Xiao-Feng He , Tian-Ze Li , Yun-Bao Ma , Meng-Fei Wang , Ji-Jun Chen
{"title":"黄花蒿中不寻常的涉及卡丁烷的倍半萜二聚体及其抗肝癌作用","authors":"Xiao-Feng He , Tian-Ze Li , Yun-Bao Ma , Meng-Fei Wang , Ji-Jun Chen","doi":"10.1016/j.phytochem.2024.114216","DOIUrl":null,"url":null,"abstract":"<div><p><em>Artemisia annua</em> L. (“Qinghao” in Chinese) is a famous traditional Chinese medicinal herb and has been used to treat malaria and various tumors. Our preliminary screening indicated that the EtOAc extract of <em>A. annua</em> manifested activity against HepG2, Huh7, and SK-Hep-1 cell lines with inhibitory ratios of 53.2%, 52.1%, and 59.6% at 200 μg/mL, respectively. Bioassay-guided isolation of <em>A. annua</em> afforded 14 unusual cadinane-involved sesquiterpenoid dimers, artemannuins A‒N (<strong>1</strong>–<strong>14</strong>), of which the structures were elucidated by extensive spectral analyses, ECD calculations, and single-crystal X-ray diffraction. Structurally, these compounds were classified into five different types based on the coupled modes of two monomeric sesquiterpenoids. Among them, compounds <strong>1</strong>–<strong>9</strong> represented the first examples of sesquiterpenoid dimers formed <em>via</em> the C-3‒C-3′ single bond of two 5(4 → 3)-<em>abeo</em>-cadinane sesquiterpenoid monomers, while compounds <strong>13</strong> and <strong>14</strong> were dimers fused by cadinane and humulane sesquiterpenoids <em>via</em> an ester bond. Methylated derivatives of <strong>1</strong>, <strong>4</strong>, <strong>6</strong>, and <strong>8</strong> showed antihepatoma activity against HepG2, Huh7, and SK-Hep-1 cell lines with IC<sub>50</sub> values ranging from 30.5 to 57.2 μM.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-07-06","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Unusual cadinane-involved sesquiterpenoid dimers from Artemisia annua and their antihepatoma effect\",\"authors\":\"Xiao-Feng He , Tian-Ze Li , Yun-Bao Ma , Meng-Fei Wang , Ji-Jun Chen\",\"doi\":\"10.1016/j.phytochem.2024.114216\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p><em>Artemisia annua</em> L. (“Qinghao” in Chinese) is a famous traditional Chinese medicinal herb and has been used to treat malaria and various tumors. Our preliminary screening indicated that the EtOAc extract of <em>A. annua</em> manifested activity against HepG2, Huh7, and SK-Hep-1 cell lines with inhibitory ratios of 53.2%, 52.1%, and 59.6% at 200 μg/mL, respectively. Bioassay-guided isolation of <em>A. annua</em> afforded 14 unusual cadinane-involved sesquiterpenoid dimers, artemannuins A‒N (<strong>1</strong>–<strong>14</strong>), of which the structures were elucidated by extensive spectral analyses, ECD calculations, and single-crystal X-ray diffraction. Structurally, these compounds were classified into five different types based on the coupled modes of two monomeric sesquiterpenoids. Among them, compounds <strong>1</strong>–<strong>9</strong> represented the first examples of sesquiterpenoid dimers formed <em>via</em> the C-3‒C-3′ single bond of two 5(4 → 3)-<em>abeo</em>-cadinane sesquiterpenoid monomers, while compounds <strong>13</strong> and <strong>14</strong> were dimers fused by cadinane and humulane sesquiterpenoids <em>via</em> an ester bond. Methylated derivatives of <strong>1</strong>, <strong>4</strong>, <strong>6</strong>, and <strong>8</strong> showed antihepatoma activity against HepG2, Huh7, and SK-Hep-1 cell lines with IC<sub>50</sub> values ranging from 30.5 to 57.2 μM.</p></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-07-06\",\"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/S003194222400253X\",\"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/S003194222400253X","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}
Unusual cadinane-involved sesquiterpenoid dimers from Artemisia annua and their antihepatoma effect
Artemisia annua L. (“Qinghao” in Chinese) is a famous traditional Chinese medicinal herb and has been used to treat malaria and various tumors. Our preliminary screening indicated that the EtOAc extract of A. annua manifested activity against HepG2, Huh7, and SK-Hep-1 cell lines with inhibitory ratios of 53.2%, 52.1%, and 59.6% at 200 μg/mL, respectively. Bioassay-guided isolation of A. annua afforded 14 unusual cadinane-involved sesquiterpenoid dimers, artemannuins A‒N (1–14), of which the structures were elucidated by extensive spectral analyses, ECD calculations, and single-crystal X-ray diffraction. Structurally, these compounds were classified into five different types based on the coupled modes of two monomeric sesquiterpenoids. Among them, compounds 1–9 represented the first examples of sesquiterpenoid dimers formed via the C-3‒C-3′ single bond of two 5(4 → 3)-abeo-cadinane sesquiterpenoid monomers, while compounds 13 and 14 were dimers fused by cadinane and humulane sesquiterpenoids via an ester bond. Methylated derivatives of 1, 4, 6, and 8 showed antihepatoma activity against HepG2, Huh7, and SK-Hep-1 cell lines with IC50 values ranging from 30.5 to 57.2 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.