Selective inhibition of prenylated flavonoids from Sophora flavescens against BACE1 and cholinesterases

American Journal of Chinese Medicine

Volumn 38, Issue 2, 2010, Pages 415-429

  Jung, Hyun Ah ^a   Yokozawa, Takako ^b   Kim, Byung Woo ^c,d   Jung, Jee H ^e   Choi, Jae Sue ^a,d  

^a Pukyong National University   (South Korea)

^b UNIVERSITY OF TOYAMA   (Japan)

^c Dong Eui University   (South Korea)

^d Blue Bio Industry RIC   (South Korea)

^e Pusan National University   (South Korea)

Author keywords

Acetylcholinesterase; Alzheimer's Disease; BACE1; Butyrylcholinesterase; Prenylated Flavonoid; Sophora flavescens

Indexed keywords

2' METHOXYKURARINONE; 8 LAVANDULYLKAEMPFEROL; ACETIC ACID ETHYL ESTER; ACETYLCHOLINESTERASE; BETA SECRETASE 1; CHALCONE DERIVATIVE; CHOLINESTERASE; DESMETHYLANHYDROICARITIN; DICHLOROMETHANE; FLAVANONE DERIVATIVE; FLAVONOL DERIVATIVE; ISOXANTHOHUMOL; KURARIDIN; KURARIDINOL; KURARINOL; KURARINONE; KUSHENOL; KUSHENOL E; LEACHIANONE; MAACKIAIN; MATRINE; OXYMATRINE; PHYSOSTIGMINE; PTEROCARPAN DERIVATIVE; QUINOLIZIDINE DERIVATIVE; SOPHORA FLAVESCENS EXTRACT; SOPHORAFLAVANONE; TRIFOLIRHIZIN; UNCLASSIFIED DRUG; UNINDEXED DRUG; XANTHOHUMOL;

ALZHEIMER DISEASE; ARTICLE; CHOLINESTERASE INHIBITION; CONTROLLED STUDY; DRUG ISOLATION; DRUG MECHANISM; DRUG SCREENING; DRUG STRUCTURE; ENZYME ACTIVITY; ENZYME INHIBITION; IC 50; IN VITRO STUDY; LIPOPHILICITY; MOLECULAR WEIGHT; PLANT ROOT; PRENYLATION; STRUCTURE ACTIVITY RELATION;

AMYLOID PRECURSOR PROTEIN SECRETASES; ASPARTIC ACID ENDOPEPTIDASES; CHOLINESTERASES; CHROMATOGRAPHY, LIQUID; ENZYME INHIBITORS; FLAVONOIDS; MAGNETIC RESONANCE SPECTROSCOPY; PLANT EXTRACTS; SOPHORA; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 77951675664     PISSN: 0192415X     EISSN: None     Source Type: Journal    
DOI: 10.1142/S0192415X10007944     Document Type: Article

References (35)

