Sorbicillin analogues and related dimeric compounds from Penicillium notatum
Sorbicillin analogues and related dimeric compounds from Penicillium notatum
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DOI：
10.1021/np040137t
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发表时间：
2005-06-01
影响因子：
5.1
通讯作者：
Laatsch, H
中科院分区：
文献类型：
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作者：
Maskey, RP;Grün-Wollny, I;Laatsch, H
在我们筛选微生物以获得新的天然产物中，真菌Penicillium notatum递送了山梨西林家族的其他成员，即，sohirnones A [3，1- 10]。（2，4-二羟基-5-甲基苯基）己-4-烯-1-酮]、B [4a，1-（2，4，5-三羟基-3，6-二甲基苯基）己-2，4-二酮-1-酮]和C [5，1-（2，4，5-三羟基-3，6-二甲基苯基）己-4-烯-1-酮]。氧代山梨醇（7）的一个稳定的互变异构体被表征为6，最近描述的7-去乙酰氧基yanuthone（8）被重新分离。另外分离的rezishanones A-D（12- 13 c）是山梨西林醇（1）与与1无关的亲二烯体的第一个天然Diels-Alder产物。单体和二聚体表现出较弱的抗菌活性，但对真菌和藻类无活性。通过光谱方法并通过将NMR数据与结构相关的2 '，3'-二氢山梨西林（2）的NMR数据进行比较，以及在4a的情况下，通过转化为已知的sorrentanone（4 b）来确定结构。
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).