Betulinic acid and its derivatives: A review on their biological properties

Current Medicinal Chemistry

Volumn 12, Issue 6, 2005, Pages 657-666

  Yogeeswari, Perumal ^a   Sriram, Dharmarajan ^a  

^a BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

Author keywords

Anti HIV derivatives; Anti HIV mechanism; Anticancer derivates; Anticancer mechanism; Antiinflammatory; Antimalarial; Betulinic acid; Biotransformation

Indexed keywords

ALANINE DERIVATIVE; AMIDE; ANTIINFECTIVE AGENT; ANTINEOPLASTIC AGENT; ANTIVIRUS AGENT; BETULIC ACID; BETULIN; CD4 ANTIGEN; CHEMOKINE RECEPTOR; CHEMOKINE RECEPTOR CCR4; CHEMOKINE RECEPTOR CCR5; CYTOCHROME C; DECANOIC ACID DERIVATIVE; DIHYDROBETULINIC ACID; DOXORUBICIN; ENVELOPE PROTEIN; GLYCOPROTEIN; GLYCOPROTEIN GP 120; GLYCOPROTEIN GP 41; HERBACEOUS AGENT; INTEGRASE; N' [N [36 HYDROXYL 20(29)ENE 28 OYL] 8 AMINOOCTANOYL] 1 STATIN; PROTEIN P53; PROTEINASE; RNA DIRECTED DNA POLYMERASE; SUCCINIC ACID DERIVATIVE; SYZRGIUM CLAVIFLORUM EXTRACT; TRITERPENOID; UNCLASSIFIED DRUG; UNINDEXED DRUG; YK FH312;

ANTHELMINTIC ACTIVITY; ANTIBACTERIAL ACTIVITY; ANTIINFLAMMATORY ACTIVITY; ANTIMALARIAL ACTIVITY; ANTINEOPLASTIC ACTIVITY; ANTIOXIDANT ACTIVITY; ANTIVIRAL ACTIVITY; BIRCH; DOSE RESPONSE; DRUG MECHANISM; DRUG STRUCTURE; DRUG SYNTHESIS; HUMAN; HUMAN IMMUNODEFICIENCY VIRUS; MEDICINAL PLANT; NONHUMAN; OVARY CARCINOMA; PHYTOCHEMISTRY; PROTEIN FUNCTION; PROTEIN STRUCTURE; REVIEW; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; SYZRGIUM CLAVIFLORUM;

EID: 14744293458     PISSN: 09298673     EISSN: None     Source Type: Journal    
DOI: 10.2174/0929867053202214     Document Type: Review

References (75)

