ABSTRACT
The present study was conducted to investigate anti-nociceptive and anti-inflammatory effects of the leaves of Ilex latifolia Thunb (I. latifolia) in in vivo and in vitro. Writhing responses induced by acetic acid and formalin- and thermal stimuli (tail flick and hot plate tests)-induced pain responses for nociception were evaluated in mice. I. latifolia (50 – 200 mg/kg, p.o.) and ibuprofen (100 mg/kg, p.o.), a positive non-steroidal anti-inflammatory drug (NSAID), inhibited the acetic acid-induced writhing response and the second phase response (peripheral inflammatory response) in the formalin test, but did not protect against thermal nociception and the first phase response (central response) in the formalin test. These results show that I. latifolia has a significant anti-nociceptive effect that appears to be peripheral, but not central. Additionally, I. latifolia (50 and 100 µg/mL) and 3,5-di-caffeoyl quinic acid methyl ester (5 µM) isolated from I. latifolia as an active compound significantly inhibited LPS-induced NO production and mRNA expression of the pro-inflammatory mediators, iNOS and COX-2, and the pro-inflammatory cytokines, IL-6 and IL-1β, in RAW 264.7 macrophages. These results suggest that I. latifolia can produce antinociceptive effects peripherally, but not centrally, via anti-inflammatory activity and supports a possible use of I. latifolia to treat pain and inflammation.
Subject(s)
Animals , Mice , Acetic Acid , Cyclooxygenase 2 , Cytokines , Ibuprofen , Ilex , In Vitro Techniques , Inflammation , Interleukin-6 , Macrophages , Nitric Oxide , Nociception , Pain Measurement , Quinic Acid , RNA, MessengerABSTRACT
To explore the effect of total extract of Chrysanthemum morifolium on lipopolysaccharide (LPS)-induced acute lung injury in mice, we studied the effects of three caffeoyl quinic acids isolated from Chrysanthemum morifolium on vascular endothelial cell injury and their mechanisms of action. All animal experiments were carried out strictly in accordance with the National Animal Welfare Ethics and Protection Regulations. A mouse model of acute lung injury was established by intranasal instillation of LPS. After 6 days of oral administration of chrysanthemum extract, the lung wet weight/dry weight ratio, tumour necrosis factor-α (TNF-α), interleukin-6 (IL-6), and interleukin-1β (IL-1β) were measured in mouse bronchoalveolar lavage fluid. Human umbilical vein endothelial cells (HUVEC) were serum starved for 12 h and treated with 2.5 μg·mL-1 LPS for 24 h to establish the in vitro model of vascular endothelial cell injury. After 24 h of treatment of caffeoyl quinic acids from Chrysanthemum morifolium, the levels of TNF-α, IL-6, IL-1β, vascular cell adhesion molecule-1 (VCAM-1) and endothelin-1 (ET-1) were measured by ELISA in the cell culture supernatant, the malondialdehyde (MDA) level was detected by TBA method, the superoxide dismutase (SOD) level was determined by hydroxylamine method, and the nitric oxide (NO) level was assayed by a one-step method. The levels of p-MEK1/2, MEK1/2, p-ERK1/2, ERK1/2, p-JNK, JNK, p-P38 and P38 of mitogen-activated protein kinase (MAPK) signaling pathway were detected by Western blot. The total extract of Chrysanthemum morifolium can significantly reduce the wet weight/dry weight ratio of lung in mice and the levels of TNF-α, IL-6 and IL-1β in alveolar lavage fluid. The caffeoyl quinic acids from Chrysanthemum morifolium significantly increased the levels of SOD and NO, decreased the levels of TNF-α, IL-6, IL-1β, VCAM-1, ET-1 and MDA, and significantly reduced the levels of p-MEK1/2, p-ERK1/2. In conclusion, total extracts of Chrysanthemum morifolium exhibit certain protective effect on mice with acute lung injury, and three caffeoyl quinic acids from Chrysanthemum morifolium may improve LPS-induced vascular endothelial cell injury by inhibiting inflammatory cytokines and oxidative stress, and regulating inter-cellular adhesion molecule and vasomotor factors through ERK/MAPK signaling pathway.
