Phenolic Constituents and Their Anti-inflammatory Activity from Echinochloa utilis Grains

Duc Hung Nguyen; Bing Tian Zhao; Duc Dat Le; Ki Yun Kim; Young Ho Kim; Young Ho Yoon; Jee Youn Ko; Koan Sik Woo; Mi Hee Woo

doi:10.20307/nps.2016.22.2.140

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Nguyen, Zhao, Le, Kim, Kim, Yoon, Ko, Woo, and Woo: Phenolic Constituents and Their Anti-inflammatory Activity from Echinochloa utilis Grains

Original Article

Natural Product Sciences 2016;22(2):140-145.

Published online: 17 December 2016

DOI: https://doi.org/10.20307/nps.2016.22.2.140

Phenolic Constituents and Their Anti-inflammatory Activity from Echinochloa utilis Grains

Duc Hung Nguyen^1,⁴, Bing Tian Zhao¹, Duc Dat Le¹, Ki Yun Kim², Young Ho Kim², Young Ho Yoon³, Jee Youn Ko³, Koan Sik Woo³, Mi Hee Woo^∗,¹

¹College of Pharmacy, Catholic University of Daegu, Gyeongsan 38430, Republic of Korea

²Laboratory of Immunobiology, School of Life Science and Biotechnology, College of Natural Sciences, Kyungpook National University, Daegu 39061, Republic of Korea

³Functional Cereal Crop research Division, Department of Functional Crop, NICS, RDA, 50426, Republic of Korea

⁴Phu Tho College of Pharmacy, Viettri City, Phutho Province 290000, Vietnam

^∗Author for correspondence Mi Hee Woo, College of Pharmacy, Catholic University of Daegu, Gyeongsan 38430, Republic of Korea Tel: +82-53-850-3620; E-mail: woomh@cu.ac.kr

Received 8 December 2015 Revised 2 February 2016 Accepted 4 February 2016

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

Seven phenolic compounds including p-coumaric acid (1), 4-hydroxybenzoic acid (2), 4-hydroxy-benzaldehyde (3), vanillic acid (4), luteolin (5), acacetin (6), and tricin (7), were isolated from the methylene chloride and ethyl acetate fractions of Echinochloa utilis grains. Compounds (1–4, 6) were isolated for the first time from this plant. These compounds were tested for inhibitory activities against LPS-induced NO production in RAW 264.7 cells. Compounds 5 and 6 displayed significant inhibitory effects, with IC₅₀ values of 27.9 ± 2.6 and 14.0 ± 1.1 µM, respectively. The results suggested that E. utilis ethanolic extract may be used as a potential source of anti-inflammatory agents and functional foods for the treatment of allergic diseases.

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Keywords: Echinochloa utilis, Phenolic compounds, NO production

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Fig. 1.

Chemical structures of compounds 1–7 isolated from the grains of E. utilis.

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Fig. 2.

The effects of compounds 5 and 6 on LPS-induced rise of iNOS and COX-2 levels in RAW 264.7 cells. The RAW 264.7 cells were pretreated with LPS (0.1 µg/mL) for 30 min, followed by concentrations of 2.5, 5.0, and 10.0 µg/mL for 5 and 1.25, 2.5, and 5.0 µg/mL for 6 for 24 h. Whole-cell lysates were blotted with the indicated antibodies. β-Actin level was used as a loading control. The expressions of iNOS and COX-2 were assessed by Western blotting analysis using specific antibodies for individual proteins. The results are representatives of three independent experiments.

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Table 1.

Effects of IC₅₀ values of isolated compounds 1–7 from E. utilis on LPS-stimulated NO production and cell viability.

Compounds	NO production and cell viability^b
Compounds	IC₅₀ value (µM)	Survival rate (%)
1	> 100	> 99
2	> 100	> 99
3	> 100	> 99
4	> 100	100
5	27.9 ± 2.6	> 99
6	14.0 ± 1.1	100
7	> 100	> 99
Dexamethasone^a	0.4 ± 0.05	100

^a Dexamethasone was used as a positive control. Data are present as mean ± SD (n = 3). IC₅₀ values, concentrations inhibiting NO production by 50%.

^b Nitrite was measured using Griess reaction at 20 h after treatment of LPS (0.1 µg/mL) in the presence or absence of various concentrations (1.25–100 µg/mL) of each compounds. Survival rates were carried out at concentration of 100 µg/mL and deter-mine by the MTT colorimetric assay.

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