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Citrus and berry flavonoids inhibit dipeptidyl peptidase‐IV enzymatic activity by binding to the catalytic site
Author(s) -
Fan Junfeng,
Johnson Michelle,
Mejia Elvira Gonzalez
Publication year - 2013
Publication title -
the faseb journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.709
H-Index - 277
eISSN - 1530-6860
pISSN - 0892-6638
DOI - 10.1096/fasebj.27.1_supplement.637.8
Subject(s) - chemistry , hesperidin , naringin , naringenin , luteolin , hesperetin , nobiletin , flavanone , kaempferol , isoflavonoid , berry , stereochemistry , cyanidin , flavonoid , apigenin , catechin , morin , biochemistry , polyphenol , chromatography , alternative medicine , pathology , medicine , botany , biology , antioxidant
We investigated 25 citrus and berry flavonoids on inhibition of DPP‐IV, contributing to decrease glucose absorption. Heperetin, nobiletin, tangeretin, cyanidin, petunidin, genistein and EGCG could bind to DPP‐IV active sites. Binding energies (kcal/mol), hesperetin (−5.8), nobiletin (−5.7), petunidin (−5.1) and tangeretin (− 4.9) were lower than diprotin A (−4.8), indicating more potency in inhibiting DPP‐IV. This was attributed to H bonds between hydroxyl groups on flavone aromatic rings and amino acid residues in the enzyme, and đ‐interactions of flavonoids aromatic ring B and DPP‐IV arg125, phe357 and arg669. Aglycone flavonoids (luteolin, apigenin, quercetin, kaempferol, flavone, naringenin, catechin, gallocatechin, epicatechin) and glycosylated flavonoids (cyanidin‐3‐glucoside, delphinidin‐3‐glucoside, dephinidin‐3‐ arabinoside, malvinidin‐3‐galactoside, malvinidin‐3‐arabinoside) could bind their aromatic B‐ring to DPP‐IV active sites, inhibiting its activity. Flavonoinds with disaccharides (naringin, rutin and narirutin) could not bind DPP‐IV due to unfavorable sugars steric obstacle. Biochemical kinetics showed blueberry and blackberry anthocyanins effectively reduced DPP‐IV activity (IC 50 4.0 μM C3G), comparable to the known inhibitor (IC 50 4.3 mg/mL). Citrus and berry flavonoids can bind DPP‐IV active pockets with potential as antidiabetes therapy. USDA