Antioxidant and anti-inflammatory activities of 3,5-dicaffeoylquinic acid isolated from Ligularia fischeri leavesby Sunghyun Hong, Taewoo Joo, Jin-Woo Jhoo

Food Sci Biotechnol

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Year
2015
DOI
10.1007/s10068-015-0034-y
Subject
Applied Microbiology and Biotechnology / Food Science / Biotechnology

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Food Sci. Biotechnol. 24(1): 257-263 (2015)

DOI 10.1007/s10068-015-0034-y

Antioxidant and Anti-inflammatory Activities of 3,5-Dicaffeoylquinic

Acid Isolated from Ligularia fischeri Leaves

Sunghyun Hong, Taewoo Joo, and Jin-Woo Jhoo

Received March 17, 2014; revised July 1, 2014; accepted August 21, 2014; published online February 28, 2015 © KoSFoST and Springer 2015

Abstract A potent anti-inflammatory compound was isolated and identified from leaves of Ligularia fischeri.

The ethyl acetate fraction was used for purification of the compound and yielded 3,5-dicaffeoylquinic acid (DCQA).

The identity of the compound was confirmed using 1H, 13C

NMR, and MS analysis. DCQA showed strong DPPH (IC50=4.26 µg/mL), ABTS (TEAC value=0.9974) radical scavenging, and FRAP activities (=3.84 mmole of Trolox equivalent/g). DCQA effectively inhibited production of

NO in RAW 264.7 cells induced using lipopolysaccharide (LPS) in a concentration dependent manner (50-250 µg/ mL). DCQA significantly suppressed (p<0.05) up-regulation of inducible NO synthase (iNOS), cyclooxygenase-2 (COX2), and tumor necrosis factor-α (TNF-α) gene expressions.

The isolated DCQA can be useful for development of effective anti-inflammatory agents.

Keywords: anti-inflammatory, antioxidant, 3,5-dicaffeoylquinic acid, Ligularia fischeri, nitric oxide

Introduction

Inflammation is a complex biological response initiated by different factors that results in cell damage or death and contributes to the cause of many chronic diseases, including diabetes, Alzheimer’s disease, asthma, and atherosclerosis (1). A variety of biological molecules, such as reactive oxygen species (ROS), nitric oxide (NO), prostaglandin E2 (PGE2), tumor necrosis factor alpha (TNF-α), and interleukins (ILs) are involved in development of inflammation (2).

Macrophages are major inflammatory and immune cells that play a vital role by providing an immediate defense against invading agents, including bacteria, viruses, and fungi, and a response to pathogen attack by release of different inflammatory mediators, including ROS and NO (3). NO is a short-lived free radical that is essential for the host defense response against pathogens. Under normal physiological conditions, NO is intimately involved in regulation of different biological activities involving neuronal communication, vasodilatation, and neurotoxicity (4). However, excessive production of NO by the macrophage defensive system can cause oxidative damage to a host associated with development of inflammatory diseases, such as rheumatoid arthritis and autoimmune disorders. In this regard, there has been much effort to develop antiinflammatory drugs, and demands remain for development of novel inhibitory agents against NO production related to treatments for chronic inflammatory diseases.

A number of studies have reported that over-production of NO can stimulate a variety of proteins and enzymes crucial to inflammatory reactions, including nuclear transcription factor-kappa B (NF-κB) and mitogen-activated protein kinase (MAPKs) pathways. Previous reports have stated that MAPKs mediate activation of transcriptional factor

NF-κB (5) and, consequently, regulate cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) expressions (6). In addition, iNOS and COX-2 are important enzymes that regulate inflammatory processes. Hence, these inflammatory mediators may be valuable targets for inflammatory disease treatments.

Previously, many studies have reported mechanisms behind the actions of natural antioxidants for inhibition of

NO production. Therefore, considerable attention has been focused on use of natural antioxidants, especially from plant sources, to inhibit NO production. The genus Ligularia (Asteraceae) comprises approximately 130 species, most

Sunghyun Hong, Taewoo Joo, Jin-Woo Jhoo ()

Department of Animal Products and Food Science, Kangwon National

University, Chuncheon, Gangwon 200-701, Korea

Tel: +82-33-250-8649; Fax +82-33-251-7719

E-mail: jjhoo@kangwon.ac.kr

RESEARCH ARTICLE 258 Hong et al. growing in Asia. The different species of Ligularia are known to produce a variety of bioactive components.

Ligularia fischeri Turcz. var. spiciformis is predominantly distributed in damp shady regions besides brooks and sloping fields in the southeast areas of China, Korea, and

Japan. The leaves of L. fischeri Turcz. are consumed as an important vegetable in Korea and the Yanbian region of

China (7). In Korean traditional systems of medicine, leaves of this plant have been used for treatment of jaundice, cough, inflammation, scarlet-fever, emptysis, diuresis, rheumatoidal arthritis, and hepatic diseases (8,9). Choi and

Kim (9) investigated the effects of L. fischeri leaf extracts against collagen-induced arthritis (CIA) in mice. Park et al. (10) reported isolation of a eudesmane-type sesquiterpene, (+)-intermedeol and 6-oxoeremophilenolide from leaves of

L. fischeri. Piao et al. (11) isolated potent antioxidant compounds, such as flavonoids, hyperoside, and 200acetylhyperoside from methanol extracts of this plant.

Intermedeol isolated from leaves of L. fischeri was reported to induce differentiation of leukemia HL-60 cells (12).

Based on the highly acclaimed properties of L. fischeri, this study aimed to isolate the effective anti-inflammatory compound from L. fischeri leaves. The antioxidant compound was identified in vitro and inhibition of NO production and gene expressions of iNOS, COX-2, and TNF-α by the isolated compound were determined in LPS-stimulated

RAW 264.7 cells

Materials and Methods

Chemicals and plant materials All solvents were of

HPLC grade from Fisher Scientific Korea Ltd. (Seoul,

Korea). DPPH, ABTS, Trolox, TPTZ, penicillin-streptomycin solution, lipopolysaccharide (LPS), and 3,5-dicaffeoylquinic acid standards were purchased from Sigma-Aldrich (St.

Louis, MO, USA). Dulbecco’s modified Eagle’s medium (DMEM), fetal bovine serum (FBS), and phosphate buffered saline (PBS) were obtained from HyClone Laboratories,