[关键词]
[摘要]
目的 对猫须草Clerodendranthus spicatus全草的化学成分进行分离鉴定并测定其抗菌活性。方法 利用硅胶、Sephadex LH-20、MCI柱色谱以及制备型高效液相色谱等进行分离纯化,并运用核磁数据和文献比对等方法对化合物进行结构鉴定。采用梯度稀释法,对分离所得的化合物进行抗蜡样芽胞杆菌、金黄色葡萄球菌、耐甲氧西林金黄色葡萄球菌(MRSA)以及大肠杆菌的活性评价。结果 从猫须草醋酸乙酯萃取部位分离得到26个化合物,分别鉴定为1-[1-oxo-9(3,4-methylenedioxyphenyl)-2E,4E,8E-nonatrienyl]-pyrrolidine(1)、piperchabamide B(2)、piperolein B(3)、dehydropipernonaline(4)、胡椒碱(5)、guineensine(6)、piperflaviflorine A(7)、胡椒酸甲酯(8)、胡椒酸乙酯(9)、methyl(2E,4E)-7-(1,3-benzodioxol-5-yl)-2,4-heptadienoate(10)、(1S,2S)-1,2,3-trihydroxy-1-(3,4-methylenedioxyphenyl)propane(11)、反式对羟基肉桂酸乙酯(12)、咖啡酸乙烯酯(13)、邻苯二甲酸正丁异丁酯(14)、eupomatenoid-7(15)、licarin A(16)、(7R,8R)-7,8-dihydro-7-(3,4-dihydroxyphenyl)-3′-methoxy-8-methyl-1′-(E-propenyl) benzofuran(17)、denudatin A(18)、futokadsurin C(19)、3-(3,4-dihydroxyphenyl)-acrylic acid-1-(3,4-dihydroxyphenyl)-2-methoxycarbonylethyl ester(20)、sibiriaester A(21)、2-(3',4'-dihydroxyphenyl)-1,3-benzodioxole-5-aldehyde(22)、glechomol A(23)、4-hydroxy-2,3-dimethyl-2-nonen-4-olide(24)、(+)-芝麻素(25)、细辛脂素(26)。与阳性药万古霉素相比,化合物15~18对蜡样芽胞杆菌、金黄色葡萄球菌、耐甲氧西林金黄色葡萄球菌(methicillin-resistant Staphylococcus aureus,MRSA)以及大肠杆菌都具有明显的抗菌活性,能够有效抑制4种菌株的生长和繁殖。结论 化合物1~4、6~12、16~19、21、24均为首次从唇形科中分离得到,化合物5、13~15、20、22、23、25、26为首次从猫须草植物中分离得到;化合物15~18在抗菌方面表现出较为显著的活性,可为后续研究和开发相关新药提供物质基础和科学依据。
[Key word]
[Abstract]
Objective The chemical constituents of the whole plant of Maoxucao (Clerodendranthus spicatus) were isolated and identified, and their antibacterial activities were determined. Methods The compounds were isolated and purified by silica gel, Sephadex LH-20, MCI column chromatography and preparative high performance liquid chromatography, and their structures were identified by NMR data and literature comparison. The activities of the isolated compounds against Bacillus cereus, Staphylococcus aureus, methicillin-resistant S. aureus (MRSA) and Escherichia coli were evaluated by gradient dilution method. Results A total of 26 compounds were isolated from the ethyl acetate extract and identified as 1-[1-oxo-9 (3,4-methylenedioxyphenyl)-2E,4E,8E-nonatrienyl]-pyrrolidine (1), piperchabamide B (2), piperolein B (3), dehydropipernonaline (4), piperine (5), guineensine (6), piperflaviflorine A (7), methyl piperate (8), ethyl piperate (9), methyl (2E,4E)-7-(1,3-benzodioxol-5-yl)-2,4-heptadienoate (10), (1S,2S)-1,2,3-trihydroxy-1-(3,4-methylenedioxyphenyl) propane (11), trans-p-hydroxyl ethyl cinnamate (12), caffeic acid ethylene ester (13), phthalic acid butyl isobutyl ester (14), eupomatenoid-7 (15), licarin A (16), (7R,8R)-7,8-dihydro-7-(3,4-dihydroxyphenyl)-3′-methoxy-8-methyl-1′-(E-propenyl) benzofuran (17), denudatin A (18), futokadsurin C (19), 3-(3,4-dihydroxyphenyl)-acrylic acid-1-(3,4-dihydroxyphenyl)-2-methoxycarbonylethyl ester (20), sibiriaester A (21), 2-(3′,4′-dihydroxyphenyl)-1,3-benzodioxole-5-aldehyde (22), glechomol A (23), 4-hydroxy-2,3-dimethyl-2-nonen-4-olide (24), (+)-sesamin (25), asarinin (26). Compared with the positive drug vancomycin, compounds 15—18 have obvious antibacterial activity against B. cereus, S. aureus, MRSA and E. coli, and can effectively inhibit the growth and reproduction of the four strains. Conclusion Compounds 1—4, 6—12, 16—19, 21 and 24 were isolated from Labiatae for the first time, and compounds 5, 13—15, 20, 22, 23, 25, 26 were isolated firstly from C. spicatus. Compounds 15—18 showed significant antibacterial activity, which can provide material basis and scientific basis for subsequent research and development of related new drugs.
[中图分类号]
R284.1
[基金项目]
国家自然科学基金资助项目(81903509)