Yanan Yang , Xiao Han , Peiling Cai , Congcong Zhao , Anran Fu , Kun Liu , Xuli Tang , Guoqiang Li
{"title":"戊萜素A-D,从海洋真菌单纯青霉中提取的戊萜素型戊萜类。","authors":"Yanan Yang , Xiao Han , Peiling Cai , Congcong Zhao , Anran Fu , Kun Liu , Xuli Tang , Guoqiang Li","doi":"10.1016/j.phytochem.2025.114680","DOIUrl":null,"url":null,"abstract":"<div><div>Four previously undescribed terretonin-type meroterpenoids, peniterretonins A–D (<strong>1</strong>–<strong>4</strong>), possessing unprecedented 6/6/6/6/6 pentacyclic systems, were isolated from the marine-derived fungus <em>Penicillium simplicissimum</em>. Peniterretonins B–D (<strong>2</strong>–<strong>4</strong>) represent the first examples of 21-<em>nor</em>-terretonin meroterpenoids, of which <strong>2</strong> and <strong>3</strong> bear a 10-hydroperoxyl group. Their structures were established by detailed analyses of the spectroscopic data, as well as by single-crystal X-ray diffraction analysis (Cu K<em>α</em>), DP4+ probability analyses, and ECD quantum chemistry calculations. In the bioassays, compounds <strong>1</strong>, <strong>3</strong>, <strong>4</strong> exhibited significant inhibitory activity against LPS-induced NO release with IC<sub>50</sub> values ranging from 2.51 to 3.98 μM.</div></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":"241 ","pages":"Article 114680"},"PeriodicalIF":3.4000,"publicationDate":"2025-09-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Peniterretonins A-D, terretonin-type meroterpenoids from the marine-derived fungus Penicillium simplicissimum\",\"authors\":\"Yanan Yang , Xiao Han , Peiling Cai , Congcong Zhao , Anran Fu , Kun Liu , Xuli Tang , Guoqiang Li\",\"doi\":\"10.1016/j.phytochem.2025.114680\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Four previously undescribed terretonin-type meroterpenoids, peniterretonins A–D (<strong>1</strong>–<strong>4</strong>), possessing unprecedented 6/6/6/6/6 pentacyclic systems, were isolated from the marine-derived fungus <em>Penicillium simplicissimum</em>. Peniterretonins B–D (<strong>2</strong>–<strong>4</strong>) represent the first examples of 21-<em>nor</em>-terretonin meroterpenoids, of which <strong>2</strong> and <strong>3</strong> bear a 10-hydroperoxyl group. Their structures were established by detailed analyses of the spectroscopic data, as well as by single-crystal X-ray diffraction analysis (Cu K<em>α</em>), DP4+ probability analyses, and ECD quantum chemistry calculations. In the bioassays, compounds <strong>1</strong>, <strong>3</strong>, <strong>4</strong> exhibited significant inhibitory activity against LPS-induced NO release with IC<sub>50</sub> values ranging from 2.51 to 3.98 μM.</div></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":\"241 \",\"pages\":\"Article 114680\"},\"PeriodicalIF\":3.4000,\"publicationDate\":\"2025-09-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Phytochemistry\",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0031942225003036\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Phytochemistry","FirstCategoryId":"99","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0031942225003036","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Peniterretonins A-D, terretonin-type meroterpenoids from the marine-derived fungus Penicillium simplicissimum
Four previously undescribed terretonin-type meroterpenoids, peniterretonins A–D (1–4), possessing unprecedented 6/6/6/6/6 pentacyclic systems, were isolated from the marine-derived fungus Penicillium simplicissimum. Peniterretonins B–D (2–4) represent the first examples of 21-nor-terretonin meroterpenoids, of which 2 and 3 bear a 10-hydroperoxyl group. Their structures were established by detailed analyses of the spectroscopic data, as well as by single-crystal X-ray diffraction analysis (Cu Kα), DP4+ probability analyses, and ECD quantum chemistry calculations. In the bioassays, compounds 1, 3, 4 exhibited significant inhibitory activity against LPS-induced NO release with IC50 values ranging from 2.51 to 3.98 μM.
期刊介绍:
Phytochemistry is a leading international journal publishing studies of plant chemistry, biochemistry, molecular biology and genetics, structure and bioactivities of phytochemicals, including ''-omics'' and bioinformatics/computational biology approaches. Phytochemistry is a primary source for papers dealing with phytochemicals, especially reports concerning their biosynthesis, regulation, and biological properties both in planta and as bioactive principles. Articles are published online as soon as possible as Articles-in-Press and in 12 volumes per year. Occasional topic-focussed special issues are published composed of papers from invited authors.