Chemical transformations of characteristic hop secondary metabolites in relation to beer properties and the brewing process: A review

被引：124

作者：

Steenackers, Bart ^{[1
]}

De Cooman, Luc ^{[2
]}

De Vos, Dirk ^{[1
]}

机构：

[1] Katholieke Univ Leuven, Ctr Surface Sci & Catalysis, B-3001 Leuven, Belgium

[2] KaHo St Lieven, Lab Enzyme & Brewing Technol, B-9000 Ghent, Belgium

来源：

FOOD CHEMISTRY | 2015年 / 172卷

关键词：

Hop alpha acids; Hop beta acids; Hop sesquiterpenes; Chemical transformation; Brewing process; Beer properties; Humulone; Lupulone; Xanthohumol; Alpha-humulene; Beta-caryophyllene; HUMULUS-LUPULUS L; ISO-ALPHA-ACIDS; OXIDATION-PRODUCTS; BITTER ACIDS; DIRECT EPISULFIDATION; BETA-CARYOPHYLLENE; PHYTOESTROGEN; 8-PRENYLNARINGENIN; CATALYZED ISOMERIZATION; ABSOLUTE-CONFIGURATION; PREPARATIVE SEPARATION;

D O I：

10.1016/j.foodchem.2014.09.139

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The annual production of hops (Humulus lupulus L.) exceeds 100,000 mt and is almost exclusively consumed by the brewing industry. The value of hops is attributed to their characteristic secondary metabolites; these metabolites are precursors which are transformed during the brewing process into important bittering, aromatising and preservative components with rather low efficiency. By selectively transforming these components off-line, both their utilisation efficiency and functionality can be significantly improved. Therefore, the chemical transformations of these secondary metabolites will be considered with special attention to recent advances in the field. The considered components are the hop alpha-acids, hop beta-acids and xanthohumol, which are components unique to hops, and alpha-humulene and beta-caryophyllene, sesquiterpenes which are highly characteristic of hops. (C) 2014 Elsevier Ltd. All rights reserved.

引用

页码：742 / 756

页数：15

共 107 条

[31] Comparison of odor-active compounds in the spicy fraction of hop (Humulus lupulus L.) essential oil from four different varieties [J].

Eyres, Graham T. ;

Marriott, Philip J. ;

Dufour, Jean-Pierre .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2007, 55 (15) :6252-6261

[32] REARRANGEMENT OF (-)-BETA-CARYOPHYLLENE - A PRODUCT ANALYSIS AND FORCE-FIELD STUDY [J].

FITJER, L ;

MALICH, A ;

PASCHKE, C ;

KLUGE, S ;

GERKE, R ;

RISSOM, B ;

WEISER, J ;

NOLTEMEYER, M .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1995, 117 (36) :9180-9189

[33]

Giersch K. W., 1994, HELV CHIM ACTA, V77, P36

[34] The oxygenated sesquiterpenoid fraction of hops in relation to the spicy hop character of beer [J].

Goiris, K ;

De Ridder, M ;

De Rouck, G ;

Boeykens, A ;

Van Opstaele, F ;

Aerts, G ;

De Cooman, L ;

De Keukeleire, D .

JOURNAL OF THE INSTITUTE OF BREWING, 2002, 108 (01) :86-93

[35]

Goldstein H., 1982, U. S. patent, Patent No. [4,324,810, 4324810]

[36]

Grant H. L., 1978, [No title captured], Patent No. [US 4123561, 4123561]

[37] Polyterpenes by ring opening metathesis polymerization of caryophyllene and humulene [J].

Grau, Etienne ;

Mecking, Stefan .

GREEN CHEMISTRY, 2013, 15 (05) :1112-1115

[38] CONVERSION OF HUMULENE INTO CARYOPHYLLENE [J].

GREENWOOD, JM ;

SUTHERLA.JK ;

TORRE, A .

CHEMICAL COMMUNICATIONS, 1965, (17) :410-+

[39] Identification and RP-HPLC-ESI-MS/MS Quantitation of Bitter-Tasting β-Acid Transformation Products in Beer [J].

Haseleu, Gesa ;

Intelmann, Daniel ;

Hofmann, Thomas .

JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY, 2009, 57 (16) :7480-7489

[40]

Hay B. A, 1991, U. S. patent, Patent No. [5,013,571, 5013571]

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