Jin-Yao Yong , Mi Li , Wen-Rui Li , Rong-Mei Gao , Guo-Zhu Su , Hai-Qiang Wang , Jia Yang , Li Li , Yu-Huan Li , Peter Scott , Ru-Bing Wang , Xiao-Jing Wang , Shuang-Gang Ma
{"title":"具有抗病毒活性的二倍半萜和橡果烷型倍半萜","authors":"Jin-Yao Yong , Mi Li , Wen-Rui Li , Rong-Mei Gao , Guo-Zhu Su , Hai-Qiang Wang , Jia Yang , Li Li , Yu-Huan Li , Peter Scott , Ru-Bing Wang , Xiao-Jing Wang , Shuang-Gang Ma","doi":"10.1016/j.bioorg.2022.106324","DOIUrl":null,"url":null,"abstract":"<div><p>Chemical investigation of an alcohol extract from the twigs and leaves of <em>Illicium henryi</em> Diels resulted in the isolation of two new acorane-related <em>seco</em>-sesquiterpenes (<strong>1</strong> and <strong>3</strong>), two new acorane-related <em>seco</em>-norsesquiterpenes (<strong>2</strong> and <strong>4</strong>), one new 2-<em>epi</em>-cedrane sesquiterpene (<strong>5</strong>), eight new acorane-type sesquiterpenes (<strong>6</strong>–<strong>13</strong>), and a known major constituent of acorenone B (<strong>14</strong>). Their structures were established by interpreting extensive spectroscopic data, including HRESIMS, NMR (<sup>1</sup>H and <sup>13</sup>C NMR, <sup>1</sup>H-<sup>1</sup>H COSY, HSQC, and HMBC), and NOE difference spectra analysis. The absolute configurations of <strong>1</strong>, <strong>2</strong>, <strong>4</strong>–<strong>7</strong>, <strong>9</strong>, <strong>10</strong>, and <strong>14</strong> were determined by X-ray crystallography, while chemical transformation methods were performed with compound <strong>14</strong> as the starting material to elegantly solve the absolute configuration issue of compounds <strong>8</strong> and <strong>11</strong>–<strong>13</strong>. Notably, <strong>1</strong> and <strong>2</strong> are <em>seco</em>-sesquiterpenes that are related to acorane and possess an unusual ketal-linked hemiacetal in a 6,8-dioxabicyclo[3.2.1]octan-7-ol scaffold ring system. Plausible biosynthetic pathways for compounds <strong>1</strong>–<strong>14</strong>, which were derived from the acorane skeleton, were proposed. All the isolated compounds (<strong>1</strong>–<strong>14</strong>) were evaluated for their antiviral and cytotoxic activities.</p></div>","PeriodicalId":257,"journal":{"name":"Bioorganic Chemistry","volume":null,"pages":null},"PeriodicalIF":4.5000,"publicationDate":"2023-02-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"seco-Sesquiterpenes and acorane-type sesquiterpenes with antiviral activity from the twigs and leaves of Illicium henryi Diels\",\"authors\":\"Jin-Yao Yong , Mi Li , Wen-Rui Li , Rong-Mei Gao , Guo-Zhu Su , Hai-Qiang Wang , Jia Yang , Li Li , Yu-Huan Li , Peter Scott , Ru-Bing Wang , Xiao-Jing Wang , Shuang-Gang Ma\",\"doi\":\"10.1016/j.bioorg.2022.106324\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Chemical investigation of an alcohol extract from the twigs and leaves of <em>Illicium henryi</em> Diels resulted in the isolation of two new acorane-related <em>seco</em>-sesquiterpenes (<strong>1</strong> and <strong>3</strong>), two new acorane-related <em>seco</em>-norsesquiterpenes (<strong>2</strong> and <strong>4</strong>), one new 2-<em>epi</em>-cedrane sesquiterpene (<strong>5</strong>), eight new acorane-type sesquiterpenes (<strong>6</strong>–<strong>13</strong>), and a known major constituent of acorenone B (<strong>14</strong>). Their structures were established by interpreting extensive spectroscopic data, including HRESIMS, NMR (<sup>1</sup>H and <sup>13</sup>C NMR, <sup>1</sup>H-<sup>1</sup>H COSY, HSQC, and HMBC), and NOE difference spectra analysis. The absolute configurations of <strong>1</strong>, <strong>2</strong>, <strong>4</strong>–<strong>7</strong>, <strong>9</strong>, <strong>10</strong>, and <strong>14</strong> were determined by X-ray crystallography, while chemical transformation methods were performed with compound <strong>14</strong> as the starting material to elegantly solve the absolute configuration issue of compounds <strong>8</strong> and <strong>11</strong>–<strong>13</strong>. Notably, <strong>1</strong> and <strong>2</strong> are <em>seco</em>-sesquiterpenes that are related to acorane and possess an unusual ketal-linked hemiacetal in a 6,8-dioxabicyclo[3.2.1]octan-7-ol scaffold ring system. Plausible biosynthetic pathways for compounds <strong>1</strong>–<strong>14</strong>, which were derived from the acorane skeleton, were proposed. All the isolated compounds (<strong>1</strong>–<strong>14</strong>) were evaluated for their antiviral and cytotoxic activities.