Bao-Bao Shi , Fan Xu , Guang-Ru Zhang , Yu He , Qing Liu , Meng-Lin Feng , Zheng-Hui Li , Ji-Kai Liu
{"title":"从 Ophiorrhiza japonica 中提取的具有黄嘌呤氧化酶抑制活性的糖醛酸单萜吲哚生物碱。","authors":"Bao-Bao Shi , Fan Xu , Guang-Ru Zhang , Yu He , Qing Liu , Meng-Lin Feng , Zheng-Hui Li , Ji-Kai Liu","doi":"10.1016/j.phytochem.2024.114169","DOIUrl":null,"url":null,"abstract":"<div><p>Continued interest in the bioactive alkaloids led to the isolation of five undescribed alkaloids (<strong>1–5</strong>), ophiorglucidines A-E, and seven known analogues (<strong>6–12</strong>) from the water-soluble fraction of <em>Ophiorrhiza japonica.</em> The structures were elucidated based on spectroscopic data and quantum calculations as well as X-ray crystallographic analysis. The structure of <strong>1</strong> was characterized as a hexacyclic skeleton including a double bridge linking the indole and the monoterpene moieties, which is the first report of a single crystal with this type of structure. Moreover, the inhibitory effect of zwitterionic indole alkaloid glycosides on xanthine oxidase was found for the first time. The alkaloids <strong>2</strong> and <strong>3</strong>, both of which have a pentacyclic zwitterionic system, were more active than the reference inhibitor, allopurinol (IC<sub>50</sub> = 11.1 <em>μ</em>M) with IC<sub>50</sub> values of 1.0 <em>μ</em>M, and 2.5 <em>μ</em>M, respectively. Structure-activity relationships analyses confirmed that the carbonyl group at C-14 was a key functional group responsible for the inhibitory effects of these alkaloids.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-05-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Glucoconjugated monoterpene indole alkaloids with xanthine oxidase inhibitory activity from Ophiorrhiza japonica\",\"authors\":\"Bao-Bao Shi , Fan Xu , Guang-Ru Zhang , Yu He , Qing Liu , Meng-Lin Feng , Zheng-Hui Li , Ji-Kai Liu\",\"doi\":\"10.1016/j.phytochem.2024.114169\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Continued interest in the bioactive alkaloids led to the isolation of five undescribed alkaloids (<strong>1–5</strong>), ophiorglucidines A-E, and seven known analogues (<strong>6–12</strong>) from the water-soluble fraction of <em>Ophiorrhiza japonica.</em> The structures were elucidated based on spectroscopic data and quantum calculations as well as X-ray crystallographic analysis. The structure of <strong>1</strong> was characterized as a hexacyclic skeleton including a double bridge linking the indole and the monoterpene moieties, which is the first report of a single crystal with this type of structure. Moreover, the inhibitory effect of zwitterionic indole alkaloid glycosides on xanthine oxidase was found for the first time. The alkaloids <strong>2</strong> and <strong>3</strong>, both of which have a pentacyclic zwitterionic system, were more active than the reference inhibitor, allopurinol (IC<sub>50</sub> = 11.1 <em>μ</em>M) with IC<sub>50</sub> values of 1.0 <em>μ</em>M, and 2.5 <em>μ</em>M, respectively. Structure-activity relationships analyses confirmed that the carbonyl group at C-14 was a key functional group responsible for the inhibitory effects of these alkaloids.</p></div>\",\"PeriodicalId\":20170,\"journal\":{\"name\":\"Phytochemistry\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":3.2000,\"publicationDate\":\"2024-05-31\",\"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/S0031942224002061\",\"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/S0031942224002061","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}
Glucoconjugated monoterpene indole alkaloids with xanthine oxidase inhibitory activity from Ophiorrhiza japonica
Continued interest in the bioactive alkaloids led to the isolation of five undescribed alkaloids (1–5), ophiorglucidines A-E, and seven known analogues (6–12) from the water-soluble fraction of Ophiorrhiza japonica. The structures were elucidated based on spectroscopic data and quantum calculations as well as X-ray crystallographic analysis. The structure of 1 was characterized as a hexacyclic skeleton including a double bridge linking the indole and the monoterpene moieties, which is the first report of a single crystal with this type of structure. Moreover, the inhibitory effect of zwitterionic indole alkaloid glycosides on xanthine oxidase was found for the first time. The alkaloids 2 and 3, both of which have a pentacyclic zwitterionic system, were more active than the reference inhibitor, allopurinol (IC50 = 11.1 μM) with IC50 values of 1.0 μM, and 2.5 μM, respectively. Structure-activity relationships analyses confirmed that the carbonyl group at C-14 was a key functional group responsible for the inhibitory effects of these alkaloids.
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.