Diterpenes of Pinus pinaster aiton with anti-inflammatory, analgesic, and antibacterial activities.

The P. pinaster species, known as 'Pino nigral or rodeno', is used in the treatment of colds, asthma, flu, and tuberculosis. This study determined the anti-inflammatory, analgesic, and antibacterial activities of the P. pinaster resin, identifying the compounds with higher biological activity. A bio-guided isolation of the compounds of P. pinaster was carried out by selecting the most active extracts with anti-inflammatory and analgesic effects in the HBEC3-KT, MRC-5, and THP-1 cell lines. The antibacterial activity was determined against the S. aureus, S. pneumoniae, K. pneumoniae and P. aeruginosa strains. The following compounds were identified by NMR: dehydroabietic acid (1), ( + )-cis-abienol (2), pimaric acid (3), isopimaric acid (4), 7α-hydroxy-dehydroabietic acid (5), 7-oxo-dehydroabietic acid (6), 15-hydroxy-abietic acid (7), 7-oxo-15-hydroxy-dehydroabietic acid (8), 13-oxo-8 (14)-podocarpen-18-oic acid (9), and pinyunin A (10). Regarding their anti-inflammatory activity, all compounds inhibited NF-κB. Compound 9 was the most active (IC This study managed to identify, for the first time, six diterpenes from the resin of P. pinaster, with anti-inflammatory, analgesic, and antibacterial activity. Among the identified compounds, compound 9 was the most active, being considered a promising candidate as an antagonist of the tachykinin NK-1 receptor and as an analgesic agent against inflammation and neuropathic pain. It also had an antibacterial effect against Gram negative bacteria.

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Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper.