Mechanistic Study of the Biomimetic Synthesis of Flavonolignan Diastereoisomers in Milk Thistle

Autor:	Maria Elena Meza-Aviña, Mitchell P. Croatt, Hanan S. Althagafy, Nicholas H. Oberlies
Rok vydání:	2013
Předmět:	Molecular Structure Milk Thistle Chemistry Organic Chemistry Diastereomer Stereoisomerism Article Flavonolignans chemistry.chemical_compound Biomimetic Materials Biomimetic synthesis Flavonolignan Organic chemistry Taxifolin Moiety Coniferyl alcohol
Zdroj:	The Journal of Organic Chemistry. 78:7594-7600
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo4011377
Popis:	The mechanism for the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle is proposed to proceed by single-electron oxidation of coniferyl alcohol, subsequent reaction with one of the oxygen atoms of taxifolin's catechol moiety, and finally, further oxidation to form four of the major components of silymarin: silybin A, silybin B, isosilybin A, and isosilybin B. This mechanism is significantly different from a previously proposed process that involves the coupling of two independently formed radicals.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::62631ac98d76286373b750f4453cbbeb https://doi.org/10.1021/jo4011377 Zobrazit plný text záznamu