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@#Using syringaldehyde as raw material, the phosphine ylide intermediate was efficiently synthesized through acetylated hydroxyl protection, aldehyde group reduction, chlorination and reaction with triphenylphosphine. On this basis, moscatilin (MST) and its 12 analogs (MST-1-MST-12) were synthesized by wittig reaction, deacetylation and double bond reduction. All the structures were confirmed by 1H NMR, 13C NMR and ESI-MS. Bacterial lipopolysaccharide-induced mouse macrophage RAW264.7 inflammation model was used to conduct preliminary anti-inflammatory activity tests in vitro for the target compounds. Results showed that all compounds could inhibit the production of inflammatory factor NO, and that MST-5 exhibited the strongest anti-inflammatory activity (IC50= 0.428 μmol/L).Further exploration is expected for the study of the anti-inflammatory mechanism of MST-5.
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Objective: To investigate the chemical constituents of leaves of Dendrobiumofficinale. Methods: Compounds were isolated from the leaves of D.officinale by column chromatography over Sephadex LH-20, MCI GEL CHP-20P, and ODS as well as by preparative HPLC. Their structures were identified by the analysis of their physical and chemical properties and the spectra data of NMR and MS. Results: Twenty-four compounds were isolated from the leaves of the plant, namely 3,4-dihydroxy-5,4'-dimethoxy bibenzyl (1), moscatilin (2), 4,4'-dihydroxy-3,5-dimethoxybibenzyl (3), densiflorol A (4), (S)-3,4,α-trihydroxy-5,4'-dimethoxybibenzyl (5), gigantol (6), dendrocandin U (7), dendrocandin B (8), loliolide (9), (6R,9S)-dihydroxy-megastigma-4,7-dien-3-one-9-O-β-D-glucopyranoside (10), (6R,9S)-9-hydroxy-megastigma-4,7-dien-3-one-9-O-β-D-glucopyranoside (11), (+)-syringaresinol (12), rutin (13), 2-benzothiazolol (14), p-hydroxyacetophenone (15), p-hydroxyl-benzoic acid (16), protocatechuic acid (17), catechol (18), ethyl p-hydroxyhydrocinnamate (19), 1-glycerol linolenate (20), 2-butoxyethyl linolenate (21), palmitic acid (22), octadecadienoic acid-2,3-dihydroxypropyl ester (23), and urticifolene (24). Conclusion: Itis the first report of the occurrence of compounds 10, 11, 14-23 in Orchidaceae family. Compounds 1, 2, 4, and 6are found in D. officinale for the first time.
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Three bibenzyls 1-3 and six other compounds 4-9 were firstly isolated from Dendrobium huoshanense stems. They were identified as 3',4-dihydroxy-3,5'-dimethoxybibenzyl(1), batatasin Ⅲ(2), 3,4'-dihydroxy-5-methoxy bibenzyl(3), dihydroconiferyl dihydro-p-coumarate(4), syringaresinol(5), 3-(4-hydroxyphenyl)-propionic acid ethyl ester(6),(3-ethylphenyl)-1,2-ethanediol(7),(S)-5-hydroxy-3,4-dimethyl-5-pentylfuran-2(5H)-one(8) and loliolide(9). Anti-inflammation assay showed that bibenzyls 1-3 could significantly inhibit the production of nitric oxide(NO) and the expression of tumor necrosis factor α(TNF-α) and interleukin 1β(IL-1β) mRNA in LPS-induced RAW264.7 macrophages. Mechanism study exhibited that the phosphorylation of nuclear factor kappa B(NF-κB) p65, inhibitor of κB(IκB), extracellular regulatedprotein kinase(ERK), c-Jun N-terminalkinase(JNK), p38 and Akt of LPS-induced RAW264.7 macrophages could be remarkably reduced by 1. These results suggested that the inflammatory response of LPS-induced RAW264.7 macrophages could be significantly inhibited by 1-3. Additionally, the anti-inflammatory effect of 1 might be contributed to its ability on the regulation of NF-κB, MAPKs and Akt signaling pathways.
