Phenolic compounds in different barley varieties: identification by tandem mass spectrometry (QStar) and NMR; quantification by liquid chromatography triple quadrupole-linear ion trap mass spectrometry (Q-Trap)

Kamilla Klausen; Anne Garfield Mortensen; Bente Birgitte Laursen; Kim Haselmann; Birthe P Møller Jespersen; Inge S. Fomsgaard

Phenolic compounds in different barley varieties: identification by tandem mass spectrometry (QStar) and NMR; quantification by liquid chromatography triple quadrupole-linear ion trap mass spectrometry (Q-Trap)

Kamilla Klausen, Anne Garfield Mortensen, Bente Birgitte Laursen, Kim Haselmann, Birthe P Møller Jespersen, Inge S. Fomsgaard

21 Citations (Scopus)

3 Downloads (Pure)

Abstract

Barley (Hordeum vulgare) is an important cereal that has many applications; as a human food, in malt products and as livestock feed. The content of soluble health-promoting fibers, β-glucans, varies substantially among barley varieties. In the present study, the content of secondary metabolites with potential positive health effects in different high- and low-β-glucan barley varieties was studied. Five different flavanols were isolated and identified: (2R,3S)-catechin-7-O-β-D-glucopyranoside (1), prodelphinidin B3 (2), procyanidin B3 (3), (+)-catechin (4) and procyanidin B1 (5). Procyanidin B1 has never been reported in barley grains before. The compounds were identified using ¹H NMR and quadrupolar time-of-flight mass spectrometry. A quantitative analytical method was developed for prodelphinidin B3, procyanidin B3 and (+)-catechin in liquid chromatography triple quadrupole-linear ion trap mass spectrometry and these compounds were quantified in all varieties, together with four phenolic acids: ferulic acid, vanillic acid, p-coumaric acid and p-hydroxybenzoic acid. Catechin was the compound that was present at the highest concentration in all varieties. The variation, between cultivars, in catechin concentration varied four fold. A Principal Component Analysis indicated no correlation between concentrations of β-glucan and secondary metabolites. Concentrations of catechin and prodelphinidin B3 were strongly correlated, whereas the concentration of procyanidin B3 was not correlated with that of catechin or prodelphinidin B3. Either two different enzymes could be responsible for the dimerization of prodelphinidin B3 and procyanidin B3, or the affinity of the enzyme could be different whether the dimerization is between two catechin units or between units of gallocatechin and catechin.

Original language	English
Journal	Natural Product Communications
Volume	5
Issue number	3
Pages (from-to)	407-414
Number of pages	8
ISSN	1934-578X
Publication status	Published - 2010

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Phenolic compounds in different barley varieties : identification by tandem mass spectrometry (QStar) and NMR; quantification by liquid chromatography triple quadrupole-linear ion trap mass spectrometry (Q-Trap). / Klausen, Kamilla; Mortensen, Anne Garfield; Laursen, Bente Birgitte et al.

In: Natural Product Communications, Vol. 5, No. 3, 2010, p. 407-414.

Research output: Contribution to journal › Journal article › Research › peer-review

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title = "Phenolic compounds in different barley varieties: identification by tandem mass spectrometry (QStar) and NMR; quantification by liquid chromatography triple quadrupole-linear ion trap mass spectrometry (Q-Trap)",

abstract = "Barley (Hordeum vulgare) is an important cereal that has many applications; as a human food, in malt products and as livestock feed. The content of soluble health-promoting fibers, β-glucans, varies substantially among barley varieties. In the present study, the content of secondary metabolites with potential positive health effects in different high- and low-β-glucan barley varieties was studied. Five different flavanols were isolated and identified: (2R,3S)-catechin-7-O-β-D-glucopyranoside (1), prodelphinidin B3 (2), procyanidin B3 (3), (+)-catechin (4) and procyanidin B1 (5). Procyanidin B1 has never been reported in barley grains before. The compounds were identified using 1H NMR and quadrupolar time-of-flight mass spectrometry. A quantitative analytical method was developed for prodelphinidin B3, procyanidin B3 and (+)-catechin in liquid chromatography triple quadrupole-linear ion trap mass spectrometry and these compounds were quantified in all varieties, together with four phenolic acids: ferulic acid, vanillic acid, p-coumaric acid and p-hydroxybenzoic acid. Catechin was the compound that was present at the highest concentration in all varieties. The variation, between cultivars, in catechin concentration varied four fold. A Principal Component Analysis indicated no correlation between concentrations of β-glucan and secondary metabolites. Concentrations of catechin and prodelphinidin B3 were strongly correlated, whereas the concentration of procyanidin B3 was not correlated with that of catechin or prodelphinidin B3. Either two different enzymes could be responsible for the dimerization of prodelphinidin B3 and procyanidin B3, or the affinity of the enzyme could be different whether the dimerization is between two catechin units or between units of gallocatechin and catechin.",

author = "Kamilla Klausen and Mortensen, {Anne Garfield} and Laursen, {Bente Birgitte} and Kim Haselmann and Jespersen, {Birthe P M{\o}ller} and Fomsgaard, {Inge S.}",

