{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,5]],"date-time":"2026-03-05T06:24:11Z","timestamp":1772691851230,"version":"3.50.1"},"reference-count":31,"publisher":"Elsevier BV","license":[{"start":{"date-parts":[[2025,7,1]],"date-time":"2025-07-01T00:00:00Z","timestamp":1751328000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/tdm\/userlicense\/1.0\/"},{"start":{"date-parts":[[2025,7,1]],"date-time":"2025-07-01T00:00:00Z","timestamp":1751328000000},"content-version":"tdm","delay-in-days":0,"URL":"https:\/\/www.elsevier.com\/legal\/tdmrep-license"},{"start":{"date-parts":[[2025,7,1]],"date-time":"2025-07-01T00:00:00Z","timestamp":1751328000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-017"},{"start":{"date-parts":[[2025,7,1]],"date-time":"2025-07-01T00:00:00Z","timestamp":1751328000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2025,7,1]],"date-time":"2025-07-01T00:00:00Z","timestamp":1751328000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-012"},{"start":{"date-parts":[[2025,7,1]],"date-time":"2025-07-01T00:00:00Z","timestamp":1751328000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2025,7,1]],"date-time":"2025-07-01T00:00:00Z","timestamp":1751328000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-004"}],"funder":[{"DOI":"10.13039\/501100004731","name":"Zhejiang Province Natural Science Foundation","doi-asserted-by":"publisher","award":["LY22H040010"],"award-info":[{"award-number":["LY22H040010"]}],"id":[{"id":"10.13039\/501100004731","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/100007835","name":"Wenzhou Medical University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007835","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["82301813"],"award-info":[{"award-number":["82301813"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001809","name":"National Natural Science Foundation of China","doi-asserted-by":"publisher","award":["82371610"],"award-info":[{"award-number":["82371610"]}],"id":[{"id":"10.13039\/501100001809","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["elsevier.com","sciencedirect.com"],"crossmark-restriction":true},"short-container-title":["Bioorganic Chemistry"],"published-print":{"date-parts":[[2025,7]]},"DOI":"10.1016\/j.bioorg.2025.108630","type":"journal-article","created":{"date-parts":[[2025,5,24]],"date-time":"2025-05-24T06:24:53Z","timestamp":1748067893000},"page":"108630","update-policy":"https:\/\/doi.org\/10.1016\/elsevier_cm_policy","source":"Crossref","is-referenced-by-count":3,"special_numbering":"C","title":["Structure activity relationship of Aristolochic acid analogues: Inhibitory effect on human and rat gonadal 3\u03b2-Hydroxysteroid dehydrogenases"],"prefix":"10.1016","volume":"162","author":[{"given":"Weijian","family":"Zhu","sequence":"first","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zhuoqi","family":"Chen","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Shaowei","family":"Wang","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Yang","family":"Zhu","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Ren-shan","family":"Ge","sequence":"additional","affiliation":[],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"78","reference":[{"issue":"2","key":"10.1016\/j.bioorg.2025.108630_bb0005","doi-asserted-by":"crossref","first-page":"261","DOI":"10.1016\/j.bpobgyn.2007.07.009","article-title":"Polycystic ovary syndrome","volume":"22","author":"Homburg","year":"2008","journal-title":"Best Pract. Res. Clin. Obstet. Gynaecol."},{"issue":"45","key":"10.1016\/j.bioorg.2025.108630_bb0010","doi-asserted-by":"crossref","first-page":"42795","DOI":"10.1074\/jbc.M208537200","article-title":"Structure\/function relationships responsible for the kinetic differences between human type 1 and type 2 3beta-hydroxysteroid dehydrogenase and for the catalysis of the type 1 activity","volume":"277","author":"Thomas","year":"2002","journal-title":"J. Biol. Chem."