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Kim, Kim, Syed, Jung, and Kim: Rapid Identification of Methylglyoxal Trapping Constituents from Onion Peels by Pre-column Incubation Method
Original Article

Natural Product Sciences 2017;23(4):247-252.

Published online: 20 January 2017

DOI: https://doi.org/10.20307/nps.2017.23.4.247

Rapid Identification of Methylglyoxal Trapping Constituents from Onion Peels by Pre-column Incubation Method

Ji Hoon Kim1, Myeong Il Kim1, Ahmed Shah Syed1, 2, Kiwon Jung3, Chul Young Kim1, ∗

1College of Pharmacy and Institute of Pharmaceutical Science and Technology, Hanyang University, Ansan, Gyeonggi-do 15588, Republic of Korea

2Department of Pharmacognosy, Faculty of Pharmacy, University of Sindh, Jamshoro, Pakistan

3College of Pharmacy, CHA University, Sungnam 13844, Republic of Korea

∗Author for correspondence Chul Young Kim, College of Pharmacy and Institute of Pharmaceutical Science and Technology, Hanyang University, Ansan, Gyeonggi-do 15588, Republic of Korea Tel: +82-31-400-5809; E-mail: chulykim@hanyang.ac.kr

Received 2 August 2017       Revised 11 September 2017       Accepted 12 September 2017

Copyright © 2017 The Korean Society of Pharmacognosy

This is an Open Access article distributed under the terms of the Creative Commons Attribution Non-Commercial License (http://creativecommons.org/licenses/by-nc/3.0) which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited.

Abstract

The methylglyoxal (MGO) trapping constituents from onion (Allium cepa L.) peels were investigated using pre-column incubation of MGO and crude extract followed by HPLC analysis. The peak areas of MGO trapping compounds decreased, and their chemical structures were identified by HPLC-ESI/MS. Among major constituents in outer scale of onion, 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (2) was more effective MGO scavenger than quercetin (6) and its 4'-glucoside, spiraeoside (3). After 1 h incubation, compound 2 trapped over 90% MGO at a concentration of 0.5 mM under physiological conditions, but compounds 3 and 6 scavenged 45%, 16% MGO, respectively. HPLC-ESI/MS showed that compound 2 trapped two molecules of MGO to form a di-MGO adduct and compounds 3 and 6 captured one molecule of MGO to form mono-MGO adducts, and the positions 6 and 8 of the A ring of flavonoids were major active sites for trapping MGO.

Keywords: Allium cepa L., Methylglyoxal trapping, Pre-column incubation, Flavonoids

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Fig. 1.
Scavenging of MGO by onion peel extracts (0.05, 0.25 and 0.5 mg/ml) under physiological conditions (pH 7.4, 37oC). Data are presented as the mean ± S.E. of three replications.
nps-23-247f1.tif
Fig. 2.
Chemical structures of the identified components from onion peel extract. The compounds No. are the same as in Fig. 3. and Table 1.
nps-23-247f2.tif
Fig. 3.
HPLC-DAD chromatograms of the onion peel extract. Onion peel extract dissolved in methanol (A), after incubation with PBS (100 mM, pH 7.4) for 12 h (B) and 10 mM MGO for 12 h, in PBS (C) at 37oC. The peaks designated as asterisk (∗) were potential MGO scavengers. Peaks 2-a, 3-a and 6-a appeared after reaction.
nps-23-247f3.tif
Fig. 4.
MGO scavenging capacity of isolated compounds 2, 3 and 6 under physiological conditions (pH 7.4, 37oC). Purified compounds 2, 3 and 6 (0.25 or 0.5 mM) were incubated with MGO (0.33 mM) for up to 4 h. (A) 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone (2). (B) spiraeoside (3). (C) quercetin (6).
nps-23-247f4.tif
Fig. 5.
MS spectra of MGO adducts and proposed structures mono- or di-MGO adducts of compounds 2 (A), 3 (B) and 6 (C) under physiological conditions (pH 7.4, 37oC).
nps-23-247f5.tif
Table 1.
Peak assignment for the components from onion peel extract
No. Retention time (min) Compound identity ()ESI-MS m/z UV ëmax (nm)
1 6.20 protocatechuic acid 152.7 [M-H]− 259, 293
2 16.6 2-(3,4-dihydroxybenzoyl)-2,4,6-trihydroxy-3(2H)-benzofuranone 316.8 [M-H]− 292
3 30.2 spiraeoside (quercetin 4'-O-β-D-glucopyranoside) 463.0 [M-H]− 253, 368
4 35.8 condensation products of quercetin with protocatechuic acid 452.8 [M-H]− 291
5 36.5 condensation products of quercetin with protocatechuic acid 452.8 [M-H]− 292
6 37.7 quercetin 300.9 [M-H]− 255, 367
7 44.2 adduct of quercetin with quercetin 4'-O-β-D-glucopyranoside 762.8 [M-H]− 303, 369
8 48.3 4'-O-β-D-glucopyranoside of quercetin dimer 762.8 [M-H]− 303, 364

Peak assignment for the components from onion peel extract.

The compounds No. are the same as in Fig. 2.

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