ABSTRACT
@#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.
ABSTRACT
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.