1. Ancelin, M.L., Y. Christen and K. Ritchie. Is antioxidant therapy a viable alternative for mild cognitive impairment? Examination of the evidence. Dement. Geriatr. Cogn. Disord. 24: 1-19, 2007.
2. Butterfield, D.A., T. Reed, S.F. Newman and R. Sultana. Roles of amyloid β-peptide-associated oxidative stress and brain protein modifications in the pathogenesis of Alzheimer's disease and mild cognitive impairment. Free Radic. Biol. Med. 43: 658-677, 2007.
3. Chen, C.C., P.C. Tsai, B.L. Wei and W.F. Chiou. 8-Prenylkaempferol suppresses inducible nitric oxide synthase expression through interfering with JNK-mediated AP-1 pathway in murine macrophages. Eur. J. Pharmacol. 590: 430-436, 2008.
4. Das, U.N. Acetylcholinesterase and butyrylcholinesterase as possible markers of low-grade systemic inflammation. Med. Sci. Monit. 13: RA214-RA221, 2007.
5. Ellman, G.L., K.D. Courtney, V. Jr. Andres and R.M. Featherstone. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem. Pharmacol. 7: 88-95, 1961.
6. Greig N.H., T. Utsuki, D.K. Ingram, Y. Wang, G. Pepeu, C. Scali, Q.S. Yu, J. Mamczarz, H.W. Holloway, T. Giordano, D. Chen, K. Furukawa, K. Sambamurti, A. Brossi and D.K. Lahiri. Selective butyrylcholinesterase inhibition elevates brain acetylcholine, augments learning and lowers Alzheimer β-amyloid peptide in rodent. Proc. Natl. Acad. Sci. USA 102: 17213-17218, 2005.
7. Hwang, E.M., Y.B. Ryu, H.Y. Kim, D.G. Kim, S.G. Hong, J.H. Lee, M.J. Curtis-Long, S.H. Jeong, J.Y. Park and K.H. Park. BACE1 inhibitory effects of lavandulyl flavanones from Sophora flavescens. Bioorg. Med. Chem. 16: 6669-6674, 2008.
8. Jeong, G.S., B. Li, D.S. Lee, E. Byun, R.B. An, H.O. Pae, H.T. Chung, K.H. Youn and Y.C. Kim. Lavandulyl flavanones from Sophora flavescens protect mouse hippocampal cells against glutamate-induced neurotoxicity via the induction of heme oxygenase-1. Biol. Pharm. Bull. 31: 1964-1967, 2008a.
9. Jeong, T.S., Y.B. Ryu, H.Y. Kim, M.J. Curtis-Long, S.J. An, J.H. Lee, W.S. Lee and K.H. Park. Low density lipoprotein (LDL)-antioxidant flavonoids from roots of Sophora flavescens. Biol. Pharm. Bull. 31: 2097-2102, 2008b.
10. Jung, C.H., S. Zhou, G.X. Ding, J.H. Kim, M.H. Hong, Y.C. Shin, G.J. Kim and S.G. Ko. Antihyper-glycemic activity of herb extracts on streptozotocin-induced diabetic rats. Biosci. Biotechnol. Biochem. 70: 2556-2559, 2006.
11. Jung, H.A., D.M. Jeong, H.Y. Chung, H.A. Lim, J.Y. Kim, N.Y. Yoon and J.S. Choi. Re-evaluation of the antioxidant prenylated flavonoids from the roots of Sophora flavescens. Biol. Pharm. Bull. 31: 908-915, 2008a.
12. Jung, H.A., N.Y. Yoon, S.S. Kang, Y.S. Kim and J.S. Choi. Inhibitory activities of prenylated flavonoids from Sophora flavescens against aldose reductase and advanced glycation endproducts generation. J. Pharm. Pharmacol. 60: 1227-1236, 2008b.
13. - scavenging activities from Sophora flavescens. Arch. Pharm. Res. 28: 1333-1336, 2005a.
14. - scavengers from Sophora flavescens. Arch. Pharm. Res. 28: 534-540, 2005b.
15. Jung, M.J., S.S. Kang, H.A. Jung, G.J. Kim and J.S. Choi. Isolation of flavonoids and a cerebroside from the stem bark of Albizzia julibrissin. Arch. Pharm. Res. 27: 593-599, 2004.
16. Kim, D.W., Y.S. Chi, K.H. Son, H.W. Chang, J.S. Kim, S.S. Kang and H.P. Kim. Effects of sophoraflavanone G, a prenylated flavonoid from Sophora flavescens, on cyclooxygenase-2 and in vivo inflammatory response. Arch. Pharm. Res. 25: 329-335, 2002.
17. Kim, J.H., Y.B. Ryu, N.S. Kang, B.W. Lee, J.S. Heo, I.Y. Jeong and K.H. Park. Glycosidase inhibitory flavonoids from Sophora flavescens. Biol. Pharm. Bull. 29: 302-305, 2006.
