Medicinal flowers.: VI.: Absolute stereostructures of two new flavanone glycosides and a phenylbutanoid glycoside from the flowers of Chrysanthemum indicum L.:: Their inhibitory activities for rat lens aldose reductase

被引:142
作者
Matsuda, H [1 ]
Morikawa, T [1 ]
Toguchida, I [1 ]
Harima, S [1 ]
Yoshikawa, M [1 ]
机构
[1] Kyoto Pharmaceut Univ, Yamashina Ku, Kyoto 6078412, Japan
关键词
aldose reductase inhibitor; Chrysanthemum indicum; medicinal flower; (2S)-eriodictyol 7-O-beta-D-glueopyranosiduronic; acid; (2R)-eriodictyol 7-O-beta-D-glucopyranosiduronic acid; (2S,3S)-1-phenyl-2,3-butanediol 3-O-beta-D-glucopyranoside;
D O I
10.1248/cpb.50.972
中图分类号
R914 [药物化学];
学科分类号
100701 ;
摘要
Two new flavanone glycosides, (2S)- and (2R)-eriodictyol 7-O-beta-D-glucopyranosiduronic acids, and a new phenylbutanoid glycoside, (2S,3S)-1-phenyl-2,3-butanediol 3-O-beta-D-glucopyranoside, were isolated from the flowers of Chrysanthemum indicum L. cultivated in China together with eight flavonoids. The absolute stereostructures of the new compounds were determined on the basis of chemical and physicochemical evidence. Both of the new flavanone glycosides were found to show inhibitory activity for rat lens aldose reductase.
引用
收藏
页码:972 / 975
页数:4
相关论文
共 22 条
[1]   SYNTHESIS OF ALL 4 POSSIBLE STEREOISOMERS OF 1-PHENYL-2,3-BUTANEDIOL AND BOTH ENANTIOMERS OF 3-HYDROXY-4-PHENYL-2-BUTANONE TO DETERMINE THE ABSOLUTE-CONFIGURATION OF THE NATURAL CONSTITUENTS [J].
AWANO, K ;
YANAI, T ;
WATANABE, I ;
TAKAGI, Y ;
KITAHARA, T ;
MORI, K .
BIOSCIENCE BIOTECHNOLOGY AND BIOCHEMISTRY, 1995, 59 (07) :1251-1254
[2]   CONSTITUENTS OF A FERN, DAVALLIA-MARIESII MOORE .1. ISOLATION AND STRUCTURES OF DAVALLIALACTONE AND A NEW FLAVANONE GLUCURONIDE [J].
CUI, CB ;
TEZUKA, Y ;
KIKUCHI, T ;
NAKANO, H ;
TAMAOKI, T ;
PARK, JH .
CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38 (12) :3218-3225
[4]  
HARA S, 1986, CHEM PHARM BULL, V34, P1843
[5]   GLUCOSYLATION OF QUERCETIN BY A CELL-SUSPENSION CULTURE OF VITIS SP [J].
KODAMA, T ;
ISHIDA, H ;
KOKUBO, T ;
YAMAKAWA, T ;
NOGUCHI, H .
AGRICULTURAL AND BIOLOGICAL CHEMISTRY, 1990, 54 (12) :3283-3288
[6]   Medicinal flowers.: IV.: Marigold.: (2):: Structures of new ionone and sesquiterpene glycosides from Egyptian Calendula officinalis [J].
Marukami, T ;
Kishi, A ;
Yoshikawa, M .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (08) :974-978
[7]   Hepatoprotective principles from the flowers of Tilia argentea (Linden):: Structure requirements of tiliroside and mechanisms of action [J].
Matsuda, H ;
Ninomiya, K ;
Shimoda, H ;
Yoshikawa, M .
BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (03) :707-712
[8]   Antidiabetic principles of natural medicines.: V. Aldose reductase inhibitors from Myrcia multiflora DC. (2):: Structures of myrciacitrins III, IV, and V [J].
Matsuda, H ;
Nishida, N ;
Yoshikawa, M .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2002, 50 (03) :429-431
[9]   Medicinal foodstuffs. XXVIII. Inhibitors of nitric oxide production and new sesquiterpenes, zedoarofuran, 4-epicurcumenol, neocurcumenol, gajutsulactones A and B, and zedoarolides A and B, from Zedoariae Rhizoma [J].
Matsuda, H ;
Morikawa, T ;
Toguchida, I ;
Ninomiya, K ;
Yoshikawa, M .
CHEMICAL & PHARMACEUTICAL BULLETIN, 2001, 49 (12) :1558-1566
[10]  
Matsuda H, 2001, HETEROCYCLES, V55, P1499