STOMACHIC PRINCIPLES IN GINGER .2. PUNGENT AND ANTIULCER EFFECTS OF LOW POLAR CONSTITUENTS ISOLATED FROM GINGER, THE DRIED RHIZOMA OF ZINGIBER-OFFICINALE ROSCOE CULTIVATED IN TAIWAN - THE ABSOLUTE STEREOSTRUCTURE OF A NEW DIARYLHEPTANOID

被引：38

作者：

YAMAHARA, J ^{[1
]}

HATAKEYAMA, S ^{[1
]}

TANIGUCHI, K ^{[1
]}

KAWAMURA, M ^{[1
]}

YOSHIKAWA, M ^{[1
]}

机构：

[1] KYOTO PHARMACEUT UNIV, YAMASHINA KU, KYOTO 607, JAPAN

来源：

YAKUGAKU ZASSHI-JOURNAL OF THE PHARMACEUTICAL SOCIETY OF JAPAN | 1992年 / 112卷 / 09期

关键词：

GINGER; ZINGIBERIS-RHIZOMA; ZINGIBER-OFFICINALE; ZINGIBERACEAE; ANTIULCER EFFECT; PUNGENT EFFECT; DIARYLHEPTANOID; (3S; 5S)-DIHYDROXY-1-(4'-HYDROXY-3'-5'-DIMETHOXYPHENYL)-7-(4''-HYDROXY-3''-METHOXYPHENYL)HEPTANE; BISABOLANE SESQUITERPENE; BENZOATE CHIRALITY METHOD;

D O I：

10.1248/yakushi1947.112.9_645

中图分类号：

R9 [药学];

学科分类号：

1007 ;

摘要：

By using the effects on HCI/ethanol-induced gastric lesions in rats, beta-sesquiphellandrene (2), beta-bisabolene (3), ar-curcumene (4) and 6-shogaol (5) were isolated as anti-ulcer active principles in ginger, the dried rhizoma of Zingiber officinale RoscoE (Shokyo in Japanese) which was cultivated in Taiwan, together with nine known compounds and a new diarylheptanoid. The absolute stereostructure of the diarylheptanoid was characterized as (3S,5S)-dihydroxy-1-(4'-hydroxy-3',5'-dimethoxyphenyl)-7-(4"-hydroxy-3"-methoxyphenyl)heptane (15) on the basis of chemical and spectroscopic evidence which included the application of the benzoate chirality method. The pungent effects of several constituents isolated from ginger were examined.

引用

页码：645 / 655

页数：11

共 17 条

[1]

CHEN CC, 1987, J CHROMATOGR, V387, P499, DOI 10.1016/S0021-9673(01)94559-5

[2] CHROMATOGRAPHIC ANALYSES OF ISOMERIC SHOGAOL COMPOUNDS DERIVED FROM ISOLATED GINGEROL COMPOUNDS OF GINGER (ZINGIBER-OFFICINALE ROSCOE) [J].

CHEN, CC ;

ROSEN, RT ;

HO, CT .

JOURNAL OF CHROMATOGRAPHY, 1986, 360 (01) :175-184

[3]

CONNELL DW, 1966, AUST J CHEM, V19, P283

[4] A RE-EXAMINATION OF GINGEROL SHOGAOL AND ZINGERONE PUNGENT PRINCIPLES OF GINGER (ZINGIBER OFFICINALE ROSCOE) [J].

CONNELL, DW ;

SUTHERLAND, MD .

AUSTRALIAN JOURNAL OF CHEMISTRY, 1969, 22 (05) :1033-+

[5] SYNTHESES OF THE (+/-)-[N]-GINGEROLS (PUNGENT PRINCIPLES OF GINGER) AND RELATED-COMPOUNDS THROUGH REGIOSELECTIVE ALDOL CONDENSATIONS - RELATIVE PUNGENCY ASSAYS [J].

DENNIFF, P ;

MACLEOD, I ;

WHITING, DA .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1981, (01) :82-87

[6]

Gall T. L., 1989, TETRAHEDRON LETT, V30, P6521

[7] A CD METHOD FOR DETERMINATION OF THE ABSOLUTE STEREOCHEMISTRY OF ACYCLIC GLYCOLS .1. APPLICATION OF THE CD EXCITON CHIRALITY METHOD TO ACYCLIC 1,3-DIBENZOATE SYSTEMS [J].

HARADA, N ;

SAITO, A ;

ONO, H ;

GAWRONSKI, J ;

GAWRONSKA, K ;

SUGIOKA, T ;

UDA, H ;

KURIKI, T .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (10) :3842-3850

[8]

HAUNG Q, 1991, CHEM PHARM BULL, V39, P397

[9]

KIKUZAKI H, 1991, CHEM PHARM BULL, V39, P120, DOI 10.1248/cpb.39.120

[10] INHIBITION OF PROSTAGLANDIN AND LEUKOTRIENE BIOSYNTHESIS BY GINGEROLS AND DIARYLHEPTANOIDS [J].

KIUCHI, F ;

IWAKAMI, S ;

SHIBUYA, M ;

HANAOKA, F ;

SANKAWA, U .

CHEMICAL & PHARMACEUTICAL BULLETIN, 1992, 40 (02) :387-391

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