黄柏与关黄柏的化学成分及生物活性研究进展
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摘要
黄皮树Phellodendron chinense、黄檗P. amurense的干燥树皮分别作为黄柏、关黄柏入药,二者在2005、2010、2015年版《中国药典》被分别收录。从这两种药材中分离出来的化学成分主要包括生物碱类、柠檬苦素类、酚酸类、萜类、苯丙素类、挥发性类等,具有抗菌、抗癌、抗糖尿病、保护心脑血管等多种生物活性。综述近年来对黄柏、关黄柏化学成分、生物活性的研究进展,为进一步研究两者药效物质基础、药理作用及临床合理用药提供参考依据。
The original plant of Phellodendri Chinensis Cortex was Phellodendron chinense, and the original plant of Phellodendri Amurensis Cortex was P. amurense. The two kinds of medicinal materials were recorded in the Pharmacopoeia of China in the 2005,2010, 2015 edition as different species, and the chemical constituents isolated from the two medicinal materials mainly include alkaloids, limonoids, phenolic acids, terpenoids, phenylpropanoids, volatiles. They had many biological activities, such as antibacterial, anti-cancer, anti-diabetes, protection of cardiovascular and cerebrovascular. Recent advances in chemical constituents and biological activities of Phellodendri Chinensis Cortex and Phellodendri Amurensis Cortex were reviewed, which could provide references for further study on the pharmacodynamic material basis, pharmacological effects and rational clinical use of drugs with Phellodendri Chinensis Cortex and Phellodendri Amurensis Cortex.
The original plant of Phellodendri Chinensis Cortex was Phellodendron chinense, and the original plant of Phellodendri Amurensis Cortex was P. amurense. The two kinds of medicinal materials were recorded in the Pharmacopoeia of China in the 2005,2010, 2015 edition as different species, and the chemical constituents isolated from the two medicinal materials mainly include alkaloids, limonoids, phenolic acids, terpenoids, phenylpropanoids, volatiles. They had many biological activities, such as antibacterial, anti-cancer, anti-diabetes, protection of cardiovascular and cerebrovascular. Recent advances in chemical constituents and biological activities of Phellodendri Chinensis Cortex and Phellodendri Amurensis Cortex were reviewed, which could provide references for further study on the pharmacodynamic material basis, pharmacological effects and rational clinical use of drugs with Phellodendri Chinensis Cortex and Phellodendri Amurensis Cortex.
引文
[1]中国药典[S].一部, 2015.
[2]张冠英,董瑞娟,廉莲.川黄柏、关黄柏的化学成分及药理活性研究进展[J].沈阳药科大学学报, 2012, 29(10):812-821.
[3]雷华平,卜晓英,田向荣,等.超临界二氧化碳萃取川黄柏挥发性成分及其GC-MS分析[J].中国野生植物资源, 2009, 28(6):61-62.
[4]徐敏,万德光.川黄柏中微量元素的主成分分析和聚类分析[J].时珍国医国药, 2008, 19(1):151-153.
[5] Wang K, Chai L W, Ding L Q, et al. Identification of metabolites of palmatine in rats after oral administration using ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry[J]. Rap Comm Mass Spec, 2017, 31(6):523-537.
[6] Wang H Y, Sun H, Zhang A H, et al. Rapid identification and comparativeanalysis of the chemical constituents andmetabolites of Phellodendri amurensis cortex and Zhibaidihuang Pill by ultra-performance liquid chromatography with quadrupole TOF-MS[J]. J Sep Sci,2013, 36:3874-3882.
[7] Xiao T T, Yu C Z, Zhi X L, et al. Systematic and comprehensive strategy for metabolite profiling in bioanalysis using software-assisted HPLC-Q-TOF:magnoflorine as an example[J]. Anal Bioanal Chem,2016, 408:2239-2254.
[8] Xiang Q Y, Hashi Y, Chen Zi L. Simultaneous detection of eight activecomponents in Radix Tinosporae by ultra high performance liquid chromatographycoupled with electrospray tandem mass spectrometry[J]. J Sep Sci,2016, 39:2036-2042.
[9] Cai W, Guan Y, Zhou Y, et al. Detection and characterization of the metabolites of rutaecarpine in rats based on ultra-highperformance liquid chromatography with linear ion trap-Orbitrap mass spectrometer[J].Pharm Biol, 2016, 55(1):294-298.
[10]李丹丹,江培,杨书美,等.黄柏的化学成分、药理作用及临床应用研究进展[J].黑龙江医药, 2014, 27(3):601-605.
[11] Wang P, Zhao Y L, ZHU Y D, et al. Metabolism of dictamnine in liver microsomes from mouse, rat, dog,monkey, and human[J]. J Pharm Biomed Anal, 2016,119:166-174.
