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