通过 OSMAC 方法从北极来源真菌 sp. D-1 中获得的细胞松弛素衍生物。

Cytosporin Derivatives from Arctic-Derived Fungus sp. D-1 via the OSMAC Approach.

机构信息

Naval Medical Center of PLA, Department of Marine Biomedicine and Polar Medicine, Naval Medical University, Shanghai 200433, China.

Basic Medical Experimental Teaching Center, College of Basic Medical Sciences, Naval Medical University, Shanghai 200433, China.

出版信息

Mar Drugs. 2023 Jun 28;21(7):382. doi: 10.3390/md21070382.

DOI:10.3390/md21070382

PMID:37504913

原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10381684/

Abstract

A chemical investigation of the Arctic-derived fungus sp. D-1 based on the OSMAC (one strain many compounds) approach resulted in the isolation of five cytosporin polyketides (compounds - and -) from rice medium and eight cytosporins (compounds and -) from solid defined medium. The structures of the seven new compounds, eutypelleudesmane A (), cytosporin Y (), cytosporin Z (), cytosporin Y (), cytosporin Y (), cytosporin Y (), and cytosporin E (), were elucidated by analyzing their detailed spectroscopic data. Structurally, cytosporin Y () may be a key intermediate in the biosynthesis of the isolated cytosporins, rather than an end product. Compound contained a unique skeleton formed by the ester linkage of two moieties, cytosporin F () and the eudesmane-type sesquiterpene dihydroalanto glycol. Additionally, the occurrence of cyclic carbonate moieties in compounds and was found to be rare in nature. The antibacterial, immunosuppressive, and cytotoxic activities of all compounds derived from sp. D-1 were evaluated. Unfortunately, only compounds , , , and - displayed immunosuppressive activity, with inhibitory rates of 62.9%, 59.5%, 67.8%, 55.8%, and 68.7%, respectively, at a concentration of 5 μg/mL.

摘要

基于 OSMAC（一种菌株多种化合物）方法对源自北极的真菌 sp. D-1 进行的化学研究，从大米培养基中分离出五种细胞松弛素聚酮（化合物 - 和 -），从固体限定培养基中分离出八种细胞松弛素（化合物和 -）。通过分析其详细的光谱数据，阐明了这七种新化合物的结构，即 eutypelleudesmane A ()、细胞松弛素 Y ()、细胞松弛素 Z ()、细胞松弛素 Y ()、细胞松弛素 Y ()、细胞松弛素 Y ()和细胞松弛素 E ()。从结构上看，细胞松弛素 Y () 可能是分离出的细胞松弛素生物合成的关键中间体，而不是终产物。化合物含有一个独特的骨架，由两个部分的酯键连接而成，即细胞松弛素 F () 和薁型倍半萜二氢阿尔烷醇。此外，还发现化合物和中存在环状碳酸酯部分，这在自然界中很少见。评估了源自 sp. D-1 的所有化合物的抗菌、免疫抑制和细胞毒性活性。不幸的是，只有化合物、、、和 - 具有免疫抑制活性，在 5 μg/mL 浓度下的抑制率分别为 62.9%、59.5%、67.8%、55.8%和 68.7%。