{"title":"深海来源真菌青霉SH0301的青霉烷a- f，青霉烷型倍半萜","authors":"Lu-Jia Yang, Ling Lv, Zhuang Han, Yu-Cheng Gu, Xin Li, Chang-Lun Shao, Zhi-Qing Liu, Chang-Yun Wang","doi":"10.1002/cjoc.202400836","DOIUrl":null,"url":null,"abstract":"<div>\n \n <p>Six new acorane-type sesquiterpenes, named penijanacoranes A—F (<b>1</b>—<b>6</b>), as well as one known eudesmane sesquiterpenoid 1<i>α</i>,6<i>β</i>,11-eudesm-triol (<b>7</b>) have been isolated from a deep-sea-derived fungus <i>Penicillium janthinellum</i> SH0301. Their structures and absolute configurations were established by the comprehensive spectroscopic analysis, TDDFT-ECD calculations, and X-ray diffraction. Penijanacorane A (<b>1</b>) was identified as a rare acorane-type sesquiterpene lactone featuring a novel 6/5/6 tricyclic system, while penijanacoranes E and F (<b>5</b> and <b>6</b>) represented undescribed examples of nor-acorane sesquiterpenes at C-1. Penijanacorane C (<b>3</b>) exhibited significant inhibitory activity against LPS-induced NO production in Raw264.7 macrophages with an IC<sub>50</sub> value of 6.23 μM, which was more potent than that of positive control dexamethasone (IC<sub>50</sub> = 11.49 μM). This study expanded the chemical diversity of acorane-type sesquiterpenoids and revealed that compound <b>3</b> was a potential molecule for anti-inflammatory agents.</p>\n <p>\n </p>\n </div>","PeriodicalId":151,"journal":{"name":"Chinese Journal of Chemistry","volume":"43 3","pages":"268-274"},"PeriodicalIF":5.5000,"publicationDate":"2024-10-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Penijanacoranes A—F, Acorane-Type Sesquiterpenes from a Deep Sea-Derived Fungus Penicillium janthinellum SH0301\",\"authors\":\"Lu-Jia Yang, Ling Lv, Zhuang Han, Yu-Cheng Gu, Xin Li, Chang-Lun Shao, Zhi-Qing Liu, Chang-Yun Wang\",\"doi\":\"10.1002/cjoc.202400836\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div>\\n \\n <p>Six new acorane-type sesquiterpenes, named penijanacoranes A—F (<b>1</b>—<b>6</b>), as well as one known eudesmane sesquiterpenoid 1<i>α</i>,6<i>β</i>,11-eudesm-triol (<b>7</b>) have been isolated from a deep-sea-derived fungus <i>Penicillium janthinellum</i> SH0301. Their structures and absolute configurations were established by the comprehensive spectroscopic analysis, TDDFT-ECD calculations, and X-ray diffraction. Penijanacorane A (<b>1</b>) was identified as a rare acorane-type sesquiterpene lactone featuring a novel 6/5/6 tricyclic system, while penijanacoranes E and F (<b>5</b> and <b>6</b>) represented undescribed examples of nor-acorane sesquiterpenes at C-1. Penijanacorane C (<b>3</b>) exhibited significant inhibitory activity against LPS-induced NO production in Raw264.7 macrophages with an IC<sub>50</sub> value of 6.23 μM, which was more potent than that of positive control dexamethasone (IC<sub>50</sub> = 11.49 μM). This study expanded the chemical diversity of acorane-type sesquiterpenoids and revealed that compound <b>3</b> was a potential molecule for anti-inflammatory agents.</p>\\n <p>\\n </p>\\n </div>\",\"PeriodicalId\":151,\"journal\":{\"name\":\"Chinese Journal of Chemistry\",\"volume\":\"43 3\",\"pages\":\"268-274\"},\"PeriodicalIF\":5.5000,\"publicationDate\":\"2024-10-17\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Chinese Journal of Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://onlinelibrary.wiley.com/doi/10.1002/cjoc.202400836\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q2\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chinese Journal of Chemistry","FirstCategoryId":"92","ListUrlMain":"https://onlinelibrary.wiley.com/doi/10.1002/cjoc.202400836","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
Penijanacoranes A—F, Acorane-Type Sesquiterpenes from a Deep Sea-Derived Fungus Penicillium janthinellum SH0301
Six new acorane-type sesquiterpenes, named penijanacoranes A—F (1—6), as well as one known eudesmane sesquiterpenoid 1α,6β,11-eudesm-triol (7) have been isolated from a deep-sea-derived fungus Penicillium janthinellum SH0301. Their structures and absolute configurations were established by the comprehensive spectroscopic analysis, TDDFT-ECD calculations, and X-ray diffraction. Penijanacorane A (1) was identified as a rare acorane-type sesquiterpene lactone featuring a novel 6/5/6 tricyclic system, while penijanacoranes E and F (5 and 6) represented undescribed examples of nor-acorane sesquiterpenes at C-1. Penijanacorane C (3) exhibited significant inhibitory activity against LPS-induced NO production in Raw264.7 macrophages with an IC50 value of 6.23 μM, which was more potent than that of positive control dexamethasone (IC50 = 11.49 μM). This study expanded the chemical diversity of acorane-type sesquiterpenoids and revealed that compound 3 was a potential molecule for anti-inflammatory agents.
期刊介绍：
The Chinese Journal of Chemistry is an international forum for peer-reviewed original research results in all fields of chemistry. Founded in 1983 under the name Acta Chimica Sinica English Edition and renamed in 1990 as Chinese Journal of Chemistry, the journal publishes a stimulating mixture of Accounts, Full Papers, Notes and Communications in English.
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