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T1 - Phenolic compounds in different barley varieties

T2 - identification by tandem mass spectrometry (QStar) and NMR; quantification by liquid chromatography triple quadrupole-linear ion trap mass spectrometry (Q-Trap)

AU - Klausen, Kamilla

AU - Mortensen, Anne Garfield

AU - Laursen, Bente Birgitte

AU - Haselmann, Kim

AU - Jespersen, Birthe P Møller

AU - Fomsgaard, Inge S.

PY - 2010

Y1 - 2010

N2 - Barley (Hordeum vulgare) is an important cereal that has many applications; as a human food, in malt products and as livestock feed. The content of soluble health-promoting fibers, β-glucans, varies substantially among barley varieties. In the present study, the content of secondary metabolites with potential positive health effects in different high- and low-β-glucan barley varieties was studied. Five different flavanols were isolated and identified: (2R,3S)-catechin-7-O-β-D-glucopyranoside (1), prodelphinidin B3 (2), procyanidin B3 (3), (+)-catechin (4) and procyanidin B1 (5). Procyanidin B1 has never been reported in barley grains before. The compounds were identified using 1H NMR and quadrupolar time-of-flight mass spectrometry. A quantitative analytical method was developed for prodelphinidin B3, procyanidin B3 and (+)-catechin in liquid chromatography triple quadrupole-linear ion trap mass spectrometry and these compounds were quantified in all varieties, together with four phenolic acids: ferulic acid, vanillic acid, p-coumaric acid and p-hydroxybenzoic acid. Catechin was the compound that was present at the highest concentration in all varieties. The variation, between cultivars, in catechin concentration varied four fold. A Principal Component Analysis indicated no correlation between concentrations of β-glucan and secondary metabolites. Concentrations of catechin and prodelphinidin B3 were strongly correlated, whereas the concentration of procyanidin B3 was not correlated with that of catechin or prodelphinidin B3. Either two different enzymes could be responsible for the dimerization of prodelphinidin B3 and procyanidin B3, or the affinity of the enzyme could be different whether the dimerization is between two catechin units or between units of gallocatechin and catechin.

AB - Barley (Hordeum vulgare) is an important cereal that has many applications; as a human food, in malt products and as livestock feed. The content of soluble health-promoting fibers, β-glucans, varies substantially among barley varieties. In the present study, the content of secondary metabolites with potential positive health effects in different high- and low-β-glucan barley varieties was studied. Five different flavanols were isolated and identified: (2R,3S)-catechin-7-O-β-D-glucopyranoside (1), prodelphinidin B3 (2), procyanidin B3 (3), (+)-catechin (4) and procyanidin B1 (5). Procyanidin B1 has never been reported in barley grains before. The compounds were identified using 1H NMR and quadrupolar time-of-flight mass spectrometry. A quantitative analytical method was developed for prodelphinidin B3, procyanidin B3 and (+)-catechin in liquid chromatography triple quadrupole-linear ion trap mass spectrometry and these compounds were quantified in all varieties, together with four phenolic acids: ferulic acid, vanillic acid, p-coumaric acid and p-hydroxybenzoic acid. Catechin was the compound that was present at the highest concentration in all varieties. The variation, between cultivars, in catechin concentration varied four fold. A Principal Component Analysis indicated no correlation between concentrations of β-glucan and secondary metabolites. Concentrations of catechin and prodelphinidin B3 were strongly correlated, whereas the concentration of procyanidin B3 was not correlated with that of catechin or prodelphinidin B3. Either two different enzymes could be responsible for the dimerization of prodelphinidin B3 and procyanidin B3, or the affinity of the enzyme could be different whether the dimerization is between two catechin units or between units of gallocatechin and catechin.

M3 - Journal article

SN - 1934-578X

VL - 5

SP - 407

EP - 414

JO - Natural Product Communications

JF - Natural Product Communications

IS - 3

ER -