Biological activity of oleanane triterpene derivatives obtained by chemical derivatization

Molecules

Volumn 18, Issue 10, 2013, Pages 13003-13019

  Cheng, Shi Yie ^a   Wang, Chao Min ^b   Cheng, Hsueh Ling ^c   Chen, Hui Jye ^b   Hsu, Yuan Man ^b   Lin, Yu Chi ^d   Chou, Chang Hung ^b,d  

^a NATIONAL UNIVERSITY OF KAOHSIUNG   (Taiwan)

^b CHINA MEDICAL UNIVERSITY   (Taiwan)

^c NATIONAL PINGTUNG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Taiwan)

^d NATIONAL CHENG KUNG UNIVERSITY   (Taiwan)

Author keywords

Anti hepatitis B virus (HBV); Antibacterial; Cytotoxic; Fatsia polycarpa Hayata; Hypoglycaemic; Oleanane triterpenoids; Wnt responsive reporter activities

Indexed keywords

ANTIDIABETIC AGENT; ANTIINFECTIVE AGENT; ANTIVIRUS AGENT; DRUG DERIVATIVE; GLUCOSE; OLEANOLIC ACID;

ARALIACEAE; ARTICLE; CELL STRAIN HEPG2; CHEMICAL STRUCTURE; CHEMISTRY; CONFORMATION; DRUG EFFECT; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HEPATITIS B VIRUS; HUMAN; IC 50; METABOLISM; MICROBIAL SENSITIVITY TEST; SYNTHESIS; WNT SIGNALING PATHWAY; ANALOGS AND DERIVATIVES; DRUG EFFECTS; HEPG2 CELL LINE; IC50;

ANTI-BACTERIAL AGENTS; ANTIVIRAL AGENTS; ARALIACEAE; GLUCOSE; GRAM-NEGATIVE BACTERIA; GRAM-POSITIVE BACTERIA; HEP G2 CELLS; HEPATITIS B VIRUS; HUMANS; HYPOGLYCEMIC AGENTS; INHIBITORY CONCENTRATION 50; MICROBIAL SENSITIVITY TESTS; MODELS, MOLECULAR; MOLECULAR CONFORMATION; OLEANOLIC ACID; WNT SIGNALING PATHWAY;

EID: 84886636985     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules181013003     Document Type: Article

References (31)