1. Maurya, S.K.; Devi, S.; Pandey, V.B. Fitother., 1989 60, 468.
2. O'Connel, M.M.; Bently, M.D.; Campbell, C.S. Phytochem. 1998, 27, 2175.
3. Cole, B.J.W.; Bently, M.D. Holzforsch., 1991, 45, 265.
4. Kim, D.S.H.L.; Chen, Z.; Nguyen, V.T.; Pezzuto, J.M.; Qiu, S.; Lu, Z. Synth. Commun., 1997, 27, 1607.
5. Fujioka, T.; Kashiwada, Y.; Kilkuskie, R.E.; Consentino, L.M.; Ballas, L.M.; Jiang, J.B.; Janzen, W.P.; Chen, I.S.; Lee, K.H. J. Nat. Prod., 1994, 57, 243.
6. Pisha, E.; Chai, H.; Lee, I.S.; Chagwedera, T.E.; Farnsworth, N.R.; Cordell, G.A.; Beecher, C.W.; Fong, H.H.; Kinghorn, A.D.; Brown, D.H. Nat. Med., 1995, 10, 1046.
7. Kwon, H.C.; Min, Y.D.; Kim, K.R.; Bang, E.J.; Lee, C.S.; Lee, K.R. Arch. Pharm. Res., 2003, 26, 275.
8. Prakash, C.V.S.; Schilling, J.K.; Johnson, R.K.; Kingston, D.G. J. Nat. Prod., 2003, 66, 419.
9. Woldemichael, G.M.; Singh, M.P.; Maiese, W.M.; Timmermann, B.N. Z. Naturforsch., 2003, 58, 70.
10. Chandramu, C.; Manohar, R.D.; Krupadanam, D.G.; Dashavantha, R.V. Phytother. Res., 2003, 17, 129.
11. Kim, D.K.; Nam, I.Y.; Kim, J.W.; Shin, T.Y.; Lim, J.P. Arch. Pharm. Res., 2002, 25, 617.
12. Yamashita, K.; Lu, H.; Lu, J.; Chen, G.; Yokoyama, T.; Sagara, Y.; Manabe, M.; Kodama, H. Clin. Chim. Acta, 2002, 325, 91.
13. De Oliveira, B.H.; Santos, C.A.; Espindola, A.P. Phytochem. Anal., 2002, 13, 95.
14. Zhang, Z.; Elsohly, H.N.; Jacob, M.R.; Pasco, D.S.; Walker, L.A.; Clark, A.M. Planta Med., 2002, 68, 49.
15. Guo, X.; Zhang, L.; Quan, S.; Hong, Y.; Sun, L.; Liu, M. Zhogguo Zhong Yao Za Zhi, 1998, 23, 546.
16. Enwerem, N.M.; Okogun, J.I.; Wambebe, C.O.; okorie, D.A.; Akah, P.A. Phytomed., 2001, 8, 112.
17. Tezuka, Y.; Stampoulis, P.; Banskota, A.H.; Awale, S.; Tran, K.Q.; Saiki, I.; Kadota, S. Chem. Pharm. Bull., 2000, 48 1711.
18. Siddiqui, B.S.; Sultana, I.; Begum, S. Phytochem., 2000, 54, 861.
19. Kim, Y.K.; Yoon, S.K.; Ryu, S.Y. Planta Med., 2000 66, 485.
20. Yi, J.H.; Zhang, G.L.; Li, B.G.; Chen, Y.Z. Phytochem., 2000, 53, 1001.
21. Setzer, W.N.; Setzer, M.C.; Bates, R.B.; Jackes, B.R. Planta Med., 2000, 66, 176.
22. Banskota, A.H.; Tezuka, Y.; Adnyana, I.K.; Xiong, Q.; Hase, K.; Tran, K.Q.; Tanaka, K.; Saiki, I.; Kadota, S. Biol. Pharm. Bull. 2000, 23, 456.
23. Ma, J.; Starck, S.R.; Hecht, S.M. J. Nat. Prod., 1999, 62, 1660.
24. Schuhly, W.; Heilmann, J.; Callis, I.; Sticher, O. Planta Med., 1999, 65, 740.
25. Steele, J.C.; Warhurst, D.C.; Kirby, G.C.; Simmonds, M.S. Phytother. Res., 1999, 13, 115.
26. Krogh, R.; Kroth, R.; Berti, C.; Madeira, A.O.; Sourza, M.M.; Cechinel-Felho, V.; Delle-Monache, F.; Yunes, R.A. Pharmazie, 1999, 54, 464.
27. Bringmann, G.; Saeb, W.; Assi, L.A.; Francois, G.; Narayanan, A.S.S.; Peters, K.; Peters, E.M. Planta Med., 1997, 63, 255.