18. Kim, J.S., S.J. Han, J.H. Byun, Y.N. Xu, S.W. Yoo, S.S. Kang, K.H. Son, H.W. Chang and H.P. Kim. Minor constituents from the roots of Sophora flavescens. Nat. Prod. Sci. 7: 5-8, 2001.
19. Ling, J.Y., G.Y. Zhang, Z.J. Cui and C.K. Zhang. Supercritical fluid extraction of quinolizidine alkaloids from Sophora flavescens Ait. and purification by high-speed counter-current chromatography. J. Chromatogr. A 1145: 123-127, 2007.
20. Pacher, P., I.G. Obrosova, J.G. Mabley and C. Szabó. Role of nitrosative stress and peroxynitrite in the pathogenesis of diabetic complications. Emerging new therapeutical strategies. Curr. Med. Chem. 12: 267-275, 2005.
21. Parihar, M.S. and T. Hemnani. Alzheimer's disease pathogenesis and therapeutic interventions. J. Clin. Neurosci. 11: 456-467, 2004.
22. Park, J.A., H.J. Kim, C.B. Jin, K.T. Lee and Y.S. Lee, A new pterocarpan, (-)-maackiain sulfate, from the root of Sophora subprostrata. Arch. Pharm. Res. 26: 1009-1013, 2003.
23. Ramassamy, C. Emerging role of polyphenolic compounds in the treatment of neurodegenerative diseases: a review of their intracellular targets. Eur. J. Pharmacol. 545: 51-64, 2006.
24. Rao, A.A., G.R. Sridhar and U.N. Das. Elevated butyrylcholinesterase and acetylcholinesterase may predict the development of type 2 diabetes mellitus and Alzheimer's disease. Med. Hypotheses 69: 1272-1276, 2007.
25. Ryu, S.Y., H.S. Lee, Y.K. Kim and S.H. Kim. Determination of isoprenyl and lavandulyl positions of flavonoids from Sophora flavescens by NMR experiment. Arch. Pharm. Res. 20: 491-495, 1997.
26. +-Glucose cotransporter (SGLT) inhibitory flavonoids from the roots of Sophora flavescens. Bioorg. Med. Chem. 15: 3445-3449, 2007.
27. Scarpini, E., P. Scheltens and H. Feldman. Treatment of Alzheimer's disease: current status and new perspectives. Lancet Neurol. 2: 539-547, 2003.
28. Shimmyo, Y., T. Kihara, A. Akaike, T. Niidome and H. Sugimoto. Flavonols and flavones as BACE-1 inhibitors: structure-activity relationship in cell-free, cell-based and in silico studies reveal novel pharmacophore features. Biochim. Biophys. Acta 1780: 819-825, 2008.
29. Singh, M., M. Arseneault, T. Sanderson, V. Murthy and C. Ramassamy. Challenges for research on polyphenols from foods in Alzheimer's disease: bioavailability, metabolism, and cellular and molecular mechanisms. J. Agric. Food Chem. 56: 4855-4873, 2008.
30. Sugimoto, H. The new approach in development of anti-Alzheimer's disease drugs via the cholinergic hypothesis. Chem. Biol. Interact. 175: 204-208, 2008.
31. Tang W. and G. Eisenbrand. Chinese Drugs of Plant Origin: Chemistry, Pharmacology, and Use in Traditional and Modern Medicine. Springer-Verlag, Berlin, 1992, pp. 931-943.
32. Tweedie D, K. Sambamurti and N.H. Greig. TNF-α inhibition as a treatment strategy for neurodegenerative disorders: new drug candidates and targets. Curr. Alzheimer Res. 4: 378-385, 2007.
33. Vassar, R. β-Secretase (BACE) as a drug target for Alzheimer's disease. Adv. Drug Deliv. Rev. 54: 1589-1602, 2002.
34. Wu, L., T. Miyase, U. Akira, M. Kuroyanagi and T. Noro. Studies on the constituents of Sophora flavescens. Chem. Pharm. Bull. 33: 3231-3236, 1985.
35. Yan, R., M.J. Bienkowski, M.E. Shuck, H. Miao, M.C. Tory, A.M. Pauley, J.R. Brashier, N.C. Stratman, W.R. Mathews, A.E. Buhl, D.B. Carter, A.G. Tomasselli, L.A. Parodi, R.L. Heinrikson and M.E. Gurney. Membrane-anchored aspartyl protease with Alzheimer's disease β-secretase activity. Nature 402: 533-537, 1999.