Characterization of aromatase binding agents from the dichloromethane extract of Corydalis yanhusuo using ultrafiltration and liquid chromatography tandem mass spectrometry

Molecules

Volumn 15, Issue 5, 2010, Pages 3556-3566

  Shi, Jing ^a   Zhang, Xiaoyu ^b   Ma, Zhongjun ^b   Zhang, Min ^b   Sun, Fang ^b  

^a ZHEJIANG UNIVERSITY SCHOOL OF MEDICINE   (China)

^b ZHEJIANG UNIVERSITY   (China)

Author keywords

Alkaloids; Aromatase; Corydalis yanhusuo; Ultrafiltration LC MS

Indexed keywords

AROMATASE; DICHLOROMETHANE; PLANT EXTRACT; PROTEIN BINDING;

ARTICLE; CHEMISTRY; CORYDALIS; LIQUID CHROMATOGRAPHY; METABOLISM; PROTEIN BINDING; TANDEM MASS SPECTROMETRY; ULTRAFILTRATION;

AROMATASE; CHROMATOGRAPHY, LIQUID; CORYDALIS; METHYLENE CHLORIDE; PLANT EXTRACTS; PROTEIN BINDING; TANDEM MASS SPECTROMETRY; ULTRAFILTRATION;

EID: 77952855053     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules15053556     Document Type: Article

References (35)

