岗梅茎中的酚类成分研究
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摘要
综合运用多种色谱技术从岗梅茎的水提物中分离得到了18个酚类成分,经波谱学方法鉴定其结构,包括2个木脂素类(1,2),5个苯丙素类(3～7),6个绿原酸类(8～13),5个苯甲酸类似物(14～18),其中3～7,9,11,13,14,17,18为首次从冬青属中分离得到,2,8,10,15,16为首次从岗梅中分离得到。抗炎活性筛选结果显示,8,9,11,13,15对RAW264.7细胞中的NO生成显示有一定的抑制作用,其IC_(50)为51.1～85.8μmol·L~(-1)。该研究为进一步阐明岗梅茎的抗炎药效物质及药材的质量评价研究提供了参考。
Phytochemical investigation on Ilex asprella stems by using various chromatographic techniques led to the isolation of 18 phenolic constituents. Based on spectroscopic data analyses and/or comparison of the spectroscopic data with those in literature, these constituents were identified, including two lignans(1, 2), five phenylpropanes(3-7), six chlorogenic analogues(8-13), and five benzoic analogues(14-18). Among them, compounds 3-7, 9, 11, 13, 14, 17, and 18 were isolated from genus Ilex for the first time, and 2, 8, 10, 15, and 16 were isolated from this species for the first time. The in vitro anti-inflammatory assay results showed that compounds 8, 9, 11, 13, and 15 possessed moderate inhibition on the NO production in RAW264.7 cells with IC_(50) values of 51.1-85.8 μmol·L~(-1). The present study brought preliminary reference for the clarification of therapeutic ingredients of I. asprella with anti-inflammatory efficacy and its quality evaluation.
Phytochemical investigation on Ilex asprella stems by using various chromatographic techniques led to the isolation of 18 phenolic constituents. Based on spectroscopic data analyses and/or comparison of the spectroscopic data with those in literature, these constituents were identified, including two lignans(1, 2), five phenylpropanes(3-7), six chlorogenic analogues(8-13), and five benzoic analogues(14-18). Among them, compounds 3-7, 9, 11, 13, 14, 17, and 18 were isolated from genus Ilex for the first time, and 2, 8, 10, 15, and 16 were isolated from this species for the first time. The in vitro anti-inflammatory assay results showed that compounds 8, 9, 11, 13, and 15 possessed moderate inhibition on the NO production in RAW264.7 cells with IC_(50) values of 51.1-85.8 μmol·L~(-1). The present study brought preliminary reference for the clarification of therapeutic ingredients of I. asprella with anti-inflammatory efficacy and its quality evaluation.
引文
[1] 杜冰曌, 杨鑫瑶, 冯晓, 等. 岗梅的化学成分和药理作用研究进展[J]. 中国中药杂志, 2017, 42 (1): 20.
[2] Yang X, Gao X, Du B, et al. The Ilex asprella aqueous extracts exert in vivo anti-inflammatory potential by regulating NF-κB, JAK2/STAT3, and MAPK signaling pathways [J]. J Ethnopharmacol, 2018, 225: 234.
[3] 杜冰曌, 张和新歌, 杨鑫瑶, 等. 岗梅茎的化学成分研究[J]. 中国中药杂志, 2017, 42 (21): 4154.
[4] Zhang H, Du B, Zhao F, et al. Three new triterpenoid saponins from the stems of Ilex asprella [J]. J Asian Nat Prod Res, 2018, 20: 439.
[5] Du B, Zhao F, Zhang H, et al. Asprenols A-H, phenolic constituents from the stems of Ilex asprella [J].Fitoterapia, 2018, 129: 220.
[6] Kim T H, Ito H, Hayashi K, et al. Aromatic constituents from the heartwood of Santalum album [J]. Chem Pharm Bull, 2005, 53(6): 641.
[7] Shu J, Liang F, Zhu G, et al. Lignan glycosides from the rhizomes of Smilax trinervula and their biological activities [J]. Phytochem Lett, 2017, 20: 1.
[8] Xu Z, Chai X, Bai C, et al. Xylocosides A-G, phenolic glucosides from the stems of Xylosma controversum [J]. Helv Chim Acta, 2008, 91(7): 1346.
[9] Yang X, Zhao P, Ma Y, et al. Mixed lignan-neolignans from Tarenna attenuate [J]. J Nat Prod, 2007, 70(4): 521.
[10] Lee T, Kuo Y, Wang G, et al. Five new phenolics from the roots of Ficus beecheyana [J]. J Nat Prod, 2002, 65(10): 1497.
[11] 苏东敏. 薄叶山柑水溶性化学成分研究[J]. 中国中药杂志, 2008, 33(9): 1021.
[12] Somwong P, Suttisri R, Buakeaw A. New sesquiterpenes and phenolic compound from Ficus foveolata [J]. Fitoterapia, 2013, 85(1): 1.
