Skip to main page content
U.S. flag

An official website of the United States government

Dot gov

The .gov means it’s official.
Federal government websites often end in .gov or .mil. Before sharing sensitive information, make sure you’re on a federal government site.

Https

The site is secure.
The https:// ensures that you are connecting to the official website and that any information you provide is encrypted and transmitted securely.

Access keys NCBI Homepage MyNCBI Homepage Main Content Main Navigation
. 2020 Nov 20;25(22):5437.
doi: 10.3390/molecules25225437.

Assembling the Puzzle of Taxifolin Polymorphism

Roman P Terekhov  1 , Irina A Selivanova  1 , Nonna A Tyukavkina  1 , Igor R Ilyasov  1 , Anastasiya K Zhevlakova  1 , Alexander V Dzuban  2 , Anatoliy G Bogdanov  3 , Georgiy N Davidovich  3 , Gennadii V Shylov  4 , Andrey N Utenishev  1   4 , Dmitriy Yu Kovalev  5 , Anatoliy A Fenin  6 , Tatyana G Kabluchko  7
Affiliations

Assembling the Puzzle of Taxifolin Polymorphism

Roman P Terekhov et al. Molecules. .

Abstract

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.

Keywords: X-ray diffraction; active pharmaceutical ingredient; flavonoids; polymorphism; scanning electron microscopy; taxifolin; thermal analysis; variable-temperature powder X-ray diffraction.

PubMed Disclaimer

Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structure of taxifolin.
Figure 2
Figure 2
Photomicrography of different taxifolin forms: (a) raw taxifolin at 250× magnification; (b) raw taxifolin at 10,000× magnification; (c) taxifolin microtubes at 250× magnification; (d) taxifolin microtubes at 10,000× magnification; (e) taxifolin microspheres at 250× magnification; (f) taxifolin microspheres at 10,000× magnification.
Figure 3
Figure 3
Cumulative undersize distribution of particles of different taxifolin forms.
Figure 4
Figure 4
Thermograms of different taxifolin forms: (a) raw taxifolin; (b) taxifolin microtubes; (c) taxifolin microspheres.
Figure 4
Figure 4
Thermograms of different taxifolin forms: (a) raw taxifolin; (b) taxifolin microtubes; (c) taxifolin microspheres.
Figure 5
Figure 5
X-ray powder diffraction (XRPD) of different taxifolin forms at room temperature: (a) raw taxifolin; (b) taxifolin microtubes; (c) taxifolin microspheres.
Figure 5
Figure 5
X-ray powder diffraction (XRPD) of different taxifolin forms at room temperature: (a) raw taxifolin; (b) taxifolin microtubes; (c) taxifolin microspheres.
Figure 6
Figure 6
In situ variable-temperature XRPD patterns for different taxifolin forms: (a) raw taxifolin; (b) taxifolin microtubes; (c) taxifolin microspheres.
Figure 6
Figure 6
In situ variable-temperature XRPD patterns for different taxifolin forms: (a) raw taxifolin; (b) taxifolin microtubes; (c) taxifolin microspheres.
See this image and copyright information in PMC

Similar articles

See all similar articles

Cited by

See all "Cited by" articles

References

    1. Scannell J.W., Blanckley A., Boldon H., Warrington B. Diagnosing the decline in pharmaceutical R&D efficiency. Nat. Rev. Drug Discov. 2012;11:191–200. doi: 10.1038/nrd3681. - DOI - PubMed
    1. Scannell J.W., Hinds S., Evance R. Financial Returns on R&D: Looking Back at History, Looking Forward to Adaptive Licensing. Rev. Recent Clin. Trials. 2015;10:28–43. doi: 10.2174/1574887110666150430151751. - DOI - PubMed
    1. Savaliya R., Singh P., Singh S. Pharmacological Drug Delivery Strategies for Improved Therapeutic Effects: Recent Advances. Curr. Pharm. Des. 2016;22:1506–1520. doi: 10.2174/1381612822666151210123546. - DOI - PubMed
    1. Chadha R., Saini A., Arora P., Bhandari S. Pharmaceutical Cocrystals: A Novel Approach for Oral Bioavailability Enhancement of Drugs. Crit. Rev. Ther. Drug Carrier Syst. 2012;29:183–218. doi: 10.1615/CritRevTherDrugCarrierSyst.v29.i3.10. - DOI - PubMed
    1. Vernadsky V.I. O Polimorfizme Kak Obshchem Svojstve Materii. Univ. Tip.; Moscow, Russia: 1891. (In Russian)

LinkOut - more resources