Study of the crystalline structure of dihydroquercetin

Селиванова, И. А.; Tyukavkina, N. A.; Kolesnik, Yu. A.; Нестеров, В. Н.; Kuleshova, L. N.; Khutoryanskii, V. A.; Bazhenov, B. N.; Saibotalov, M. Yu.

doi:10.1007/bf02509946

Cited by 12 publications

(18 citation statements)

References 8 publications

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“…The molecular structure and unit-cell parameters of taxifolin are consistent with those reported previously (Selivanova et al, 1999).…”

Section: X-ray Crystallographysupporting

confidence: 89%

“…Taxifolin is a commercial product and is characterized by a wide range of pharma-cological effects and antioxidant properties (Asmi et al, 2017;Ilyasov et al, 2018;Plotnikov et al, 2005) and nontoxicity (Schauss et al, 2015). Commercially available taxifolin as an active pharmaceutical ingredient (API) is known to exist in crystalline form, in which the taxifolin molecules are linked to each other and to the water molecules via intermolecular hydrogen bonds forming three-dimensional structural patterns (Selivanova et al, 1999). The identifier of crystalline taxifolin in the Cambridge Structural Database (CCDC; Groom et al, 2016) is LORKEI.…”

Section: Introductionmentioning

confidence: 99%

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Taxifolin tubes: crystal engineering and characteristics

Terekhov

Селиванова

Tyukavkina

et al. 2019

Acta Crystallogr B Struct Sci Cryst Eng Mater

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Taxifolin, also known as dihydroquercetin, is the major flavonoid in larch wood. It is well known as an antioxidant and a bioactive substance. Taxifolin as an active pharmaceutical ingredient is produced industrially in crystalline form during the processing of larch wood. Some information is available on nano-and microstructured particles of taxifolin. This paper reports on the generation of a new form of taxifolin as microtubes. These self-assembled tubes were obtained from raw taxifolin by crystal engineering with urea at ambient temperature and pressure. The parameters of temperature, pH value, molar ratio of taxifolin and urea, and time duration were optimized for yield enhancement of the microtubes. The water solubility and melting point of the new form of taxifolin were established. The microtubes were characterized by X-ray diffraction, X-ray powder diffraction, microscopy, mass spectrometry, 1 H NMR spectroscopy, UV spectroscopy and Fourier transform infrared spectroscopy methods. The experimental results demonstrate that the microtubes and raw taxifolin both exist in crystalline form with the same structure of the crystal unit. However, they are characterized by different morphological and physicochemical properties. Computer simulation was performed to explain the mechanism of the selfassembly process. research papers Acta Cryst. (2019). B75, 175-182 Roman P. Terekhov et al. Taxifolin tubes: crystal engineering and characteristics 181 Figure 6 Molecular surface of taxifolin nanoparticle model: (a) nanoparticle surface and (b) cross-sectional view.

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“…The molecular structure and unit-cell parameters of taxifolin are consistent with those reported previously (Selivanova et al, 1999).…”

Section: X-ray Crystallographysupporting

confidence: 89%

Section: Introductionmentioning

confidence: 99%

Taxifolin tubes: crystal engineering and characteristics

Terekhov

Селиванова

Tyukavkina

et al. 2019

Acta Crystallogr B Struct Sci Cryst Eng Mater

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“…Rather limited differences in the steric hindrance of the two molecules may account for this competitive binding mode. The deviation from planarity of the fused rings A and C of DHQ remains limited (the highest deviation from the mean plane is 0.56 Å ; Selivanova et al, 1999) and the B phenyl ring can adopt different orientations relative to the heterocyclic system, so that the active site is able to accommodate each molecule without drastic structural changes.…”

Section: Discussionmentioning

confidence: 99%

“…are rigorously planar in flavonols (Rossi et al, 1986), those of dihydroflavonols exhibit only a slight distortion with a halfchair configuration of ring C and a maximum deviation of atoms with respect to the average plane of less than 0.57 Å (Wilmouth et al, 2002;Petit et al, 2007;Selivanova et al, 1999;Xu et al, 2007). Finally, in comparison with dihydroflavonols, flavonols present a higher degree of unsaturation of ring C, which modifies the electrophilic and nucleophilic character of the carbonyl in position 4, preventing hydride transfer from the nicotinamide ring of NADPH.…”

Section: Introductionmentioning

confidence: 99%

Structural evidence for the inhibition of grape dihydroflavonol 4-reductase by flavonols

Trabelsi

Petit

Manigand

et al. 2008

Acta Crystallogr D Biol Cryst

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Dihydroflavonol 4-reductase (DFR) is a key enzyme of the flavonoid biosynthesis pathway which catalyses the NADPH-dependent reduction of 2R,3R-trans-dihydroflavonols to leucoanthocyanidins. The latter are the precursors of anthocyans and condensed tannins, two major classes of phenolic compounds that strongly influence the organoleptic properties of wine. DFR has been investigated in many plant species, but little was known about its structural properties until the three-dimensional structure of the Vitis vinifera enzyme complexed with NADP(+) and its natural substrate dihydroquercetin (DHQ) was described. In the course of the study of substrate specificity, crystals of DFR-NADP(+)-flavonol (myricetin and quercetin) complexes were obtained. Their structures exhibit major changes with respect to that of the abortive DFR-NADP(+)-DHQ complex. Two flavonol molecules bind to the catalytic site in a stacking arrangement and alter its geometry, which becomes incompatible with enzymatic activity. The X-ray structures of both DFR-NADP(+)-myricetin and DFR-NADP(+)-quercetin are reported together with preliminary spectroscopic data. The results suggest that flavonols could be inhibitors of the activity of DFR towards dihydroflavonols.

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“…In order to obtain a standard sample, a complex investigation of taxifolin was performed. There exist several articles that focus on the X-ray analysis of such samples, produced by a different manufacturer [ 33 , 34 ]. Physicochemical properties of taxifolin have previously been adjusted using chemical and physical modification [ 35 , 36 ], lyophilization [ 37 ], and nanodispersion formation [ 38 ].…”

Section: Introductionmentioning

confidence: 99%

Assembling the Puzzle of Taxifolin Polymorphism

et al. 2020

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A large amount of the current literature dedicated to solid states of active pharmaceutical ingredients (APIs) pays special attention to polymorphism of flavonoids. Taxifolin (also known as dihydroquercetin) is an example of a typical flavonoid. Some new forms of taxifolin have been reported previously, however it is still unclear whether they represent polymorphic modifications. In this paper, we tried to answer the question about the taxifolin polymorphism. Taxifolin microtubes and taxifolin microspheres were synthesized from raw taxifolin API using several methods of crystal engineering. All forms were described with the help of spectral methods, scanning electron microscopy (SEM), X-ray powder diffraction (XRPD), and thermal analysis (TA). SEM reveals that the morphology of the solid phase is very specific for each sample. Although XRPD patterns of raw taxifolin and microtubes look similar, their TA profiles differ significantly. At the same time, raw taxifolin and microspheres have nearly identical thermograms, while XRPD shows that the former is a crystalline and the latter is an amorphous substance. Only the use of complex analyses allowed us to put the puzzle together and to confirm the polymorphism of taxifolin. This article demonstrates that taxifolin microtubes are a pseudopolymorphic modification of raw taxifolin.

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Study of the crystalline structure of dihydroquercetin

Cited by 12 publications

References 8 publications

Taxifolin tubes: crystal engineering and characteristics

Taxifolin tubes: crystal engineering and characteristics

Structural evidence for the inhibition of grape dihydroflavonol 4-reductase by flavonols

Assembling the Puzzle of Taxifolin Polymorphism

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