樟子松针叶化学成分研究

Chemical constituents in Pinus sylvestris needles

关键词:  樟子松针叶, 化学成分, 抑菌活性, 松叶酸, 7-羟基脱氢枞酸, 杜松醇

Key words:  Pinus sylvestris needles, chemical constituents, antibacterial activity, pinifolic acid, 7-hydroxydehydroabietic acid, cadinol

摘要:

该研究以采自黑龙江省齐齐哈尔市的樟子松(Pinus sylvestris)针叶为对象,采用溶剂提取法对樟子松针叶中的化学成分进行提取,应用硅胶柱色谱、制备薄层色谱和高效液相色谱等现代色谱技术对提取浸膏中的化学成分进行分离和纯化,运用质谱,核磁(¹H-NMR和¹³C-NMR)等波谱技术,鉴定了化合物结构,并对提取浸膏的抑菌活性进行了测试。结果表明:从樟子松针叶提取物中分离得到15个化合物,分别鉴定为松叶酸(1)、松叶酸甲酯(2)、18α-acetoxylabd-8(17)-en-15-oic acid(3)、4-eplimbricataloic acid(4)、15-乙基-18-松叶酸甲酯(5)、15-acetoxy-labda-8(17),13E-dien-18-al(6)、7β-羟基脱氢枞酸(7)、7α-羟基脱氢枞酸(8)、endo-peroxide(9)、α-杜松醇(10)、β-谷甾醇(11)、邻苯二甲酸二丁酯(12)、7R,11R-phytol(13)、正二十四烷醇(14)、N-octacosan7β-ol(15)。其中,化合物9,13,14和15为首次从该属植物中分离得到。抑菌活性结果表明,正己烷萃取浸膏在浓度为5～100 mg·mL^-1时对大肠杆菌和枯草芽孢菌的抑菌率分别为53%～71%和56%～70%,在浓度为50 mg·mL^-1和100 mg·mL^-1时对金黄色葡萄球菌的抑菌率分别为51%和69%。该研究课题进一步明确了樟子松针叶中的化学成分,为其活性测试及应用研究提供依据。

Abstract:

The chemical constituents of Pinus sylvestris needles collected from Qiqihar City in Heilongjiang Province were studied. The chemical components in the needles were extracted by solvent method. The use of column chromatography, prepared TLC, and HPLC technique led to the separation and purification of the chemical constituents in the extract. The structures for the isolated pure compounds were elucidated by analysis of spectroscopic of MS and NMR(¹H-NMR and ¹³C-NMR). The antibacterial activity of the extract was also scanned. The results were as follows: 15 compounds were isolated and identified as pinifolic acid(1), monomethyl pinifolate(2), 18α-acetoxylabd-8(17)-en-15-oic acid(3), 4-eplimbricataloic acid(4), 15-ethyl-18-methyl pinifolate(5), 15-acetoxy-labda-8(17), 13E-dien-18-al(6), 7β-hydroxydehydroabietic acid(7), 7α-hydroxydehydroabietic acid(8), endo-peroxide(9), α-cadinol(10), β-sitosterol(11), dibutyl phthalate(12), 7R,11R-phytol(13), tetracosanol(14), and N-octacosan7β-ol(15). Compounds 9, 13, 14, and 15 were isolated from the genus Pinus for the first time. The result of antibacterial activity indicated that the inhibition rate of hexane extract to Escherichia coli and Bacillus subtilis was 53%-71% and 56%-70%, respectively, on the concentration range of 5-100 mg·mL^-1. And the inhibition rate to Staphylococcus aureus was 51% and 69% on the concentration of 50 mg·mL^-1 and 100 mg·mL^-1, respectively. This research reported the isolated chemical constituents from Pinus sylvestris needles which will provide theoretical basis for the further investigation of active components and application of drugs.