Rui-Li Huang , Wei Tang , Chaoqun Wang , Cong Yan , Yun Hu , Hai-Xia Yang , Hai-Yang Xiang , Xiao-Jun Huang , Li-Jun Hu , Wen-Cai Ye , Jian-Guo Song , Ying Wang
{"title":"Antiviral C-geranylated flavonoids from Artocarpus communis","authors":"Rui-Li Huang , Wei Tang , Chaoqun Wang , Cong Yan , Yun Hu , Hai-Xia Yang , Hai-Yang Xiang , Xiao-Jun Huang , Li-Jun Hu , Wen-Cai Ye , Jian-Guo Song , Ying Wang","doi":"10.1016/j.phytochem.2024.114165","DOIUrl":null,"url":null,"abstract":"<div><p>Ten <em>C</em>-geranylated flavonoids, along with three known analogues, were isolated from the leaves of <em>Artocarpus communis</em>. The chemical structures of these compounds were unambiguously determined via comprehensive spectroscopic analysis, single-crystal X-ray diffraction experiments, and quantum chemical electronic circular dichroism calculations. Structurally, artocarones A–I (<strong>1</strong>–<strong>9</strong>) represent a group of unusual, highly modified <em>C</em>-geranylated flavonoids, in which the geranyl chain is cyclised with the <em>ortho</em>-hydroxy group of flavonoids to form various heterocyclic scaffolds. Notably, artocarones E and G–I (<strong>5</strong> and <strong>7</strong>–<strong>9</strong>) feature a 6<em>H</em>-benzo[<em>c</em>]chromene core that is hitherto undescribed in <em>C</em>-geranylated flavonoids. Artocarone J (<strong>10</strong>) is the first example of C-9–C-16 connected <em>C</em>-geranylated aurone. Meanwhile, the plausible biosynthetic pathways for these rare <em>C</em>-geranylated flavonoids were also proposed. Notably, compounds <strong>1</strong>, <strong>2</strong>, <strong>4</strong>, <strong>8</strong>, <strong>11</strong>, and <strong>12</strong> exhibited promising <em>in vitro</em> inhibitory activities against respiratory syncytial virus and herpes simplex virus type 1.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-05-28","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/S0031942224002024","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}
引用次数: 0
Abstract
Ten C-geranylated flavonoids, along with three known analogues, were isolated from the leaves of Artocarpus communis. The chemical structures of these compounds were unambiguously determined via comprehensive spectroscopic analysis, single-crystal X-ray diffraction experiments, and quantum chemical electronic circular dichroism calculations. Structurally, artocarones A–I (1–9) represent a group of unusual, highly modified C-geranylated flavonoids, in which the geranyl chain is cyclised with the ortho-hydroxy group of flavonoids to form various heterocyclic scaffolds. Notably, artocarones E and G–I (5 and 7–9) feature a 6H-benzo[c]chromene core that is hitherto undescribed in C-geranylated flavonoids. Artocarone J (10) is the first example of C-9–C-16 connected C-geranylated aurone. Meanwhile, the plausible biosynthetic pathways for these rare C-geranylated flavonoids were also proposed. Notably, compounds 1, 2, 4, 8, 11, and 12 exhibited promising in vitro inhibitory activities against respiratory syncytial virus and herpes simplex virus type 1.
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.