4,5‐Di‐O‐Caffeoylquinic Acid from <i>Ligularia fischeri</i> Suppresses Inflammatory Responses Through TRPV1 Activation

Kim, Yiseul; Kim, Jung Tae; Park, Joonwoo; Son, Hee Jin; Kim, Eun Young; Lee, Young Joo; Rhyu, Mee-Ra

doi:10.1002/ptr.5885

Cited by 20 publications

(6 citation statements)

References 21 publications

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“…Results indicated that the methanol extract of in vitro cultured roots was the richest in 3,5-O-DCQA content, whose concentration was 6 times higher than that in the extract obtained from roots of wild-growing tansy. This is a noticeable result in the manner of industrial production of biologically active 3,5-O-DCQA, which has been shown to have antioxidant, hepatoprotective, antimutagenic, and immunomodulatory activity (Peluso et al 1995;Tatefuji et al 1996;Basnet et al 1996;Yoshimoto et al 2002;Juan-Badaturuge et al 2009;Kim et al 2012Kim et al , 2017. It has also been reported that 3,5-O-DCQA improves pancreatic function in type 2 diabetic mice (Yin et al 2018) and is a potent inhibitor of HIV-1 integrase, an enzyme that is essential for viral replication and subsequent HIV infection of humans (Tamura et al 2006).…”

Section: Discussionmentioning

confidence: 99%

In vitro cultivation of tansy (Tanacetum vulgare L.): a tool for the production of potent pharmaceutical agents

et al. 2020

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In this study, tansy (Tanacetum vulgare L.) in vitro culture was established from seeds collected from natural populations. The multiplication of plantlets was conducted through shoot tips that exhibited potent apical growth and regeneration capacities on basal medium (BM), without the addition of any plant growth regulators (PGRs). PGRs were also omitted for the establishment and cultivation of tansy root cultures. Both abaxial and adaxial leaf surfaces of in vitro micropropagated plantlets were covered with glandular biseriate trichomes. Histochemical staining showed that glandular secretions were rich in lipid and terpene compounds, confirmed by GC-MS analysis of essential oil (EO). In the total EO, similar portions of oxygenated monoterpenes (38.5% m/m) and oxygenated sesquiterpenes (22.6% m/m) were detected. Chemical profiles of methanol extracts of in vitro cultured tansy shoots and roots varied in quantity and quality from those obtained from wild-growingtansy. HPLC analysis indicated that the methanol extracts of in vitro cultured roots were the richest in 3,5-O-dicaffeoylquinic acid (3,5-O-DCQA), in which the concentration was 6 times higher (10.220 mg/g DW) than that in the extract obtained from roots of wild-growing tansy (1.684 mg/g DW). This result is noticeable in the manner of industrial production of biologically active 3,5-O-DCQA that has been shown to have antioxidant, hepatoprotective, antiviral, antimutagenic, and immunomodulatory activity. Biotechnological interventions on secondary metabolite production taking place in trichomes could further enhance the production of some important tansy metabolites and further investigation will be directed toward the elucidation of the pharmaceutical potential of tansy in vitro obtained metabolites, as mixtures or single moieties.

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Section: Discussionmentioning

confidence: 99%

In vitro cultivation of tansy (Tanacetum vulgare L.): a tool for the production of potent pharmaceutical agents

et al. 2020

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“…132 Another promising target for the treatment of inflammation is transient receptor potential vanilloid 1 (TRPV1). Kim et al 133 demonstrated that 4,5-DCQA (75) from Ligularia fischeri (Ledeb.) Turcz.…”

Section: Biological Activities Of Natural Cqasmentioning

confidence: 99%

“…esterification of quinide(133) with acid chloride(120) provided a mixture of compounds 134 and 135 (58 and 42%, respectively). The former (134) using H 2 O as a deprotecting agent under reflux led to compound 69 in 27% yield (Scheme 7).…”

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confidence: 99%

Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Liu

Zhang

et al. 2020

J. Agric. Food Chem.

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Caffeoylquinic acids (CQAs) are a broad class of secondary metabolites that have been found in edible and medicinal plants from various families. It has been 100 years since the discovery of chlorogenic acid in 1920. In recent years, a number of naturally derived CQAs have been isolated and structurally elucidated. Accumulated evidence demonstrate that CQAs have a wide range of biological activities, such as antioxidation, antibacterial, antiparasitic, neuroprotective, anti-inflammatory, anticancer, antiviral, and antidiabetic effects. Up to date, some meaningful progresses on the biosynthesis and total synthesis of CQAs have also been made. Therefore, it is necessary to comprehensively summarize the structure, biological activity, biosynthesis, and chemical synthesis of CQAs. This review provides extensive coverage of naturally occurring CQAs discovered from 1990 until 2020. Modern isolation techniques, chemical data (including structure, biosynthesis, and total synthesis), and bioactivity are summarized. This would be helpful for further research of CQAs as potential pharmaceutical agents.

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“…LFT is mainly used to treat coughs, ulcers, and tuberculosis as a clinical therapeutic agent [2]. The chemical constituents and pharmacological effects of LFT have been studied previously [3][4][5][6][7]. The plant roots are rich in aroma and volatile oils.…”

Section: Introductionmentioning

confidence: 99%

Molecular mechanism underlying the anti-inflammatory effects of volatile components of Ligularia fischeri (Ledeb) Turcz based on network pharmacology

Huang

Gao

Feng

et al. 2020

BMC Complement Med Ther

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Background: Ligularia fischeri (Ledeb) Turcz (LFT) is a well-known expectorant and active anti-inflammatory agent in Chinese traditional medicine. LFT's expectorant effect is closely related to its anti-inflammatory effects. This study aimed to evaluate the differential composition and anti-inflammatory mechanisms of the volatile components in LFT from different production areas. Method: Headspace solid-phase microextraction-gas chromatography-mass spectrometry analysis of volatile components, as well as chemometric methods, including similarity analysis, hierarchical clustering analysis, and principal component analysis, were performed to identify LFT produced in different areas. The molecular mechanism underlying the anti-inflammatory effects of these components was determined by network pharmacology analysis. Results: We observed significant differences in the chemical constituents and percentage contents in samples with different origins. Eighteen volatile components were identified in four different producing areas, among which the highest content of olefinic components was the main component of the aroma of LFT. The mechanisms of these pharmacological effects involved multiple targets and pathways. Twenty-seven potential target proteins and 65 signaling pathways were screened, and a "component-target-disease" interaction network map was constructed. The volatile components of the LFT function mainly by inhibiting the production of inflammatory factors. Conclusion: This study provides a theoretical framework for further development and application of LFT used in traditional Chinese medicine.

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4,5‐Di‐O‐Caffeoylquinic Acid from Ligularia fischeri Suppresses Inflammatory Responses Through TRPV1 Activation

Cited by 20 publications

References 21 publications

In vitro cultivation of tansy (Tanacetum vulgare L.): a tool for the production of potent pharmaceutical agents

In vitro cultivation of tansy (Tanacetum vulgare L.): a tool for the production of potent pharmaceutical agents

Current Advances in Naturally Occurring Caffeoylquinic Acids: Structure, Bioactivity, and Synthesis

Molecular mechanism underlying the anti-inflammatory effects of volatile components of Ligularia fischeri (Ledeb) Turcz based on network pharmacology

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