{"title":"UPLC-Q-TOF-MS/MS analysis of ophiobolins sesterterpenoids and bioactive analogs from Bipolaris eleusines","authors":"","doi":"10.1016/j.phytochem.2024.114267","DOIUrl":null,"url":null,"abstract":"<div><p>In order to elucidate the mass fragmentation patterns and unveil more undescribed ophiobolin analogs, the mass fragmentation patterns of ophiobolins were analyzed based on UPLC-Q-TOF-MS/MS experiments. Different kinds of rearrangements (including McLafferty rearrangement) were the main cleavage patterns. Twenty-six (<strong>9</strong>–<strong>31</strong>) analogs were then tentatively characterized based on their mass analysis, and three undescribed ophiobolins (<strong>6</strong>–<strong>8</strong>) and a known analogue (<strong>5</strong>) were isolated in target. Compound <strong>5</strong> possesses a rare polycyclic carbon skeleton only recently reported, and compound <strong>6</strong> contains an undescribed lactone ring system fused with A/B ring at C-3/C-21, whereas compounds <strong>7</strong> and <strong>8</strong> have a peroxyl group in the side chain, which is the first reported in all ophiobolins. Compounds <strong>5</strong> and <strong>7</strong> displayed significant cytotoxicity against MCF-7 cancer cells.</p></div>","PeriodicalId":20170,"journal":{"name":"Phytochemistry","volume":null,"pages":null},"PeriodicalIF":3.2000,"publicationDate":"2024-08-30","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/S0031942224003042","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
In order to elucidate the mass fragmentation patterns and unveil more undescribed ophiobolin analogs, the mass fragmentation patterns of ophiobolins were analyzed based on UPLC-Q-TOF-MS/MS experiments. Different kinds of rearrangements (including McLafferty rearrangement) were the main cleavage patterns. Twenty-six (9–31) analogs were then tentatively characterized based on their mass analysis, and three undescribed ophiobolins (6–8) and a known analogue (5) were isolated in target. Compound 5 possesses a rare polycyclic carbon skeleton only recently reported, and compound 6 contains an undescribed lactone ring system fused with A/B ring at C-3/C-21, whereas compounds 7 and 8 have a peroxyl group in the side chain, which is the first reported in all ophiobolins. Compounds 5 and 7 displayed significant cytotoxicity against MCF-7 cancer cells.
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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