Objective To investigate the chemical constituents from the ethanol extract of the bark of Spondias pinnata and preliminarily evaluate their anti-inflammatory activity. Methods Various chromatographic techniques were employed to isolate and purify the constituents from the extract. Their structures were elucidated by spectroscopic methods including NMR spectroscopy, as well as GFN2NMR and computational chemistry approaches. The anti-inflammatory activity of the new compound was evaluated using an LPS/IFN-γ-induced MH-S cell inflammation model in vitro. Results Ten compounds were isolated from the ethanol extract of the bark of S. pinnata and identified as (5R,6S)-6-[(7E,9R)-9-hydroxy-10-({(15R,16R)-17-butoxycarbonyl-15,16-dihydroxypropoxy})but-7-en-7-yl]-6-hydroxy-1,1-dimethylcyclohexan-3-one (1), ampelopsisionoside (2), (2E,4E,1'R,3'S,5'R,8'S)-dihydrophaseic acid 3'-O-β-D-glucopyranoside (3), N-benzoyl-D-phenylalanine (2R)-2-(benzoylamino)-3-phenylpropyl ester (4), isolariciresinol-4-O-β-D-glucopyranoside (5), (+)-lyoniresin-4-yl-β-D-glucopyranoside (6), demethoxymatteucinol (7), 4'-hydroxy-3-O-β-D-glucopyranoside flavone (8), (2S)-2-hydroxynaringenin-4'-O-β-D-glucoside (9), and (S)-(-)-N-benzoylphenylalaninol (10). Compound 1 significantly inhibited the expression of TNF-α (P < 0.05) and IL-6 (P < 0.01) at a concentration of 10 μmol/L. Moreover, at 20 μmol/L, it markedly ameliorated the LPS/IFN-γ-induced morphological changes in MH-S cells. Conclusion Compound 1 is a new compound, named as spondias A. Compounds 2—4 and 7—10 were isolated from the genus Spondias for the first time, while compounds 5—6 were obtained from this species for the first time. The bioassay results indicate that compound 1 inhibits the transformation of MH-S cells to the M1 phenotype, suggesting its potential anti-inflammatory activity.

Spondias pinnata (L. f.) Kurz.  /  anti-inflammatory activity  /  spondias A  /  demethoxymatteucinol  /  4'-hydroxy-3-O-β-D-glucopyranoside flavone  /  (S)-(-)-N-benzoylphenylalaninol