青花椒根皮中1个新的香豆素类化合物
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摘要
目的对青花椒Zanthoxylum schinifolium根皮中抗炎活性成分进行跟踪分离研究。方法采用硅胶、Sephadex LH-20、MCI以及半制备HPLC等色谱方法进行分离纯化,根据理化性质和现代谱学技术鉴定化合物的结构,以脂多糖(LPS)诱导的RAW264.7细胞炎症模型进行抗炎活性评价。结果从青花椒根皮的醋酸乙酯部位中共分离得到4个香豆素类化合物,分别鉴定为青花椒素A(1)、7-甲氧基香豆素(2)、异东莨菪内酯(3)和秦皮乙素(4)。在LPS诱导RAW264.7细胞产生一氧化氮(NO)的模型中,化合物1～4均对NO的产生具有抑制作用,半数抑制浓度(IC50)值分别为(0.21±0.03)、(0.92±0.16)、(0.15±0.02)和(0.26±0.04)μmol/L。结论化合物1为新化合物,是1个罕见的香豆素类化合物,命名为青花椒素A。化合物3为首次从该属植物中分离得到,所有化合物均具有较强的抗NO生成活性。
Objective To study the anti-inflammatory components from the root barks of Zanthoxylum schinifolium. Methods The compounds were isolated and purified by silica gel, MCI, Sephadex LH-20 column chromatographies, and semi-preparative HPLC,and their structures were elucidated by physical and spectroscopic analysis. The anti-inf1 ammatory activity was evaluated by the levels of NO in LPS-induced RAW264.7 tested by Griess reagent. Results Four coumarins, namely zantholin A(1), 7-methoxycoumarin(2), isoscopoletin(3), and esculetin(4), were isolated from the root barks of Z. schinifolium. Compounds 1—4 exhibited anti-inflammatory activities on inhibition of lipopolysaccharide(LPS)-induced NO production in RAW 264.7 macrophages with IC50 values of(0.21 ± 0.03),(0.92 ± 0.16),(0.15 ± 0.02), and(0.26 ± 0.04) μmol/L, respectively. Conclusion Compound 1 is a new compound, a rare terpenylated coumarin named zantholin A, and compounds 3 is obtained from this plant for the first time. All compounds exhibited anti-inflammatory activities.
Objective To study the anti-inflammatory components from the root barks of Zanthoxylum schinifolium. Methods The compounds were isolated and purified by silica gel, MCI, Sephadex LH-20 column chromatographies, and semi-preparative HPLC,and their structures were elucidated by physical and spectroscopic analysis. The anti-inf1 ammatory activity was evaluated by the levels of NO in LPS-induced RAW264.7 tested by Griess reagent. Results Four coumarins, namely zantholin A(1), 7-methoxycoumarin(2), isoscopoletin(3), and esculetin(4), were isolated from the root barks of Z. schinifolium. Compounds 1—4 exhibited anti-inflammatory activities on inhibition of lipopolysaccharide(LPS)-induced NO production in RAW 264.7 macrophages with IC50 values of(0.21 ± 0.03),(0.92 ± 0.16),(0.15 ± 0.02), and(0.26 ± 0.04) μmol/L, respectively. Conclusion Compound 1 is a new compound, a rare terpenylated coumarin named zantholin A, and compounds 3 is obtained from this plant for the first time. All compounds exhibited anti-inflammatory activities.
引文
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[5]Min B K,Hyun D G,Jeong S Y,et al.A new cytotoxic coumarin,7-[(E)-3′,7′-dimethyl-6′-oxo-2′,7′-octadienyl]oxycoumarin,from the leaves of Zanthoxylum schinifolium[J].Arch Pharm Res,2011,34(5):723-726.
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[7]Tsai I L,Lin W Y,Teng C M,et al.Coumarins and antiplatelet constituents from the root bark of Zanthoxylum schinifolium[J].Planta Med,2000,66(7):618-623.
[8]Dao T T,Tran T L,Kim J,et al.Terpenylated coumarins as SIRT1 activators isolated from Ailanthus altissima[J].J Nat Prod,2012,75(7):1332-1338.
[9]王倩,王丰,薛松,等.茵陈中7-甲氧基香豆素的分离与含量测定[J].沈阳药科大学学报,2003,20(1):12-14.
[10]王清吉,王友绍,何磊,等.厚藤Ipomoea Pes-Caprae(L.)Sweet的化学成分研究(I)[J].中国海洋药物,2006,25(3):15-17.
[11]许洪波,杨康,刘澳昕,等.11种中药提取物对脂多糖诱导的RAW264.7细胞生成一氧化氮的影响[J].中南药学,2018,16(1):72-75.
[2]中国药典[S].一部.2015.
[3]刘锁兰,魏璐雪,王动,等.青花椒化学成分的研究[J].药学学报,1991,26(11):836-840.
[4]Nguyen P H,Zhao B T,Kim O,et al.Anti-inflammatory terpenylated coumarins from the leaves of Zanthoxylum schinifolium withα-glucosidase inhibitory activity[J].JNat Med,2016,70(2):276-281.
[5]Min B K,Hyun D G,Jeong S Y,et al.A new cytotoxic coumarin,7-[(E)-3′,7′-dimethyl-6′-oxo-2′,7′-octadienyl]oxycoumarin,from the leaves of Zanthoxylum schinifolium[J].Arch Pharm Res,2011,34(5):723-726.
[6]Jo Y S,Huong D T L,Bae K H,et al.Monoamine oxidase inhibitory coumarin from Zanthoxylum schinifolium[J].Planta Med,2002,68(1):84-85.
[7]Tsai I L,Lin W Y,Teng C M,et al.Coumarins and antiplatelet constituents from the root bark of Zanthoxylum schinifolium[J].Planta Med,2000,66(7):618-623.
[8]Dao T T,Tran T L,Kim J,et al.Terpenylated coumarins as SIRT1 activators isolated from Ailanthus altissima[J].J Nat Prod,2012,75(7):1332-1338.
[9]王倩,王丰,薛松,等.茵陈中7-甲氧基香豆素的分离与含量测定[J].沈阳药科大学学报,2003,20(1):12-14.
[10]王清吉,王友绍,何磊,等.厚藤Ipomoea Pes-Caprae(L.)Sweet的化学成分研究(I)[J].中国海洋药物,2006,25(3):15-17.
[11]许洪波,杨康,刘澳昕,等.11种中药提取物对脂多糖诱导的RAW264.7细胞生成一氧化氮的影响[J].中南药学,2018,16(1):72-75.