</p></div>\",\"PeriodicalId\":257,\"journal\":{\"name\":\"Bioorganic Chemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.5000,\"publicationDate\":\"2023-02-01\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Bioorganic Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0045206822007313\",\"RegionNum\":2,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Bioorganic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0045206822007313","RegionNum":2,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
seco-Sesquiterpenes and acorane-type sesquiterpenes with antiviral activity from the twigs and leaves of Illicium henryi Diels
Chemical investigation of an alcohol extract from the twigs and leaves of Illicium henryi Diels resulted in the isolation of two new acorane-related seco-sesquiterpenes (1 and 3), two new acorane-related seco-norsesquiterpenes (2 and 4), one new 2-epi-cedrane sesquiterpene (5), eight new acorane-type sesquiterpenes (6–13), and a known major constituent of acorenone B (14). Their structures were established by interpreting extensive spectroscopic data, including HRESIMS, NMR (1H and 13C NMR, 1H-1H COSY, HSQC, and HMBC), and NOE difference spectra analysis. The absolute configurations of 1, 2, 4–7, 9, 10, and 14 were determined by X-ray crystallography, while chemical transformation methods were performed with compound 14 as the starting material to elegantly solve the absolute configuration issue of compounds 8 and 11–13. Notably, 1 and 2 are seco-sesquiterpenes that are related to acorane and possess an unusual ketal-linked hemiacetal in a 6,8-dioxabicyclo[3.2.1]octan-7-ol scaffold ring system. Plausible biosynthetic pathways for compounds 1–14, which were derived from the acorane skeleton, were proposed. All the isolated compounds (1–14) were evaluated for their antiviral and cytotoxic activities.
期刊介绍:
Bioorganic Chemistry publishes research that addresses biological questions at the molecular level, using organic chemistry and principles of physical organic chemistry. The scope of the journal covers a range of topics at the organic chemistry-biology interface, including: enzyme catalysis, biotransformation and enzyme inhibition; nucleic acids chemistry; medicinal chemistry; natural product chemistry, natural product synthesis and natural product biosynthesis; antimicrobial agents; lipid and peptide chemistry; biophysical chemistry; biological probes; bio-orthogonal chemistry and biomimetic chemistry.
For manuscripts dealing with synthetic bioactive compounds, the Journal requires that the molecular target of the compounds described must be known, and must be demonstrated experimentally in the manuscript. For studies involving natural products, if the molecular target is unknown, some data beyond simple cell-based toxicity studies to provide insight into the mechanism of action is required. Studies supported by molecular docking are welcome, but must be supported by experimental data. The Journal does not consider manuscripts that are purely theoretical or computational in nature.
The Journal publishes regular articles, short communications and reviews. Reviews are normally invited by Editors or Editorial Board members. Authors of unsolicited reviews should first contact an Editor or Editorial Board member to determine whether the proposed article is within the scope of the Journal.