甲基丁香酚的大鼠肝微粒体生物转化

doi:10.5246/jcps.2014.05.043

中国药学(英文版) ›› 2014, Vol. 23 ›› Issue (5): 311-316.DOI: 10.5246/jcps.2014.05.043

甲基丁香酚的大鼠肝微粒体生物转化

曹桂云, 杨秀伟^*

北京大学医学部天然药物及仿生药物国家重点实验室; 药学院天然药物学系, 北京 100191

收稿日期:2013-10-03 修回日期:2013-10-23 出版日期:2014-05-23 发布日期:2013-11-05
通讯作者: Tel.: 86-10-82801569; E-mail: xwyang@bjmu.edu.cn
基金资助:
National Natural Science Foundation of China (Grant No. 30973863; 81161120429) and National Key Technology R & D Program of China (Grant No. 2011BAI07B08).

Biotransformation of methyleugenol by rat hepatic microsomes

Guiyun Cao, Xiuwei Yang^*

State Key Laboratory of Natural and Biomimetic Drugs; Department of Natural Medicines, School of Pharmaceutical Sciences, Peking University Health Science Center, Beijing 100191, China

Received:2013-10-03 Revised:2013-10-23 Online:2014-05-23 Published:2013-11-05
Contact: Tel.: 86-10-82801569; E-mail: xwyang@bjmu.edu.cn
Supported by:
National Natural Science Foundation of China (Grant No. 30973863; 81161120429) and National Key Technology R & D Program of China (Grant No. 2011BAI07B08).

摘要/Abstract

摘要：

甲基丁香酚(1)是中药肉豆蔻的主要成分之一, 将其与大鼠肝微粒体共温孵, 从温孵物中通过色谱方法得到原形化合物1和8个转化产物 (2–9), 根据谱学数据并与文献报道数据比较, 确定它们分别为(R)-1'-甲氧基甲基丁香酚(2)、3-(3,4-二甲氧基苯基)-l-甲氧基-2-丙烯(3)、顺式-3,4-二甲氧基桂皮酰乙酯(4)、反式-3,4-二甲氧基桂皮酰乙酯(5)、(R)-1′-羟基甲基丁香酚(6)、反式-3,4-二甲氧基桂皮醇(7)、顺式-3,4-二甲氧基桂皮醇(8)、(R)-3-(3,4-二甲氧基苯基)-丙烷-1,2-二醇(9)。化合物7和8的¹³C NMR数据为首次报道。本文结果为甲基丁香酚的应用提供了有用的信息。

关键词: 甲基丁香酚, 肉豆蔻, 生物转化, 大鼠肝微粒体

Abstract:

Methyleugenol (1), one of the main bioactive constituents of the seeds of Myristica fragrans Houtt. (family: Myristicaceae),was incubated with rat hepatic microsomes from rats pretreated with sodium phenobarbital. Eight biotransformation products named (R)-1'-methoxymethyleugenol (2), 3-(3,4-dimethoxyphenyl)-l-methoxyprop-2-ene (3), cis-3,4-dimethoxycinnamyl acetate (4), trans-3,4-dimethoxycinnamyl acetate (5), (R)-1'-hydroxymethyleugenol (6), trans-3,4-dimethoxycinnamyl alcohol (7), cis-3,4-dimethoxycinnamyl alcohol (8), and (R)-3-(3,4-dimethoxyphenyl)-propane-1,2-diol (9) were obtained and their structures were elucidated by NMR and MS data analysis and by comparison with the previously reported data. The biotransformation of 1 may provide valuable information for the use of methyleugenol. The NMR data of compounds 4 and 6 were reported for the first time.

Key words: Methyleugenol, Myristica fragrans, Biotransformation, Rat hepatic microsomes

中图分类号:

R915

Supporting: National Natural Science Foundation of China (Grant No. 30973863; 81161120429) and National Key Technology R & D Program of China (Grant No. 2011BAI07B08).

曹桂云, 杨秀伟. 甲基丁香酚的大鼠肝微粒体生物转化[J]. 中国药学(英文版), 2014, 23(5): 311-316.