[12] Servillo L, Giovane A, D'Onofrio N, et al. N-Methylated Derivatives of tyramine in Citrus genus plants identification of N,N,N-trimethyltyramine(candicine)[J].J Agric Food Chem, 2014, 62:2679-2684.
[13] Luo X M, Qi S H, Yin H, et al. Alkaloids from the stem bark of Micromelum falcatum[J]. Chem Pharm Bull,2009, 57(6):600-602.
[14] Nishiyama Y, Moriyasua M, Ichimarua M, et al.Quaternary isoquinoline alkaloids from Xylopia parviflora[J]. Phytochemistry, 2004, 65, 939-944.
[15]李行诺,翟文丰,周孟宇,等.黄柏化学成分研究[J].浙江工业大学学报, 2012, 40(3):244-246.
[16] Roberta G, Maria M C, Giovanni L, et al. The Chemistry and pharmacology of citrus limonoids[J]. Molecules,2016, 21:1530-1569.
[17] Kawaguchi H, Kim M, Ishida, et al. Several antifeedants from phellodendron amurense against Reticulitermes speratus[J]. Agric Biol Chem, 1989, 53(10):2635-2640.
[18] Miyake M, Inaba N, Ayano S, et al. Limonoids in Phellodendron amurense(Kihada)[J]. Yakugaku Zasshi,1992, 112(5):343-347.
[19] Balachandran C, Em N, Arun Y, et al. In vitro anticancer activity of methyl caffeate isolated from Solanum torvum Swartz. fruit[J]. Chem Biol Int, 2015, 242(5):81-90.
[20]侯冬岩,回瑞华.黄柏果中挥发性成分的研究[J].质谱学报, 2001, 21(3):61-65.
[21] Hung Y C, Tian S W, Sheng F S, et al. Marked decrease of cyclosporin absorption caused by phellamurin in rats[J]. Plant Med, 2002, 68(2):138-141.
[22] Lee S H, Lee J Y, Kwon Y I, et al. Anti-osteoclastic activity of Artemisia capillaries Thunb. extract depends upon attenuation of osteoclast differentiation and bone resorption-associated acidification due to chlorogenic acid, hyperoside, and scoparone[J]. Int J Mol Sci, 2017,18(2):322.
[23] Lian R Y, Xin M, Xiao J Y, et al. Simultaneous determination of anemoside B4, phellodendrine,berberine, palmatine, obakunone, esculin, esculetin in rat plasma by UPLC–ESI–MS/MS and its application to a comparative pharmacokinetic study in normal and ulcerative colitis rats[J]. J Pharm Biomed Anal, 2017,134:43-52.
[24] Cristiane M C, Vanessa C D, Jaqueline R B, et al.Isolation of xanthyletin, an inhibitor of ants'symbiotic fungus, by high-speed counter-current chromatography[J]. J Chromatogr A, 2009, 1216:4307-4312.
[25]郭书好,周明辉,李素梅.川黄柏果挥发油化学成分研究[J].暨南大学学报:自然科学与医学版, 1998, 3:61-63.
[26] Sack R B, Froehlich J L. Berberine inhibits intestinal secretory response of Vibrio cholerae and Escherichia coli enterotoxins[J]. Infect Immun, 1982, 35:471-475.
[27]胡俊青,胡晓.黄柏化学成分和药理作用的现代研究[J].当代医学, 2009, 15(7):139-141.
[28]吴嘉瑞,张冰,张光敏,等.黄柏药理作用研究进展[J].北京中医药大学学报, 2009, 5(11):160-162.
[29]郭志坚,郭书好,何康明,等.黄柏叶中黄酮醇甙含量测定及其抑菌实验[J].暨南大学学报:自然科学版, 2002, 23(5):64.
[30]闫玉鑫.川黄柏的抗肿瘤活性成分研究[J].云南师范大学学报:自然科学版, 2015, 5(35):75-78.
[31] Kim S J, Kim O Y, Ko K H, et al. Butanol extract of 1:1mixture of Phellodendron Cortex and Aralia Cortex stimulates PI3-Kinase and ERK2 with increase of Glycogen Levels in HepG2cells[J]. Phytother Res, 1998,12:255-260.
[32]王春波,陆付耳,冷三华,等.小檗碱对HepG2细胞葡萄糖激酶活性及其mRNA表达的影响[J].中国药理学通报, 2007, 23(90):1145-1147.
[33]齐梁煜,黄月维,黄莹.黄柏提取物对大鼠心肌损伤的保护作用[J].中国药师, 2016, 19(7):1259-1262.
