{"title":"Acremosides A-G, Sugar Alcohol-Conjugated Acyclic Sesquiterpenes from a Sponge-Derived Acremonium Species.","authors":"Xiaomeng Hao, Shasha Li, Jianrui Li, Guiyang Wang, Jiao Li, Zonggen Peng* and Maoluo Gan*, ","doi":"10.1021/acs.jnatprod.4c00015","DOIUrl":null,"url":null,"abstract":"<p >Seven new sugar alcohol-conjugated acyclic sesquiterpenes, acremosides A–G (<b>1</b>–<b>7</b>), were isolated from the cultures of the sponge-associated fungus <i>Acremonium</i> sp. IMB18-086 cultivated with heat-killed <i>Pseudomonas aeruginosa</i>. The structures were determined by comprehensive analyses of 1D and 2D NMR spectroscopic data. The relative configurations were established by <i>J</i>-based configuration analysis and acetonide derivatization. The absolute configurations were elucidated by the Mosher ester method and ECD calculations. The structures of acremosides E–G (<b>5</b>–<b>7</b>) featured the linear sesquiterpene skeleton with a tetrahydrofuran moiety attached to a sugar alcohol. Acremosides A (<b>1</b>) and C–E (<b>3</b>–<b>5</b>) showed significant inhibitory activities against hepatitis C virus (EC<sub>50</sub> values of 4.8–8.8 μM) with no cytotoxicity (CC<sub>50</sub> of >200 μM).</p>","PeriodicalId":47,"journal":{"name":"Journal of Natural Products ","volume":null,"pages":null},"PeriodicalIF":3.3000,"publicationDate":"2024-04-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Acremosides A–G, Sugar Alcohol-Conjugated Acyclic Sesquiterpenes from a Sponge-Derived Acremonium Species\",\"authors\":\"Xiaomeng Hao, Shasha Li, Jianrui Li, Guiyang Wang, Jiao Li, Zonggen Peng* and Maoluo Gan*, \",\"doi\":\"10.1021/acs.jnatprod.4c00015\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p >Seven new sugar alcohol-conjugated acyclic sesquiterpenes, acremosides A–G (<b>1</b>–<b>7</b>), were isolated from the cultures of the sponge-associated fungus <i>Acremonium</i> sp. IMB18-086 cultivated with heat-killed <i>Pseudomonas aeruginosa</i>. The structures were determined by comprehensive analyses of 1D and 2D NMR spectroscopic data. The relative configurations were established by <i>J</i>-based configuration analysis and acetonide derivatization. The absolute configurations were elucidated by the Mosher ester method and ECD calculations. The structures of acremosides E–G (<b>5</b>–<b>7</b>) featured the linear sesquiterpene skeleton with a tetrahydrofuran moiety attached to a sugar alcohol. Acremosides A (<b>1</b>) and C–E (<b>3</b>–<b>5</b>) showed significant inhibitory activities against hepatitis C virus (EC<sub>50</sub> values of 4.8–8.8 μM) with no cytotoxicity (CC<sub>50</sub> of >200 μM).</p>\",\"PeriodicalId\":47,\"journal\":{\"name\":\"Journal of Natural Products \",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.3000,\"publicationDate\":\"2024-04-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Journal of Natural Products \",\"FirstCategoryId\":\"99\",\"ListUrlMain\":\"https://pubs.acs.org/doi/10.1021/acs.jnatprod.4c00015\",\"RegionNum\":2,\"RegionCategory\":\"生物学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MEDICINAL\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Natural Products ","FirstCategoryId":"99","ListUrlMain":"https://pubs.acs.org/doi/10.1021/acs.jnatprod.4c00015","RegionNum":2,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
Acremosides A–G, Sugar Alcohol-Conjugated Acyclic Sesquiterpenes from a Sponge-Derived Acremonium Species
Seven new sugar alcohol-conjugated acyclic sesquiterpenes, acremosides A–G (1–7), were isolated from the cultures of the sponge-associated fungus Acremonium sp. IMB18-086 cultivated with heat-killed Pseudomonas aeruginosa. The structures were determined by comprehensive analyses of 1D and 2D NMR spectroscopic data. The relative configurations were established by J-based configuration analysis and acetonide derivatization. The absolute configurations were elucidated by the Mosher ester method and ECD calculations. The structures of acremosides E–G (5–7) featured the linear sesquiterpene skeleton with a tetrahydrofuran moiety attached to a sugar alcohol. Acremosides A (1) and C–E (3–5) showed significant inhibitory activities against hepatitis C virus (EC50 values of 4.8–8.8 μM) with no cytotoxicity (CC50 of >200 μM).
期刊介绍:
The Journal of Natural Products invites and publishes papers that make substantial and scholarly contributions to the area of natural products research. Contributions may relate to the chemistry and/or biochemistry of naturally occurring compounds or the biology of living systems from which they are obtained.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.
When new compounds are reported, manuscripts describing their biological activity are much preferred.
Specifically, there may be articles that describe secondary metabolites of microorganisms, including antibiotics and mycotoxins; physiologically active compounds from terrestrial and marine plants and animals; biochemical studies, including biosynthesis and microbiological transformations; fermentation and plant tissue culture; the isolation, structure elucidation, and chemical synthesis of novel compounds from nature; and the pharmacology of compounds of natural origin.