New coumarins from the roots of Angelica dahurica var. formosana cv. Chuanbaizhi and their inhibition on NO production in LPS-activated RAW264.7 cells

Deng, Gai-Gai; Wei, Wei; Yang, Xiu‐Wei; Zhang, You-Bo; Xu, Wei; Gong, Ningbo; Liu, Yang; Wang, Feng-Feng

doi:10.1016/j.fitote.2015.01.016

Cited by 36 publications

(18 citation statements)

References 32 publications

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“…Although isopentane-derived groups are likely to reduce the inhibition of histamine release, the 2,3-dihydroxyisopentane group has little effects on this. Similarly, the 6,7-furanocoumarin scaffold is necessary and the methoxyl group at the C-5 position largely contributes to reduce the secretion of TNF-α, IL-1β and IL-4, which is in accordance with the previous results on anti-inflammatory coumarins in A. dahurica (18,33,34). The isopentenyl group also shows a positive effect on the secretion of cytokines, which makes compounds 1 and 2 display potent activity.…”

Section: Discussionsupporting

confidence: 89%

“…Furthermore, pharmacological studies have shown that it has antimicrobial (11), hepatoprotective (12), antioxidative (13) and cholinesterase inhibitory activities (14), and activates dendritic cells (15) and the actions of lipolytic hormones (16). Furthermore, it inhibits the production of prostaglandin E 2 (17) and nitric oxide (NO) (18,19), and reduces the release of histamine (20). In addition, the ethanolic extract of A. dahurica displayed anti-inflammatory effects by the upregulation of heme oxygenase-1, particularly in mice with asthma (21,22).…”

Section: Introductionmentioning

confidence: 99%

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Coumarins from the roots of Angelica dahurica cause anti-allergic inflammation

Liu

2017

Experimental and Therapeutic Medicine

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Abstract. Allergic inflammation is induced by allergens and leads to various allergic diseases, including rhinitis, asthma and conjunctivitis. Histamine is important in the pathogenesis of an immunoglobulin E-dependent allergic reaction and results in the secretion of cytokines associated with inflammation. Angelica dahurica (A. dahurica) is a medicinal plant widely used in China for the treatment of symptoms related to allergic inflammation. The present study investigated the chemical constituents from A. dahurica and evaluated their reductive effect on allergic inflammation. As a result, 15 compounds including 13 coumarins have been identified as isoimperatorin (1), imperatorin (2), oxypeucedanin (3), oxypeucedanin hydrate (4), bergapten (5), byakangelicin (6), phellopterin (7), byakangelicol (8), isopimpinellin (9), xanthotoxol (10), xanthotoxin (11), pimpinellin (12), scopoletin (13), β-sitosterol (14) and daucosterol (15). Compounds 1-13 were able to reduce the release of histamine, with compounds 4-6 exhibiting the most potent activity. Furthermore, compounds 1-12 were able to inhibit the secretion of tumor necrosis factor-α, interleukin (IL)-1β and IL-4, with compounds 5 and 7 exhibiting the strongest inhibitory effects. These compounds implemented the inhibitory effects on the expression of inflammatory cytokine genes through the inhibition of nuclear factor-κB activation. Virtual screening by a docking program indicated that compound 3 is a potent histamine H 1 receptor antagonist. Additionally, the calculated physicochemical properties of these compounds support most furanocoumarins to be delivered to binding sites and permeate the cell membrane. The present findings contribute to understanding how A. dahurica attenuates allergic inflammation.

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Section: Discussionsupporting

confidence: 89%

Section: Introductionmentioning

confidence: 99%

Coumarins from the roots of Angelica dahurica cause anti-allergic inflammation

Liu

2017

Experimental and Therapeutic Medicine

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“…As part of our project to find natural structures with inhibitory activity on overproduction of NO, all of the isolated compounds were evaluated against NO release in LPS-activated RAW264.7 macrophage cell model [ 12 , 14 ]. The compounds 1 – 9 were initially assayed for cytotoxic effects in RAW264.7 cells by the 3-(4,5-dimethyl-2-thiazolyl)-2,5-diphenyl-2 H -tetrazolium bromide (MTT) assay.…”

Section: Resultsmentioning

confidence: 99%

“…A low concentration of NO participates in neurotransmission and vasodilation, whereas overproduction of NO by NOS was responsible for inflammation [ 11 ]; therefore, NO inhibitor is believed to have therapeutic potential for the treatment of inflammation accompanying overproduction of NO. Our previous studies showed anti-inflammatory activities of some coumarins [ 12 , 13 ], sesquiterpenoids [ 14 ], polyacetylenes [ 15 ], and neolignans [ 16 , 17 ]. As part of an ongoing effort to search for natural anti-inflammatory agents, herein we describe the isolation and structural elucidation of one new and eight known phenolic acid esters from the dried roots and rhizomes of N. incisium , together with predicted absorbability, using a human intestinal Caco-2 cell monolayer model [ 18 ] and their inhibitory effects against NO production induced by lipopolysaccharide (LPS) in RAW 264.7 macrophage cells.…”

