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Inhibitory activity of caffeoylquinic acids from the aerial parts of Artemisia princes on rat lens aldose reductase and on the formation of advanced glycation end products

Journal of the Korean Society for Applied Biological Chemistry volume 52, pages 655–662 (2009)Cite this article

Abstract

Caffeoylquinic acids -3,4-di-O-caffeoylquinic acid (1); 1,3,5-tri-O-caffeoylquinic acid (2); and 3,4,5-tri-O-caffeoylqunic acid (3)- were isolated from an acetone-soluble fraction of the aerial parts of Artemisia princes. Their structures were determined spectroscopically using 1D- and 2D-nuclear magnetic resonance (NMR) studies, as well as by comparing the NMR results with previously published structures. All the isolates were subjected to in vitro bioassays to evaluate their efficacy in inhibiting rat lens aldose reductase (RLAR) activity and the formation of advanced glycation end products (AGEs). We found 1,3,5-tri-O-caffeoylquinic acid (2) to be the most potent AGE inhibitor, and the concentration that resulted in 50% inhibition (IC50) was 22.18 ±1.46 mM, as compared to the aminoguanidine and chlorogenic acid controls, which had IC50 values of 1,093.11±10.95 and 117.63±0.20 mM, respectively. In the RLAR assay, the three caffeoylquinic acids were found to have IC50 values in the range of 1.78-2.40 μM, demonstrating a 5- to 10-fold greater efficacy in RLAR inhibition as compared to the quercetin control, which had an IC50 value of 17.91 μM.

Abbreviations

AGEs:

advanced glycation end products

A. princeps:

Artemisia princes

AR:

aldose reductase

BSA-MGO:

methylglyoxal-modified bovine serum albumin

ESI-MS:

electron spray ionization-mass spectrophotometer

HMBC:

heteronuclear multiple bond coherence

HMQC:

heteronuclear multiple quantum coherence

IC50 :

half maximal inhibitory concentration

MGO:

methylglyoxal

NADPH:

nicotinamide adenine dinucleotide phosphate

NMR:

nuclear magnetic resonance

RLAR:

rat lens aldose reductase

SD:

Sprague-Dawley

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Authors and Affiliations

  1. Department of Agriculture, Yanbian University, Yan Ji, 133000, Jilin Prov, China

    Cheng-Bi Cui

  2. Medical & Bio-material Research Center and Department of Food Science and Nutrition, Hallym University, 200-702, Chuncheon, Republic of Korea

    Seung Kyoung Jeong, Il-Jun Kang & Soon Sung Lim

  3. Center for Efficacy Assessment and Development of Functional Foods and Drugs, Hallym University, 200-702, Chuncheon, Republic of Korea

    Yeon Sil Lee, Il-Jun Kang & Soon Sung Lim

  4. Department of Hotel Cuisine, Korea Tourism College, 467-745, Icheon, Republic of Korea

    Soon Ok Lee

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  1. Cheng-Bi Cui
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  2. Seung Kyoung Jeong
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  5. Il-Jun Kang
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Correspondence to Il-Jun Kang or Soon Sung Lim.

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Cui, CB., Jeong, S.K., Lee, Y.S. et al. Inhibitory activity of caffeoylquinic acids from the aerial parts of Artemisia princes on rat lens aldose reductase and on the formation of advanced glycation end products. J. Korean Soc. Appl. Biol. Chem. 52, 655–662 (2009). https://doi.org/10.3839/jksabc.2009.109

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  • DOI: https://doi.org/10.3839/jksabc.2009.109

Key words

  • advanced glycation end products
  • Artemisia princes
  • caffeoylquinic acids
  • rat lens aldose reductase