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

共 50 条

[31] HiFSA Fingerprinting Applied to Isomers with Near-Identical NMR Spectra: The Silybin/Isosilybin Case [J].

Napolitano, Jose G. ;

Lankin, David C. ;

Graf, Tyler N. ;

Friesen, J. Brent ;

Chen, Shao-Nong ;

McAlpine, James B. ;

Oberlies, Nicholas H. ;

Pauli, Guido F. .

JOURNAL OF ORGANIC CHEMISTRY, 2013, 78 (07) :2827-2839

[32] New insight into the biosynthesis of flavanolignans in the white-flowered variant of Silybum marianum [J].

Nyiredy, Sz. ;

Samu, Zs. ;

Szuecs, Z. ;

Gulacsi, K. ;

Kurtan, T. ;

Antus, S. .

JOURNAL OF CHROMATOGRAPHIC SCIENCE, 2008, 46 (02) :93-96

[33]

PELTER A, 1968, TETRAHEDRON LETT, P2911

[34] STRUCTURE OF SILYBIN .1. DEGRADATIVE EXPERIMENTS [J].

PELTER, A ;

HANSEL, R .

CHEMISCHE BERICHTE-RECUEIL, 1975, 108 (03) :790-802

[35] Silymarin for HCV infection [J].

Polyak, Stephen J. ;

Oberlies, Nicholas H. ;

Pecheur, Eve-Isabelle ;

Dahari, Harel ;

Ferenci, Peter ;

Pawlotsky, Jean-Michel .

ANTIVIRAL THERAPY, 2013, 18 (02) :141-147

[36] Hepatoprotective and antiviral functions of silymarin components in hepatitis C virus infection [J].

Polyak, Stephen J. ;

Ferenci, Peter ;

Pawlotsky, Jean-Michel .

HEPATOLOGY, 2013, 57 (03) :1262-1271

[37] A BIOMIMETIC ROUTE TO LIGNIN MODEL COMPOUNDS VIA SILVER(I) OXIDE OXIDATION .1. SYNTHESIS OF DILIGNOLS AND NONCYCLIC BENZYL ARYL ETHERS [J].

QUIDEAU, S ;

RALPH, J .

HOLZFORSCHUNG, 1994, 48 (01) :12-22

[38] A new synthesis of (Z)-coniferyl alcohol, and characterization of its derived synthetic lignin [J].

Ralph, J ;

Zhang, YS .

TETRAHEDRON, 1998, 54 (08) :1349-1354

[39]

Ralph J, 2008, REC ADV POLYPHEN RES, V1, P36

[40] Multitargeted therapy of cancer by silymarin [J].

Ramasamy, Kumaraguruparan ;

Agarwal, Rajesh .

CANCER LETTERS, 2008, 269 (02) :352-362

← 1 2 3 4 5 →