大果木姜子果实倍半萜类成分及生物活性研究

Sesquiterpenoids from the fruits of Cinnamomum migao and their biological activities

关键词:  大果木姜子, 倍半萜, PC12, 神经保护活性, α-葡萄糖苷酶

Key words:  Cinnamomum migao, sesquiterpenoid, PC12, neuroprotective activity, α-glucosidase

摘要:

为探究大果木姜子(Cinnamomum migao)果实的化学成分及生物活性,该研究采用硅胶柱层析、反相柱色谱和半制备高效液相等色谱技术对大果木姜子果实乙醇提取物进行分离纯化,通过理化性质与核磁共振波谱数据,并结合参考文献鉴定这些化合物的结构,以及检测了部分化合物的神经保护作用和降糖活性。结果表明:(1)从大果木姜子果实中分离得到29个倍半萜类化合物,分别鉴定为 dehydrocarissone(1)、揽香醇(2)、eremophil-6-en-11-ol(3)、11-hydroxy-1-oxo-4α,5α,7β,10β-eremophilane(4)、1β-hydroxy-4(15),5E,10(14)-germacratriene(5)、(1R,5S,6R,10R)-4-methylene-10-methyl-6-(2-methylprop-1-en-1-yl)octahydro-1H-inden-1-ol(6)、1β-acetoxy-4-eudesmen-11-ol(7)、shiluone H(8)、7α,11-dihydroxy-cadin-10(14)-ene(9)、kobusone(10)、humulene diepoxide A(11)、madolins A(12)、holostylactone(13)、4-(2,2,5-trimethyl-2,3,4,5,6,7-hexahydrocyclopentapyran-3-yl)butan-2-one(14)、litsemnolide D(15)、桉油烯醇(16)、isospathulenol(17)、aromadendrane-4α-10α-diol(18)、aromadendrane-4β-10β-diol(19)、litseachromolaevane A(20)、phacadinane E(21)、rel-(5R,7R)-10-desmethyl-1-methyl-1,10-dioxo-1,10-seco-11-eudesmene(22)、chimonol C(23)、10-hydroxy-6,10-epoxy-7(14)-isodaucane(24)、1,5-epoxy-4(14)-salvialene(25)、4-hydroxy-4,7- dimethyl-1-tetralone(26)、(4S^*,5E,10R^*)-7-oxo-tri-nor-eudesm-5-en-4β-ol(27)、trans-4,5-dihydroxycorocalane(28)、5,11-epoxycadalene(29)。其中,化合物1-10、12-15、17、19-22、24、25、27、29均为首次从该植物中分离得到。(2)化合物1、4、5、8、11、16、22在30 μmol·L^-1下对N-methyl-D-aspartic acid(NMDA)损伤的PC12细胞具有保护作用。(3)化合物 5 具有α-葡萄糖苷酶抑制作用,IC₅₀ 值均为(33.3±0.71)μmol·L^-1。该研究结果丰富了大果木姜子化学成分库,为进一步研究与开发利用大果木姜子提供了一定的科学依据。

Abstract:

In order to explore the chemical constituents from the fruits of Cinnamomum migao and their biological activities, the ethanol extract from the fruits of C. migao was isolated and purified by silica gel column chromatography, reversed phase column chromatography, semi-preparative HPLC and other column chromatography technologies. Their structures were identified by physicochemical properties, comprehensive spectral data combined with relevant literatures. Some compounds have been tested for their neuroprotective effects and α-glucosidase inhibitory activity. The results were as follows:(1)Twenty-nine sesquiterpenoids were isolated from the fruits of C. migao, which were identified as dehydrocarissone(1), elemol(2), eremophil-6-en-11-ol(3), 11-hydroxy-1-oxo-4α,5α,7β,10β-eremophilane(4), 1β-hydroxy-4(15), 5E,10(14)-germacratriene(5),(1R,5S,6R,10R)-4-methylene-10-methyl-6-(2-methylprop-1-en-1-yl)octahydro-1H-inden-1-ol(6), 1β-acetoxy-4-eudesmen-11-ol(7), shiluone H(8), 7α,11- dihydroxy-cadin-10(14)-ene(9), kobusone(10), humulene diepoxide A(11), madolins A(12), holostylactone(13), 4-(2,2,5-trimethyl-2,3,4,5,6,7-hexahydrocyclopentapyran-3-yl)butan-2-one(14), litsemnolide D(15), spathulenol(16), isospathulenol(17), aromadendrane-4α-10α-diol(18), aromadendrane-4β-10β-diol(19), litseachromolaevane A(20), phacadinane E(21), rel-(5R,7R)-10-desmethyl-1-methyl-1,10-dioxo-1,10-seco-11-eudesmene(22), chimonol C(23), 10-hydroxy-6,10-epoxy-7(14)-isodaucane(24), 1,5-epoxy-4(14)-salvialene(25), 4-hydroxy-4,7-dimethyl-1-tetralone(26),(4S^*,5E,10R^*)-7-oxo-tri-nor-eudesm-5-en-4β-ol(27), trans-4,5-dihydroxycorocalane(28), 5,11-epoxycadalene(29). Compounds 1-10, 12-15, 17, 19-22, 24、25, 27, 29 were isolated from this plant for the first time.(2)Compounds 1, 4, 5, 8, 11, 16, 22 showed protective activities against NMDA-induced neurotoxicity in PC12 cells.(3)Compound 5 exhibited α-glucosidase inhibitory activity with IC₅₀ value of(33.3±0.71)μmol·L^-1. The results of this study enrich the chemical composition of C. migao, and provide a certain scientific reference for further study, development and utilization of the plant resource in the future.