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

IF 4.8 3区化学 Q1 CHEMISTRY, MEDICINAL

Natural Products and Bioprospecting Pub Date : 2024-05-21 DOI:10.1007/s13659-024-00449-9

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

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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.

Graphical Abstract

Abstract Image

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通过 OSMAC（一种菌株多种化合物）策略从海洋源真菌 Penicillium velutinum ZK-14 中发现新的哌嗪衍生物 helvamides B-C。

根据 OSMAC（一种菌株多种化合物）策略，通过金属离子胁迫条件获得了来自海洋的真菌 Penicillium velutinum J.F.H. Beyma 的四种提取物。利用 LC/UV、LC/MS 和生物活性数据分析等现代方法，并结合硅学计算，分析了金属应激因素对短毛青霉代谢物谱变化的影响。从 velutinum 青霉菌的乙酸乙酯提取物中分离出了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-guaia-1(2),9(10)-dien（4）。它们的结构是根据光谱方法确定的。通过结合 X 射线分析和电子圆二色性（ECD）光谱的时间相关密度泛函理论（TD-DFT）计算，确定了氦酰胺 B（1）的绝对构型为 2R、5R。检测了分离化合物对人类前列腺癌 PC-3 细胞和人类胚胎肾 HEK-293 细胞的细胞毒活性，以及对类酵母真菌白色念珠菌的生长抑制活性。

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来源期刊

Natural Products and Bioprospecting CHEMISTRY, MEDICINAL-

CiteScore

8.30

自引率

2.10%

发文量

审稿时长

13 weeks

期刊介绍： Natural Products and Bioprospecting serves as an international forum for essential research on natural products and focuses on, but is not limited to, the following aspects: Natural products: isolation and structure elucidation Natural products: synthesis Biological evaluation of biologically active natural products Bioorganic and medicinal chemistry Biosynthesis and microbiological transformation Fermentation and plant tissue cultures Bioprospecting of natural products from natural resources All research articles published in this journal have undergone rigorous peer review. In addition to original research articles, Natural Products and Bioprospecting publishes reviews and short communications, aiming to rapidly disseminate the research results of timely interest, and comprehensive reviews of emerging topics in all the areas of natural products. It is also an open access journal, which provides free access to its articles to anyone, anywhere.