Subject(s)
Humans , Anti-Inflammatory Agents , Therapeutic Uses , Dendrobium , Inflammation , Drug Therapy , Lipopolysaccharides , Macrophages , NF-kappa B , Nitric Oxide , Nitric Oxide Synthase Type IIABSTRACT
OBJECTIVE: To provide scientific basis for variety evaluation and selection of Dendrobium officinale. METHODS: The agronomic traits of D. officinale were measured. The chemical compositions of D. officinale stem were analyzed. The dynamic changes of plant biomass and chemical composition content during mycorrhizal cultivation with M2 (Mycena sp.)were observed. RESULTS: There were significant differences between D. officinale phenotype A and B in stem length, internode length, leaf width and leaf shape index (P<0.05), and in the content of polysaccharide and ethanol soluble extract (P<0.05). Moreover, the contents of 4, 4'-dihydroxy-3, 5-dimethoxybibenzyl and 3, 4'-dihydroxy-5-methoxybibenzyl were always very different between phenotype A and B during plant growth. After 12 months of growth, the stem dry weight and plant dry weight of M-A group were significantly higher than those of CK-A group(P<0.01), increasing by 37.6% and 37.3%, respectively. The contents of polysaccharide and six marker compounds of M-A group were increased by 36.8% and 5%-50% than those in CK-A group, respectively. After 12 months of growth, the contents of polysaccharide and six marker compounds of M-B group were increased by 16.7% and 25%-170% than those in CK-B group, respectively. CONCLUSION: The bibenzyl content and the response ability to mycorrhizal fungi M2 of D. officinale phenotype A and B are different.
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In this study, seven bibenzyl compounds were isolated from the stem of Dendrobium nobile by silica gel, MCI column chromatographic and preparative HPLC technology. By using spectroscopic techniques including NMR and MS, these compounds were identified as 4, α-dihydroxy-3, 5, 3'-trimethoxybibenzyl (1), 4, 5-dihydroxy-3, 3', α-trimethoxybibenzyl (2), 4, 4'-dihydroxy-3, 5, 3'-trimethoxybibenzyl (3), 4, 5-dihydroxy-3, 3'-dimethoxybibenzyl (4), 4, 3'-dihydroxy-3, 5-dimethoxybibenzyl (5), 5, 4'-dihydroxy-3, 3'-dimethoxybibenzyl (6) and 5, 3'-dihydroxy-3-methoxybibenzyl (7). Compound 1 is a new compound and compound 4 was isolated from this plant for the first time.
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Objective:To study the polar chemical constituents of Blettila striata(Thunb.) Reichb.f. Methods:The constituents in N-butanol moiety were separated and purified by column chromatography with silica gel and SephadexLH-20, and were identified by spectral analysis. Results:Five compounds were identified as: militarine(1);7-hydroxy-4-methoxy-phenanthrene-2-O-?-D-glucoside(2);4-methoxyphenanthrene-2,7-O-?-D-diglucoside(3);7-hydroxy-2,4-dimethoxyphenanthrene-3-O-glucoside(4);3′-hydroxy-5-methoxybibenzyl-3-O-?-glucopyranoside(5). Conclusion:Compound 1,5 were isolated from this plant for the first time.
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Objective To study the chemical constituents of the whole plant of Pholidota yunnanensis and to examine the inhibitory effects of the isolated compounds on nitric oxide(NO) production in activated rat macrophage-like cell line(RAW 264.7).Methods Various chromatographic techniques were used to separate and purify the constituents,and their structures were elucidated on the basis of spectroscopic analysis. The inhibitory effects of these compounds on NO production in RAW 264.7 cells of rats activated by lipopolysaccharide(LPS) and interferon-?(IFN-?) were tested in vitro by microplate ultraviolet-colorimetric method.Results Seven compounds were isolated and identified as trans-3,3′,5-trihydroxy-2′-methoxystilbene(Ⅰ),cis-3,3′-dihydroxy-5-methoxystilbene(Ⅱ),trans-3,3′, 5-trihydroxystilbene(Ⅲ),3,3′-dihydroxy-5-methoxybibenzyl(batatasin-Ⅲ,Ⅳ),3,4′-dihydroxy-3′,5-dimethoxybibenzyl(gigantol,Ⅴ),3,3′,5-trihydroxybibenzyl(Ⅵ),2,7-dihydroxy-4-methoxy-9,10-dihydrophenanthrene(coelonin,Ⅶ).Conclusion Compounds Ⅱ,Ⅳ,and Ⅵ show favorable inhibitory effects on NO production,compounds Ⅰ and Ⅱ are new compounds,and compounds Ⅲ-Ⅶ are isolated from this genus for the first time.
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Objective: To study the chemical constituents of Bletilla striata (Thunb. ) Reichb. f. Methods: The con-stituents were separated and purified by column chromatography with silica gel and Sephadex LH-20,and were identified byspectral analysis. Results: Five compounds were identified as: 2, 7-dihydroxy-4-methoxy-9, 10-dihydrophenanthrene (1), 2, 7-dihydroxy-3, 4-dimethoxyphenanthrene (2), 3, 7-dihydroxy-2, 4-dimethoxyphenanthrene (3 ), 3', 3--dihydroxy--5-methoxybiben-zyl(4), p-hydroxybenzaldehyde (5), Conclusion: Compound 2, 3, 4 are isolated from this plant for the first time.