{"title":"Kopsileuconines A−D: Bisindole alkaloids with cytotoxic activity from Kopsia hainanensis","authors":"","doi":"10.1016/j.phytochem.2024.114245","DOIUrl":null,"url":null,"abstract":"<div><p>Kopsileuconines A−D (<strong>1</strong>−<strong>4</strong>), four monoterpenoid bisindole alkaloids with unprecedented skeletons, along with their biosynthetically related precursors (<strong>5</strong>−<strong>8</strong>) were isolated from the roots of <em>Kopsia hainanensis</em>. Compound <strong>1</strong> possessed an undescribed C-6−C-5′ dimerization pattern of aspidofractinine-type alkaloids. Compounds <strong>2</strong>−<strong>4</strong> were rhazinilam-kopsine (<strong>2</strong>) and rhazinilam-aspidofractinine type (<strong>3</strong> and <strong>4</strong>) bisindole alkaloids with undescribed skeletons, respectively. Their structures with absolute configurations were fully accomplished by extensive spectroscopic analysis, quantum-chemical calculations, and X-ray crystallography. A plausible biosynthetic pathway for <strong>1</strong>−<strong>4</strong> was proposed. Compound <strong>2</strong> exhibited a significant inhibitory effect against human lung cancer cell lines PC9 (EGFR mutant), with an IC<sub>50</sub> value of 15.07 ± 1.19 μM.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-08-10","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/S0031942224002826","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
Kopsileuconines A−D (1−4), four monoterpenoid bisindole alkaloids with unprecedented skeletons, along with their biosynthetically related precursors (5−8) were isolated from the roots of Kopsia hainanensis. Compound 1 possessed an undescribed C-6−C-5′ dimerization pattern of aspidofractinine-type alkaloids. Compounds 2−4 were rhazinilam-kopsine (2) and rhazinilam-aspidofractinine type (3 and 4) bisindole alkaloids with undescribed skeletons, respectively. Their structures with absolute configurations were fully accomplished by extensive spectroscopic analysis, quantum-chemical calculations, and X-ray crystallography. A plausible biosynthetic pathway for 1−4 was proposed. Compound 2 exhibited a significant inhibitory effect against human lung cancer cell lines PC9 (EGFR mutant), with an IC50 value of 15.07 ± 1.19 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.
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