11β-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational approaches

Bioorganic and Medicinal Chemistry

Volumn 18, Issue 4, 2010, Pages 1507-1515

  Rollinger, Judith M ^a   Kratschmar, Denise V ^b   Schuster, Daniela ^a   Pfisterer, Petra H ^a   Gumy, Christel ^b   Aubry, Evelyne M ^b   Brandstötter, Sarah ^a   Stuppner, Hermann ^a   Wolber, Gerhard ^a   Odermatt, Alex ^b  

^a UNIVERSITY OF INNSBRUCK   (Austria)

^b UNIVERSITY OF BASEL   (Switzerland)

Author keywords

11 HSD1; Diabetes; Eriobotrya japonica; Glucocorticoid receptor; Metabolic syndrome

Indexed keywords

11BETA HYDROXYSTEROID DEHYDROGENASE 1; 11BETA HYDROXYSTEROID DEHYDROGENASE 2; 2 ALPHA HYDROXY 3 OXO URS 12 EN 28 OIC ACID; 3 EPICOROSOLIC ACID METHYL ESTER; 3 O CIS 4 COUMAROYLTORMENTIC ACID; 3 O TRANS 4 COUMAROYLTORMENTIC ACID; COROSOLIC ACID METHYL ESTER; MASLINIC ACID; OXIDOREDUCTASE INHIBITOR; PENTACYCLIC TRITERPENE; SITOSTEROL; TORMENTIC ACID; TORMENTIC ACID METHYL ESTER; UNCLASSIFIED DRUG; URSOLIC ACID; URSOLIC ACID METHYL ESTER; UVAOL; ENZYME INHIBITOR;

ARTICLE; CATALYSIS; CELL LYSATE; COMPUTER MODEL; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG DETERMINATION; DRUG IDENTIFICATION; DRUG SCREENING; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; LOQUAT; MOLECULAR MODEL; NONHUMAN; PHARMACOPHORE; PHYTOCHEMISTRY; PLANT LEAF; STRUCTURE ACTIVITY RELATION; BIOASSAY; CELL LINE; CHEMICAL STRUCTURE; CHEMISTRY; DATA BASE; DRUG ANTAGONISM; ELECTROSPRAY MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY;

ERIOBOTRYA JAPONICA;

11-BETA-HYDROXYSTEROID DEHYDROGENASE TYPE 1; BIOLOGICAL ASSAY; CELL LINE; DATABASE MANAGEMENT SYSTEMS; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; ERIOBOTRYA; HUMANS; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 75849158958     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2010.01.010     Document Type: Article

References (56)

