Journal
JOURNAL OF AGRICULTURAL AND FOOD CHEMISTRY
Volume 68, Issue 33, Pages 8797-8811Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.jafc.0c02122
Keywords
Allium cepa skins; antioxidant; alpha-glucosidase; PTP1B; kinetic; molecular docking
Funding
- National Research Foundation of Korea (NRF) - Ministry of Science and ICT, Korea [2015M3A9A5031271, 2020R1F1A1072001]
- National Research Foundation of Korea [2015M3A9A5031271, 2020R1F1A1072001] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
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The onion, known as the bulb onion or common onion, is not only a key ingredient in many tasty and healthy vegetarian meals but also many traditional medicines. Nine new flavonoids [cepaflavas A, B (5, 6), cepadials A-D (7-9 and 14), and cepabiflas A-C (10-12)] and six known compounds (1-4, 13, 15) were obtained from the outer skins of Allium cepa L. Among them, compounds 5, 6, and 9 might be artificial products formed during extraction and isolation. New compounds were structurally elucidated using various spectroscopy/spectrometry techniques, including NMR and HRMS, and computational methods. Their absolute configurations were determined using time-dependent density functional theory calculations, combined with ECD spectroscopy, optical rotation calculation, and statistical procedures (CP3 and DP4 analysis). The free radical scavenging assays revealed that the new compounds 10-12 possessed considerable antioxidant activities with IC50 values of 4.25-8.88 and 7.12-8.14 mu M against DPPH and ABTS(center dot+), respectively. Compounds 13-15 showed substantial inhibitory activities against both alpha-glucosidase and protein tyrosine phosphatase 1B (PTP1B), with IC50 values of 0.89-6.80 and 1.13-6.82 mu M, respectively. On the basis of molecular docking studies, 13 and 15 were predicted to have high binding capacity and strong affinity toward the active site of PTP1B.
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