Plant Physiology Area, Department of Engineering and Agricultural Sciences, Faculty of Biological and Environmental Sciences, Universidad de León, Campus Vegazana, 24007, León, Spain.
Department of Organic Chemistry, Faculty of Sciences, University Autónoma of Madrid, Cantoblanco, 28049, Madrid, Spain; Organic Chemistry Unit, Department of Chemistry in Pharmaceutical Sciences, Faculty of Pharmacy, Universidad Complutense de Madrid. Plza, Ramón y Cajal S/n, 28040, Madrid, Spain.
J Ethnopharmacol. 2024 Jan 10;318(Pt B):117021. doi: 10.1016/j.jep.2023.117021. Epub 2023 Aug 9.
ETHNO-PHARMACOLOGICAL RELEVANCE: 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 = 3.90-12.06 μM). Concerning the analgesic activity, all the compounds inhibited NK-1, yet compound 9 was the most active (IC = 0.28-0.33 μM). Finally, compounds 6 (MIC = 12.80-25.55 μM) and 9 (MIC = 9.80-24.31 μM) were the most promising antibacterial compounds in all strains.
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.
石栗（Pinus pinaster），又名“黑松或罗登”，被用于治疗感冒、哮喘、流感和肺结核。
本研究旨在确定石栗树脂的抗炎、镇痛和抗菌活性，鉴定出具有更高生物活性的化合物。
通过选择对 HBEC3-KT、MRC-5 和 THP-1 细胞系具有抗炎和镇痛作用的最活跃提取物，对石栗化合物进行生物导向分离。针对金黄色葡萄球菌、肺炎链球菌、肺炎克雷伯菌和铜绿假单胞菌菌株，测定了其抗菌活性。
通过 NMR 鉴定出以下化合物：去氢枞酸（1）、（+）-顺-贝壳杉烯醇（2）、枞酸（3）、异枞酸（4）、7α-羟基去氢枞酸（5）、7-氧代去氢枞酸（6）、15-羟基枞酸（7）、7-氧代-15-羟基去氢枞酸（8）、13-氧代-8（14）-贝壳松烷-18-酸（9）和皮云林 A（10）。关于其抗炎活性，所有化合物均抑制 NF-κB。化合物 9 最为活跃（IC=3.90-12.06 μM）。关于镇痛活性，所有化合物均抑制 NK-1，而化合物 9 最为活跃（IC=0.28-0.33 μM）。最后，化合物 6（MIC=12.80-25.55 μM）和 9（MIC=9.80-24.31 μM）在所有菌株中是最有前景的抗菌化合物。
本研究首次从石栗树脂中鉴定出六种二萜类化合物，具有抗炎、镇痛和抗菌活性。在所鉴定的化合物中，化合物 9 最为活跃，被认为是一种有前途的候选物，可作为速激肽 NK-1 受体拮抗剂和针对炎症和神经病理性疼痛的镇痛剂。它还对革兰氏阴性菌具有抗菌作用。
