Oxidation of flavonolignan silydianin to unexpected lactone-acid derivative

Biedermann, David; Moravcová, Veronika; Valentová, Kateřina; Kuzma, Marek; Petrásková, Lucie; Císařová, I.; Křen, Vladimír

doi:https://dx.doi.org/10.1016/j.phytol.2019.01.006

Number of the records: 1

Oxidation of flavonolignan silydianin to unexpected lactone-acid derivative

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SYSNO ASEP	0504011
Document Type	J - Journal Article
R&D Document Type	Journal Article
Subsidiary J	Článek ve WOS
Title	Oxidation of flavonolignan silydianin to unexpected lactone-acid derivative
Author(s)	Biedermann, David (MBU-M)_{RID, ORCID} Moravcová, Veronika (MBU-M) Valentová, Kateřina (MBU-M)_{RID, ORCID} Kuzma, Marek (MBU-M)_{ORCID, RID} Petrásková, Lucie (MBU-M)_ORCID Císařová, I. (CZ) Křen, Vladimír (MBU-M)_{RID, ORCID}
Source Title	Phytochemistry Letters. - : Elsevier - ISSN 1874-3900 Roč. 30, APR (2019), s. 14-20
Number of pages	7 s.
Language	eng - English
Country	NL - Netherlands
Keywords	Silymarin ; Silydianin ; Flavonoid
Subject RIV	CC - Organic Chemistry
OECD category	Organic chemistry
R&D Projects	GA18-00150S GA ČR - Czech Science Foundation (CSF)
	LTC18071 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
	LTC17009 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
	LTC18003 GA MŠMT - Ministry of Education, Youth and Sports (MEYS)
Method of publishing	Limited access
Institutional support	MBU-M - RVO:61388971
UT WOS	000461363900004
EID SCOPUS	85059505000
DOI	10.1016/j.phytol.2019.01.006
Annotation	One of the main flavonolignans from silymarin, an extract of the fruits of the milk thistle (Silybum marianum), is silydianin possessing an unusual bicyclic structure with the keto group next to the hemiacetal moiety. As its oxidation product 2,3-dehydrosilydianin was found to display strong chemoprotective activity and Na+/K+ ATPase inhibitory activity, the present work aims at the optimization of silydianin oxidation. The isolated yield of the optimized reaction was improved from 10 to 22% in a considerably shorter reaction time (24 vs. 192 h). The formation of a new compound, a lactone-acid, was observed during the optimization experiments. The structure of this new compound was elucidated and its antioxidant activity compared with those of silydianin and 2,3-dehydrosilydianin. Moreover, the high resolution crystal structure of silydianin is shown here for the first time.
Workplace	Institute of Microbiology
Contact	Eliška Spurná, eliska.spurna@biomed.cas.cz, Tel.: 241 062 231
Year of Publishing	2020
Electronic address	https://www.sciencedirect.com/science/article/pii/S1874390018306323?via%3Dihub

Number of the records: 1