Rui Guo , Cun-Lin Wang , Xiao-Juan Cao , Xiao-Juan Yao , Xin Qiao , Ya-Tian Meng , Tong Zhang , Qiong Zhang
{"title":"Rare oxoisoaporphine alkaloids from Menispermum dauricum with potential anti-inflammatory activity","authors":"Rui Guo , Cun-Lin Wang , Xiao-Juan Cao , Xiao-Juan Yao , Xin Qiao , Ya-Tian Meng , Tong Zhang , Qiong Zhang","doi":"10.1016/j.phytochem.2024.114170","DOIUrl":null,"url":null,"abstract":"<div><p>Eleven alkaloids including four previously undescribed oxoisoaporphine alkaloids, menisoxoisoaporphines A-D (<strong>1</strong>–<strong>4</strong>), four known analogues (<strong>5</strong>–<strong>8</strong>), and three aporphine alkaloids (<strong>9</strong>–<strong>11</strong>), were isolated and identified from the rhizomes of <em>Menispermum dauricum</em>. Their structures were elucidated by extensive spectroscopic data and single-crystal X-ray diffraction analyses. Among them, compounds <strong>1</strong> and <strong>4</strong> were the first samples of oxoisoaporphine with C-6 isopentylamino moiety, and <strong>2</strong> was a rare C-4 methylation product of oxoisoaporphine alkaloid. The in vitro anti-inflammatory activity of compounds <strong>1</strong>–<strong>11</strong> was performed by evaluating the inhibition of NO level in LPS-induced RAW264.7 macrophages. Among them, compound <strong>4</strong> exhibited the most potent NO inhibition activity with an IC<sub>50</sub> value of 1.95 ± 0.33 <em>μ</em>M. The key structure-activity relationships of those oxoisoaporphine alkaloids for anti-inflammatory effects have been summarized.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-06-01","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/S0031942224002073","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
Eleven alkaloids including four previously undescribed oxoisoaporphine alkaloids, menisoxoisoaporphines A-D (1–4), four known analogues (5–8), and three aporphine alkaloids (9–11), were isolated and identified from the rhizomes of Menispermum dauricum. Their structures were elucidated by extensive spectroscopic data and single-crystal X-ray diffraction analyses. Among them, compounds 1 and 4 were the first samples of oxoisoaporphine with C-6 isopentylamino moiety, and 2 was a rare C-4 methylation product of oxoisoaporphine alkaloid. The in vitro anti-inflammatory activity of compounds 1–11 was performed by evaluating the inhibition of NO level in LPS-induced RAW264.7 macrophages. Among them, compound 4 exhibited the most potent NO inhibition activity with an IC50 value of 1.95 ± 0.33 μM. The key structure-activity relationships of those oxoisoaporphine alkaloids for anti-inflammatory effects have been summarized.
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.