Cytochalasans Produced by the Coculture of Aspergillus flavipes and Chaetomium globosum
Cytochalasans Produced by the Coculture of Aspergillus flavipes and Chaetomium globosum
复制标题
黄曲霉和球毛壳菌共培养产生的细胞松弛素
DOI：
10.1021/acs.jnatprod.8b00110
复制
发表时间：
2018-07-01
影响因子：
5.1
通讯作者：
Zhang, Yonghui
中科院分区：
文献类型：
--
作者：
Wang, Wenjing;Gong, Jiaojiao;Zhang, Yonghui
将细胞松弛素的丰富来源--黄足曲霉和球毛壳菌（Chaetomium globosum）在固体水稻培养基上共培养，产生了13种新的高度氧化的细胞松弛素，即Aspochalasinol A-D（1-4）和oxichaetoglobosins A-I（5-13），以及7种已知化合物（1 - 4 -20）。在这些化合物中，13是一种新的细胞松弛素，具有意想不到的2-去甲吲哚基团。分离的化合物，其特征在于通过NMR光谱，单晶X-射线晶体学，和ECD实验。化合物1-4代表了具有C-12羟基的Asp型细胞松弛素的第一个实例，这可能是共培养的结果，因为羟基化的Me-12基团经常在来自C. globosum。此外，5-10是不常见的具有含氧C-10的细胞松弛素。有趣的是，13是天然存在的细胞松弛素的第一个例子，它具有独特的降解吲哚环，衍生自球毛藻素W，11和12都作为其生物合成中间体。在A. flavipes和C. globosum中，这些细胞松弛素中的大多数比正常的细胞松弛素功能更强，并且潜在的原因可能引起合成生物学家的大量关注。对5种人癌细胞株（SW 480、HL-60、A549、MCF-7和SMMC-7721）进行了体外细胞毒性和免疫调节活性的评价。
The cocultivation of Aspergillus flavipes and Chaetomium globosum, rich sources of cytochalasans, on solid rice medium, resulted in the production of 13 new, highly oxygenated cytochalasans, aspochalasinols A-D (1-4) and oxichaetoglobosins A-I (5-13), as well as seven known compounds (14-20). Of these compounds, 13 is a novel cytochalasan with an unexpected 2-norindole group. The isolated compounds were characterized by NMR spectroscopy, single-crystal X-ray crystallography, and ECD experiments. Compounds 1-4 represent the first examples of Asp-type cytochalasans with C-12 hydroxy groups, which may be a result of the coculture, as hydroxylated Me-12 groups are frequently found in Chae-type cytochalasans from C. globosum. In addition, 5-10 are unusual cytochalasans with an oxygenated C-10. Interestingly, 13 is the first example of a naturally occurring cytochalasan possessing a uniquely degraded indole ring that is derived from chaetoglobosin W, with 11 and 12 both serving as its biosynthetic intermediates. In the coculture of A. flavipes and C. globosum, most of these cytochalasans are more functionalized than normal cytochalasans, and the underlying causes may attract substantial attention from synthetic biologists. The cytotoxicities against five human cancer cell lines (SW480, HL-60, A549, MCF-7, and SMMC-7721) and the immunomodulatory activities of these new compounds were evaluated in vitro.