Maskey Rajendra P, Grün-Wollny Iris, Laatsch Hartmut
Department of Organic and Biomolecular Chemistry, University of Göttingen, Germany.
J Nat Prod. 2005 Jun;68(6):865-70. doi: 10.1021/np040137t.
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-dien-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).
在我们对微生物产生新型天然产物的筛选过程中，真菌点青霉产生了山梨素家族的其他成员，即索霍宁 A [3, 1-(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-2,4-二烯-1-酮] 和 C [5, 1-(2,4,5-三羟基-3,6-二甲基苯基)己-4-烯-1-酮]。氧代山梨素醇 (7) 的一种稳定互变异构体被鉴定为 6，并且重新分离出了最近报道的 7-脱乙酰基雅努酮 (8)。另外分离得到的瑞芝山酮 A-D (12 - 13c) 是山梨素醇 (1) 与非 1 相关亲双烯体形成的首批天然狄尔斯-阿尔德产物。单体和二聚体显示出微弱的抗菌活性，但对真菌和藻类无活性。结构通过光谱方法以及将 NMR 数据与结构相关的 2',3'-二氢山梨素 (2) 的数据进行比较来确定，对于 4a 的情况，通过转化为已知的索伦他酮 (4b) 来确定。