},{"issue":"4","key":"10.1016\/j.bioorg.2025.108630_bb0015","doi-asserted-by":"crossref","first-page":"525","DOI":"10.1210\/er.2002-0050","article-title":"Molecular biology of the 3beta-hydroxysteroid dehydrogenase\/delta5-delta4 isomerase gene family","volume":"26","author":"Simard","year":"2005","journal-title":"Endocr. Rev."},{"key":"10.1016\/j.bioorg.2025.108630_bb0020","doi-asserted-by":"crossref","DOI":"10.1016\/j.ejmech.2024.116523","article-title":"Exploring fluorine-substituted piperidines as potential therapeutics for diabetes mellitus and Alzheimer's diseases","volume":"273","author":"Mughal","year":"2024","journal-title":"Eur. J. Med. Chem."},{"key":"10.1016\/j.bioorg.2025.108630_bb0025","doi-asserted-by":"crossref","DOI":"10.2174\/0109298673309489240816063313","article-title":"The investigation of Nf\u03bab inhibitors to block cell proliferation in OSCC cells lines","author":"Cheng","year":"2024","journal-title":"Curr. Med. Chem."},{"issue":"14","key":"10.1016\/j.bioorg.2025.108630_bb0030","doi-asserted-by":"crossref","first-page":"10484","DOI":"10.1039\/D4RA08558B","article-title":"Comprehensive assessment of 3-benzyloxyflavones as \u03b2-glucosidase inhibitors: in vitro, in vivo, kinetic","volume":"15","author":"Naeem","year":"2025","journal-title":"SAR and computational studies, RSC Adv"},{"issue":"1","key":"10.1016\/j.bioorg.2025.108630_bb0035","doi-asserted-by":"crossref","DOI":"10.3892\/mmr.2024.13387","article-title":"Research progress on antioxidants and protein aggregation inhibitors in cataract prevention and therapy (review)","volume":"31","author":"Wang","year":"2025","journal-title":"Mol. Med. Rep."},{"issue":"1","key":"10.1016\/j.bioorg.2025.108630_bb0040","doi-asserted-by":"crossref","first-page":"108","DOI":"10.1016\/j.jep.2009.05.028","article-title":"Local uses of Aristolochia species and content of nephrotoxic aristolochic acid 1 and 2--a global assessment based on bibliographic sources","volume":"125","author":"Heinrich","year":"2009","journal-title":"J. Ethnopharmacol."},{"issue":"6","key":"10.1016\/j.bioorg.2025.108630_bb0045","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1039\/b303648k","article-title":"Naturally occurring aristolactams, aristolochic acids and dioxoaporphines and their biological activities","volume":"20","author":"Kumar","year":"2003","journal-title":"Nat. Prod. Rep."},{"issue":"4","key":"10.1016\/j.bioorg.2025.108630_bb0050","doi-asserted-by":"crossref","first-page":"249","DOI":"10.1016\/S2225-4110(16)30111-0","article-title":"Chemical constituents and pharmacology of the Aristolochia (madou ling) species","volume":"2","author":"Kuo","year":"2012","journal-title":"J. Tradit. Complement. Med."},{"issue":"18","key":"10.1016\/j.bioorg.2025.108630_bb0055","doi-asserted-by":"crossref","first-page":"52446","DOI":"10.1007\/s11356-023-26018-0","volume":"30","author":"Lalrinzuali","year":"2023","journal-title":"Environ. Sci. Pollut. Res. Int."},{"key":"10.1016\/j.bioorg.2025.108630_bb0060","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1007\/978-3-030-41283-8_9","article-title":"Biotransformation and toxicities of Aristolochic acids","volume":"1241","author":"Sidorenko","year":"2020","journal-title":"Adv. Exp. Med. Biol."},{"key":"10.1016\/j.bioorg.2025.108630_bb0065","doi-asserted-by":"crossref","DOI":"10.1016\/j.tox.2022.153228","article-title":"Oral subacute nephrotoxicity of aristololactam I in rats","volume":"475","author":"Wang","year":"2022","journal-title":"Toxicology"},{"key":"10.1016\/j.bioorg.2025.108630_bb0070","doi-asserted-by":"crossref","DOI":"10.1016\/j.phymed.2022.154257","article-title":"Aristolone in Nardostachys jatamansi DC. Induces mesenteric vasodilation and ameliorates hypertension via activation of the K(ATP) channel and PDK1-Akt-eNOS pathway","volume":"104","author":"Fang","year":"2022","journal-title":"Phytomedicine : international journal of phytotherapy and phytopharmacology"},{"issue":"2","key":"10.1016\/j.bioorg.2025.108630_bb0075","first-page":"253","article-title":"Aristolactams, 1-(2-C-methyl-beta-D-ribofuranosyl)-uracil and other bioactive constituents of Toussaintia orientalis","volume":"5","author":"Odalo","year":"2010","journal-title":"Nat. Prod. Commun."