Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners
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...
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doaj-4e6b6464b61a47f19c9144888bf23cc42021-08-06T15:24:38ZengMDPI AGInternational Journal of Molecular Sciences1661-65961422-00672021-07-01227885788510.3390/ijms22157885Chirality Matters: Biological Activity of Optically Pure Silybin and Its CongenersVladimír Křen0Laboratory of Biotransformation, Institute of Microbiology of the Czech Academy of Sciences, Vídeňská 1083, 142 20 Prague, Czech RepublicThis 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.https://www.mdpi.com/1422-0067/22/15/7885silymarinsilybin<i>Silybum marianum</i>milk thistlediastereomerchirality |
collection |
DOAJ |
language |
English |
format |
Article |
sources |
DOAJ |
author |
Vladimír Křen |
spellingShingle |
Vladimír Křen Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners International Journal of Molecular Sciences silymarin silybin <i>Silybum marianum</i> milk thistle diastereomer chirality |
author_facet |
Vladimír Křen |
author_sort |
Vladimír Křen |
title |
Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners |
title_short |
Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners |
title_full |
Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners |
title_fullStr |
Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners |
title_full_unstemmed |
Chirality Matters: Biological Activity of Optically Pure Silybin and Its Congeners |
title_sort |
chirality matters: biological activity of optically pure silybin and its congeners |
publisher |
MDPI AG |
series |
International Journal of Molecular Sciences |
issn |
1661-6596 1422-0067 |
publishDate |
2021-07-01 |
description |
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. |
topic |
silymarin silybin <i>Silybum marianum</i> milk thistle diastereomer chirality |
url |
https://www.mdpi.com/1422-0067/22/15/7885 |
work_keys_str_mv |
AT vladimirkren chiralitymattersbiologicalactivityofopticallypuresilybinanditscongeners |
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