[34]孔令东,杨澄,仇熙,等.黄柏炮制品清除自由基和抗脂质过氧化作用[J].中国中药杂志, 2001, 26(4):245-247.
[35]王飞,郭力,杨奎,等.加味三妙胶囊及黄柏对前列腺渗透作用的实验观察[J].成都医药, 2003, 29(1):42-43.
[36]杨澄,朱继孝,王颖,等.盐制对黄柏抗通风作用的影响[J].中国中药杂志, 2005, 30(2):145-148.
[37]张冠英,董瑞娟,廉莲.川黄柏、关黄柏的化学成分及药理活性研究进展[J].沈阳药科大学学报, 2012, 10:812-821.
[38]胡俊青,胡晓.黄柏化学成分和药理作用的现代研究[J].当代医学, 2009, 7:139-141.
[39]张凡,吴琦,鞠成国,等.产地加工炮制一体化与传统黄柏饮片的化学成分比较研究[J].中草药, 2018, 49(20):4748-4752.
[40]武卫党,张星艳,魏滋鸿,等.小檗碱对有机阴离子转运体抑制作用及双向跨膜转运研究[J].药物评价研究,2017, 40(6):778-782.
[2]张冠英,董瑞娟,廉莲.川黄柏、关黄柏的化学成分及药理活性研究进展[J].沈阳药科大学学报, 2012, 29(10):812-821.
[3]雷华平,卜晓英,田向荣,等.超临界二氧化碳萃取川黄柏挥发性成分及其GC-MS分析[J].中国野生植物资源, 2009, 28(6):61-62.
[4]徐敏,万德光.川黄柏中微量元素的主成分分析和聚类分析[J].时珍国医国药, 2008, 19(1):151-153.
[5] Wang K, Chai L W, Ding L Q, et al. Identification of metabolites of palmatine in rats after oral administration using ultra-high performance liquid chromatography/quadrupole time-of-flight mass spectrometry[J]. Rap Comm Mass Spec, 2017, 31(6):523-537.
[6] Wang H Y, Sun H, Zhang A H, et al. Rapid identification and comparativeanalysis of the chemical constituents andmetabolites of Phellodendri amurensis cortex and Zhibaidihuang Pill by ultra-performance liquid chromatography with quadrupole TOF-MS[J]. J Sep Sci,2013, 36:3874-3882.
[7] Xiao T T, Yu C Z, Zhi X L, et al. Systematic and comprehensive strategy for metabolite profiling in bioanalysis using software-assisted HPLC-Q-TOF:magnoflorine as an example[J]. Anal Bioanal Chem,2016, 408:2239-2254.
[8] Xiang Q Y, Hashi Y, Chen Zi L. Simultaneous detection of eight activecomponents in Radix Tinosporae by ultra high performance liquid chromatographycoupled with electrospray tandem mass spectrometry[J]. J Sep Sci,2016, 39:2036-2042.
[9] Cai W, Guan Y, Zhou Y, et al. Detection and characterization of the metabolites of rutaecarpine in rats based on ultra-highperformance liquid chromatography with linear ion trap-Orbitrap mass spectrometer[J].Pharm Biol, 2016, 55(1):294-298.
[10]李丹丹,江培,杨书美,等.黄柏的化学成分、药理作用及临床应用研究进展[J].黑龙江医药, 2014, 27(3):601-605.
[11] Wang P, Zhao Y L, ZHU Y D, et al. Metabolism of dictamnine in liver microsomes from mouse, rat, dog,monkey, and human[J]. J Pharm Biomed Anal, 2016,119:166-174.
[12] Servillo L, Giovane A, D'Onofrio N, et al. N-Methylated Derivatives of tyramine in Citrus genus plants identification of N,N,N-trimethyltyramine(candicine)[J].J Agric Food Chem, 2014, 62:2679-2684.
[13] Luo X M, Qi S H, Yin H, et al. Alkaloids from the stem bark of Micromelum falcatum[J]. Chem Pharm Bull,2009, 57(6):600-602.
[14] Nishiyama Y, Moriyasua M, Ichimarua M, et al.Quaternary isoquinoline alkaloids from Xylopia parviflora[J]. Phytochemistry, 2004, 65, 939-944.
[15]李行诺,翟文丰,周孟宇,等.黄柏化学成分研究[J].浙江工业大学学报, 2012, 40(3):244-246.
[16] Roberta G, Maria M C, Giovanni L, et al. The Chemistry and pharmacology of citrus limonoids[J]. Molecules,2016, 21:1530-1569.
[17] Kawaguchi H, Kim M, Ishida, et al. Several antifeedants from phellodendron amurense against Reticulitermes speratus[J]. Agric Biol Chem, 1989, 53(10):2635-2640.