},{"issue":"4","key":"10.1016\/j.bioorg.2025.108630_bb0080","doi-asserted-by":"crossref","first-page":"519","DOI":"10.1038\/aja.2010.18","article-title":"Effects of genistein and equol on human and rat testicular 3beta-hydroxysteroid dehydrogenase and 17beta-hydroxysteroid dehydrogenase 3 activities","volume":"12","author":"Hu","year":"2010","journal-title":"Asian J. Androl."},{"key":"10.1016\/j.bioorg.2025.108630_bb0085","doi-asserted-by":"crossref","DOI":"10.1016\/j.tox.2022.153334","article-title":"Structure-activity relationship analysis of perfluoroalkyl carbonic acids on human and rat placental 3beta-hydroxysteroid dehydrogenase activity","volume":"480","author":"Wang","year":"2022","journal-title":"Toxicology"},{"key":"10.1016\/j.bioorg.2025.108630_bb0090","doi-asserted-by":"crossref","DOI":"10.3389\/fendo.2021.765251","article-title":"Effects of midazolam on the development of adult Leydig cells from stem cells in vitro","volume":"12","author":"Zhao","year":"2021","journal-title":"Front. Endocrinol."},{"issue":"W1","key":"10.1016\/j.bioorg.2025.108630_bb0095","doi-asserted-by":"crossref","first-page":"W296","DOI":"10.1093\/nar\/gky427","article-title":"SWISS-MODEL: homology modelling of protein structures and complexes","volume":"46","author":"Waterhouse","year":"2018","journal-title":"Nucleic Acids Res."},{"issue":"1","key":"10.1016\/j.bioorg.2025.108630_bb0100","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1038\/nmeth.4067","article-title":"CHARMM36m: an improved force field for folded and intrinsically disordered proteins","volume":"14","author":"Huang","year":"2017","journal-title":"Nat. Methods"},{"issue":"10","key":"10.1016\/j.bioorg.2025.108630_bb0105","doi-asserted-by":"crossref","first-page":"6281","DOI":"10.1021\/acs.jctc.1c00645","article-title":"gmx_MMPBSA: a new tool to perform end-state free energy calculations with GROMACS","volume":"17","author":"Valdes-Tresanco","year":"2021","journal-title":"J. Chem. Theory Comput."},{"issue":"9","key":"10.1016\/j.bioorg.2025.108630_bb0110","doi-asserted-by":"crossref","first-page":"3314","DOI":"10.1021\/ct300418h","article-title":"MMPBSA.Py: an efficient program for end-state free energy calculations","volume":"8","author":"Miller","year":"2012","journal-title":"J. Chem. Theory Comput."},{"key":"10.1016\/j.bioorg.2025.108630_bb0115","doi-asserted-by":"crossref","DOI":"10.1016\/j.fct.2023.114028","article-title":"Azole fungicides inhibit human and rat gonadal 3beta-hydroxysteroid dehydrogenases: structure-activity relationship and in silico docking analysis","volume":"180","author":"Sang","year":"2023","journal-title":"Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association"},{"key":"10.1016\/j.bioorg.2025.108630_bb0120","doi-asserted-by":"crossref","DOI":"10.1016\/j.ecoenv.2023.115461","article-title":"Benzene ring bisphenol a substitutes potently inhibit human, rat, and mouse gonadal 3beta-hydroxysteroid dehydrogenases: structure-activity relationship and in silico docking analysis","volume":"264","author":"Yu","year":"2023","journal-title":"Ecotoxicol. Environ. Saf."},{"key":"10.1016\/j.bioorg.2025.108630_bb0125","doi-asserted-by":"crossref","first-page":"20","DOI":"10.1016\/j.toxlet.2023.09.002","article-title":"Halogenated bisphenol a derivatives potently inhibit human, rat, and mouse gonadal 3beta-hydroxysteroid dehydrogenases: structure-activity relationship and in silico molecular docking analysis","volume":"386","author":"Yu","year":"2023","journal-title":"Toxicol. Lett."