{"title":"Discovery of Indole Alkaloids Crienamides A and B from Penicillium citrinum by a Simulated MS/MS-Guided Molecular Network Strategy","authors":"Yuanyang Peng, Shang Luo, Qin Li, Yongqi Li, Jiale Zhang, Nanjin Ding, Weiguang Sun, Chunmei Chen, Junjun Liu, Ying Ye, Hucheng Zhu, Yonghui Zhang","doi":"10.1021/acs.orglett.5c00564","DOIUrl":null,"url":null,"abstract":"The building blocks-based molecular network (BBMN) strategy is effective for targeted natural product identification but depends on existing MS/MS data. To address this, we propose the simulated MS/MS-guided molecular network (SMMN) strategy, which combines virtual molecule design and MS/MS simulation to identify novel compounds containing target building blocks. We developed the MZmol Analyzer, a user-friendly web tool, to automate the SMMN strategy. Using this approach and the target 6-methyl-<span>l</span>-pipecolate (6-MeP), we identified two new indole alkaloid hybrids, crienamides A and B. <i>In vitro</i> immunosuppressive assays showed that both compounds inhibited ConA-induced cell proliferation, with IC<sub>50</sub> values of 2.86 ± 1.33 μM and 0.96 ± 1.22 μM, respectively.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"20 1","pages":""},"PeriodicalIF":5.0000,"publicationDate":"2025-04-02","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.5c00564","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0
Abstract
The building blocks-based molecular network (BBMN) strategy is effective for targeted natural product identification but depends on existing MS/MS data. To address this, we propose the simulated MS/MS-guided molecular network (SMMN) strategy, which combines virtual molecule design and MS/MS simulation to identify novel compounds containing target building blocks. We developed the MZmol Analyzer, a user-friendly web tool, to automate the SMMN strategy. Using this approach and the target 6-methyl-l-pipecolate (6-MeP), we identified two new indole alkaloid hybrids, crienamides A and B. In vitro immunosuppressive assays showed that both compounds inhibited ConA-induced cell proliferation, with IC50 values of 2.86 ± 1.33 μM and 0.96 ± 1.22 μM, respectively.
期刊介绍：
Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
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