Section: Introductionmentioning

confidence: 99%

Anti-Inflammatory Phenolic Acid Esters from the Roots and Rhizomes of Notopterygium incisium and Their Permeability in the Human Caco-2 Monolayer Cell Model

Wei

Yang

et al. 2017

Molecules

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A new ferulic acid ester named 4-methyl-3-trans-hexenylferulate (1), together with eight known phenolic acid esters (2–9), was isolated from the methanolic extract of the roots and rhizomes of Notopterygium incisium. Their structures were elucidated by extensive spectroscopic techniques, including 2D NMR spectroscopy and mass spectrometry. 4-Methoxyphenethyl ferulate (8) NMR data is reported here for the first time. The uptake and transepithelial transport of the isolated compounds 1–9 were investigated in the human intestinal Caco-2 cell monolayer model. Compounds 2 and 6 were assigned for the well-absorbed compounds, compound 8 was assigned for the moderately absorbed compound, and compounds 1, 3, 4, 5, 7, and 9 were assigned for the poorly absorbed compounds. Moreover, all of the isolated compounds were assayed for the inhibitory effects against nitric oxide (NO) production in the lipopolysaccharide-activated RAW264.7 macrophages model and L-N6-(1-iminoethyl)-lysine (L-NIL) was used as a positive control. Compounds 1, 5, 8, and 9 exhibited potent inhibitory activity on NO production with the half maximal inhibitory concentration (IC50) values of 1.01, 4.63, 2.47, and 2.73 μM, respectively, which were more effective than L-NIL with IC50 values of 9.37 μM. These findings not only enriched the types of anti-inflammatory compounds in N. incisum but also provided some useful information for predicting their oral bioavailability and their suitability as drug leads or promising anti-inflammatory agents.

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“…Steamed Rehmannia glutinosa , which is a modified form of Rehmannia root, has been used to treat inflammatory diseases [ 15 ]. Angelica dahurica has various types of total coumarins, which were reported to possess anti-inflammatory and anti-oxidant effects [ 16 ]. Ferulic acid is regarded as the main active constituent of Cimicifuga heracleifolia , which was found to inhibit the production of macrophage inflammatory protein-2 in Raw 264.7 cells [ 17 ].…”

Section: Introductionmentioning

confidence: 99%

Topical application of herbal formula for the treatment of ligature-induced periodontitis

Kim

Choi

Lee

et al. 2015

J Periodontal Implant Sci

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PurposeThe aim of this study was to investigate the therapeutic effects of a herbal formula, PerioH-035, containing Angelica sinensis, steamed Rehmannia glutinosa, Angelica dahurica, Cimicifuga heracleifolia, and Zanthoxylum piperitum on the periodontal breakdown in a well-established ligature-induced periodontitis model in rats.MethodsSprague-Dawley rats were randomly assigned to 1 of 4 groups: NL (non-ligatured), L (ligatured), P1 (ligatured and treated with 1 mg/mL PerioH-035), P100 (ligatured and treated with 100 mg/mL PerioH-035). Periodontitis was induced by placing a ligature around the mandibular first molars. PerioH-035 was topically applied to both sides of the first molar for 2 weeks. The right side of the mandibles was retrieved for micro-computed tomography (CT) and methylene blue staining to analyze alveolar bone loss. The left side of the mandibles was histologically analyzed by TRAP and H&E staining. The MMP-9 mRNA level in gingival tissue was investigated by RT-PCR.ResultsAlveolar bone resorption was significantly reduced in the PerioH-035-treated groups. The number of dense multi-nucleated cells found to be TRAP-positive by staining in the ligatured rats was markedly decreased by PerioH-035 application. In addition, periodontal tissue destruction, especially cementum demineralization, was ameliorated in the P1 and P100 groups. Moreover, gingival tissue from the PerioH-035-treated group showed a decrease in the MMP-9 mRNA level, resulting in recovery of collagen degradation.ConclusionsThese results suggest that PerioH-035 has therapeutic effects on periodontitis, and thus, PerioH-035 shows promise as a treatment for periodontitis.Graphical Abstract

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New coumarins from the roots of Angelica dahurica var. formosana cv. Chuanbaizhi and their inhibition on NO production in LPS-activated RAW264.7 cells

Cited by 36 publications

References 32 publications

Coumarins from the roots of Angelica dahurica cause anti-allergic inflammation

Coumarins from the roots of Angelica dahurica cause anti-allergic inflammation

Anti-Inflammatory Phenolic Acid Esters from the Roots and Rhizomes of Notopterygium incisium and Their Permeability in the Human Caco-2 Monolayer Cell Model

Topical application of herbal formula for the treatment of ligature-induced periodontitis

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