Isolation of a Unique Monoterpene Diperoxy Dimer From Ziziphora clinopodioides subsp. bungeana Together With Triterpenes With Antidiabetic Properties
Malaník M. Treml J. Kubínová R. Vávrová G. Oravec M. Marek J. Zhaparkulova K. Ibragimova L. Bekezhanova T. Karaubayeva A. Sakipova Z. Šmejkal K.
June 2025John Wiley and Sons Ltd
Phytochemical Analysis
2025#36Issue 41223 - 1230 pp.
Introduction: Ziziphora clinopodioides subsp. bungeana (Juz.) Rech.f. is used in traditional medicine for various purposes. Previous phytochemical studies focused on phenolic compounds, but triterpenoids were almost overlooked. Objective: The study focused on the isolation of compounds with dual antidiabetic activity from the aerial parts of Z. clinopodioides subsp. bungeana. Materials and Methods: Separation of CHCl3-soluble fraction by silica gel column chromatography using different mobile phases and purification of compounds by semi-preparative HPLC or preparative TLC. The structures of pure compounds were elucidated by 1D and 2D NMR experiments along with HRMS. Compound 1 was additionally identified by the single crystal X-ray diffraction method. α-Glucosidase inhibitory assay and GLUT4 expression and translocation in C2C12 myotubes were conducted to evaluate antidiabetic potential of isolated compounds. Results: This phytochemical study led to the isolation of 20 compounds, including a unique monoterpene diperoxy dimer (1). Compounds 7 and 9–11 displayed more potent α-glucosidase inhibitory activity (IC50 45.3–135.3 μM) than acarbose used as a positive control (IC50 264.7 μM), while only pomolic acid (5) increased GLUT4 translocation in C2C12 myotubes in a significant manner. Conclusion: Extensive chromatographic separation led to the isolation and identification of a unique monoterpene diperoxy dimer (1) from aerial parts of Z. clinopodioides subsp. bungeana. Some triterpenes inhibited α-glucosidase, another increased GLUT4 translocation. Although none of the isolated compounds demonstrated dual antidiabetic activity, selected triterpenes proved to be potent antidiabetic agents in vitro.
antidiabetic , GLUT4 , pomolic acid , triterpenes , Ziziphora , α-glucosidase
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Department of Natural Drugs, Faculty of Pharmacy, Masaryk University, Brno, Czech Republic
Department of Molecular Pharmacy, Faculty of Pharmacy, Masaryk University, Brno, Czech Republic
Global Change Research Institute of the Czech Academy of Sciences, Brno, Czech Republic
Core Facility Biomolecular Interactions and Crystallography, CEITEC MU, Masaryk University, Brno, Czech Republic
Department of Chemistry, Faculty of Science, Masaryk University, Brno, Czech Republic
School of Pharmacy, Asfendiyarov Kazakh National Medical University, Almaty, Kazakhstan
Department of Natural Drugs
Department of Molecular Pharmacy
Global Change Research Institute of the Czech Academy of Sciences
Core Facility Biomolecular Interactions and Crystallography
Department of Chemistry
School of Pharmacy
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