Isolation of two novel terpenoid glucose esters from Riesling wine

被引：39

作者：

Bonnländer, B ^{[1
]}

Baderschneider, B ^{[1
]}

Messerer, M ^{[1
]}

Winterhalter, P ^{[1
]}

机构：

[1] Univ Erlangen Nurnberg, Inst Pharm & Lebensmittelchem, D-91052 Erlangen, Germany

来源：

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY | 1998年 / 46卷 / 04期

关键词：

(E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid glucose ester; (2E,6E)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoic acid glucose ester; aroma precursor; wine lactone; multilayer coil countercurrent chromatography; Riesling wine;

D O I：

10.1021/jf9706033

中图分类号：

S [农业科学];

学科分类号：

09 ;

摘要：

A glycosidic isolate of Riesling wine was separated with multilayer coil countercurrent chromatography (MLCCC). After acetylation and subsequent purification by high-performance liquid chromatography (HPLC), the glucose esters of (E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid (1) and (2E,6E)-10,11-dihydroxy-3,7,11-trimethyl-2,6-dodecadienoic acid (2) were identified for the first time as nine constituents. The identification was achieved by mass spectrometry (DCI-MS) as well as nuclear magnetic resonance spectroscopy (H-1 NMR, C-13 NMR, COSY, HMBC). In biomimetic studies carried out with (E)-2,6-dimethyl-6-hydroxyocta-2,7-dienoic acid the potent nine aroma compound 3a,4,5,7a-tetrahydro-3,6-dimethylbenzofuran-2(3H)-one (wine lactone) was formed, thus revealing an important aroma precursor function for glucoconjugate 1.

引用

页码：1474 / 1478

页数：5

共 23 条

[11] GLYCOSIDICALLY BOUND NORISOPRENOIDS FROM VITIS-VINIFERA CV RIESLING LEAVES [J].

SKOUROUMOUNIS, GK ;

WINTERHALTER, P .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1994, 42 (05) :1068-1072

[12]

SOUTHWELL I A, 1975, Tetrahedron Letters, V24, P1885

[13] RAPID CHROMATOGRAPHIC TECHNIQUE FOR PREPARATIVE SEPARATIONS WITH MODERATE RESOLUTION [J].

STILL, WC ;

KAHN, M ;

MITRA, A .

JOURNAL OF ORGANIC CHEMISTRY, 1978, 43 (14) :2923-2925

[14] NOVEL MONOTERPENE DIOLS AND DIOL GLYCOSIDES IN VITIS-VINIFERA GRAPES [J].

STRAUSS, CR ;

WILSON, B ;

WILLIAMS, PJ .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1988, 36 (03) :569-573

[15] APPLICATION OF DROPLET COUNTERCURRENT CHROMATOGRAPHY TO THE ANALYSIS OF CONJUGATED FORMS OF TERPENOIDS, PHENOLS, AND OTHER CONSTITUENTS OF GRAPE JUICE [J].

STRAUSS, CR ;

GOOLEY, PR ;

WILSON, B ;

WILLIAMS, PJ .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1987, 35 (04) :519-524

[16]

Versini G, 1996, VITIS, V35, P15

[17]

WALDMANN D, 1992, VITIS, V31, P169

[18]

Williams PJ., 1993, FLAVOR SCI SENSIBLE, P287

[19]

Winterhalter P, 1997, VITIS, V36, P55

[20] 2-DIMENSIONAL GC-DCCC ANALYSIS OF THE GLYCOCONJUGATES OF MONOTERPENES, NORISOPRENOIDS, AND SHIKIMATE-DERIVED METABOLITES FROM RIESLING WINE [J].

WINTERHALTER, P ;

SEFTON, MA ;

WILLIAMS, PJ .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 1990, 38 (04) :1041-1048

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