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

被引：64

作者：

Althagafy, Hanan S. ^{[1
]}

Meza-Avina, Maria Elena ^{[1
]}

Oberlies, Nicholas H. ^{[1
]}

Croatt, Mitchell P. ^{[1
]}

机构：

[1] Univ N Carolina, Dept Chem & Biochem, Greensboro, NC 27402 USA

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 15期

基金：

美国国家卫生研究院;

关键词：

SILYBUM-MARIANUM L; PROSTATE-CANCER; ISOSILYBIN-B; SILYMARIN; STEREOCHEMISTRY; ANTIOXIDANT; FLAVONOIDS; GROWTH;

D O I：

10.1021/jo4011377

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

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.

引用

页码：7594 / 7600

页数：7

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