Key Laboratory of Experimental Marine Biology, Center for Ocean Mega-Science , Institute of Oceanology, Chinese Academy of Sciences , Nanhai Road 7 , Qingdao 266071 , People's Republic of China.
Laboratory of Marine Biology and Biotechnology , Qingdao National Laboratory for Marine Science and Technology , Wenhai Road 1 , Qingdao 266237 , People's Republic of China.
J Nat Prod. 2019 Jun 28;82(6):1535-1541. doi: 10.1021/acs.jnatprod.8b01091. Epub 2019 Apr 30.
Four new 12-membered macrolides, thiocladospolides A-D (1-4), each possessing a sulfur substitution at C-2, along with the known congener pandangolide 3 (5) and the possible hydrolysis product seco-patulolide C (6), were isolated and identified from the culture extract of Cladosporium cladosporioides MA-299, an endophytic fungus obtained from the leaves of the mangrove plant Bruguiera gymnorrhiza. Their structures were established by interpretation of the NMR spectroscopic and mass spectrometric data. X-ray crystallographic analysis of compound 1, which represents the first crystal structure described for a sulfur-containing 12-membered macrolide, confirmed its structure and absolute configuration. The proposed sulfur side chain at C-3 in pandangolide 3 (5) was revised to be at C-2 by detailed analysis of the NMR data and by a comparison with data for thiocladospolide A (1). The structures for pandangolides 2 and 4 should also be considered for revisions. The isolated compounds were evaluated for the antimicrobial activities against aquatic bacteria and plant pathogens.
从内生真菌 Cladosporium cladosporioides MA-299 的培养物提取物中分离并鉴定了四个新的 12 元大环内酯类化合物，分别为硫代克拉多斯波内酯 A-D（1-4），每个化合物在 C-2 位都有硫取代，以及已知的同类物 pandangolide 3（5）和可能的水解产物 seco-patulolide C（6）。这些化合物的结构是通过对 NMR 光谱和质谱数据的解释确定的。化合物 1 的 X 射线晶体结构分析，代表了第一个描述的含硫 12 元大环内酯的晶体结构，证实了其结构和绝对构型。通过对 NMR 数据的详细分析和与硫代克拉多斯波内酯 A（1）数据的比较，对 pandangolide 3（5）中 C-3 上的拟硫侧链进行了修订，确定其位于 C-2 位。pandangolide 2 和 4 的结构也应该考虑进行修订。对分离得到的化合物进行了水生细菌和植物病原菌的抗菌活性评价。