[18] Miyake M, Inaba N, Ayano S, et al. Limonoids in Phellodendron amurense(Kihada)[J]. Yakugaku Zasshi,1992, 112(5):343-347.
[19] Balachandran C, Em N, Arun Y, et al. In vitro anticancer activity of methyl caffeate isolated from Solanum torvum Swartz. fruit[J]. Chem Biol Int, 2015, 242(5):81-90.
[20]侯冬岩,回瑞华.黄柏果中挥发性成分的研究[J].质谱学报, 2001, 21(3):61-65.
[21] Hung Y C, Tian S W, Sheng F S, et al. Marked decrease of cyclosporin absorption caused by phellamurin in rats[J]. Plant Med, 2002, 68(2):138-141.
[22] Lee S H, Lee J Y, Kwon Y I, et al. Anti-osteoclastic activity of Artemisia capillaries Thunb. extract depends upon attenuation of osteoclast differentiation and bone resorption-associated acidification due to chlorogenic acid, hyperoside, and scoparone[J]. Int J Mol Sci, 2017,18(2):322.
[23] Lian R Y, Xin M, Xiao J Y, et al. Simultaneous determination of anemoside B4, phellodendrine,berberine, palmatine, obakunone, esculin, esculetin in rat plasma by UPLC–ESI–MS/MS and its application to a comparative pharmacokinetic study in normal and ulcerative colitis rats[J]. J Pharm Biomed Anal, 2017,134:43-52.
[24] Cristiane M C, Vanessa C D, Jaqueline R B, et al.Isolation of xanthyletin, an inhibitor of ants'symbiotic fungus, by high-speed counter-current chromatography[J]. J Chromatogr A, 2009, 1216:4307-4312.
[25]郭书好,周明辉,李素梅.川黄柏果挥发油化学成分研究[J].暨南大学学报:自然科学与医学版, 1998, 3:61-63.
[26] Sack R B, Froehlich J L. Berberine inhibits intestinal secretory response of Vibrio cholerae and Escherichia coli enterotoxins[J]. Infect Immun, 1982, 35:471-475.
[27]胡俊青,胡晓.黄柏化学成分和药理作用的现代研究[J].当代医学, 2009, 15(7):139-141.
[28]吴嘉瑞,张冰,张光敏,等.黄柏药理作用研究进展[J].北京中医药大学学报, 2009, 5(11):160-162.
[29]郭志坚,郭书好,何康明,等.黄柏叶中黄酮醇甙含量测定及其抑菌实验[J].暨南大学学报:自然科学版, 2002, 23(5):64.
[30]闫玉鑫.川黄柏的抗肿瘤活性成分研究[J].云南师范大学学报:自然科学版, 2015, 5(35):75-78.
[31] Kim S J, Kim O Y, Ko K H, et al. Butanol extract of 1:1mixture of Phellodendron Cortex and Aralia Cortex stimulates PI3-Kinase and ERK2 with increase of Glycogen Levels in HepG2cells[J]. Phytother Res, 1998,12:255-260.
[32]王春波,陆付耳,冷三华,等.小檗碱对HepG2细胞葡萄糖激酶活性及其mRNA表达的影响[J].中国药理学通报, 2007, 23(90):1145-1147.
[33]齐梁煜,黄月维,黄莹.黄柏提取物对大鼠心肌损伤的保护作用[J].中国药师, 2016, 19(7):1259-1262.
[34]孔令东,杨澄,仇熙,等.黄柏炮制品清除自由基和抗脂质过氧化作用[J].中国中药杂志, 2001, 26(4):245-247.
[35]王飞,郭力,杨奎,等.加味三妙胶囊及黄柏对前列腺渗透作用的实验观察[J].成都医药, 2003, 29(1):42-43.
[36]杨澄,朱继孝,王颖,等.盐制对黄柏抗通风作用的影响[J].中国中药杂志, 2005, 30(2):145-148.
[37]张冠英,董瑞娟,廉莲.川黄柏、关黄柏的化学成分及药理活性研究进展[J].沈阳药科大学学报, 2012, 10:812-821.
[38]胡俊青,胡晓.黄柏化学成分和药理作用的现代研究[J].当代医学, 2009, 7:139-141.
[39]张凡,吴琦,鞠成国,等.产地加工炮制一体化与传统黄柏饮片的化学成分比较研究[J].中草药, 2018, 49(20):4748-4752.
[40]武卫党,张星艳,魏滋鸿,等.小檗碱对有机阴离子转运体抑制作用及双向跨膜转运研究[J].药物评价研究,2017, 40(6):778-782.