28. Recio, M.C.; Giner, R.M.; Manez, S.; Gueho, J.; Julien, H.R.; Hostettmann, K.; Rios, J.L. Planta Med., 1995, 61, 9.
29. Son, L.B.; Kaplan, A.P.; Spilevskii, A.A.; Andiia-Pravdivyi, I.; Alekseeva, S.B.; Griborev, V.B.; Shvets, V.I. Bioorg. Khim., 1998, 24, 787.
30. Fujoka, T.; Kashiwada, Y.; Kilkushi, R.E.; Consentino, L.M.; Ballas, L.M.; Jiang, J.B.; Janzen, W.P.; Chen, I.S.; Lee, K.H. J. Nat. Prod., 1994, 57, 243.
31. Mayaux, J.F.; Bousseau, A.; Pauwels, R.; Huet, T.; Henin, Y.; Dereu, N.; Evers, M.; Soler, F.; Poujado, C.; De Clercq, E.; Le Pecq, J.B. Proc. Natl. Acad. Sci., 1994, 91, 3564.
32. Xu, H.X.; Zeng, F.Q.; Wan, M.; Sim, K.Y. J. Nat. Prod., 1996, 59, 643.
33. Pengsuparp, T.; Cai, L.; Fong, H.H.S.; Kinghorn, A.D.; Pezzuto, J.M.; Wani, M.; Wall, M.E. J. Nat. Prod., 1994, 57, 415.
34. Kashiwada, Y.; Hashimota, F.; Cosentina, L.M.; Chen, C.H.; Garren, P.E.; Lee, K.H. J. Med. Chem., 1996, 39, 1016.
35. Evers, M.; Poujade, C.; Soler, F.; Ribeill, Y.; James, C.; Lelievre, Y.; Gueguen, J.C.; Reisdorf, D.; Morize, I.; Pauwels, R.; De Clercq, E.; Henin, Y.; Bousseau, A.; Mayaux, J.F.; Le Pecq, J.B.; Dereu, N. J. Med. Chem., 1996, 39, 1056.
36. Soler, F.; Poujade, C.; Evers, M.; Carry, J.C.; Henin, Y.; Bousseau, A.; Huet, H.; Pauwels, R.; De Clercq, E.; Mayaux, J.F.; Le Pecq, J.B.; Dereu, N. J. Med. Chem., 1996, 39, 1069.
37. Sun, I.C.; Wang, H.K.; Kashiwada, Y.; Shen, J.K.; Cosentino, L.M.; Chen, C.H.; Yang, L.M.; Le, K.H. J. Med. Chem., 1998, 41, 4648.
38. Kashiwada, Y.; Chiyo, J.; Ikeshino, Y.; Nagao, T.; Okabe, H.; Cosentino, L.M.; Fowke, K.; Lee, K.H. Bioorg. Med. Chem. Lett., 2001, 11, 183.
39. Sun, I.C.; Chen, C.H.; Kashiwada, Y.; wu, J.H.; Wang, H.K.; Lee, K.H. J. Med. Chem., 2002, 45, 4271.
40. Freed, E.O.; Martin, M.A. J. Biol. Chem., 1995, 270, 23883.
41. Berger, E.A.; Murphy, P.M.; Farber, J.M. Annu. Rev. Immunol., 1999, 17, 657.
42. Sattentau, Q.J.; Moore, J.P. J. Exp. Med., 1991, 174, 407.
43. Moore, J.P.; McKeating, J.H.; Huang, Y.; Ashkenazi, A.; Ho, D. D. J. Virol., 1992, 66, 235.
44. Gallaher, W.R.; Ball, J.M.; Garry, R.T.; Grittin, M.C.; Montelaro, R.C. AIDS Res. Hum. Retroviruses, 1989, 67, 5939.
45. Helseth, E.; Olshevsky, U.; Furman, C.; Sodroski, J. J. Virol., 1991, 65, 2119.
46. Chan, D.C.; Fass, D.; Berger, J.M.; Kim, P.S. Cell, 1997, 89, 263.
47. Caffrey, M.; Cai, M.; Kaufman, J.; Stahl, S.J.; Wingfield, P.T.; Covell, D.G.; Gronenborn, A.M.; Clore, G.M. EMBO J, 1998 17, 4572.
48. Freed, E.O.; Myers, D.J.; Risser, R. J. Virol., 1991 63, 190.
49. Wild, C.; Oas, T.; McDanal, C.; Bolognesi, D.; Matthews, T. Proc. Natl. Acad. Sci. USA, 1992, 89, 10537.
50. Kanamoto, T.; Kashiwada, Y.; Kanbara, K.; Gotoh, K.; Yoshimori, M.; Goto, T.; Sano, K.; Nakashima, H. Antimicrob. Agents Chemother., 2001, 45, 1225.
