The modern approaches of analysis of dihydroquercetin stereoisomeric composition
- Authors: Terekhov R.P.1, Savina A.D.1, Pankov D.I.1, Nikitin I.D.1, Selivanova I.A.1
-
Affiliations:
- FSAEI of HE I.M.Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University)
- Issue: Vol 73, No 2 (2024)
- Pages: 5-12
- Section: Review
- URL: https://journals.eco-vector.com/0367-3014/article/view/629388
- DOI: https://doi.org/10.29296/25419218-2024-02-01
- ID: 629388
Cite item
Abstract
Dihydroquercetin (DHQ) is a representative of the flavonoid family. This natural polyphenol is known for its high ability to bind active oxygen species, which is used to explain its wide range of biological activities. However, the fact that DHQ has two chiral centers in the positions 2 and 3 of the pyranone ring is often ignored. By the way, such structure allowing this compound to exist in four stereoisomers. The current literature review was prepared to systemize the information for the analysis of DHQ stereoisomers to control the quality of future chiral remedies. During the study, it was found that relying on polarimetry results for research and the development of regulatory documentation is difficult due to the heterogeneity of data on the optical activity of flavanonol molecules. Information on the NMR spectroscopy of DHQ diastereomers is more reliable, but this method does not allow for the identification of individual stereoisomers and is not implemented in routine pharmaceutical analysis. Among all the methods considered, only HPLC is currently characterized by sufficient enantioselectivity. The results of the literature review indicate that chromatography is the most promising method for quality control of chiral pharmaceuticals, which can be developed based on DHQ. Referring to the history of pharmaceutical science, it seems unnecessary to remind the important role of the stereochemical composition of active pharmaceutical ingredient in ensuring the efficacy and safety of drugs. The results of our review are intended to draw the attention of the scientific community to significant gaps in the current system of knowledge and regulatory documentation.
Full Text
About the authors
Roman P. Terekhov
FSAEI of HE I.M.Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University)
Author for correspondence.
Email: terekhov_r_p@staff.sechenov.ru
ORCID iD: 0000-0001-9206-8632
PhD in pharmaceutical sciences, associate professor at the Department of Chemistry of Nelyubin Institute of Pharmacy
Russian Federation, Trubetskaya str., 8/2, Mosсow, 119991Anastasiya D. Savina
FSAEI of HE I.M.Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University)
Email: savina_a_d@student.sechenov.ru
ORCID iD: 0009-0000-5123-8746
student at Nelyubin Institute of Pharmacy
Russian Federation, Trubetskaya str., 8/2, Mosсow, 119991Denis I. Pankov
FSAEI of HE I.M.Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University)
Email: pankov_d_i@staff.sechenov.ru
ORCID iD: 0009-0007-6195-6400
assistant professor at the Department of Chemistry of Nelyubin Institute of Pharmacy
Russian Federation, Trubetskaya str., 8/2, Mosсow, 119991Ilya D. Nikitin
FSAEI of HE I.M.Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University)
Email: nikitin_i_d@student.sechenov.ru
ORCID iD: 0000-0001-8044-0548
student at Nelyubin Institute of Pharmacy