[13] 关焕玉, 兰燕宇, 廖尚高, 等. 羊耳菊中咖啡酰基奎宁酸类化学成分研究[J]. 天然产物研究与开发, 2014, 26(12): 1948.
[14] 刘玉峰, 杨秀伟, 武滨, 等. 款冬花化学成分的研究[J]. 中国中药杂志, 2007, 32(22): 2378.
[15] 郭林新,马养民,李梦云, 等. 三叶木通利尿活性部位筛选及其化学成分[J]. 中国实验方剂学杂志, 2017, 23(3): 66.
[16] 赵志勇, 杨姣. 中药连翘的酚酸类化学成分研究[J]. 辽宁医学院学报, 2016, 37(3):12.
[17] 陈艳. 半枝莲的化学成分研究[D]. 沈阳:沈阳药科大学, 2007.
[18] 董礼, 陈敏, 李梅, 等. 柴胡红景天中一个新氰苷类化合物[J]. 药学学报, 2009, 44(12): 1383.
[19] Sande J S. Part A: synthesis of acetophenones with possible applications in anthocyanin synthesis. Part B: synthesis and ring opening of selected strained gem-dihalocyclopropyl ethers [D]. Stavanger:University of Stavanger, 2011.
[20] Guo Q, Zeng K, Gao X, et al. Chemical constituents with NO production inhibitory and cytotoxic activities from Litsea cubeba [J]. J Nat Med, 2015, 69 (1): 94.
[2] Yang X, Gao X, Du B, et al. The Ilex asprella aqueous extracts exert in vivo anti-inflammatory potential by regulating NF-κB, JAK2/STAT3, and MAPK signaling pathways [J]. J Ethnopharmacol, 2018, 225: 234.
[3] 杜冰曌, 张和新歌, 杨鑫瑶, 等. 岗梅茎的化学成分研究[J]. 中国中药杂志, 2017, 42 (21): 4154.
[4] Zhang H, Du B, Zhao F, et al. Three new triterpenoid saponins from the stems of Ilex asprella [J]. J Asian Nat Prod Res, 2018, 20: 439.
[5] Du B, Zhao F, Zhang H, et al. Asprenols A-H, phenolic constituents from the stems of Ilex asprella [J].Fitoterapia, 2018, 129: 220.
[6] Kim T H, Ito H, Hayashi K, et al. Aromatic constituents from the heartwood of Santalum album [J]. Chem Pharm Bull, 2005, 53(6): 641.
[7] Shu J, Liang F, Zhu G, et al. Lignan glycosides from the rhizomes of Smilax trinervula and their biological activities [J]. Phytochem Lett, 2017, 20: 1.
[8] Xu Z, Chai X, Bai C, et al. Xylocosides A-G, phenolic glucosides from the stems of Xylosma controversum [J]. Helv Chim Acta, 2008, 91(7): 1346.
[9] Yang X, Zhao P, Ma Y, et al. Mixed lignan-neolignans from Tarenna attenuate [J]. J Nat Prod, 2007, 70(4): 521.
[10] Lee T, Kuo Y, Wang G, et al. Five new phenolics from the roots of Ficus beecheyana [J]. J Nat Prod, 2002, 65(10): 1497.
[11] 苏东敏. 薄叶山柑水溶性化学成分研究[J]. 中国中药杂志, 2008, 33(9): 1021.
[12] Somwong P, Suttisri R, Buakeaw A. New sesquiterpenes and phenolic compound from Ficus foveolata [J]. Fitoterapia, 2013, 85(1): 1.
[13] 关焕玉, 兰燕宇, 廖尚高, 等. 羊耳菊中咖啡酰基奎宁酸类化学成分研究[J]. 天然产物研究与开发, 2014, 26(12): 1948.
[14] 刘玉峰, 杨秀伟, 武滨, 等. 款冬花化学成分的研究[J]. 中国中药杂志, 2007, 32(22): 2378.
[15] 郭林新,马养民,李梦云, 等. 三叶木通利尿活性部位筛选及其化学成分[J]. 中国实验方剂学杂志, 2017, 23(3): 66.
[16] 赵志勇, 杨姣. 中药连翘的酚酸类化学成分研究[J]. 辽宁医学院学报, 2016, 37(3):12.
[17] 陈艳. 半枝莲的化学成分研究[D]. 沈阳:沈阳药科大学, 2007.
[18] 董礼, 陈敏, 李梅, 等. 柴胡红景天中一个新氰苷类化合物[J]. 药学学报, 2009, 44(12): 1383.
[19] Sande J S. Part A: synthesis of acetophenones with possible applications in anthocyanin synthesis. Part B: synthesis and ring opening of selected strained gem-dihalocyclopropyl ethers [D]. Stavanger:University of Stavanger, 2011.
[20] Guo Q, Zeng K, Gao X, et al. Chemical constituents with NO production inhibitory and cytotoxic activities from Litsea cubeba [J]. J Nat Med, 2015, 69 (1): 94.