1. Atanasov A.G., and Odermatt A. Endocr. Metab. Immune Disord.: Drug Targets 7 (2007) 125-140
2. Masuzaki H., Paterson J., Shinyama H., Morton N.M., Mullins J.J., Seckl J.R., and Flier J.S. Science 294 (2001) 2166-2170
3. Masuzaki H., Yamamoto H., Kenyon C.J., Elmquist J.K., Morton N.M., Paterson J.M., Shinyama H., Sharp M.G.F., Fleming S., Mullins J.J., Seckl J.R., and Flier J.S. J. Clin. Invest. 112 (2003) 83-90
4. Hadoke P.W.F., Iqbal J., and Walker B.R. Br. J. Pharmacol. 156 (2009) 689-712
5. Boyle C.D., and Kowalski T.J. Expert Opin. Ther. Pat. 19 (2009) 801-825
6. St. Jean Jr. D.J., Wang M., and Fotsch C. Curr. Top. Med. Chem. 8 (2008) 1508-1523
7. Odermatt A., and Gumy C. Biochem. Pharmacol. 76 (2008) 1184-1193
8. Gumy C., Thurnbichler C., Aubry E.M., Balazs Z., Pfisterer P., Baumgartner L., Stuppner H., Odermatt A., and Rollinger J.M. Fitoterapia 80 (2009) 200-205
9. Li W.L., Zheng H.C., Bukuru J., and De Kimpe N. J. Ethnopharmacol. 92 (2004) 1-21
10. Chen J., Li W.L., Wu J.L., Ren B.R., and Zhang H.Q. Phytomedicine 15 (2008) 98-102
11. De Tommasi N., De Simone F., Cirino G., Cicala C., and Pizza C. Planta Med. 57 (1991) 414-416
12. Li W.-L., Wu J.-L., Ren B.-R., Chen J., and Lu C.-G. Am. J. Chin. Med. 35 (2007) 705-711
13. Lu H., Chen J., Li W.L., Ren B.R., Wu J.L., Kang H.Y., Zhang H.Q., Adams A., and De Kimpe N. J. Ethnopharmacol. 122 (2009) 486-491
14. Lu H., Chen J., Li W.L., Ren B.R., Wu J.L., and Zhang H.Q. Phytomedicine 16 (2009) 967-971
15. Noreen W., Wadood A., Hidayat H.K., and Wahid S.A. Planta Med. 54 (1988) 196-199
16. Schuster D., Maurer E.M., Laggner C., Nashev L.G., Wilckens T., Langer T., and Odermatt A. J. Med. Chem. 49 (2006) 3454-3466
17. Rollinger J.M., Steindl T.M., Schuster D., Kirchmair J., Anrain K., Ellmerer E.P., Langer T., Stuppner H., Wutzler P., and Schmidtke M. J. Med. Chem. 51 (2008) 842-851
18. Amico V., Barresi V., Condorelli D., Spatafora C., and Tringali C. J. Agric. Food Chem. 54 (2006) 810-814
19. Ganguly S.N. Phytochemistry 11 (1972) 2893
20. He X., and Liu R.H. J. Agric. Food Chem. 55 (2007) 4366-4370
21. Li E.-N., Luo J.-G., and Kong L.-Y. Phytochem. Anal. 20 (2009) 338-343
22. Liang Z., Aquino R., De Feo V., De Simone F., and Pizza C. Planta Med. 56 (1990) 330-332
23. Banno N., Akihisa T., Tokuda H., Yasukawa K., Taguchi Y., Akazawa H., Ukiya M., Kimura Y., Suzuki T., and Nishino H. Biol. Pharm. Bull. 28 (2005) 1995-1999
24. Ito H., Kobayashi E., Li S.-H., Hatano T., Sugita D., Kubo N., Shimura S., Itoh Y., and Yoshida T. J. Nat. Prod. 64 (2001) 737-740
25. Biessels H.W.A., Van der Kerk-Van Hoof A.C., Kettenes-Van den Bosch J.J., and Salemink C.A. Phytochemistry 13 (1974) 203-207
26. Fu L., Zhang S., Li N., Wang J., Zhao M., Sakai J., Hasegawa T., Mitsui T., Kataoka T., Oka S., Kiuchi M., Hirose K., and Ando M. J. Nat. Prod. 68 (2005) 198-206
27. Tsichritzis F., and Jakupovic J. Phytochemistry 29 (1990) 3173-3187
28. Seo S., Tomita Y., and Tori K. Tetrahedron Lett. (1975) 7-10
29. Lontsi D., Ngounou N.F., Tapondjou A.L., Sondengam B.L., Bodo B., and Martin M.-T. Phytochemistry 49 (1998) 2473-2476
30. Shimizu M., Fukumura H., Tsuji H., Tanaami S., Hayashi T., and Morita N. Chem. Pharm. Bull. 34 (1986) 2614-2617
