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Seo, Jung, and Shim: Aldose Reductase Inhibitory Alkaloids from Corydalis ternata
Original Article

Natural Product Sciences 2016;22(2):102-106.

Published online: 17 December 2016

DOI: https://doi.org/10.20307/nps.2016.22.2.102

Aldose Reductase Inhibitory Alkaloids from Corydalis ternata

Wonse Seo1, Sang Hoon Jung2, Sang Hee Shim3, ∗

1School of Biotechnology, Yeungnam University, Gyeongsan 38541, Korea

2Natural Products Research Center, Korea Institute of Science and Technology (KIST) Gangreung Institute, Gangreung 25451, Korea

3College of Pharmacy, Duksung Women's University, Seoul 01369, Korea

∗Author for correspondence Sang Hee Shim, College of Pharmacy, Duksung Women's University, Seoul 01369, Korea Tel: +82-2-901-8774; E-mail: sangheeshim@duksung.ac.kr

Received 9 November 2015       Revised 17 December 2015       Accepted 24 December 2015

Copyright © 2016 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

A methanolic extract of Corydalis ternata having aldose reductase inhibitory activity was examined as a possible aldose reductase (ALR2) inhibitor, a key enzyme involved in diabetic complications. Seven alkaloids, tetrahydrocoptisine (1), corydaline (2), tetrahydropalmatine (3), isocorybulbine (4), corybulbine (5), dehydrocory-daline (6), and N-methyltetrahydroberbinium (7) were isolated from CHCl3 fraction of C. ternata methanol extract. Among them, compounds 1, 5, and 7 exhibited 5.04 ± 1.97%, 5.00 ± 1.26%, and 1.80 ± 2.33% inhibitions, respectively at 40 µ M. The activities of the single compounds were not comparable to that of the whole extract, suggesting that the whole combination of each single compound was responsible for the activity of the extract as shown in many cases of natural medicines. Even though this is the second report on aldose reductase inhibition activity of C. ternata, recombinant human aldose reductase was employed in this study unlike in the previous report. Furthermore, the aldose reductase inhibitory activities of isocorybulbine, corybulbine, and N-methy-ltetrahydroberbinium, to the best of our knowledge, were evaluated for the first time in this study. These results suggest a use of the extract of C. ternata for ameliorating diabetic complications.

Keywords: Corydalis ternata, Aldose reductase inhibition activity, Isoquinoline alkaloids

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Fig. 1.
Chemical structures of the compounds isolated from C. ternata.
nps-22-102f1.tif
Table 1.
Effects of methanolic extracts and fractions of Corydalis tuber on rhALR2
Ex./Frs. Conc. (µ g/ml) Inhibition1 (%)
MeOH ex. 100 75.4 ± 5.2
50 32.5 ± 2.1
25 11.4 ± 1.3
CHCl3 fr. 100 63.4 ± 4.2
50 25.8 ± 3.4
25 58.7 ± 1.1
EtOAc fr. 100 57.5 ± 1.6
50 −2
25 −2
Water fr. 100 −2

1 Inhibitory rate was calculated as a percentage relative to the control value and expressed as the mean ± standard deviation of triplicate experiments.

2 Inhibition (%) was less than 1%.

Table 2.
Inhibitory effect of compounds isolated from C. ternata on rhALR2 activity
Compounds Conc. (µ M) Inhibition2 (%) IC503 (µ M)
TMG1 40 72.62 ± 0.10  
20 62.56 ± 1.28  
10 51.38 ± 1.43 10.06
55 36.74 ± 2.20  
1 40 55.04 ± 1.97 >40
2 40 −4 >40
3 40 −4 >40
4 40 −4 >40
5 40 55.00 ± 1.26 >40
6 40 −4 >40
7 40 51.80 ± 2.33 >40

1 Tetramethylene glutaric acid (TMG) was used as a positive control.

2 Inhibitory rate was calculated as a percentage relative to the control value and expressed as the mean ± standard deviation of triplicate experiments.

3 The concentration of each test sample resulting in 50% inhibition of activity (IC50) was estimated from the least-squares regression line of the logarithmic concentration plotted against inhibitory activity.

4 Inhibition (%) was less than 1%.

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