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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.

SUBMITTER: Althagafy HS 

PROVIDER: S-EPMC3855429 | biostudies-literature | 2013 Aug

REPOSITORIES: biostudies-literature

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Mechanistic study of the biomimetic synthesis of flavonolignan diastereoisomers in milk thistle.

Althagafy Hanan S HS   Meza-Aviña Maria Elena ME   Oberlies Nicholas H NH   Croatt Mitchell P MP  

The Journal of organic chemistry 20130722 15


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 indep  ...[more]

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