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通过OSMAC（一株多化合物）策略从海洋来源真菌绒毛青霉ZK-14中发现的新型哌嗪衍生物helvamides B-C。

New piperazine derivatives helvamides B-C from the marine-derived fungus Penicillium velutinum ZK-14 uncovered by OSMAC (One Strain Many Compounds) strategy.

作者信息

Borkunov Gleb V, Leshchenko Elena V, Berdyshev Dmitrii V, Popov Roman S, Chingizova Ekaterina A, Shlyk Nadezhda P, Gerasimenko Andrey V, Kirichuk Natalya N, Khudyakova Yuliya V, Chausova Viktoria E, Antonov Alexandr S, Kalinovsky Anatoly I, Chingizov Artur R, Yurchenko Ekaterina A, Isaeva Marina P, Yurchenko Anton N

机构信息

G.B. Elyakov Pacific Institute of Bioorganic Chemistry, Far Eastern Branch of the Russian Academy of Sciences, 159 Prospect 100-Letiya Vladivostoka, Vladivostok, 690022, Russian Federation.

Far Eastern Federal University, Vladivostok, 690922, Russian Federation.

出版信息

Nat Prod Bioprospect. 2024 May 21;14(1):32. doi: 10.1007/s13659-024-00449-9.

DOI:10.1007/s13659-024-00449-9
PMID:38769256
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11106049/
Abstract

Four extracts of the marine-derived fungus Penicillium velutinum J.F.H. Beyma were obtained via metal ions stress conditions based on the OSMAC (One Strain Many Compounds) strategy. Using a combination of modern approaches such as LC/UV, LC/MS and bioactivity data analysis, as well as in silico calculations, influence metal stress factors to change metabolite profiles Penicillium velutinum were analyzed. From the ethyl acetate extract of the P. velutinum were isolated two new piperazine derivatives helvamides B (1) and C (2) together with known saroclazin A (3) (4S,5R,7S)-4,11-dihydroxy-guaia-1(2),9(10)-dien (4). Their structures were established based on spectroscopic methods. The absolute configuration of helvamide B (1) as 2R,5R was determined by a combination of the X-ray analysis and by time-dependent density functional theory (TD-DFT) calculations of electronic circular dichroism (ECD) spectra. The cytotoxic activity of the isolated compounds against human prostate cancer PC-3 and human embryonic kidney HEK-293 cells and growth inhibition activity against yeast-like fungi Candida albicans were assayed.

摘要

基于“一种菌株，多种化合物”（OSMAC）策略，通过金属离子胁迫条件从海洋来源的真菌绒毛青霉J.F.H. Beyma中获得了四种提取物。采用液相色谱/紫外（LC/UV）、液相色谱/质谱（LC/MS）和生物活性数据分析等现代方法相结合，以及计算机模拟计算，分析了金属胁迫因素对绒毛青霉代谢产物谱变化的影响。从绒毛青霉的乙酸乙酯提取物中分离出两种新的哌嗪衍生物helvamides B（1）和C（2），以及已知的saroclazin A（3）、（4S,5R,7S）-4,11-二羟基愈创木-1（2）,9（10）-二烯（4）。它们的结构通过光谱方法确定。helvamide B（1）的绝对构型为2R,5R，通过X射线分析和电子圆二色（ECD）光谱的含时密度泛函理论（TD-DFT）计算相结合来确定。测定了分离得到的化合物对人前列腺癌PC-3细胞和人胚肾HEK-293细胞的细胞毒性活性以及对酵母样真菌白色念珠菌的生长抑制活性。

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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c7b0/11106049/536d649ce3c3/13659_2024_449_Fig9_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c7b0/11106049/c212e74b15c7/13659_2024_449_Fig10_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c7b0/11106049/57fbc25a65e0/13659_2024_449_Fig11_HTML.jpg
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