Abdur Rahman Khan , Zainab Aziz , Amir Iqbal , Sheema , Afsana Rashid Khan , Salman Zafar
{"title":"琥珀酸氢化可的松与紫斑门氏菌和棘皮莞氏菌全细胞培养物的生物转化","authors":"Abdur Rahman Khan , Zainab Aziz , Amir Iqbal , Sheema , Afsana Rashid Khan , Salman Zafar","doi":"10.1016/j.steroids.2024.109466","DOIUrl":null,"url":null,"abstract":"<div><p>Hydrocortisone succinate (<strong>1</strong>) is a synthetic anti-inflammatory drug and key intermediate in the synthesis of other steroidal drugs. This work is based on the fungal biotransformation of <strong>1</strong>, using <em>Monascus purpureus</em> and <em>Cunninghamella echinulata</em> strains. Comopound <strong>1</strong> was transformed into four metabolites, identified as hydrocortisone (<strong>2</strong>), 11β-hydroxyandrost-4-en-3,17-dione (<strong>3</strong>), Δ<sup>1</sup>-cortienic acid (<strong>4</strong>), and hydrocortisone-17-succinate (<strong>5</strong>), obtained through side chain cleavage, hydrolysis, dehydrogenation, and oxidation reactions. These compounds have previously been synthesized either chemically or enzymatically from different precursors. Though this is not the first report on the biotransformation of <strong>1</strong>, but it obviously is a first, where the biotransformed products of compound <strong>1</strong> have been characterized structurally with the help of modern spectroscopic techniques. It is noteworthy that these products have already shown biological potential, however a more thorough investigation of the anti-inflammatory properties of these metabolites would be of high value. These results not only emphasize upon the immense potential of biotransformation in catalysis of reactions, otherwise not-achievable chemically, but also holds promise for the development of novel anti-inflammatory compounds.</p></div>","PeriodicalId":21997,"journal":{"name":"Steroids","volume":"209 ","pages":"Article 109466"},"PeriodicalIF":2.1000,"publicationDate":"2024-06-30","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Biotransformation of hydrocortisone succinate with whole cell cultures of Monascus purpureus and Cunninghamella echinulata\",\"authors\":\"Abdur Rahman Khan , Zainab Aziz , Amir Iqbal , Sheema , Afsana Rashid Khan , Salman Zafar\",\"doi\":\"10.1016/j.steroids.2024.109466\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><p>Hydrocortisone succinate (<strong>1</strong>) is a synthetic anti-inflammatory drug and key intermediate in the synthesis of other steroidal drugs. This work is based on the fungal biotransformation of <strong>1</strong>, using <em>Monascus purpureus</em> and <em>Cunninghamella echinulata</em> strains. Comopound <strong>1</strong> was transformed into four metabolites, identified as hydrocortisone (<strong>2</strong>), 11β-hydroxyandrost-4-en-3,17-dione (<strong>3</strong>), Δ<sup>1</sup>-cortienic acid (<strong>4</strong>), and hydrocortisone-17-succinate (<strong>5</strong>), obtained through side chain cleavage, hydrolysis, dehydrogenation, and oxidation reactions. These compounds have previously been synthesized either chemically or enzymatically from different precursors. Though this is not the first report on the biotransformation of <strong>1</strong>, but it obviously is a first, where the biotransformed products of compound <strong>1</strong> have been characterized structurally with the help of modern spectroscopic techniques. It is noteworthy that these products have already shown biological potential, however a more thorough investigation of the anti-inflammatory properties of these metabolites would be of high value. These results not only emphasize upon the immense potential of biotransformation in catalysis of reactions, otherwise not-achievable chemically, but also holds promise for the development of novel anti-inflammatory compounds.</p></div>\",\"PeriodicalId\":21997,\"journal\":{\"name\":\"Steroids\",\"volume\":\"209 \",\"pages\":\"Article 109466\"},\"PeriodicalIF\":2.1000,\"publicationDate\":\"2024-06-30\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Steroids\",\"FirstCategoryId\":\"3\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0039128X24001041\",\"RegionNum\":4,\"RegionCategory\":\"医学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q4\",\"JCRName\":\"BIOCHEMISTRY & MOLECULAR BIOLOGY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Steroids","FirstCategoryId":"3","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0039128X24001041","RegionNum":4,"RegionCategory":"医学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q4","JCRName":"BIOCHEMISTRY & MOLECULAR BIOLOGY","Score":null,"Total":0}
Biotransformation of hydrocortisone succinate with whole cell cultures of Monascus purpureus and Cunninghamella echinulata
Hydrocortisone succinate (1) is a synthetic anti-inflammatory drug and key intermediate in the synthesis of other steroidal drugs. This work is based on the fungal biotransformation of 1, using Monascus purpureus and Cunninghamella echinulata strains. Comopound 1 was transformed into four metabolites, identified as hydrocortisone (2), 11β-hydroxyandrost-4-en-3,17-dione (3), Δ1-cortienic acid (4), and hydrocortisone-17-succinate (5), obtained through side chain cleavage, hydrolysis, dehydrogenation, and oxidation reactions. These compounds have previously been synthesized either chemically or enzymatically from different precursors. Though this is not the first report on the biotransformation of 1, but it obviously is a first, where the biotransformed products of compound 1 have been characterized structurally with the help of modern spectroscopic techniques. It is noteworthy that these products have already shown biological potential, however a more thorough investigation of the anti-inflammatory properties of these metabolites would be of high value. These results not only emphasize upon the immense potential of biotransformation in catalysis of reactions, otherwise not-achievable chemically, but also holds promise for the development of novel anti-inflammatory compounds.
期刊介绍:
STEROIDS is an international research journal devoted to studies on all chemical and biological aspects of steroidal moieties. The journal focuses on both experimental and theoretical studies on the biology, chemistry, biosynthesis, metabolism, molecular biology, physiology and pharmacology of steroids and other molecules that target or regulate steroid receptors. Manuscripts presenting clinical research related to steroids, steroid drug development, comparative endocrinology of steroid hormones, investigations on the mechanism of steroid action and steroid chemistry are all appropriate for submission for peer review. STEROIDS publishes both original research and timely reviews. For details concerning the preparation of manuscripts see Instructions to Authors, which is published in each issue of the journal.