Guiyun Cao, Xiuwei Yang. Biotransformation of methyleugenol by rat hepatic microsomes[J]. Journal of Chinese Pharmaceutical Sciences, 2014, 23(5): 311-316.

参考文献

[1] Han, Y.S.; Kim, M.S.; Hwang, J.K. Inflammation. 2012, 35, 1723–1731.

[2] Jin, D.Q.; Lim, C.S.; Hwang, J.K.; Ha, I.; Han, J.S. Biochem. Biophys. Res. Commun. 2005, 331, 1264–1269.

[3]Leem, H.H; Kim, E.O.; Seo, M.J.; Choi, S.W. J. Korean Soc. Food Sci. Nutr. 2011, 40, 1361–1370.

[4] Chatterjee, S.; Niaz, Z.; Gautam, S.; Adhikari, S.; Variyar, P.S.; Sharma A. Food Chem. 2007, 101, 515–523.

[5] Sohn, J.H.; Han, K.L.; Choo, J.H.; Hwang, J.K. BioFactors. 2007, 29, 1–10.

[6] Morita, T.; Jinno, K.; Kawagishi, H.; Arimoto, Y.; Suganuma, H.; Inakuma, T.; Sugiyama, K. J. Agric. Food Chem–1565.. 2003, 51, 1560

[7] Han, K.L.; Choi, J.S.; Lee, J.Y.; Song, J.; Joe, M.K.; Jung, M.H.; Hwang, J.K. Diabetes. 2008, 57, 737–745.

[8] Patil, S.B.; Ghadyale, V.A.; Taklikar, S.S.; Kulkarni, C.R.; Arvindekar, A.U. Plant Food Hum. Nutr. 2011, 66, 85–90.

[9] El-Alfy, A.T.; Wilson, L.; Elsohly, M.A.; Abourashed, E.A. J. Ethnopharmacol. 2009, 126, 280–286.

[10] Tan, K.H.; Nishida, R. J. Insect Sci. 2012, 12, 1–60.

[11] de Vincenzi, M.; Silano, M.; Stacchini, P.; Scazzocchio, B. Fitoterapia. 2000, 71, 216–221.

[12] Yang, X.W.; Huang, X.; Ahmat, M. China J. Chin. Mater. Med. 2008, 33, 397–402.

[13] Li, Y.; Yang, X.W. Fitoterapia. 2013, 85, 95–100.

[14] Lowry, O.H.; Rosebrough, N.J.; Farr, A.L.; Randall, R.J. J. Biol. Chem. 1951, 193, 265–275.

[15] Omura, T.; Sato, R. J. Biol. Chem. 1964, 239, 2379–2385.

[16] Yang, X.W.; Ahmat, M.; Li, Q.; Xu, W.; Yang, Z.; Xiao, S.Y. Chin. Tradit. Herb. Drugs. 2003, 34, 93–96.

[17] Pistelli, L.; Bilia, A.R.; Bertoli, A.; Morelli, I.; Marsili, A. J. Nat. Prod. 1995, 58, 112–116.

[18] Jung, Y.H.; Kim, J.D. Arch. Pharm. Res. 2003, 26, 667–678.

[19] Li, S.; Lundqist, K. Acta Chem. Scand. 1995, 49, 64–67.

[20] Chuah, C.H.; Ool, L.E.; Yong, H.S.; Goh, S.H. Biochem. Syst. Ecol. 1996, 24, 189–193.

[21] Jeurissen, S.M.F.; Bogaards, J.J.P.; Boersma, M.G.; Ter Horst, J.P.F.; Awad, H.M.; Fiamegos, Y.C.; van Beek, T.A.; Alink, G.M.; Sudhölter, E.J.R.; Cnubben, N.H.P.; Rietjens, I.M.C.M. Chem. Res. Toxicol. 2006, 19, 111–116.

[22] Nishida, R.; Shelly, T.E.; Kaneshiro, K.Y. J. Chem. Ecol. 1997, 23, 2275–2285.

