Elsevier

Food Chemistry

Volume 152, 1 June 2014, Pages 300-306
Food Chemistry

Phenolic compounds from Origanum vulgare and their antioxidant and antiviral activities

https://doi.org/10.1016/j.foodchem.2013.11.153Get rights and content

Highlights

Abstract

In the present study, six new phenolic compounds (16) along with five known ones were isolated from the ethanol extract of the whole plants of Origanum vulgare. The structures of the new compounds were identified on the basis of extensive spectroscopic analyses (UV, IR, NMR, and HRESIMS) and acid hydrolysis. Twenty-one phenolic compounds isolated from O. vulgare in our previous and present studies were evaluated for their in vitro antioxidant activity using 2,2-diphenyl-1-picryhydrazyl (DPPH) radical-scavenging and ferric-reducing antioxidant power (FRAP) assays; twelve of them including two new compounds exhibited significant antioxidant activity comparable to that of ascorbic acid. In addition, the antiviral effects against respiratory syncytial virus (RSV), Coxsackie virus B3 (CVB3) and herpes simplex virus type 1 (HSV-1) were tested by cytopathic effect (CPE) reduction assay.

Introduction

Origanum vulgare (Lamiaceae) is a perennial herb distributed in Europe, North Africa, America and Asia (Kintzios, 2002). The herb is widely used as a spice in Western diets, and is also commonly used as a traditional medicine for the treatment of various diseases, such as cold, cough, and digestive disorders (Yin, Fretté, Christensen, & Grevsen, 2012). The plant is known for its powerful antimicrobial and antioxidant activities (Lemhadri, Zeggwagh, Maghrani, Jouad, & Eddouks, 2004), which may explain its use in traditional medicine. The antimicrobial activity of O. vulgare is due to its high content of volatile oils (Esen et al., 2007, Faleiro et al., 2005, Karakaya et al., 2011). In addition, these volatile constituents significantly contribute to the aroma and flavour of the herb. The phenolic compounds including flavonoids and phenolic acids, another kind of abundant constituent in O. vulgare, are responsible for its antioxidant activity (Chou et al., 2010, Ding et al., 2010, Liang et al., 2012). Moreover, these phenolic antioxidants possess diverse biological activities, for instance, anti-ulcer, anti-inflammatory, antidiabetic, antiviral, cytotoxic and antitumour (Saxena, Saxena, & Pradhan, 2012), and they are believed to be responsible for the health effects of O. vulgare.

In this work, we report the isolation of six new phenolic compounds (16) (Fig. 1) from O. vulgare, along with five known ones: 2,5-dihydroxybenzoic acid (7) (Xie & Li, 2002), 3,4-dihydroxybenzoic acid (8) (Zhang, Fang, & Ye, 2008), rosmarinic acid (9) (Wu, Song, Zhao, & JIA, 2011a), origanoside (10) (Nakatani & Kikuzaki, 1987), and maltol 6′-O-(5-O-p-coumaroyl)-β-d-apiofuranosyl-β-d-glucopyranoside (11) (Li et al., 2008). The structures of the new compounds were identified with spectroscopic analyses and acid hydrolysis experiments. The phenolic compounds combining with the previously isolated ones E-caffeic acid (12), amburoside A (13), oresbiusin A (14), (+)-(R)-butyl rosmarinate (15), apigenin (16), apigenin 7-O-β-d-glucoside (17), luteolin (18), 6,7,4′-trihydroxyflavone (19), 5,7,3′,4′-tetrahydroxy-8-C-p-hydroxybenzylflavone (20) and didymin (21) (Guo et al., 2012) were subjected to in vitro antioxidant evaluation with 2,2-diphenyl-1-picryhydrazyl (DPPH) radical-scavenging and ferric-reducing antioxidant power (FRAP) assays. Furthermore, their antiviral activities against respiratory syncytial virus (RSV), Coxsackie virus B3 (CVB3) and herpes simplex virus type 1 (HSV-1) were determined by cytopathic effect (CPE) assay.

Section snippets

General experimental procedures

Melting points were obtained on an X-5 micro-melting point detector (Tech, Beijing, China). Optical rotation values were measured by a JASCO P-1020 polarimeter. UV spectra were recorded on a JASCO V-550 UV/VIS spectrophotometer (JASCO International Co., Ltd., Tokyo, Japan). IR spectra were measured on a JASCO FT/IR-480 plus FT-IR spectrometer. HR-ESI-MS data were determined by an Agilent 6210 ESI/TOF mass spectrometer (Agilent, Santa Clara, CA). NMR spectra were carried out on a Bruker AV-400

Identification of compounds 111

Compound 1 was isolated as amorphous powder. The molecular formula was established to be C20H22O10 by its HRESIMS m/z 445.1101 [M+Na]+ (calcd for C20H22O10Na, 445.1105). The IR spectrum indicated the presence of hydroxyl (3446 cm−1), carbonyl (1684 cm−1) and aromatic ring (1608, 1518 cm−1). The 1H NMR spectrum showed the presence of a 1,4-disubstituted benzene moiety [δH 7.05 (2H, d, J = 8.6 Hz) and 7.38 (2H, d, J = 8.4 Hz)], a 1,2,4-trisubstituted benzene moiety [δH 6.81 (1H, d, J = 8.3 Hz), 7.34 (1H, dd,

Conclusion

In summary, phytochemical analysis of the ethanol extract of O. vulgare resulted in the isolation and characterisation of six new and five known phenolic compounds. Their structures were elucidated by chemical and spectroscopic analyses, including 1D, 2D NMR and HRESI-MS. Biological studies disclosed that twelve phenolic compounds (1, 2, 79, 1215, 18, 19) from this plant exhibited potent antioxidant activity but only a few compounds showed weak antiviral activity. The result of our chemical

Acknowledgements

This work was supported financially by the Fundamental Research Funds for the Central Universities (21612417), the National Natural Science Foundation (Nos. 81273390, 81202429, 81072535) and Program of the Pearl River Young Talents of Science and Technology in Guangzhou, China.

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