{"title":"The clarification of two hydroxylation steps in the conversion of cholesterol to OSW‐1 in Ornithogalum saundersiae","authors":"Shu‐Yue Zhang, Jian‐Qiang Kong","doi":"10.1111/pbi.70080","DOIUrl":null,"url":null,"abstract":"SummaryOSW‐1 is a cholestane saponin uniquely produced in <jats:italic>Ornithogalum saundersiae</jats:italic> and exhibits a potential antitumor activity. The enzymes responsible for OSW‐1 biosynthesis in <jats:italic>O. saundersiae</jats:italic>, however, remain unclear. Herein, cholesterol was confirmed to be the precursor of OSW‐1 using stable‐isotope labeling method. Next, two cytochrome P450s, <jats:italic>Os</jats:italic>CYP90B94 and <jats:italic>Os</jats:italic>CYP90G11, and their partner cytochrome P450 reductase <jats:italic>Os</jats:italic>CPR2 were mined by comparable transcriptome analysis and demonstrated to be involved in OSW‐1 biosynthesis. Specifically, <jats:italic>Os</jats:italic>CYP90B94 catalyses cholesterol to 22<jats:italic>R</jats:italic>‐hydroxycholesterol, which is then converted to 16<jats:italic>β</jats:italic>‐hydroxy‐22‐oxo‐cholesterol, a precursor of OSW‐1 by the second P450 <jats:italic>O</jats:italic>sCYP90G11 via two consecutive oxidation reactions. Unlike their homologues, <jats:italic>Os</jats:italic>CYP90G11 and <jats:italic>Os</jats:italic>CYP90B94 displayed broader catalytic promiscuity. <jats:italic>Os</jats:italic>CYP90B94 recognizes both cholesterol and 7<jats:italic>β</jats:italic>‐hydroxycholesterol, while <jats:italic>Os</jats:italic>CYP90G11 can react with cholesterol, 22<jats:italic>R</jats:italic>‐hydroxycholesterol and 16<jats:italic>β</jats:italic>,22<jats:italic>R</jats:italic>‐dihydroxycholesterol, suggesting their involvement in more than one pathway besides OSW‐1 biosynthesis. This study lays a foundation for the complete characterization of OSW‐1 biosynthesis.","PeriodicalId":221,"journal":{"name":"Plant Biotechnology Journal","volume":"245 1","pages":""},"PeriodicalIF":10.1000,"publicationDate":"2025-06-23","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Plant Biotechnology Journal","FirstCategoryId":"5","ListUrlMain":"https://doi.org/10.1111/pbi.70080","RegionNum":1,"RegionCategory":"生物学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"BIOTECHNOLOGY & APPLIED MICROBIOLOGY","Score":null,"Total":0}
引用次数: 0
Abstract
SummaryOSW‐1 is a cholestane saponin uniquely produced in Ornithogalum saundersiae and exhibits a potential antitumor activity. The enzymes responsible for OSW‐1 biosynthesis in O. saundersiae, however, remain unclear. Herein, cholesterol was confirmed to be the precursor of OSW‐1 using stable‐isotope labeling method. Next, two cytochrome P450s, OsCYP90B94 and OsCYP90G11, and their partner cytochrome P450 reductase OsCPR2 were mined by comparable transcriptome analysis and demonstrated to be involved in OSW‐1 biosynthesis. Specifically, OsCYP90B94 catalyses cholesterol to 22R‐hydroxycholesterol, which is then converted to 16β‐hydroxy‐22‐oxo‐cholesterol, a precursor of OSW‐1 by the second P450 OsCYP90G11 via two consecutive oxidation reactions. Unlike their homologues, OsCYP90G11 and OsCYP90B94 displayed broader catalytic promiscuity. OsCYP90B94 recognizes both cholesterol and 7β‐hydroxycholesterol, while OsCYP90G11 can react with cholesterol, 22R‐hydroxycholesterol and 16β,22R‐dihydroxycholesterol, suggesting their involvement in more than one pathway besides OSW‐1 biosynthesis. This study lays a foundation for the complete characterization of OSW‐1 biosynthesis.
期刊介绍:
Plant Biotechnology Journal aspires to publish original research and insightful reviews of high impact, authored by prominent researchers in applied plant science. The journal places a special emphasis on molecular plant sciences and their practical applications through plant biotechnology. Our goal is to establish a platform for showcasing significant advances in the field, encompassing curiosity-driven studies with potential applications, strategic research in plant biotechnology, scientific analysis of crucial issues for the beneficial utilization of plant sciences, and assessments of the performance of plant biotechnology products in practical applications.