[23] Tokushima, I.; Orankanok, W.; Tan, K. H.; Ono, H.; Nishida, R. J. Chem. Ecol. 2010, 36, 1327–1334.

[24] Sawant, R.T.; Waghmode, S.B. Synth. Commun. 2010, 40, 2269–2277.

[25] Stambasky, J.; Malkov, A.V.; Kocovsky, P. J. Org. Chem. 2008, 73, 9148–9150.

[26]Li, F.; Yang, X.W.Phytochemistry. 2008, 69, 765–771.

[27]Li, F.;Yang, X.W. Planta Med. 2011, 77, 1712–1717.

[28] Al-Subeihi, A.A.A.; Alhusainy, W.; Paini, A.; Punt, A.; Vervoort, J.; van Bladeren, P.J.; Rietjens, I.M.C.M. Food Chem. Toxicol. 2013, 59, 564–571.

[29] Niu, B.J.; Ma, Z.K.; Liao, Z.X.; Ji, L.J.; Sun, H.F. Chin. Tradit. Herb. Drugs. 2013, 44, 147–152.

[30] Yuan, X.Y.; Cheng, M.C.; Gao, M.Z.; Zhuo, R.J.; Zhang, L.X.; Xiao, H.B. Phytochem. Lett. 2013, 6, 21–25.

[31] Wang, H.; Du, H.B.; Zhu, F.Y.; Shang, J.; Silafu, A.B. J. China Pharm. Univ. 2011, 42, 310–313.

甲基丁香酚的大鼠肝微粒体生物转化

Biotransformation of methyleugenol by rat hepatic microsomes

RichHTML

PDF (PC)

可视化

被引次数

摘要/Abstract

引用本文

使用本文

参考文献

相关文章 10

编辑推荐

Metrics

本文评价

[1]	谢雁景, 刘子光, 高雅宁, 王秀伶, 郝庆红, 于秀梅. 一株新分离鸡肠道厌氧细菌将染料木素转化为左旋-5羟基-雌马酚[J]. 中国药学(英文版), 2015, 24(7): 442-448.
[2]	冯金, 梁文飞, 季帅, 乔雪, 张英涛, 余四旺, 叶敏. Isoangustone A的冻土毛霉生物转化研究[J]. 中国药学(英文版), 2015, 24(5): 285-291.
[3]	吴妮, 徐嵬, 张友波, 杨秀伟. 马拉巴酮C的大鼠肝微粒体生物转化及其体外对人胃癌细胞株的细胞毒活性研究[J]. 中国药学(英文版), 2014, 23(4): 241-245.
[4]	冉丽, 吴帅, 徐嵬, 张友波, 杨秀伟^*. 柚皮苷的人肠内菌生物转化[J]. , 2013, 22(4): 329-333.
[5]	孔德涛, 凌笑梅^, 韩方斌, 龚京莉, 葛泽梅, 李润涛, 崔景荣^*. TM208在大鼠肝微粒体中代谢产物与细胞色素P450亚型代谢酶鉴别研究[J]. , 2008, 17(1): 30-34.
[6]	李莉欣, 苏艳芳, 刘晓峰, 果德安^*. 大黄毛状根对青蒿素的生物转化研究[J]. , 2002, 11(4): 122-124.
[7]	占纪勋, 郭洪祝, 戴均贵, 张元兴, 果德安^*. 刺囊毛霉对天麻素的生物转化研究[J]. , 2001, 10(4): 187-189.
[8]	董阿玲, 崔亚君, 郭洪祝, 郑俊华, 果德安^*. 人参皂苷Rg1的微生物转化研究[J]. , 2001, 10(3): 115-118.
[9]	李慧义, 罗淑荣, 周同惠. 左旋紫草素体内代谢研究[J]. , 1999, 8(3): 148-151.
[10]	匡唐永, 楼雅卿^*, 赵立安 . 地西泮、苯巴比妥、普萘洛尔和西咪替丁对大鼠肝微粒体安定氧化代谢的影响[J]. , 1997, 6(2): 90-96.