薰衣草残渣化学成分及其生物活性
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摘要
目的研究薰衣草Lavandula angustifolia Mill.残渣的化学成分及其生物活性。方法薰衣草残渣的正丁醇部位采用硅胶、Sephadex LH-20、ODS、半制备高效液相进行分离纯化,根据理化性质及波谱数据鉴定所得化合物的结构。检测抗氧化、降糖活性。结果从中分离得到10个化合物,分别鉴定为木樨草素-4′-O-β-D-葡萄糖醛酸苷(1)、木樨草素-3′-O-β-D-(6″-甲基)-葡萄糖醛酸苷(2)、木樨草素-7-O-β-D-葡萄糖醛酸苷(3)、木樨草素-7-O-β-(6″-甲基)-葡萄糖醛酸苷(4)、芹菜素-7-O-β-D-葡萄糖醛酸苷(5)、芹菜素-7-O-β-D-(6″-甲基)-葡萄糖醛酸苷(6)、芹菜素-7-O-β-D-(6″-乙基)-葡萄糖醛酸苷(7)、芹菜素-7-O-β-D-(6″-丁基)-葡萄糖醛酸苷(8)、(7S, 8R)-二氢去氢二愈创木基醇葡萄糖苷(9)、木樨草素(10)。化合物1、3～4对DPPH表现出较强的抗氧化活性,化合物3、7～8对PTP1B表现出较好的抑制作用。结论化合物1、2、5、7～10为首次从该植物中分离得到,化合物1、3、4、7～8有较强的生物活性。
AIM To study the chemical constituents from the residue of Lavandula angustifolia Mill and their biological activities.METHODS The n-butanol fraction of the residue of L. angustifolia was isolated and purified by silica,Sephadex LH-20,ODS and semi-preparative HPLC,then the structures of obtained compounds were identified by physicochemical properties and spectral data.The antioxidant and hypoglycemic activities were evaluated.RESULTS Ten compounds were isolated and identified as luteolin-4′-O-β-D-glucopyranosiduronic acid(1), luteolin-3′-O-β-D-(6′-methyl)-glucopyranosiduronic acid(2), luteolin-7-O-β-D-glucuronopyranoside(3), luteolin-7-O-β-D-(6″-methyl)-glucuronopyranoside(4), apigenin-7-O-β-D-glucronide(5), apigenin-7-O-β-D-(6″-methyl)-glucronide(6), apigenin-7-O-β-D-glucopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7 yl, ehtyl ester(7), apigenin-7-O-β-D-glucopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7 yl,ehtyl ester(8),(7S,8R)-urolignoside(9), luteolin(10).Compounds 1, 3-4 showed strong antioxidant activities against DPPH. Compounds 3, 7-8 exhibited good inhibitory activities against PTP1 B.CONCLUSION Compounds 1, 2, 5, 7-10 are isolated from this plant for the first time,and compounds 1,3,4,7-8 have strong biological activities.
AIM To study the chemical constituents from the residue of Lavandula angustifolia Mill and their biological activities.METHODS The n-butanol fraction of the residue of L. angustifolia was isolated and purified by silica,Sephadex LH-20,ODS and semi-preparative HPLC,then the structures of obtained compounds were identified by physicochemical properties and spectral data.The antioxidant and hypoglycemic activities were evaluated.RESULTS Ten compounds were isolated and identified as luteolin-4′-O-β-D-glucopyranosiduronic acid(1), luteolin-3′-O-β-D-(6′-methyl)-glucopyranosiduronic acid(2), luteolin-7-O-β-D-glucuronopyranoside(3), luteolin-7-O-β-D-(6″-methyl)-glucuronopyranoside(4), apigenin-7-O-β-D-glucronide(5), apigenin-7-O-β-D-(6″-methyl)-glucronide(6), apigenin-7-O-β-D-glucopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7 yl, ehtyl ester(7), apigenin-7-O-β-D-glucopyranosiduronic acid, 5-hydroxy-2-(4-hydroxyphenyl)-4-oxo-4H-1-benzopyran-7 yl,ehtyl ester(8),(7S,8R)-urolignoside(9), luteolin(10).Compounds 1, 3-4 showed strong antioxidant activities against DPPH. Compounds 3, 7-8 exhibited good inhibitory activities against PTP1 B.CONCLUSION Compounds 1, 2, 5, 7-10 are isolated from this plant for the first time,and compounds 1,3,4,7-8 have strong biological activities.
