黄素馨化学成分及其抗氧化活性
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摘要
对黄素馨Jasminum giraldii根皮的化学成分进行研究。采用正相硅胶、Sephadex LH-20以及Rp-HPLC制备柱色谱法,从黄素馨乙醇提取物的乙酸乙酯萃取部位中分离得到10个化合物,通过MS和NMR等谱学方法,鉴定结构为(+)-梣皮树脂醇(1),(+)-丁香树脂醇(2),(+)-丁香脂素-4'-O-β-D-葡萄糖苷(3),齐墩果酸(4),3-甲氧基-4-羟基桂皮醛(5),芥子醛(6),3,5-二甲氧基对羟基苯甲醛(7),1-(4-甲氧基苯基)乙醇(8),反式桂皮酸(9),4-(1-甲氧基乙基)苯酚(10)。化合物1~3,5~8以及10为首次从素馨属植物中分离得到;化合物4和9为首次从该植物中分离得到。采用DPPH自由基清除法对分离得到的化合物进行抗氧化活性的筛选。结果显示,化合物1显示出强的自由清除能力(IC50为55.1μmol·L-1),活性强于维生素C(IC50为59.9μmol·L-1),化合物2显示中等强度自由清除能力(IC50为79.0μmol·L-1),活性弱于维生素C,但强于2,6-二羟丁基对甲酚(IC50为236μmol·L-1)。
Ten compounds were isolated from the barks of Jasminum giraldii by means of various of chromatographic techniques such as silica gel,Sephadex LH-20 and Rp-HPLC.Their structures were identified by spectroscopic data analysis as(+)-medioresinol(1),(+)-syringaresinol(2),syringaresinol-4'-O-β-D-glucopyranoside(3),oleanic acid(4),3-methoxy-4-hydroxy-transcinnamaldehyde(5),trans-sinapaldehyde(6),syringaldehyde(7),1-(4-methoxy-phenyl)-ethanol(8),trans-cinnamic acid(9),and 4-(1-methoxyethyl)-phenol(10).Among them,compounds 1-3,5-8 and 10 were isolated from the J.genus for the first time and compounds 4 and 9 were obtained from J.giraldii for the first time.In the DPPH free radical scavenging assay,compound 1 exhibited significant activity(IC5055.1 μmol·L-1),compared with vitamin C(IC5059.9 μmol·L-1); and compound 2 showed moderate activity(IC5079.0 μmol·L-1),compared with 2,6-di-tert-butyl-4-methylphenol(IC50236 μmol·L-1).
Ten compounds were isolated from the barks of Jasminum giraldii by means of various of chromatographic techniques such as silica gel,Sephadex LH-20 and Rp-HPLC.Their structures were identified by spectroscopic data analysis as(+)-medioresinol(1),(+)-syringaresinol(2),syringaresinol-4'-O-β-D-glucopyranoside(3),oleanic acid(4),3-methoxy-4-hydroxy-transcinnamaldehyde(5),trans-sinapaldehyde(6),syringaldehyde(7),1-(4-methoxy-phenyl)-ethanol(8),trans-cinnamic acid(9),and 4-(1-methoxyethyl)-phenol(10).Among them,compounds 1-3,5-8 and 10 were isolated from the J.genus for the first time and compounds 4 and 9 were obtained from J.giraldii for the first time.In the DPPH free radical scavenging assay,compound 1 exhibited significant activity(IC5055.1 μmol·L-1),compared with vitamin C(IC5059.9 μmol·L-1); and compound 2 showed moderate activity(IC5079.0 μmol·L-1),compared with 2,6-di-tert-butyl-4-methylphenol(IC50236 μmol·L-1).
引文
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[4]Ando H,Hirai Y,Fujii M,et al.The chemical constituents of fresh Gentian root[J].J Nat Med,2007,61(3):269.
[5]Chen D,Song Y L,Nie C X,et al.Chemical constituents from Aquilaria sinensis(Lour.)Gilg[J].J Chin Pharm Sci,2012,21:88.
[6]Wang C,Yu D.Lignan and acetylenic glycosides from Aster auriculatus[J].Phytochemistry,1998,48(4):711.
[7]刘普,邓瑞雪,段宏泉,等.糙苏根的化学成分研究[J].中国中药杂志,2009,34(7):867.
[8]刘岱琳,庞发根,张家欣,等.密花石豆兰的化学成分研究[J].中国药物化学杂志,2005,15(2):103.
[9]林佳,郝小江,梁光义.毛果含笑的化学成分[J].药学学报,1999,34(3):203.
[10]王湛昌,林文瀚,张亮亮,等.福建浮宫红海榄(Rhizophorastylosa)次生代谢产物研究[J].厦门大学学报,2006,45(6):873.
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[12]许云龙,马云保,熊江.高山金粉蕨的黄酮类成分[J].Acta Botanica Yunnanica,1999,21(3):386.
[13]Camps P,González A,Muoz-Torrero D,et al.Synthesis of polysubstituted bicyclo[3.3.1]nonane-3,7-diones from cyclohexa-2,5-dienones and dimethyl 1,3-acetonedicarboxylate[J].Tetrahedron,2000,56(41):8141.
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