Protective Properties of Spheroidal Taxifolin Form in Streptozotocin-Induced Diabetic Rats

Taldaev, Amir; Savina, Anastasiya D.; Olicheva, Vera V.; Ivanov, Sergey V.; Terekhov, Roman P.; Ilyasov, Igor R.; Zhevlakova, Anastasiya K.; Selivanova, Irina A.

doi:10.3390/ijms241511962

Cited by 4 publications

(2 citation statements)

References 39 publications

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“…The spheroidal form of taxifolin (TAXs) has emerged as a promising modification in our investigations [29]. This modification is characterized by enhanced solubility up to 2.2 times, a higher safety profile, and long-term release from solid dosage forms [30,31].…”

Section: Introductionmentioning

confidence: 99%

Diastereomers of Spheroidal Form and Commercially Available Taxifolin Samples

Terekhov,

Melnikov,

Nikitin

et al. 2024

Sci. Pharm.

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Taxifolin is a natural polyphenol belonging to the class of flavonoids. The structure of this compound is characterized by the presence of two chiral centers. The spheroidal form of taxifolin (TAXs) has emerged as a promising modification due to enhanced solubility, higher safety profile, and long-term release from solid dosage forms. The study’s objective was to assess the diastereomeric content in TAXs and industrially produced samples of taxifolin. Considering the difference in the physico-chemical properties of diastereomers and based on the literature data, we developed a qualitative HPLC method. The chromatograms were recorded using a diode array detector at 290 nm and a mass spectrometer operated in negative ionization mode. Our data suggest that a biphenyl column and gradient elution using 0.1% formic acid in water and 0.2% formic acid in methanol, with the organic phase gradient from 7% to 21% and a flow rate of 0.65 mL/min for 15 min at 60 °C, provides the best conditions for the separation of taxifolin diastereomers. This method was validated for quantitative analysis. We discovered that the cis-isomer was present in all the analyzed samples, with its quantity ranging from 0.8% to 9.5%. TAXs can be considered a sample enriched with diastereomers.

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Section: Introductionmentioning

confidence: 99%

Diastereomers of Spheroidal Form and Commercially Available Taxifolin Samples

Terekhov,

Melnikov,

Nikitin

et al. 2024

Sci. Pharm.

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“…In the European Union, it is on the market as a food supplement. Various preclinical and clinical studies are ongoing in Russia, China, and Japan ( Shinozaki et al, 2023 ; Taldaev et al, 2023 ; Choi et al, 2024 ).…”

Section: Introductionmentioning

confidence: 99%

Insights into the stereoisomerism of dihydroquercetin: analytical and pharmacological aspects

Terekhov,

Savina,

Pankov

et al. 2024

Front. Chem.

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Dihydroquercetin (DHQ) is a representative of flavonoids that is available on the market as a food supplement and registered as an active pharmaceutical ingredient. The structure of this compound is characterized by the presence of two chiral centers in positions 2 and 3 of the pyranone ring. Current regulatory documentation on DHQ lacks quantitative analysis of the stereoisomers of this flavanonol. This poses potential risks for consumers of DHQ-based dietary supplements and developers of new drugs. This review was conducted to systematize data on the pharmacology of DHQ stereoisomers and the possible methods of controlling them in promising chiral drugs. We found that relying on literature data of polarimetry for the identification of DHQ stereoisomers is currently impossible due to these heterogeneities. NMR spectroscopy allows to distinguishing between trans- and cis-DHQ using chemical shifts values. Only HPLC is currently characterized by sufficient enantioselectivity. Regarding pharmacology, the most active stereoisomer of DHQ should be identified, if the substituents in chiral centers both take part in binding with the biological target. The significant impact of stereochemical structure on the pharmacokinetics of DHQ isomers was reported. The question about these toxicity of these compounds remains open. The results of the conducted review of scientific literature indicate the necessity of revising the pharmacology of DHQ taking into account its stereoisomerism.

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