Prolyl endopeptidase inhibitors from green tea

Archives of Pharmacal Research

Volumn 24, Issue 4, 2001, Pages 292-296

  Kim, Jin Hui ^a   Kim, Sang In ^a   Song, Kyung Sik ^a  

^a Kyungpook National University   (South Korea)

Author keywords

(+) Callocatechin gallate; ( ) Epicatechin gallate; ( ) Epigallocatechin gallate; Green tea leaves; Prolyl endopeptidase inhibitor

Indexed keywords

CATECHIN; DRUG DERIVATIVE; EPICATECHIN GALLATE; EPIGALLOCATECHIN GALLATE; GALLOCATECHIN GALLATE; PLANT EXTRACT; PROLYL ENDOPEPTIDASE; PROTEINASE INHIBITOR; SERINE PROTEINASE;

ARTICLE; CHEMISTRY; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; ISOLATION AND PURIFICATION; KINETICS; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; TEA; ULTRAVIOLET SPECTROPHOTOMETRY;

CAMELLIA SINENSIS; CATECHIN; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; PLANT EXTRACTS; PROTEASE INHIBITORS; SERINE ENDOPEPTIDASES; SPECTROMETRY, MASS, FAST ATOM BOMBARDMENT; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 0035434177     PISSN: 02536269     EISSN: None     Source Type: Journal    
DOI: 10.1007/BF02975094     Document Type: Article

References (32)