51. Tochikura, T.S.; Nakashima, H.; Tanabe, A.; Yamamoto, N. Virol., 1988, 164, 542.
52. Kimpton, J.; Emerman, M. J. Virol., 1992, 66 2232.
53. Kohno, T.; Fujioka, Y.; Goto, T.; Morimatsu, S.; Morita, C.; Nakano, T.; Sano, K. J. Virol. Methods, 1998, 72, 137.
54. Nakashima, H.; Ichiyama, K.; Inaazawa, K.; Ito, M.; Hayashi, H.; Nishihara, Y.; Tsujii, E.; Kino, T. Biol. Pharm. Bull., 1996 19, 405.
55. Holz-Smith, S.L.; Sun, I.C.; Jin, L.; Matthews, T.J.; Lee, K.H.; Chen, C.H. Antimicrob. Agents Chemother., 2001, 45 60.
56. Fischer, D.E. Cell, 1994, 78, 539.
57. Kroemer, G.; Zamzami, N.; Susin, S.A. Immunol. Today, 1997, 18, 44.
58. Decaudin, D.; Geley, S.; Hisch, T.; Castedo, M.; Marchelti, P.; Macho, A.; Kofler, R.; Kroemer, G. Cancer Res., 1997, 57, 62.
59. Setzer, E.; Pimental, E.; Wacheck, V.; Schlegal, W.; Pehamberger, H.; Jansen, B.; Kodym, R. J. Invest. Dermatol., 2000, 114, 935.
60. Zuco, V.; Supino, R.; Righeltis, S.C.; Cleris, L.; Marchesi, E.; Passerini, C.G.; Formelli, F. Cancer Lett., 2002, 175 17.
61. Fulda, S.; Jeremias, I.; Pietsh, T.; Debatin, K.M. Klin. Padiatr., 1999, 211, 319.
62. Fulda, S.; Jeremias, I.; Steiner, H.H.; Pietsch, T.; Debatin, K.M. Int. J. Cancer, 1999, 82, 435.
63. Jeong, H.J.; Chai, H.B.; Park, S.Y.; Kim, D.S.H.L. Bioorg. Med. Chem. Lett., 1999, 9, 1201.
64. Kim, J.Y.; Koo, H.M.; Kim, D.S.H.L. Bioorg. Med. Chem. Lett., 2001, 11, 2405.
65. Fulda, S.; Friesen, C.; Los, M.; Scaffidi, C.; Mier, W.; Benedict, M.; Nunez, G.; Krammer, P.H.; Peter, M.E.; Debatin, K.M. Cancer Res., 1997, 57, 4956.
66. Fulda, S.; Scaffidi, C.; Susin, S.A.; Krammer, P.H.; Kroemer, G.; Peters, M.E.; Debatin, K.M. J. Biol. Chem., 1998, 273 33942.
67. Chou, K.J.; Fang, H.C.; Chung, H.M.; Cheng, J.S.; Lee, K.C.; Tseng, L.L.; Tang, K.Y.; Jan, C.R. Eur. J. Pharmacol., 2000, 408, 99.
68. Baltina, L.A.; Flekhter, O.B.; Nigmatullina, L.R.; Boreko, E.I.; Pavlova, N.I.; Nikolaeva, S.N.; Savinova, O.V.; Tolstikov, G.A. Bioorg Med. Chem. Lett., 2003, 13, 3549.
69. Pavlova, N.I.; Savinova, O.V.; Nikolaeva, S.N.; Boreko, E.I.; Flekhter, O.B. Fitother., 2003, 74, 489.
70. Clark, A.M.; Hufford, C.D. Med. Res. Rev., 1991, 11, 473.
71. Chatterjee, P.; Pezzuto, J.M.; Kouzi, S.A. J. Nat. Prod. 1999, 62, 761.
72. Kouzi, S.A.; Chatterjee, P.; Pezzuto, J.M.; Hamann, M.T. J. Nat. Prod., 2000, 63, 1653.
73. Chatterjee, P.; Kouzi, S.A.; Pezzuto, J.M.; Hamann, M.T. Appl. Environ. Microbiol., 2000, 66, 3850.
74. Udeani, G.O.; Zhao, G.M.; Shin, Y.G.; Cooke, B.P.; Graham, J.; Beecher, C.W.W.; Kinghorn, A.D.; Pezzuto, J.M. Biopharm. Drug Dispos., 1999, 20, 379.
75. Cheng, X.; Shin, Y.G.; Levine, B.S.; Smith, A.C.; Tomaszewski, J.E.; Van Breemen, R.B. Rapid Commun. Mass Spectrum., 2003, 17, 2089.