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
{"title":"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。","authors":"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","doi":"10.1007/s13659-024-00449-9","DOIUrl":null,"url":null,"abstract":"<div><p>Four extracts of the marine-derived fungus <i>Penicillium velutinum</i> 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 <i>Penicillium velutinum</i> were analyzed. From the ethyl acetate extract of the <i>P. velutinum</i> were isolated two new piperazine derivatives helvamides B (<b>1</b>) and C (<b>2</b>) together with known saroclazin A (<b>3</b>) (4<i>S</i>,5<i>R</i>,7<i>S</i>)-4,11-dihydroxy-guaia-1(2),9(10)-dien (<b>4</b>). Their structures were established based on spectroscopic methods. The absolute configuration of helvamide B (<b>1</b>) as 2<i>R</i>,5<i>R</i> 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 <i>Candida albicans</i> were assayed.</p><h3>Graphical Abstract</h3>\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>","PeriodicalId":718,"journal":{"name":"Natural Products and Bioprospecting","volume":"14 1","pages":""},"PeriodicalIF":4.8000,"publicationDate":"2024-05-21","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11106049/pdf/","citationCount":"0","resultStr":"{\"title\":\"New piperazine derivatives helvamides B–C from the marine-derived fungus Penicillium velutinum ZK-14 uncovered by OSMAC (One Strain Many Compounds) strategy\",\"authors\":\"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\",\"doi\":\"10.1007/s13659-024-00449-9\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Four extracts of the marine-derived fungus <i>Penicillium velutinum</i> 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 <i>Penicillium velutinum</i> were analyzed. From the ethyl acetate extract of the <i>P. velutinum</i> were isolated two new piperazine derivatives helvamides B (<b>1</b>) and C (<b>2</b>) together with known saroclazin A (<b>3</b>) (4<i>S</i>,5<i>R</i>,7<i>S</i>)-4,11-dihydroxy-guaia-1(2),9(10)-dien (<b>4</b>). Their structures were established based on spectroscopic methods. The absolute configuration of helvamide B (<b>1</b>) as 2<i>R</i>,5<i>R</i> 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 <i>Candida albicans</i> were assayed.</p><h3>Graphical Abstract</h3>\\n<div><figure><div><div><picture><source><img></source></picture></div></div></figure></div></div>\",\"PeriodicalId\":718,\"journal\":{\"name\":\"Natural Products and Bioprospecting\",\"volume\":\"14 1\",\"pages\":\"\"},\"PeriodicalIF\":4.8000,\"publicationDate\":\"2024-05-21\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11106049/pdf/\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Natural Products and Bioprospecting\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://link.springer.com/article/10.1007/s13659-024-00449-9\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Natural Products and Bioprospecting","FirstCategoryId":"92","ListUrlMain":"https://link.springer.com/article/10.1007/s13659-024-00449-9","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
New piperazine derivatives helvamides B–C from the marine-derived fungus Penicillium velutinum ZK-14 uncovered by OSMAC (One Strain Many Compounds) strategy
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.
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.
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