Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners

0547159 - MBÚ 2022 RIV CH eng J - Journal Article
Křen, Vladimír
Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners.
International Journal of Molecular Sciences. Roč. 22, č. 15 (2021), č. článku 7885. E-ISSN 1422-0067
R&D Projects: GA ČR(CZ) GA21-01799S
Institutional support: RVO:61388971
Keywords : silymarin * silybin * Silybum marianum * milk thistle * diastereomer * chirality * isosilybin * silychristin * silydianin * silibinin * flavonolignan * flavonoid * dehydroflavonolignan
OECD category: Biochemistry and molecular biology
Impact factor: 6.208, year: 2021
Method of publishing: Open access
https://www.mdpi.com/1422-0067/22/15/7885

This review focuses on the specific biological effects of optically pure silymarin flavo-nolignans, mainly silybins A and B, isosilybins A and B, silychristins A and B, and their 2,3-dehydro derivatives. The chirality of these flavonolignans is also discussed in terms of their analysis, preparative separation and chemical reactions. We demonstrated the specific activities of the respective diastereomers of flavonolignans and also the enantiomers of their 2,3-dehydro derivatives in the 3D anisotropic systems typically represented by biological systems. In vivo, silymarin flavonolignans do not act as redox antioxidants, but they play a role as specific ligands of biological targets, according to the ´lock-and-key´ concept. Estrogenic, antidiabetic, anticancer, antiviral, and antiparasitic effects have been demonstrated in optically pure flavonolignans. Potential application of pure flavonolignans has also been shown in cardiovascular and neurological diseases. Inhibition of drug-metabolizing enzymes and modulation of multidrug resistance activity by these compounds are discussed in detail. The future of ´silymarin applications´ lies in the use of optically pure components that can be applied directly or used as valuable lead structures, and in the exploration of their true molecular effects.
Permanent Link: http://hdl.handle.net/11104/0323482