Russian Federation, Trubetskaya str., 8/2, Mosсow, 119991Irina A. Selivanova
FSAEI of HE I.M.Sechenov First Moscow State Medical University of the Ministry of Health of the Russian Federation (Sechenov University)
Email: selivanova_i_a@staff.sechenov.ru
ORCID iD: 0000-0002-2244-445X
ScD in pharmaceutical sciences, professor, professor at the Department of Chemistry of Nelyubin Institute of Pharmacy
Russian Federation, Trubetskaya str., 8/2, Mosсow, 119991References
- Aware C.B., Patil D.N., Suryawanshi S.S. et al. Natural bioactive products as promising therapeutics: A review of natural product-based drug development. Journal of South African botany. 2022; 151: 512–28. doi: 10.1016/j.sajb.2022.05.028
- Terekhov R.P., Melnikov E.S., Nikitin I.D. et al. Diastereomers of Spheroidal Form and Commercially Available Taxifolin Samples. Scientia Pharmaceutica. 2024; 92 (1): 5. doi: 10.3390/scipharm92010005
- Gaggeri R., Rossi D., Christodoulou M. et al. Chiral Flavanones from Amygdalus lycioides Spach: Structural Elucidation and Identification of TNF alpha Inhibitors by Bioactivity-guided Fractionation. Molecules. 2012; 17 (2): 1665–74. doi: 10.3390/molecules17021665
- Lundgren L.N., Theander O. Cis- and trans-dihydroquercetin glucosides from needles of Pinus sylvestris. Phytochemistry. 1988; 27 (3): 829–32. doi: 10.1016/0031-9422(88)84101-3
- Yoon K.D., Lee J.Y., Kim T.Y. et al. In Vitro and in Vivo Anti-Hyperglycemic Activities of Taxifolin and Its Derivatives Isolated from Pigmented Rice (Oryzae sativa L. cv. Superhongmi). J. Agric. Food Chem. 2020; 68 (3): 742–50. doi: 10.1021/acs.jafc.9b04962
- Sato M., Murakami K., Uno M. et al. Structure–Activity Relationship for (+)-Taxifolin Isolated from Silymarin as an Inhibitor of Amyloid β Aggregation. Biosci. Biotechnol. Biochem. 2013; 77 (5): 1100–3. doi: 10.1271/bbb.120925
- Imai T., Inoue S., Ohdaira N. et al. Heartwood extractives from the Amazonian trees Dipteryx odorata, Hymenaea courbaril, Astronium lecointei and their antioxidant activities. Journal of Wood Science. 2008; 54 (6): 470–75. doi: 10.1007/s10086-008-0975-3
- Lee E.H., Kim H.J., Song Y.S. et al. Constituents of the stems and fruits of Opuntia ficus-indica var. saboten. Arch. Pharm. Res. 2003; 26 (12): 1018–23. doi: 10.1007/BF02994752
- Inada A., Murata H., Somekawa M. et al. Phytochemical Studies of Seeds of Medicinal Plants. II. A New Dihydroflavonol Glycoside and a New 3-Methyl-1-butanol Glycoside from Seeds of Platycodon grandiflorum A. DE CANDOLLE. Chem. Pharm. Bull. (Tokyo). 1992; 40 (11): 3081–3. doi: 10.1248/CPB.40.3081
- Kuroyanagi M., Yamamoto Y., Fukushima S. et al. Chemical studies on the constituents of Polygonum nodosum. Chem. Pharm. Bull. (Tokyo). 1982; 30 (5): 1602–8. doi: 10.1248/CPB.30.1602
- Kiehlmann E., Li E.P.M. Isomerization of Dihydroquercetin. J. Nat. Prod. 1995; 58 (3): 450–5. doi: 10.1021/np50117a018
- Kasai R., Hirono S., Chou W.H. et al. Sweet dihydroflavonol rhamnoside from leaves of Engelhardtia chrysolepis, a chinese folk medicine, hung-qi. Chem. Pharm. Bull. (Tokyo). 1988; 36 (10): 4167–70. doi: 10.1248/CPB.36.4167
- Sakurai A., Okumura Y. Chemical Studies on the Mistletoe. V. The Structure of Taxillusin, a New Flavonoid Glycoside Isolated from Taxillus kaempferi. Bull. Chem. Soc. Jpn. 1983; 56 (2): 542–4. doi: 10.1246/bcsj.56.542
