Complete isolation and characterization of silybins and isosilybins from milk thistle (Silybum marianum)

被引:238
作者
Kim, NC [1 ]
Graf, TN [1 ]
Sparacino, CM [1 ]
Wani, MC [1 ]
Wall, ME [1 ]
机构
[1] Res Triangle Inst, Nat Prod Lab, Res Triangle Pk, NC 27709 USA
关键词
D O I
10.1039/b300099k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Complete separation, isolation, and structural characterization of four diastereoisomeric flavonolignans, silybins A (1) and B (2), and isosilybins A (3) and B (4) from the seeds of milk thistle (Silybum marianum) were achieved for the first time using a preparative reversed-phase HPLC method. In addition, three other flavonolignans, silychristin (5) isosilychristin (6) and silydianin (7), and a flavonoid, taxifolin (8) were isolated. Structures, including absolute stereochemistries of 1-4, were confirmed using 2D NMR and CD spectroscopy.
引用
收藏
页码:1684 / 1689
页数:6
相关论文
共 59 条
[1]  
ABRAHAM DJ, 1970, TETRAHEDRON LETT, P2675
[2]   ASYMMETRIC-SYNTHESIS OF "3-METHYL-2-PHENYL-1,4-BENZODIOXANES - ABSOLUTE-CONFIGURATION OF THE NEOLIGNANS EUSIDERIN AND EUSIDERIN-C AND EUSIDERIN-D [J].
ARNOLDI, A ;
MERLINI, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1985, (12) :2555-2557
[3]   CONSTITUENTS OF SILYBUM-MARIANUM - STRUCTURE OF ISOSILYBIN AND STEREOCHEMISTRY OF SILYBIN [J].
ARNONE, A ;
MERLINI, L ;
ZANAROTTI, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1979, (16) :696-697
[4]  
BOHRER I, 1968, TETRAHEDRON LETT, P6219
[5]  
CAPPELLETTI E M, 1983, Plantes Medicinales et Phytotherapie, V17, P209
[6]   CONFORMATIONAL ANALYSIS OF SATURATED HETEROCYCLES .26. 2-SUBSTITUTED BENZODIOXANS [J].
COOK, MJ ;
KATRITZK.AR ;
SEWELL, MJ .
JOURNAL OF THE CHEMICAL SOCIETY B-PHYSICAL ORGANIC, 1970, (06) :1207-&
[7]   THE CHEMISTRY OF BRAZILIAN LAURACEAE .91. BENZODIOXANE AND BETA-ARYLOXY-ARYLPROPANE TYPE NEOLIGNANS FROM LICARIA-CHRYSOPHYLLA [J].
DASILVA, MS ;
BARBOSAFILHO, JM ;
YOSHIDA, M ;
GOTTLIEB, OR .
PHYTOCHEMISTRY, 1989, 28 (12) :3477-3482
[8]   H-1 DELINEATION OF CONFORMATIONAL PARAMETERS OF CONSTITUENTS OF SILYBUM-MARIANUM IN SOLUTION [J].
DELFINI, M ;
DICOCCO, ME ;
GAGGELLI, E ;
LEPRI, A ;
VALENSIN, G .
SPECTROSCOPY LETTERS, 1990, 23 (08) :1007-1025
[9]   Determination of active component in silymarin by RP-LC and LC/MS [J].
Ding, TM ;
Tian, SJ ;
Zhang, ZX ;
Gu, DZ ;
Chen, YF ;
Shi, YH ;
Sun, ZP .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2001, 26 (01) :155-161
[10]  
FANG JM, 1992, PHYTOCHEMISTRY, V31, P3659, DOI 10.1016/0031-9422(92)83753-L