title: Mechanistic study of the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle.
abstract: 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.
authors.affiliation: Department of Chemistry and Biochemistry, University of North Carolina at Greensboro, 435 Sullivan Science Building, P.O. Box 26170, Greensboro, North Carolina 27402, USA.
authors.forename: Hanan S
authors.initials: HS
authors.lastname: Althagafy
authors.forename: Maria Elena
authors.initials: ME
authors.lastname: Meza-Aviña
authors.forename: Nicholas H
authors.initials: NH
authors.lastname: Oberlies
authors.forename: Mitchell P
authors.initials: MP
authors.lastname: Croatt
mesh_terms: D040761:Biomimetic Materials / Q000138:chemical synthesis* / Q000737:chemistry; D044947:Flavonolignans / Q000138:chemical synthesis* / Q000737:chemistry; D020944:Silybum marianum / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D044947:Flavonolignans