{"title":"Benzomalvin G and H, an Atropisomeric Pair of Dimethoxylated Quinazolinobenzodiazepine Alkaloids Produced by Aspergillus fumigatiaffinis.","authors":"Shinji Kishimoto, Rikuto Takahashi, Kenji Watanabe","doi":"10.1248/cpb.c25-00430","DOIUrl":null,"url":null,"abstract":"<p><p>Aspergillus and Penicillium species produce a variety of quinazolinobenzodiazepine (QBD) alkaloids by using different biosynthetic gene clusters (BGCs). During the course of metabolome analysis of Aspergillus fumigatiaffinis IFM55214, we discovered an atropisomeric pair of QBD natural products, benzomalvin G (1) and H (2), that are produced by this fungus. The isomer 1 was favored in organic solvents, and 2 was favored in aqueous solutions. The stereochemistry and conformation of these 2 compounds were determined unambiguously by Marfey's method and nuclear Overhauser effect (NOE) analysis, respectively. Furthermore, a putative BGC for 1 and 2 (Afben cluster), composed of 3 genes (AfbenX, AfbenY, and AfbenZ) shared between the ben cluster in Aspergillus terreus and 4 additional genes (methyltransferases and oxygenases), was identified in the genome of A. fumigatiaffinis IFM55214.</p>","PeriodicalId":9773,"journal":{"name":"Chemical & pharmaceutical bulletin","volume":"73 10","pages":"962-967"},"PeriodicalIF":1.3000,"publicationDate":"2025-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Chemical & pharmaceutical bulletin","FirstCategoryId":"3","ListUrlMain":"https://doi.org/10.1248/cpb.c25-00430","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"CHEMISTRY, MEDICINAL","Score":null,"Total":0}
引用次数: 0
Abstract
Aspergillus and Penicillium species produce a variety of quinazolinobenzodiazepine (QBD) alkaloids by using different biosynthetic gene clusters (BGCs). During the course of metabolome analysis of Aspergillus fumigatiaffinis IFM55214, we discovered an atropisomeric pair of QBD natural products, benzomalvin G (1) and H (2), that are produced by this fungus. The isomer 1 was favored in organic solvents, and 2 was favored in aqueous solutions. The stereochemistry and conformation of these 2 compounds were determined unambiguously by Marfey's method and nuclear Overhauser effect (NOE) analysis, respectively. Furthermore, a putative BGC for 1 and 2 (Afben cluster), composed of 3 genes (AfbenX, AfbenY, and AfbenZ) shared between the ben cluster in Aspergillus terreus and 4 additional genes (methyltransferases and oxygenases), was identified in the genome of A. fumigatiaffinis IFM55214.
期刊介绍：
The CPB covers various chemical topics in the pharmaceutical and health sciences fields dealing with biologically active compounds, natural products, and medicines, while BPB deals with a wide range of biological topics in the pharmaceutical and health sciences fields including scientific research from basic to clinical studies. For details of their respective scopes, please refer to the submission topic categories below.
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