},{"issue":"1","key":"10.1016\/j.bioorg.2025.108630_bb0130","doi-asserted-by":"crossref","first-page":"2205052","DOI":"10.1080\/14756366.2023.2205052","article-title":"Curcumin analogues exert potent inhibition on human and rat gonadal 3beta-hydroxysteroid dehydrogenases as potential therapeutic agents: structure-activity relationship and in silico docking","volume":"38","author":"Qiao","year":"2023","journal-title":"J. Enzyme Inhib. Med. Chem."},{"issue":"9","key":"10.1016\/j.bioorg.2025.108630_bb0135","doi-asserted-by":"crossref","DOI":"10.3390\/biom11091344","article-title":"Computational analysis of naturally occurring Aristolochic acid analogues and their biological sources","volume":"11","author":"Xu","year":"2021","journal-title":"Biomolecules"},{"key":"10.1016\/j.bioorg.2025.108630_bb0140","doi-asserted-by":"crossref","DOI":"10.1016\/j.toxicon.2024.108214","article-title":"In vitro nephrotoxicity and structure-toxicity relationships of eight natural aristolactams","volume":"254","author":"Xue","year":"2025","journal-title":"Toxicon"},{"key":"10.1016\/j.bioorg.2025.108630_bb0145","series-title":"Chinese Pharmacopoeia","author":"C.P. Commission","year":"2025"},{"issue":"4","key":"10.1016\/j.bioorg.2025.108630_bb0150","doi-asserted-by":"crossref","first-page":"831","DOI":"10.1016\/S0731-7085(03)00310-8","article-title":"Analysis of aristolochic acid in nine sources of Xixin, a traditional Chinese medicine, by liquid chromatography\/atmospheric pressure chemical ionization\/tandem mass spectrometry","volume":"33","author":"Jong","year":"2003","journal-title":"J. Pharm. Biomed. Anal."},{"key":"10.1016\/j.bioorg.2025.108630_bb0155","doi-asserted-by":"crossref","first-page":"215","DOI":"10.3389\/fphar.2017.00215","article-title":"Medicinally used Asarum species: high-resolution LC-MS analysis of Aristolochic acid analogs and in vitro toxicity screening in HK-2 cells","volume":"8","author":"Michl","year":"2017","journal-title":"Front. Pharmacol."}],"container-title":["Bioorganic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206825005103?httpAccept=text\/xml","content-type":"text\/xml","content-version":"vor","intended-application":"text-mining"},{"URL":"https:\/\/api.elsevier.com\/content\/article\/PII:S0045206825005103?httpAccept=text\/plain","content-type":"text\/plain","content-version":"vor","intended-application":"text-mining"}],"deposited":{"date-parts":[[2025,6,3]],"date-time":"2025-06-03T18:06:30Z","timestamp":1748973990000},"score":1,"resource":{"primary":{"URL":"https:\/\/linkinghub.elsevier.com\/retrieve\/pii\/S0045206825005103"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,7]]},"references-count":31,"alternative-id":["S0045206825005103"],"URL":"https:\/\/doi.org\/10.1016\/j.bioorg.2025.108630","relation":{},"ISSN":["0045-2068"],"issn-type":[{"value":"0045-2068","type":"print"}],"subject":[],"published":{"date-parts":[[2025,7]]},"assertion":[{"value":"Elsevier","name":"publisher","label":"This article is maintained by"},{"value":"Structure activity relationship of Aristolochic acid analogues: Inhibitory effect on human and rat gonadal 3\u03b2-Hydroxysteroid dehydrogenases","name":"articletitle","label":"Article Title"},{"value":"Bioorganic Chemistry","name":"journaltitle","label":"Journal Title"},{"value":"https:\/\/doi.org\/10.1016\/j.bioorg.2025.108630","name":"articlelink","label":"CrossRef DOI link to publisher maintained version"},{"value":"article","name":"content_type","label":"Content Type"},{"value":"\u00a9 2025 Elsevier Inc. All rights are reserved, including those for text and data mining, AI training, and similar technologies.","name":"copyright","label":"Copyright"}],"article-number":"108630"}}