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Objective To study the chemical constituents from stems of Acanthopanax henryi based on LPS-induced macrophages RAW264.7 and microglia BV2 as the bioactivity guided model. Methods The compounds were isolated and purified by silica gel and Sephadex LH-20 column chromatography, as well as Prep-TLC and recrystallization methods. Their structures were identified on the basis of their physicochemical properties and spectroscopic data. Results Eighteen compounds were obtained from A. henryi and their chemical structures were identified as p-hydroxybenzoic acid (1), trans-p-hydroxycinnamic acid (2), (E)-caffeic acid methyl ester (3), caffeic acid (4), trans-coniferyl aldehyde (5), syringaldehyde (6), vanillin (7), 6-methoxy-7-hydroxycoumarin (8), trans-sinapaldehyde (9), undecane-1,11-dioic acid monomethyl ester (10), (-)-sesamin (11), 3-O-caffeoyl-quinic acid (12), 5-O-caffeoyl-quinic acid (13), 1,3-di-O-caffeoyl-quinic acid (14), 1,4-di-O-caffeoyl-quinic acid (15), 1,5-di-O-caffeoyl-quinic acid (16), stigmasterol (17), and β-sitosterol (18), respectively. Conclusion To the best of our knowledge, compound 10 was isolated from Araliaceae for the first time. Except compounds 12, 14, 17, and 18, all of other compounds were obtained from this species for the first time.
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Objective: To study the antioxidant chemical constituents and antioxidant activity of Patrinia villosa. Methods: The 70% ethanol-water extract of the herb was separated by silica gel column chromatography, ODS column chromatography and sephadex column chromatography. Then, the compound were further purified and extracted by semi-preparative HPLC. Their structures were elucidated by physiochemical property and spectral analysis. DPPH and ABTS methods were used to determine the antioxidant bioactivities of the isolated compounds. Results: A total of ten compounds were isolated and synthesized, including chlorogenic acid butyl ester (1), 3,4-di-O-caffeoyl quinic acid methyl ester (2), luteolin-7-O-rutinoside (3), 1β-O-β-D-glucopyranosy- 15-O-(p-hydroxylphenylacetate)-5α,6βH-eudesma-3,11(13)-dien-12,6α-olide (4), 3,4-di-O-caffeoyl quinic acid ethyl ester (5), 4,5-di-O-caffeoyl quinic acid methyl ester (6), 4,5-di-O-caffeoyl quinic acid n-butyl ester (7), luteolin-7-O-β-D-glucuronide methyl ester (8), luteolin-7-O-β-D-glucuronide ethyl ester (9), and apigenin-7-O-β-D-glucuronide methyl ester (10). The DPPH radical scavenging IC50 of compounds 3, 8, and 9 were (23.95 ± 0.71), (73.09 ± 0.33), and (25.06 ± 0.65) μmol/L, respectively. The ABTS radical scavenging IC50 was (7.13 ± 0.07), (11.48 ± 0.21), (5.15 ± 0.08) mol/L, respectively. Conclusion: Eight compounds except compounds 3 and 8 are obtained from this species for the first time. Compounds 3, 8, and 9 had significant antioxidant activity.
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Objective: The chemical constituents in the methanol extract from Farfarae Flos were rapidly identified using UPLC-Q-TOF-MS in positive and negative ion modes. Methods: The analysis was performed on an Agilent Poroshell 120 EC-C18 chromatographic column (100 mm × 2.1 mm, 2.7 μm). The mobile phase consisted of acetonitrile and 0.1% aq formic acid. In positive ion mode, gradient elution: 0-1 min, 5%-17% B; 1-3 min, 17%-19% B; 3-14 min, 19%-44% B; 14-16 min, 44%-66% B; 16-26 min, 66%-87% B; 26-28 min, 87%-95% B; 28-33 min, 95% B. In negative ion mode, gradient elution: 0-2 min, 5%-14% B; 2-10 min, 14%-32% B; 10-15 min, 32% B. The flow rate was 0.4 mL/min, and the injection volume was 5 μL. The information of the compounds was analyzed by positive and negative ion modes mass spectrum information, elements composition, reference substance retention time or mass spectrum parameters of compounds in literature. Results: Thirty-four compounds in Farfarae Flos extracts were identified, combined with provided accurate molecular weight compounds by UPLC-Q-TOF-MS, including 12 kinds of terpenoids, eight kinds of flavonoids, seven kinds of phenolic acids, two kinds of pyran compounds, one kind of phenolic ketones, one kind of fat ketones, and three kinds of alkaloids. Conclusion: The method provides the theory basis for quality control and the clinical reasonable application and provides the reference for clarifying its efficacy material base.