1. 1. Bulun, S.E.; Lin, Z.; Imir, G.; Amin, S.; Demura, M.; Yilmaz, B.; Martin, R.; Utsunomiya, H.; Thung, S.; Gurates, B.; Tamura, M.; Langoi, D.; Deb, S. Regulation of aromatase expression in estrogen-responsive breast and uterine disease: from bench to treatment. Pharmacol. Rev. 2005, 57, 359-383.
2. Santen, R.J. Inhibition of aromatase: insights from recent studies. Steroids 2003, 68, 559-567.
3. Fisher, B.; Costantino, J.P.; Wickerham, D.L.; Redmond, C.K.; Kavanah, M.; Cronin, W.M.; Vogel, V.; Robidoux, A.; Dimitrov, N.; Atkins, J.; Daly, M.; Wieand, S.; Tan-Chiu, E.; Ford, L.; Wolmark, N. Tamoxifen for prevention of breast caner: Report of the National Surgical Adjuvant Breast and Bowel Project P-1 Study. J. Natl. Cancer Inst. 1998, 90, 1371-1388.
4. Brueggemeier, R.W.; Hackett, J.C.; Diaz-Cruz, E.S. Aromatase inhibitors in the treatment of breast cancer. Endocr. Rev. 2005, 26, 331-345.
5. Evans, C.T.; Ledesma, D.B.; Schulz, T.Z.; Simpson, E.R.; Mendelson, C.R. Isolation and characterization of a complementary DNA specific for human aromatase-system cytochrome P450 mRNA. Proc. Natl. Acad. Sci. USA 1986, 83, 6387-6391.
6. Brueggemeier, R.W. Update on the use of aromatase inhibitors in breast cancer. Expert Opin. Pharmacother. 2006, 7, 1919-1930.
7. Kendall, A.; Dowsett, M. Novel concepts for the chemoprevention of breast cancer through aromatase inhibition. Endocr. Relat. Cancer 2006, 13, 827-837.
8. Wong, Z.W.; Ellis, M.J. First-line endocrine treatment of breast cancer: aromatase inhibitor or antioestrogen? Brit. J. Cancer 2004, 90, 20-25.
9. Milla-Santos, A.; Milla, L.; Portella, J.; Rallo, L.; Pons, M.; Rodes, E.; Casanovas, J.; Puig-Gali, M. Anastrozole versus tamoxifen as first-line therapy in postmenopausal patients with hormone-dependent advanced breast cancer: a prospective, randomized, phase III study. Am. J. Clin. Oncol. 2003, 26, 317-322.
10. Arora, A.; Potter, J.F. Aromatase inhibitors: current indications and future prospects for treatment of postmenopausal breast cancer. J. Am. Geriatr. Soc. 2004, 52, 611-616.
11. Goss, P.E. Risks versus benefits in the clinical application of aromatase inhibitors. Endocr. Relat. Cancer 1999, 6, 325-332.
12. Gnant, M. Management of bone loss induced by aromatase inhibitors. Cancer Invest. 2006, 24, 328-330.
13. Chlebowski, R.T.; Anderson, G.L.; Geller, M.; Col, N. Coronary heart disease and stroke with aromatase inhibitor, tamoxifen, and menopausal hormone therapy use. Clin. Breast Cancer 2006, 6, 58-64.
14. Lee D.; Bhat, K.P.; Fong, H.H.; Farnsworth, N.R.; Pezzuto, J.M.; Kinghorn, A.D. Aromatase inhibitors from Broussonetiapapyrifera.J. Nat. Prod. 2001, 64,1286-1293.
15. Chen, S.; Cho, M.; Karlsberg, K.; Zhou, D.; Yuan, Y.C. Biochemical and biological characterization of a novel anti-aromatase coumarin derivative. J. Biol. Chem. 2004, 279, 48071-48078.
16. Blanco, J.G.; Gil, R.R.; Alvarea, C.I.; Patrito, L.C.; Genti-Raimondi, S.; Flury, A. A novel activity for a group of sesquiterpene lactones: inhibition of aromatase. FEBS Lett. 1997, 09, 396-400.
17. Wang, Y.; Lee, K.W.; Chan, F.L.; Chen, S.; Leung, L.K. The red wine polyphenol reseratrol displays bilevel inhibition on aromatase in breast cancer cells. Toxicol. Sci. 2006, 92, 71-77.
18. Kadohama, N.; Shintani, K.; Osawa, Y. Tobacco alkaloid derivatives as inhibitors of breast cancer aromatase. Cancer Lett. 1993, 75, 175-182.
19. Ng, P.C.; Ho, D.D.; Ng, K.H.; Kong, Y.C.; Cheng, K.F.; Stone, G. Mixed estrogenic and antiestrogenic activities of yuehchukene-a bis-indole alkaloid. Eur. J. Pharmacol. 1994, 264, 1-12.
20. Ding, B.; Zhou, T.; Fan, G.; Hong, Z.; Wu, Y. Qualitative and quantitative determination of ten alkaloids in traditional Chinese medicine Corydalisyanhusuo W.T. Wang by LC-MS/MS and LC-DAD. J. Pharm. Biomed. Anal. 2007, 45, 219-226.
21. Ma, Z.Z.; Xu, W.; Jensen, N.H.; Roth, B.L.; Liu-Chen, L.Y.; Lee, D.Y. Isoquinoline alkaloids isolated from Corydalis yanhusuo and their binding affinities at the dopamine D1 receptor. Molecules 2008, 13, 2303-2312.
22. Ou, J.; Kong, L.; Pan, C.; Su, X.; Lei, X.; Zou, H. Determination of DL-tetrahydropalmatine in Corydalis yanhusuo by L-tetrahydropalmatine imprinted monolithic column coupling with reversed-phase high performance liquid chromatography. J. Chromatogr. A 2006, 1117, 163-169. (Pubitemid 44269290)
23. Gao, J.L.; Shi, J.M.; He, K.; Zhang, Q.W.; Li, S.P.; Lee, S.M.; Wang, Y.T. Yanhusuo extract inhibits metastasis of breast cancer cells by modulating mitogen-activated protein kinase signaling pathways. Oncol. Rep. 2008, 20, 819-824.
24. Nobuyuki, K.; Keiji, S.; Yoshio, O. Tobacco alkaloid derivatives as inhibitors of breast cancer aromatase. Cancer Lett. 1993, 75, 175-182.
25. Grycova, L.; Dostal, J.; Marek, R. Quaternary protoberberine alkaloids. Phytochemistry 2007, 68, 150-175.
26. Cutter, P.S.; Miller, R.B.; Schore, N.E. Synthesis of protoberberines using a silyl-directed Pictet-Spengler cyclization. Tetrahedron 2002, 58, 1471-1478.
27. Cushman, M.; Dekow, F.W. A total synthesis of corydaline. Tetrahedron 1978, 34, 1435-1439.
28. Wada, Y.; Kaga, H.; Uchiito, S.; Kumazawa, E.; Tomiki, M.; Onozaki, Y.; Kurono, N.; Tokuda, M.; Ohkuma, T.; Orito, K. On the synthesis of protopine alkaloids. J. Org. Chem. 2007, 72, 7301-7306.
29. Van Breemen, R.B.; Huang, C.R.; Nikolic, D.; Woodbury, C.P.; Zhao, Y.Z.; Venton, D.L. Pulsed ultrafiltration mass spectrometry: A new method for screening combinatorial libraries. Anal. Chem. 1997, 69, 2159-2164. (Pubitemid 27279476)
30. Zhao, Y.Z.; van Breemen, R.B.; Nikolic, D.; Huang, C.R.; Woodbury, C.P.; Schilling, A.; Venton, D.L. Screening solution-phase combinatorial libraries using pulsed ultrafiltration/electrospray mass spectrometry. J. Med. Chem. 1997, 40, 4006-4012. (Pubitemid 28008395)
31. Nikolic, D.; Habibi-Goudarzi, S.; Corley, D.G.; Gafner, S.; Pezzuto, J.M.; van Breemen, R.B. Evalution of cyclooxygenase-2 inhibitors using pulsed ultrafiltration mass spectrometry. Anal. Chem. 2000, 72, 3853-3859.
32. Liu, J.; Burdette, J.E.; Xu, H.; Gu, C.; van Breemen, R.B.; Bhat, K.P.L.; Booth, N.; Constantinou, A.I.; Pezzuto, J.M.; Fong, H.H.S.; Farnsworth, N.R.; Bolton, J.L. Evaluation of estrogenic activity of plant extracts for the potential treatment of menopausal symptoms. J. Agric. Food Chem. 2001, 49, 2472-2479.
33. Sun, Y.; Gu, C.; Liu, X.; Liang, W.; Yao, P.; Bolton, J.L.; van Breemen, R.B. Ultrafiltration tandem mass spectrometry of estrogens for characterization of structure and affinity for human estrogen receptors. J. Am. Soc. Mass Spectrom. 2005, 16, 271-279.
34. Le Bail, J.C.; Laroche, T.; Marre-Fournier, F.; Habrioux, G. Aromatase and 17-hydroxysteroid dehydrogenase inhibition by flavonoids. Cancer Lett. 1998, 133, 101-106.
35. Sanderson, J.T.; Hordijk, J.; Denison, M.S.; Springsteel, M.F.; Nantz, M.H.; van den Berg, M. Induction and inhibition of aromatase (CYP19) activity by natural and synthetic flavonoid compounds in H295R human adrenocortical carcinoma cells. Toxicol. Sci. 2004, 82, 70-79.