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Chemical Constituents of Gold‐red Apple and Their α ‐Glucosidase Inhibitory Activities
Author(s) -
He QianQian,
Yang Liu,
Zhang JiaYu,
Ma JianNan,
Ma ChaoMei
Publication year - 2014
Publication title -
journal of food science
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.772
H-Index - 150
eISSN - 1750-3841
pISSN - 0022-1147
DOI - 10.1111/1750-3841.12599
Subject(s) - betulinic acid , chemistry , ursolic acid , pomace , oleanolic acid , terpene , chromatography , malus , electrospray ionization , food science , mass spectrometry , organic chemistry , botany , biology , medicine , genetics , alternative medicine , pathology
Ten compounds were isolated and purified from the peels of gold‐red apple ( Malus domestica ) for the 1st time. The identified compounds are 3 β , 20 β ‐dihydroxyursan‐28‐oic acid (1), 2 α ‐hydroxyoleanolic acid (2), euscaphic acid (3), 3‐ O ‐p‐coumaroyl tormentic acid (4), ursolic acid (5), 2 α ‐hydroxyursolic acid (6), oleanolic acid (7), betulinic acid (8), linolic acid (9), and α ‐linolenic acid (10). Their structures were determined by interpreting their nuclear magnetic resonance and mass spectrometry (MS) spectra, and by comparison with literature data. Compound 1 is new, and compound 2 is herein reported for the 1st time for the genus Malus . α ‐Glucosidase inhibition assay revealed 6 of the triterpenoid isolates as remarkable α ‐glucosidase inhibitors, with betulinic acid showing the strongest inhibition (IC 50 = 15.19 μM). Ultra‐performance liquid chromatography‐electrospray ionization MS analysis of the fruit peels, pomace, flesh, and juice revealed that the peels and pomace contained high levels of triterpenes, suggesting that wastes from the fruit juice industry could serve as rich sources of bioactive triterpenes.