Liana Zakirova, Alexander Poptsov, Oxana Kazakova, Irina Smirnova, Yury Gatilov, Dmitriy Polovyanenko, Irina Bagryanskaya, Denis Babkov, Roman Danilov, Andrey Lukyanov
{"title":"熊烷、齐墩烷和达马烷类型的2-氧三萜及其α-葡萄糖苷酶抑制性能。","authors":"Liana Zakirova, Alexander Poptsov, Oxana Kazakova, Irina Smirnova, Yury Gatilov, Dmitriy Polovyanenko, Irina Bagryanskaya, Denis Babkov, Roman Danilov, Andrey Lukyanov","doi":"10.1080/14786419.2025.2565286","DOIUrl":null,"url":null,"abstract":"<p><p>New 2-oxo-triterpenoids of ursane, dammarane and oleanane types were synthesised from the corresponding 3-oxo-derivatives by Willgerodte-Kindler reaction with yields of 31-42%. It was shown that their C2-oximes are formed as the equimolar mixtures of <i>syn/anti</i>-isomers in contrast to literature data for C3-oximes giving a single <i>E</i>-isomer due to the steric factors. The structures of 2-oxo- and 3-oxo-28-oxo-allobetulones as well as allobetulone 2<i>E</i>-oxime were confirmed by X-ray diffraction analysis. A regioisomer of natural erythrodiol - olean-12(13)-ene-2β,28-diol <b>19</b> was firstly synthesised by the reduction of methyl 2-oxo-oleanoate. The tested triterpenoids were more potent in α-glucosidase (from <i>S. cerevisia</i>) inhibition than acarbose (from 5 to 20 times). Erythrodiol <b>20</b> showed IC<sub>50</sub> value of 8.35 μM, while it's regioisomer <b>19</b> was found as the most active and non-cytotoxic in terms of enzyme inhibition with an IC<sub>50</sub> value of 14.19 μM.</p>","PeriodicalId":18990,"journal":{"name":"Natural Product Research","volume":" ","pages":"1-8"},"PeriodicalIF":1.6000,"publicationDate":"2025-10-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"2-Oxo-triterpenoids of ursane, oleanane and dammarane types and their α-glucosidase inhibitory properties.\",\"authors\":\"Liana Zakirova, Alexander Poptsov, Oxana Kazakova, Irina Smirnova, Yury Gatilov, Dmitriy Polovyanenko, Irina Bagryanskaya, Denis Babkov, Roman Danilov, Andrey Lukyanov\",\"doi\":\"10.1080/14786419.2025.2565286\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>New 2-oxo-triterpenoids of ursane, dammarane and oleanane types were synthesised from the corresponding 3-oxo-derivatives by Willgerodte-Kindler reaction with yields of 31-42%. It was shown that their C2-oximes are formed as the equimolar mixtures of <i>syn/anti</i>-isomers in contrast to literature data for C3-oximes giving a single <i>E</i>-isomer due to the steric factors. The structures of 2-oxo- and 3-oxo-28-oxo-allobetulones as well as allobetulone 2<i>E</i>-oxime were confirmed by X-ray diffraction analysis. A regioisomer of natural erythrodiol - olean-12(13)-ene-2β,28-diol <b>19</b> was firstly synthesised by the reduction of methyl 2-oxo-oleanoate. The tested triterpenoids were more potent in α-glucosidase (from <i>S. cerevisia</i>) inhibition than acarbose (from 5 to 20 times). Erythrodiol <b>20</b> showed IC<sub>50</sub> value of 8.35 μM, while it's regioisomer <b>19</b> was found as the most active and non-cytotoxic in terms of enzyme inhibition with an IC<sub>50</sub> value of 14.19 μM.</p>\",\"PeriodicalId\":18990,\"journal\":{\"name\":\"Natural Product Research\",\"volume\":\" \",\"pages\":\"1-8\"},\"PeriodicalIF\":1.6000,\"publicationDate\":\"2025-10-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Natural Product Research\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1080/14786419.2025.2565286\",\"RegionNum\":3,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, APPLIED\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Natural Product Research","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1080/14786419.2025.2565286","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
2-Oxo-triterpenoids of ursane, oleanane and dammarane types and their α-glucosidase inhibitory properties.
New 2-oxo-triterpenoids of ursane, dammarane and oleanane types were synthesised from the corresponding 3-oxo-derivatives by Willgerodte-Kindler reaction with yields of 31-42%. It was shown that their C2-oximes are formed as the equimolar mixtures of syn/anti-isomers in contrast to literature data for C3-oximes giving a single E-isomer due to the steric factors. The structures of 2-oxo- and 3-oxo-28-oxo-allobetulones as well as allobetulone 2E-oxime were confirmed by X-ray diffraction analysis. A regioisomer of natural erythrodiol - olean-12(13)-ene-2β,28-diol 19 was firstly synthesised by the reduction of methyl 2-oxo-oleanoate. The tested triterpenoids were more potent in α-glucosidase (from S. cerevisia) inhibition than acarbose (from 5 to 20 times). Erythrodiol 20 showed IC50 value of 8.35 μM, while it's regioisomer 19 was found as the most active and non-cytotoxic in terms of enzyme inhibition with an IC50 value of 14.19 μM.
期刊介绍：
The aim of Natural Product Research is to publish important contributions in the field of natural product chemistry. The journal covers all aspects of research in the chemistry and biochemistry of naturally occurring compounds.
The communications include coverage of work on natural substances of land and sea and of plants, microbes and animals. Discussions of structure elucidation, synthesis and experimental biosynthesis of natural products as well as developments of methods in these areas are welcomed in the journal. Finally, research papers in fields on the chemistry-biology boundary, eg. fermentation chemistry, plant tissue culture investigations etc., are accepted into the journal.
Natural Product Research issues will be subtitled either ""Part A - Synthesis and Structure"" or ""Part B - Bioactive Natural Products"". for details on this , see the forthcoming articles section.
All manuscript submissions are subject to initial appraisal by the Editor, and, if found suitable for further consideration, to peer review by independent, anonymous expert referees. All peer review is single blind and submission is online via ScholarOne Manuscripts.
求助内容：
应助结果提醒方式：
京公网安备 11010802042870号