1. Aoyagi, T., Nagai, M., Ogawa, K., Gojima, F., Okada, M., Ikeda, T., Hamada, M., and Takeuchi, T., Poststatin, a new inhibitor of prolyl endopeptidase, produced by Streptomyces viridochromogens MH534-30F3. I. Taxonomy, production, isolation, physico-chemical properties and biological activities. J. Antibiotics, 44, 949-955 (1991).
2. Aoyagi, T., Wada, T., Nagai, M., Kojima, F., Harada, S., Takeuchi, T., Takahashi, H., Hirokawa, K., and Tsumita, T., Dificiency of kallikrein-like enzyme activities in cerebral tissue of patients with Alzheimer's disease. Experientia., 46, 94-97 (1990).
3. Arai, H., Nishioka, H., Niwa, S., Yamanaka, T., Tanaka, Y., Yoshinaga, K., Kobayashi, N., Miura, N., and Ikeda, Y., Synthesis of prolyl endopeptidase inhibitors and evaluation of their structure-activity relationships: In vitro inhibition of prolyl endopeptidase from canine brain. Chem. Pharm. Bull., 41, 1583-1588 (1993).
4. Bakker, A. V., Jung, S., Spencer, R. W., Vinick, F. J., and Faraci, W. S., Stow tight-binding of prolyl endopeptidase by benzyloxycarbonyl-prolyl-prolinal. Biochem. J., 271, 559-562 (1990).
5. Behl, C., Alzheimer's disease and Oxidative stress. Implications for novel therapeutic approaches. Prog. Neurobiol., 57, 301-323 (1999).
6. Bieth, J., Spiess. C., and Camille, G. W., The synthesis and analytical use of a highly sensitive and convenient substrate of elastase. Biochem. Med., 11, 350-357 (1974).
7. Checler, F., Processing of the beta-amyloid precursor protein and its regulation in Alzheimer's disease. J. Neurochem., 65, 1431-1444 (1995).
8. Chung, C. H., Ives, H. E., Almeda, S., and Goldberg, A. L., Purification of Escherichia coli of a periplasmic protein that is a potent inhibitor of pancreatic proteases. J. Biol. Chem., 258, 11032-11038 (1983).
9. Es-Safi, N., E., Guerneve, C., L., Cheynier, V., and Moutounet, M., New phenolic compounds obtained by evolution of (+)-catechin and glyoxylic acid in hydroalcoholic medium. Tetrahedron Lett., 41, 1917-1921 (2000).
10. Fan, W., Tezuka, Y., Komatsu, K. Namaba, T., and Kadota, S., Prolyl endopeptidase inhibitors from the underground part of Rhodiola sacra S. H. Fu. Biol. Pharm. Bull., 22, 157-161 (1999).
11. Hubert, F., Gaertner, J., Antoine, J., and Puigserver, Increased activity and stability of poly (ethylene glycol)-modified trypsin. Enzyme Microb. Technol., 14, 150-155 (1992).
12. Hwang, J. -S., Song, K. -S., Kim, W. -G., Lee, T. -H., Koshino, H., and Yoo, I. -D., Polyozellin, a new inhibitor of prolyl endopeptidase from Polyozellus multiflex. J. Antibiotics, 50, 773-777 (1997).
13. Ishiura, S., Tsukahara, T., Tabira, T., Shimizu, T., Arahata, K. and Sugita, H., Identification of a putative amyloid A4-generating enzyme as a prolyl endopeptidase. FEBS., 260, 131-134 (1990).
14. Kim, S. -I. and Song, K. -S., 1,2,3,4,6-Pentagalloyl-β-D-Glucopyranose, A Prolyl Endopeptidase Inhibitor from Moutan Cortex. J. Agric. Chem. & Biotechnol., 43, 158-161 (2000).
15. Kimura, K., Kanou, F., Yoshihama, M., Koshino, H., and Uramoto, M., SNA-8073-B, a new isotetracenone antibiotic inhibits prolyl endopeptidase. J. Antibiotics, 50, 291-296 (1977a).
16. Kimura, K., Kanou, F., Takahashi, H., Esumi, Y., Uramoto, M., and Yoshihama, M., Propeptin, a new inhibitor of prolyl endopeptidase produced by Microbispora. I. Fermentation, isolation and biological properties. J. Antibiotics, 50, 373-378 (1997b).
17. Kimura, K., Kawaguchi, N., Yoshihama, M. and Kawanishi, G., Staurosporine, a prolyl endopeptidase inhibitor. Agric. Biol. Chem. 54, 3021-3022 (1990).
18. Lee, K. -H., Kwak, J. -H. Lee, B. -K., and Song, K. -S., Prolyl endopeptidase inhibitors from Caryophylli Flos. Arch. Pharm. Res., 21, 207-211 (1998).
19. 2+ homeostasis in Alzheimer's disease. Trends Neurosci., 16, 409-414 (1993).
20. Miranda, S., Opazo, C., Larrondo, L., F., Munoz, F., J., Ruiz, F., Leighton, F., and Inestrosa, N., C., The role of oxidative stress in the toxicity induced by amyloid β-peptide in Alzheimer's disease. Prog. Neurobiol., 62, 633-648 (2000).
21. Mitscher, L. A., Jung, M., Shankel. D., Dou, J., Steele, L., and Pillai, S. P., Chemoprotection: A review of the potential therapeutic antioxidant properties of green tea (Camellia sinensis) and certain of its constituents. Med. Res. Rev., 17, 327-365 (1997).
22. Nonaka, C., Kawahara, O., and Nishioka, I., Tannins and related compounds. XV. a new class of dimeric flavan-3-ol gallate, theasinensins A and B, and proanthocyanidin gallates from green tea leaf. Chem. Pharm. Bull., 31, 3906-3914 (1983).
23. Portevin, B., Benoist, A., Remond, G., Herve, Y., Vincent, M., Lepagnol, J., and De Nanteuil, G., New prolyl endopeptidase inhibitors: in vitro and in vivo activities of azabicyclo[2.2.2]octane, azabicyclo[2.2.1]heptane, and perhydroindole derivatives. J. Med. Chem., 39, 2379-2391 (1996).
24. Rennex, D., Hemmings, B. A., Hofsteenge, J., and Stone, S. R., cDNA cloning of porcine brain prolyl endopeptidase and identification of the active-site seryl residue. Biochemistry, 30, 2195-2203 (1991).
25. Saeki, K., Hayakawa, S., Isemura, M., and Miyase, T., Importance of a pyrogallol-type structure in catechin compounds for apoptosis-inducing activity. Phytochemistry, 53, 391-394 (2000).
26. Selkoe, D. J., The molecular pathology of Alzheimer's disease. Neuron, 6, 487-498 (1991).
27. Selkoe, D. J., Normal and abnormal biology of the β-amyloid precursor protein. Annu. Rev. Neurosci., 17, 489-517 (1994).
28. Toda, S., Obi, Y., Numata, K., Hamagishi, Y., Tomita, K., Komiyama, N., Kotake, C., Furumai, T., and Oki, T., Eurystatin A and B, new prolyl endopeptidase inhibitors. I. Taxonomy, production, isolation and biological activities. J. Antibiotics, 45, 1573-1579 (1992).
29. Yoshimoto, T., Kado, K., Matubara, F., Koriyama, N., Kaneto, H., and Tsuru, D., Specific inhibitors for prolyl endopeptidase and their anti-amnesic effect. J. PharmacobioDyn., 10, 730-735 (1987).
30. Yoshimoto, T., Nishimura, T., Kita, T., and Tsuru, D., Postproline cleaving enzyme (prolyl endopeptidase) from bovine brain. J. Biochem., 94, 1179-1190, (1983).
31. Yoshimoto, T., Walter, R., and Tsuru, D., Proline-specific endopeptidase from Flavobacterium. Purification and properties. J. Biol. Chem., 225, 4786-4792 (1980).
32. Yukiaki, K. and Yukihiko, H., Antimutagenic and anticarcinogenic activity of tea polyphenols. Mutat. Res. 436, 69-97, (1999).