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

作者:Althagafy Hanan S; Meza Avina Maria Elena; Oberlies Nicholas H*; Croatt Mitchell P
来源:Journal of Organic Chemistry, 2013, 78(15): 7594-7600.
DOI:10.1021/jo4011377

摘要

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.

  • 出版日期2013-8-2