1. Hill, R.A.; Connolly, J.D. Triterpenoids. Nat. Prod. Rep. 2013, 30, 1028-1065.
2. Cheng, S.Y.; Wang, C.M.; Hsu, Y.M.; Huang, T.J.; Chou, S.C.; Lin, E.H.; Chou, C.H. Oleananetype triterpenoids from the leaves and twigs of Fatsia polycarpa. J. Nat. Prod. 2011, 74, 1744-1750.
3. Sun, H.X.; Zheng, Q.F.; Tu, J. Induction of apoptosis in HeLa cells by 3β-hydroxy-12-oleanen-27-oic acid from the rhizomes of Astilbe chinensis. Bioorg. Med. Chem. 2006, 14, 1189-1198.
4. Rojas, R.; Caviedes, L.; Aponte, J.C.; Vaisberg, A.J.; Lewis, W.H.; Lamas, G.; Sarasara, C.; Gilman, R.H.; Hammond, G.B. Aegicerin, the first oleanane triterpene with wide-ranging antimycobacterial activity, isolated from Clavija procera. J. Nat. Prod. 2006, 69, 845-846.
5. Chang, C.I.; Kuo, C.C.; Chang, J.Y.; Kuo, Y.H. Three new oleanane-type triterpenes from Ludwigia octovalvis with cytotoxic activity against two human cancer cell lines. J. Nat. Prod. 2004, 67, 91-93.
6. Zeng, N.; Shen, Y.; Li, L.Z.; Jiao, W.-H.; Gao, P.Y.; Song, S.J.; Chen, W.S.; Lin, H.W. Anti-inflammatory triterpenes from the leaves of Rosa laevigata. J. Nat. Prod. 2011, 74, 732-738.
7. Wang, F.; Hua, H.; Pei, Y.; Chen, D.; Jing, Y. Triterpenoids from the resin of Styrax tonkinensis and their antiproliferative and differentiation effects in human leukemia HL-60 cells. J. Nat. Prod. 2006, 69, 807-810.
8. Djoumessi, A.V.B.; Sandjo, L.P.; Liermann, J.C.; Schollmeyer, D.; Kuete, V.; Rincheval, V.; Berhanu, A.M.; Yeboah, S.O.; Wafo, P.; Ngadjui, B.T.; Opatz, T. Donellanic acids A-C: new cyclopropanic oleanane derivatives from Donella ubanguiensis (Sapotaceae). Tetrahedron 2012, 68, 4621-4627.
9. Ho, J.C.; Chen, C.M.; Row, L.C. Oleanane-type triterpenes from the flowers, pith, leaves, and fruit of Tetrapanax papyriferus. Phytochemistry 2007, 68, 631-635.
10. Cáceres-Castillo, D.; Mena-Rejón, G.J.; Cedillo-Rivera, R.; Quijano, L. 21β-Hydroxy-oleananetype triterpenes from Hippocratea excelsa. Phytochemistry 2008, 69, 1057-1064.
11. Nishino, H.; Nishino, A.; Takayasu, J.; Hasegawa, T.; Iwashima, A.; Hirabayashi, K.; Iwata, S.; Shibata, S. Inhibition of the tumor-promoting action of 12-O-tetradecanoylphorbol-13-acetate by some oleanane-type triterpenoid compounds. Cancer Res. 1988, 48, 5210-5215.
12. Liu, J. Pharmacology of oleanolic acid and ursolic acid. J. Ethnopharmacol. 1995, 49, 57-68.
13. Kashiwada, Y.; Hashimoto, F.; Cosentino, L.M.; Chen, C.H.; Garrett, P.E.; Lee, K.H. Betulinic acid and dihydrobetulinic acid derivatives as potent anti-HIV agents. J. Med. Chem. 1996, 39, 1016-1017.
14. Qian, K.; Kuo, R.Y.; Chen, C.H.; Huang, L.; Morris-Natschke, S.L.; Lee, K.H. Anti-AIDS agents 81. Design, synthesis, and structure-activity relationship study of betulinic acid and moronic acid derivatives as potent HIV maturation inhibitors. J. Med. Chem. 2010, 53, 3133-3141.
15. Crystallographic data for 9 has been deposited with the Cambridge Crystallographic Data Centre (deposition number CCDC 837341). Copies of the data can be obtained, free of charge, on application to the Director, CCDC, 12 Union Road, Cambridge CB21EZ, UK (fax: +44-1223-336033 or e-mail: deposit@ccdc.cam.ac.uk).
16. Chen, H.J.; Lin, C.M.; Lin, C.S.; Perez-Olle, R.; Leung, C.L.; Liem, R.K. The role of microtubule actin cross-linking factor 1 (MACF1) in the Wnt signaling pathway. Genes Dev. 2006, 20, 1933-1945.
17. Volonterio, A.; Ramirez de Arellano, C.; Zanda, M. Synthesis of 1,3,5-trisubstituted hydantoins by regiospecific domino condensation/aza- Michael/O→N acyl migration of carbodiimides with activated α,β-unsaturated carboxylic acids. J. Org. Chem. 2005, 70, 2161-2170.
18. Ganem, D.; Prince, A.M. Hepatitis B virus infection - natural history and clinical consequences. N. Engl. J. Med. 2004, 350, 1118-1129.
19. Egan, B.J.; Marzio, L.; O'Connor, H.; O'Morain, C. Treatment of Helicobacter pylori infection. Helicobacter 2008, 13, 35-40.
20. Chang, J.M.; Chen, T.H. Bacterial foodborne outbreaks in central Taiwan, 1991-2000. J. Food Drug Anal. 2003, 11, 53-59.
21. Tanachatchairtana, T.; Bremner, J.B.; Chokchaisiri, R.; Suksamrarn, A. Antimycobacterial activity of cinnamate-based esters of the triterpenes betulinic, oleanolic and ursolic acids. Chem. Pharm Bull. 2008, 56, 194-198.
22. Cheng, H.L.; Huang, H.K.; Chang, C.I.; Tsai, C.P.; Chou, C.H. A cell-based screening identifies compounds from the stem of Momordica charantia that overcome insulin resistance and activate AMP-activated protein kinase. J. Agric. Food Chem. 2008, 56, 6835-6843.
23. Chang, C.I.; Tseng, H.I.; Liao, Y.W.; Yen, C.H.; Chen, T.M.; Lin, C.C.; Cheng, H.L. In vivo and in vitro studies to identify the hypoglycaemic constituents of Momordica charantia wild variant WB24. Food Chem. 2011, 125, 521-528.
24. MacDonald, B.T.; Tamai, K.; He, X. Wnt/β-catenin signaling: components, mechanisms, and diseases. Developmental cell 2009, 17, 9-26.
25. Sen, M.; Lauterbach, K.; El-Gabalawy, H.; Firestein, G.S.; Corr, M.; Carson, D.A. Expression and function of wingless and frizzled homologs in rheumatoid arthritis. Proc. Natl. Acad. Sci. USA 2000, 97, 2791-2796.
26. Sen, M.; Chamorro, M.; Reifert, J.; Corr, M.; Carson, D.A. Blockade of Wnt-5A/Frizzled 5 signaling inhibits rheumatoid synoviocyte activation. Arthritis Rheum. 2001, 44, 772-781.
27. Moon, R.T.; Kohn, A.D.; De Ferrari, G.V.; Kaykas, A. WNT and β-catenin signalling: diseases and therapies. Nat. Rev. Genet. 2004, 5, 691-701.
28. Clevers, H. Wnt/β-catenin signaling in development and disease. Cell 2006, 127, 469-480.
29. De Ferrari, G.V.; Moon, R.T. The ups and downs of Wnt signaling in prevalent neurological disorders. Oncogene 2006, 25, 7545-7553.
30. Johnson, M.L.; Rajamannan, N. Diseases of Wnt signaling. Rev. Endocr. Metab. Disord. 2006, 7, 41-49.
31. Luo, J.; Chen, J.; Deng, Z.L.; Luo, X.; Song, W.X.; Sharff, K.A.; Tang, N.; Haydon, R.C.; Luu, H.H.; He, T.C. Wnt signaling and human diseases: what are the therapeutic implications? Lab. Invest. 2007, 87, 97-103.