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3,4-Dihydroxy-7,8-dihydro-beta-ionone 3-O-beta-D-glucopyranoside and other glycosidic constituents from apple leaves.
Nat Prod Lett. 2002 Apr; 16(2):87-93.NP

Abstract

3,4-Dihydroxy-7,8-dihydro-beta-ionone 3-O-beta-D-glucopyranoside 1 has been isolated from a methanolic extract of apple (Malus domestica) leaves by XAD-2 adsorption chromatography and subsequent purification by high speed countercurrent chromatography (HSCCC) and HPLC. Under acidic conditions this glycoside gives rise to a number of volatile compounds including 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) 2, which is known as an off-flavor compound in wine. In the course of the study, six additional glycoconjugates were isolated from apple leaves, i.e. roseoside 3, 3-oxo-alpha-ionol beta-D-glucopyranoside 4, benzoic acid beta-D-glucose ester 5, kaempferol 3-O-rhamnoside 6, (+)-syringaresinol beta-D-glucopyranoside 7 and 4-hydroxy-5-(3''-methyl-2''-butenyl)-benzoic acid methylester 3-beta-D-glucopyranoside 8. The latter compound has been isolated for the first time in nature. In order to avoid the 'kerosene-off-flavor' caused by TDN, the methanolic extract has been subjected to yeast fermentation. This treatment reduced the amount of TDN formed and resulted in an improved flavor impression of the methanolic extract.

Authors+Show Affiliations

Institut für Lebensmittelchemie, TU Braunschweig, Germany.No affiliation info availableNo affiliation info available

Pub Type(s)

Journal Article

Language

eng

PubMed ID

11990433

Citation

Stingl, Carola, et al. "3,4-Dihydroxy-7,8-dihydro-beta-ionone 3-O-beta-D-glucopyranoside and Other Glycosidic Constituents From Apple Leaves." Natural Product Letters, vol. 16, no. 2, 2002, pp. 87-93.
Stingl C, Knapp H, Winterhalter P. 3,4-Dihydroxy-7,8-dihydro-beta-ionone 3-O-beta-D-glucopyranoside and other glycosidic constituents from apple leaves. Nat Prod Lett. 2002;16(2):87-93.
Stingl, C., Knapp, H., & Winterhalter, P. (2002). 3,4-Dihydroxy-7,8-dihydro-beta-ionone 3-O-beta-D-glucopyranoside and other glycosidic constituents from apple leaves. Natural Product Letters, 16(2), 87-93.
Stingl C, Knapp H, Winterhalter P. 3,4-Dihydroxy-7,8-dihydro-beta-ionone 3-O-beta-D-glucopyranoside and Other Glycosidic Constituents From Apple Leaves. Nat Prod Lett. 2002;16(2):87-93. PubMed PMID: 11990433.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - 3,4-Dihydroxy-7,8-dihydro-beta-ionone 3-O-beta-D-glucopyranoside and other glycosidic constituents from apple leaves. AU - Stingl,Carola, AU - Knapp,Holger, AU - Winterhalter,Peter, PY - 2002/5/7/pubmed PY - 2003/1/11/medline PY - 2002/5/7/entrez SP - 87 EP - 93 JF - Natural product letters JO - Nat Prod Lett VL - 16 IS - 2 N2 - 3,4-Dihydroxy-7,8-dihydro-beta-ionone 3-O-beta-D-glucopyranoside 1 has been isolated from a methanolic extract of apple (Malus domestica) leaves by XAD-2 adsorption chromatography and subsequent purification by high speed countercurrent chromatography (HSCCC) and HPLC. Under acidic conditions this glycoside gives rise to a number of volatile compounds including 1,1,6-trimethyl-1,2-dihydronaphthalene (TDN) 2, which is known as an off-flavor compound in wine. In the course of the study, six additional glycoconjugates were isolated from apple leaves, i.e. roseoside 3, 3-oxo-alpha-ionol beta-D-glucopyranoside 4, benzoic acid beta-D-glucose ester 5, kaempferol 3-O-rhamnoside 6, (+)-syringaresinol beta-D-glucopyranoside 7 and 4-hydroxy-5-(3''-methyl-2''-butenyl)-benzoic acid methylester 3-beta-D-glucopyranoside 8. The latter compound has been isolated for the first time in nature. In order to avoid the 'kerosene-off-flavor' caused by TDN, the methanolic extract has been subjected to yeast fermentation. This treatment reduced the amount of TDN formed and resulted in an improved flavor impression of the methanolic extract. SN - 1057-5634 UR - https://www.unboundmedicine.com/medline/citation/11990433/34_Dihydroxy_78_dihydro_beta_ionone_3_O_beta_D_glucopyranoside_and_other_glycosidic_constituents_from_apple_leaves_ DB - PRIME DP - Unbound Medicine ER -