].
Anderson, MG ;
Rickards, RW ;
Lacey, E .
JOURNAL OF ANTIBIOTICS, 1999, 52 (11) :1023-1028
[7]   STRUCTURES AND ABSOLUTE-CONFIGURATIONS OF ANTIBIOTICS OF THE OLIGOSPORON GROUP FROM THE NEMATODE-TRAPPING FUNGUS ARTHROBOTRYS OLIGOSPORA [J].
ANDERSON, MG ;
JARMAN, TB ;
RICKARDS, RW .
JOURNAL OF ANTIBIOTICS, 1995, 48 (05) :391-398
[8]   THE METABOLITES OF TRICHODERMA-LONGIBRACHIATUM .1. ISOLATION OF THE METABOLITES AND THE STRUCTURE OF TRICHODIMEROL [J].
ANDRADE, R ;
AYER, WA ;
MEBE, PP .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1992, 70 (10) :2526-2535
[9]  
Fleming A, 1929, BRIT J EXP PATHOL, V10, P226
[10]   ISOLATION OF 2-PYRUVOYLAMINOBENZ-AMIDE AS AN ANTIAUXIN FROM COLLETOTRICHUM LAGENARIUM [J].
KIMURA, Y ;
INOUE, T ;
TAMURA, S .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1973, 37 (09) :2213-2214