引文
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[16] 洪俊丽, 秦民坚, 吴刚, 等. 水蔓菁中的酚性成分[J]. 中国天然药物, 2008, 6(2): 126-129.
[17] Hai X K, Yong G X,Bing Y Y, et al. Lignan constituents from Chloranthus japonicus Sieb[J].Arch Pharmacal Res, 2009, 32(3): 329-334.
[18] 靳鑫, 时圣明, 张东方,等. 穿心莲化学成分的研究(Ⅱ)[J]. 中草药, 2014, 45(2): 164-169.
[2] 宋旺弟, 刘盼盼,陈文. 分子蒸馏纯化薰衣草精油主要成分的HS_SPME_GC分析[J]. 食品工业科技, 2018,39(2): 196-201,206.
[3] 尼格尔热依·亚迪卡尔. 薰衣草精油蒸馏残渣化学成分及其生物活性研究[D]. 北京: 中国科学院大学,2017.
[4] 张秋霞, 江英,张志强. 薰衣草精油的研究进展[J]. 香料香精化妆品, 2006, 12(6): 21-24.
[5] 胡喜兰, 韩照祥, 刘玉芬,等. 薰衣草挥发油的抗氧化活性测定和成分比较[J]. 食品科技, 2006, 9(3): 115-117.
[6] 胡坤. 薰衣草精油化学成分及抗菌活性研究[J]. 黑河学院学报, 2018, 9(1): 215-216.
[7] 王玉芹, 孙亚军,施献儿. 薰衣草精油的化学成分与药理活性[J]. 国外医药(植物药分册), 2004, 19(1): 5-8.
[8] 朱丽云, 高永生, 宋林珍,等. 薰衣草挥发油的响应面法优化提取及抗菌活性分析[J]. 中国食品添加剂试验研究, 2018(2): 130-137.
[9] 胡星麟. 薰衣草精油品质评价及杂花薰衣草精油蒸馏残渣化学成分的研究[D]. 南京: 南京师范大学,2014.
[10] 黄梅桂, 徐云巧, 张忠明,等. 薰衣草残渣中黄酮的超声辅助提取工艺及其抗氧化活性[J]. 食品工业科技, 2018, 39(1): 214-220.
[11] 陈斌, 周谦, 钱骅,等. 伊犁杂花薰衣草叶化学成分研究[J]. 中国野生植物资源, 2018, 37(5): 8-9,29.
[12] 易湘茜,高程海. 海草化学成分及其生物活性研究进展[J]. 天然产物研究与开发, 2013, 25(7): 1001-1005.
[13] Tadrent W, Magid A A,Kabouche A, et al. A new sulfonylated flavonoid and other bioactive compounds isolated from the aerial parts of Cotula anthemoides L[J]. Nat Prod Res, 2017, 31(12): 1437-1445.
[14] Nguyen D H, Seo U M, Bing T Z, et al. Ellagitannin and flavonoid constituents from Agrimonia pilosa Ledeb. with their protein tyrosine phosphatase and acetylcholinesterase inhibitory activities[J].Bioorg Chem, 2017, 72: 293-300.
[15] 晏小云, 殷晓静, 王国凯,等. 南苜蓿的化学成分研究[J]. 中国药学杂志, 2012, 47(6): 415-418.
[16] 洪俊丽, 秦民坚, 吴刚, 等. 水蔓菁中的酚性成分[J]. 中国天然药物, 2008, 6(2): 126-129.
[17] Hai X K, Yong G X,Bing Y Y, et al. Lignan constituents from Chloranthus japonicus Sieb[J].Arch Pharmacal Res, 2009, 32(3): 329-334.
[18] 靳鑫, 时圣明, 张东方,等. 穿心莲化学成分的研究(Ⅱ)[J]. 中草药, 2014, 45(2): 164-169.