- Nonaka G.-I., Goto Y., Kinjo J.-E. et al. Tannins and related compounds. LII Studies on the constituents of the leaves of Thujopsis dolabrata SIEB. et ZUCC. // Chem. Pharm. Bull. (Tokyo). 1987; 35 (3): 1105–8. doi: 10.1248/cpb.35.1105
- Ohmura W., Ohara S., Hashida K. et al. Hydrothermolysis of Flavonoids in Relation to Steaming of Japanese Larch Wood. Holzforschung. 2002; 56 (5): 493–7. doi: 10.1515/HF.2002.076
- Yoshida T., Zhe X.J., Okuda T. Taxifolin apioside and davuriciin M1, a hydrolysable tannin from Rosa davurica. Phytochemistry. 1989; 28 (8): 2177–81. doi: 10.1016/S0031-9422(00)97939-1
- Mohammed H.A., Almahmoud S.A., El-Ghaly E.M. et al. Comparative Anticancer Potentials of Taxifolin and Quercetin Methylated Derivatives against HCT-116 Cell Lines: Effects of O -Methylation on Taxifolin and Quercetin as Preliminary Natural Leads. ACS Omega. 2022; 7 (50): 46629–39. doi: 10.1021/acsomega.2c05565
- Braune A., Gütschow M., Engst W., Blaut M. Degradation of Quercetin and Luteolin by Eubacterium ramulus. Appl. Environ. Microbiol. 2001; 67 (12): 5558–67. doi: 10.1128/AEM.67.12.5558-5567.2001
- Trofimova N.N., Stolpovskaya E.V., Babkin V.A. et al. The structure and electrochemical properties of metal complexes with dihydroquercetin. Russian J. of Bioorganic Chemistry. 2015; 41 (7): 745–52. doi: 10.1134/S1068162015070146
- Kuspradini H., Mitsunaga T., Ohashi H. Antimicrobial activity against Streptococcus sobrinus and glucosyltransferase inhibitory activity of taxifolin and some flavanonol rhamnosides from kempas (Koompassia malaccensis) extracts. J. of Wood Science. 2009; 55 (4): 308–13. doi: 10.1007/s10086-009-1026-4
- Baderschneider B., Winterhalter P. Isolation and Characterization of Novel Benzoates, Cinnamates, Flavonoids, and Lignans from Riesling Wine and Screening for Antioxidant Activity. J. Agric. Food Chem. 2001; 49 (6): 2788–98. doi: 10.1021/jf010396d
- Turnbull J.J., Nakajima J., Welford R.W. et al. Mechanistic Studies on Three 2-Oxoglutarate-dependent Oxygenases of Flavonoid Biosynthesis. J. Biol. Chem. 2004; 279 (2): 1206–16. doi: 10.1074/jbc.M309228200
- Jiang W.-J., Ishiuchi K., Furukawa M. et al. Stereospecific inhibition of nitric oxide production in macrophage cells by flavanonols: Synthesis and the structure–activity relationship. Bioorg. Med. Chem. 2015; 23 (21): 6922–9. doi: 10.1016/j.bmc.2015.09.042
- Fedorova T.E., Fedorov S.V., Babkin V.A. Phenolic Compounds of Picea obovata Ledeb. Bark. Russian Journal of Bioorganic Chemistry. 2019; 45 (7): 927–32. doi: 10.1134/S1068162019070045
- Nifant’ev E.E., Koroteev M.P., Kaziev G.Z. et al. On the problem of identification of the dihydroquercetin flavonoid. Russian J. of general chemistry. 2006; 76 (1): 161–3. doi: 10.1134/S1070363206010324
- Wang X., Zhou H., Zeng S. Identification and assay of 3'-O-methyltaxifolin by UPLC–MS in rat plasma. J. Chromatogr. B. 2012; 911: 34–42. doi: 10.1016/j.jchromb.2012.09.006
- Elsinghorst P.W., Cavlar T., Müller A. et al. The Thermal and Enzymatic Taxifolin–Alphitonin Rearrangement. Journal of Natural Products. 2011; 74 (10): 2243–9. doi: 10.1021/np200639s
- Vega-Villa K.R., Remsberg C.M., Ohgami Y. et al. Stereospecific high-performance liquid chromatography of taxifolin, applications in pharmacokinetics, and determination in tu fu ling (Rhizoma smilacis glabrae) and apple (Malus × domestica). Biomed. Chromatogr. 2009; 23 (6): 638–46. doi: 10.1002/bmc.1165