Wu Bin, Oesker Vanessa, Wiese Jutta, Malien Susann, Schmaljohann Rolf, Imhoff Johannes F
Kieler Wirkstoff-Zentrum am GEOMAR Helmholtz Zentrum für Ozeanforschung Kiel, Kiel 24105, Germany.
Mar Drugs. 2014 Apr 1;12(4):1924-38. doi: 10.3390/md12041924.
A novel spirocyclic drimane coupled by two drimane fragment building blocks 2 and a new drimane 1 were identified in mycelia and culture broth of Stachybotrys sp. MF347. Their structures were established by spectroscopic means. This is the first example of spirocyclic drimane coupled by a spirodihydrobenzofuranlactam unit and a spirodihydroisobenzofuran unit; and the connecting position being N-C instead of an N and N connecting unit. Strain MF347 produced also the known spirocyclic drimanes stachybocin A (12) and stachybocin B (11) featured by two sesquiterpene-spirobenzofuran structural units connected by a lysine residue; the known spirocyclic drimanes chartarlactam O (5); chartarlactam K (6); F1839A (7); stachybotrylactam (8); stachybotramide (9); and 2α-acetoxystachybotrylactam acetate (10); as well as ilicicolin B (13), a known sesquiterpene. The relative configuration of two known spirobenzofuranlactams (3 and 4) was determined. All compounds were subjected to biological activity tests. The spirocyclic drimane 2, 11, and 12, as well as the sesquiterpene 13, exhibited antibacterial activity against the clinically relevant methicillin-resistant Staphylococcus aureus (MRSA).
在链格孢属菌株MF347的菌丝体和培养液中鉴定出一种由两个杜松烷片段构建单元2偶联而成的新型螺环杜松烷以及一种新的杜松烷1。它们的结构通过光谱手段得以确定。这是首例由螺二氢苯并呋喃内酰胺单元和螺二氢异苯并呋喃单元偶联而成的螺环杜松烷，且连接位置为N-C而非N与N连接单元。菌株MF347还产生了已知的螺环杜松烷——由赖氨酸残基连接的两个倍半萜-螺苯并呋喃结构单元构成的链格孢菌素A（12）和链格孢菌素B（11）；已知的螺环杜松烷查塔尔内酰胺O（5）、查塔尔内酰胺K（6）、F1839A（7）、链格孢内酯（8）、链格孢酰胺（9）以及2α-乙酰氧基链格孢内酯乙酸酯（10）；还有已知的倍半萜伊利西考林B（13）。确定了两种已知螺苯并呋喃内酰胺（3和4）的相对构型。所有化合物均进行了生物活性测试。螺环杜松烷2、11和12以及倍半萜13对临床相关的耐甲氧西林金黄色葡萄球菌（MRSA）表现出抗菌活性。
