2-Oxo-triterpenoids of ursane, oleanane and dammarane types and their α-glucosidase inhibitory properties.

IF 1.6 3区化学 Q3 CHEMISTRY, APPLIED

Natural Product Research Pub Date : 2025-10-16 DOI:10.1080/14786419.2025.2565286

Liana Zakirova, Alexander Poptsov, Oxana Kazakova, Irina Smirnova, Yury Gatilov, Dmitriy Polovyanenko, Irina Bagryanskaya, Denis Babkov, Roman Danilov, Andrey Lukyanov

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Abstract

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.

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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。

以相应的3-氧基衍生物为原料，采用Willgerodte-Kindler反应合成了新的2-氧基三萜，分别为熊烷、达玛烷和齐墩烷，产率为31-42%。结果表明，它们的c2 -肟是正/反同分异构体的等摩尔混合物，而文献中c3 -肟由于位阻因素只得到一个e -异构体。x射线衍射分析证实了2-氧-异戊二酮和3-氧-28-氧-异戊二酮以及异戊二酮二肟的结构。通过还原2-氧齐墩酸甲酯，首次合成了天然红二醇的区域异构体-齐墩酸-12(13)-烯-2β，28-二醇19。所测三萜对酿酒葡萄球菌α-葡萄糖苷酶的抑制作用比阿卡波糖强5 ~ 20倍。红二醇20的IC50值为8.35 μM，而红二醇19的IC50值为14.19 μM，是红二醇20的活性最高且无细胞毒性。

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来源期刊

Natural Product Research 化学-医药化学

CiteScore

5.10

自引率

9.10%

发文量

605

审稿时长

2.1 months

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.