Work

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

Year: 2013

Type: article

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.

Source: The Journal of Organic Chemistry

DOI: 10.1021/jo4011377

Authors: Hanan S. Althagafy, Maria Elena Meza-Aviña, Nicholas H. Oberlies, Mitchell P. Croatt

Institution: University of North Carolina at Greensboro

Language: English

Topic: Silymarin and Mushroom Poisoning

Subfield: Pulmonary and Respiratory Medicine

Field: Medicine

Domain: Health Sciences

Open Access status: green

Funders: National Institutes of Health, University of North Carolina at Greensboro, National Center for Complementary and Alternative Medicine, National Center for Complementary and Integrative Health

Awards: G1689950459, G8221667519