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Objective: To investigate the chemical constituents in the stems of Ilex cornuta and the ability of scavenging free radicals of compounds 1-9. Methods: The compounds were isolated and purified by silica gel, medium pressure column chromatography, and semi-preparative liquid chromatography, and their structures were elucidated by chemical properties and spectroscopic analyses. The antifreeradical efficiency of compounds 1-9 was evaluated by DPPH radical scavenging assay. Results: Fifteen compounds were isolated and their structures were identified as isochlorogenic acid B (1), 3,4,5-tricaffeoylquinic acid (2), 4,5-di-O-caffeoyl quinic acid methyl ester (3), 3,4-di-O-caffeoyl quinicacid methyl ester (4), 3,5-di-O-caffeoyl quinicacid methyl ester (5), 3,4,5-tri-O-caffeoyl quinic acid methyl ester (6), 3,5-dimethoxy-4-hydroxybenzaldehyde (7), ethyl gallate (8), dihydrosyringenin (9), 2,6-dimethoxy-1,4-benzoquinone (10), arctigenin (11), 1-O-(vanillic acid)-6-O-(3″, 5″-dimethoxy-galloyl)-β-D-glycoside (12), (+)-1-hydroxypinoresinol-1-O-β-D-glucopyranoside (13), (+)-(7S,8S)-syringylglycerol 8-O-β-D-glucopyranoside (14), and schaftoside (15). Compounds 1-7 had good antifreeradical efficiency. Conclusion: Compounds 6,8-10,14, and 15 are obtained from the plants of Ilex L. the first time, and compounds 2,7,11, and 12 are obtained from this plant for the first time. Compounds 1-6 have good antifreeradical efficiency.
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Objective: To investigate the chemical constituents of Erycibe schmidtii. Methods: The compounds were separated and purified by silica gel and Sephadex LH-20 column chromatography, and semipreparative HPLC. Their structures were determined by nuclear magnetic resonance (NMR) spectroscopy analysis method. The anti-inflammatory activity of some compounds was tested by relative NO productivity. Results: Twelve compounds were isolated and identified as caffeic acid (1), N-trans-p-hydroxyphenethyl ferolamine (2), chlorogenic acid (3), chlorogenic acid methyl ester (4), 4-O-caffeoylquinic acid (5), 4-O-caffeoylquinic acid methyl ester (6), 4,5-di-O-caffeoylquinic acid (7), 4,5-di-O-caffeoylquinic acid methyl ester (8), 3,5-di-O-caffeoylquinic acid (9), 3,5-di-O-caffeoylquinic acid methyl ester (10), 3,4-di-O-caffeoylquinic acid (11), and 3,4-di-O-caffeoylquinic acid methyl ester (12). Compounds 1 and 2 showed some inhibitory activity for RAW cells 264.7 releasing NO. Conclusion: Compounds 5-7, 9, 11, and 12 are obtained from the plants of Erycibe Roxb. for the first time, while compounds 1, 2, and 4-12 are separated from this plant for the first time. Compounds 1 and 2 exhibit certain anti-inflammatory activity.
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Objective Based on the activities of antihistamine release to study the compounds from Bidens parvi-flora and find biological active compounds. Methods The chemical constituents from B.parviflora were isolated by silica gel and Sphadex LH-20 column chromatographies and purified by preparative HPLC. The chemical structures had been identified by physiochemical properties and spectroscopic methods. Results Six caffeoylquinic acid derivatives were identified as 3, 5-di-O-caffeoylquinic acid ( Ⅰ ),3, 4-di-O-caffeoylquinic acid ( Ⅱ ), 4, 5-di-O-caffeoylquinic acid ( Ⅲ ), 4-O-caffeoylquinic acid ( Ⅳ ), 5-O-caffeoylquinic acid ( Ⅴ ), 4-[3-(3, 4-dihydroxy-phenyl)-acryloyloxy]-2, 3-dihydroxy-2-methyl-butyric acid ( Ⅵ ). Conclusion Compounds Ⅰ - Ⅵ are first obtained from B. parviflora and Ⅵ is new one. Some of the compounds exhibit the activities in antiallergic assays. Moreover, the structure-activity relationships of these compounds have been also discussed in this paper.