31. Taniguchi S., Imayoshi Y., Kobayashi E., Takamatsu Y., Ito H., Hatano T., Sakagami H., Tokuda H., Nishino H., Sugita D., Shimura S., and Yoshida T. Phytochemistry 59 (2002) 315-323
32. Kubota T., Asaka Y., Miura I., and Mori H. Helv. Chim. Acta 65 (1982) 611-619
33. Pardhy M.R.S., and Bhattacharyya S.C. Indian J. Chem., Sect. B 16B (1978) 176-178
34. Syamasundar K.V., Mallavarapu G.R., and Krishna E.M. Phytochemistry 30 (1991) 362-363
35. Berman H.M., Westbrook J., Feng Z., Gilliland G., Bhat T.N., Weissig H., Shindyalov I.N., and Bourne P.E. Nucleic Acids Res. 28 (2000) 235-242
36. Kim K.W., Wang Z., Busby J., Tsuruda T., Chen M., Hale C., Castro V.M., Svensson S., Nybo R., Xiong F., and Wang M. Biochim. Biophys. Acta, Proteins Proteomics 1764 (2006) 824-830
37. Wolber G., Dornhofer A.A., and Langer T. J. Comput. Aided Mol. Des. 20 (2006) 773-788
38. Hughes K.A., Webster S.P., and Walker B.R. Expert Opin. Invest. Drugs 17 (2008) 481-496
39. Dzubak P., Hajduch M., Vydra D., Hustova A., Kvasnica M., Biedermann D., Markova L., Urban M., and Sarek J. Nat. Prod. Rep. 23 (2006) 394-411
40. Miura T., Ueda N., Yamada K., Fukushima M., Ishida T., Kaneko T., Matsuyama F., and Seino Y. Biol. Pharm. Bull. 29 (2006) 585-587
41. Fukushima M., Matsuyama F., Ueda N., Egawa K., Takemoto J., Kajimoto Y., Yonaha N., Miura T., Kaneko T., Nishi Y., Mitsui R., Fujita Y., Yamada Y., and Seino Y. Diabetes Res. Clin. Pract. 73 (2006) 174-177
42. Yamaguchi Y., Yamada K., Yoshikawa N., Nakamura K., Haginaka J., and Kunitomo M. Life Sci. 79 (2006) 2474-2479
43. Wen X., Sun H., Liu J., Wu G., Zhang L., Wu X., and Ni P. Bioorg. Med. Chem. Lett. 15 (2005) 4944-4948
44. Hou W., Li Y., Zhang Q., Wei X., Peng A., Chen L., and Wei Y. Phytother. Res. 23 (2009) 614-618
45. Shi L., Zhang W., Zhou Y.-Y., Zhang Y.-N., Li J.-Y., Hu L.-H., and Li J. Eur. J. Pharmacol. 584 (2008) 21-29
46. Na M., Yang S., He L., Oh H., Kim B.S., Oh W.K., Kim B.Y., and Ahn J.S. Planta Med. 72 (2006) 261-263
47. Takagi S., Miura T., Ishibashi C., Kawata T., Ishihara E., Gu Y., and Ishida T. J. Nutr. Sci. Vitaminol. 54 (2008) 266-268
48. Jang S.-M., Yee S.-T., Choi J., Choi M.-S., Do G.-M., Jeon S.-M., Yeo J., Kim M.-J., Seo K.-I., and Lee M.-K. Int. Immunopharmacol. 9 (2009) 113-119
49. Wen X., Sun H., Liu J., Cheng K., Zhang P., Zhang L., Hao J., Zhang L., Ni P., Zographos S.E., Leonidas D.D., Alexacou K.-M., Gimisis T., Hayes J.M., and Oikonomakos N.G. J. Med. Chem 51 (2008) 3540-3554
50. Ali H., Houghton P.J., and Soumyanath A. J. Ethnopharmacol. 107 (2006) 449-455
51. Wermuth C.G., Ganellin C.R., Lindberg P., and Mitscher L.A. Pure Appl. Chem. 70 (1998) 1129-1143
52. Wolber G., and Langer T. J. Chem. Inf. Comput. Sci. 45 (2005) 160-169
53. Collins D.O., Ruddock P.L.D., Chiverton de Grasse J., Reynolds W.F., and Reese P.B. Phytochemistry 59 (2002) 479-488
54. Weng J.-R., Su H.-J., Yen M.-H., Won S.-J., and Lin C.-N. Chin. Pharm. J. 55 (2003) 267-272
55. Gnoatto S.C.B., Dassonville-Klimpt A., Da Nascimento S., Galera P., Boumediene K., Gosmann G., Sonnet P., and Moslemi S. Eur. J. Med. Chem. 43 (2008) 1865-1877
56. Ding Y., Kinjo J., Yang C., and Nohara T. Phytochemistry 30 (1991) 3703-3707