Pochodne kwasu oleanolowego i ich dzialanie farmakologiczne

• Autorzy: Choluj A , Janiszowska W.
• Języki publikacji: PL

Abstrakty

PL

Oleanolic acid, a pentacyclic triterpenoid of oleanane type, occurs free or more often as glycosides and glycoside esters in at least 120 species of the Magnoliopsydia class. These compounds arouse intense interest of pharmaceutical industry, because they occur mainly in medical plants. They have a wide spectrum of pharmaceutical activities and due to these activities seem to be promising drugs of natural origin. Their antiinflammatory, immuno­modulatory, cytotoxic, anti-tumor, antimutagenic, antihepatotoxic, antidiabetic, hemolyt­ic, antiviral, antibacterial and trypanocidal activities were described in many experiments. Moreover, in these studies, we can observe clear structure-activity relationship.

EN

Kwas oleanolowy, pentacykliczny triterpen typu oleananu, występuje w postaci wolnej lub znacznie częściej w postaci glikozydów lub glikozydoestrów w co najmniej 120 gatunkach Magnoliopsydia. Związki te występują głównie w roślinach leczniczych i wykazują działanie przeciwzapalne, immunomodulujące, cytotoksyczne, antynowotworowe, przeciwwiruso- we, bakteriobójcze lub pierwotniakobójcze, przy czym możemy zaobserwować wyraźną zależność pomiędzy ich strukturą a funkcją. W związku z tym wydają się być obiecującymi lekami pochodzenia naturalnego.

Słowa kluczowe

PL

kwas oleanolowy; saponiny; aktywnosc farmakologiczna

• Wydawca: -
• Czasopismo: Herba Polonica
• Rocznik: 2005
• Tom: 51
• Numer: 1-2
• Opis fizyczny: s.66-76,rys.,tab.,bibliogr.

Twórcy

autor

Choluj A

• Uniwersytet Warszawski, ul.Miecznikowa 1, 02-096 Warszawa

autor

Janiszowska W.

Bibliografia

• 1. Patočka J. Biologically active pentacyclic triterpenes and their current medicine signification.] App Biomed 2003; 1(1):7- 12.
• 2. Mahato SB, Nandy AK, Roy G. Triterpenoids. Phytochemistry 1992; 31(7):2199-249.
• 3. Mahato SB, Sarkar SK, Poddar G. Triterpenoid saponins. Phytochemistry 1988; 27(10);3037-67.
• 4. Ida Y, Satoh Y, Katoh M, Katsumata M, Nagasao M, Yamaguchi K et al. Achyranthosides A and B, now! cytotoxic saponins from Achyranthes faureri roots. Tetrahedron Lett 1994; 35(37):6887-90.
• 5. Massiot G, Dijoux MG, Lavaud C, Le Men-Olivier L, Connolly JD, Sheeley DM. Seco-glycosides of oleanolic acid from Beta vulgaris. Phytochemistry 1994; 37(6): 1667-70.
• 6. Zhang H, Lu Z, Tan GT, Qiu S, Farshworth NR, Pezzuto JM, Fong HS. Polyacetyleneginsenoside-Ro, a novel triterpene saponin from Panax ginseng. Tetrahedron Lett 2002; 43(6):973-7.
• 7. Liu J. Pharmacology of oleanolic acid and ursolic acid. J Ethnopharmacol 1995; 49(2). 57-68.
• 8. Kasprzyk Z, Wojciechowski Z. The structure of triterpenic glycosides from flowers of Calendula officinalis L. Phytochemistry 1967; 6(1 ):69-75.
• 9. Kasprzyk Z, Wojciechowski Z, Janiszowska W. Incorporation of 1-uC-acetate into glycosides of oleanolic acid in Calendula officinalis. Phytochemistry 1970; 9(3):561-4.
• 10. Ruszkowski D, Szakiel A, Janiszowska W. Metabolism of [3-3H]oleanolic acid in Calendula officinalis roots. APP 2003; 25(4):31l-7.
• 11. Yoshikawa M, Matsuda H, Harada E, Murakami T, Wariishi N, YamaharaJ et al. Elatoside E, a new hypoglycemic principle from the root cortex of Aralia elata: structure related hypoglycemic activity of B oleanolic acid glycosides. Chem Pharm Bull 1994; 42(6):1364-6.
• 12. Shao B, Qin G, Xu R, Wu H, Ma K. Triterpenoid saponins from Clematis chinensis. Phytochemistry 1995; 38(3);1473-5.
• 13. Thapliyal RP, Bahuguna RP. An oleanolic acid based bisglycoside from Clematis montana roots. Phytochemistry 1993; 34(3):861-2.
• 14. Hikino H, Kiso Y, Kinouchi J, Sanada S, Shoji J. Antihepatotoxic action of ginsenosides from Panax ; ginseng roots. Planta Med 1985; 51(1);62-4.
• 15. Matsuda H, Namba K, Fukada S, Tani T, Kubo M. Pharmacological study on Panax ginseng CA. Mayer. III. Effects of red ginseng on experimental dissamited intervascular coagulation. (2). Effects of ginsenosides on blood coagulative and fibrolytic system. Chem Pharm Bull 1986; 34(3):1153-7.
• 16. Matsuda H, Samukawa K, Kubo M. Anti-inflamatory activity of ginsenoside Ro. Planta Med 1989; 56(1): 19-23.
• 17. Matsuda H, Samukawa K, Fukuda S, Shimoto H, Chung-Ning T, Kubo M. Studies of Panax japonicus ] fibrinolysis. Planta Med 1989; 55(1 ):18-21.
• 18. Hasegawa H, Matsumiya S, Murakami C, Kurokawa T, Kasai R, Ischibashi S et al. Inhibitory effect of some triterpenoid saponins on glucose transport in tumor cells and its application to in vitro cytotoxic and antiviral activities. Planta Med 1994; 60(2):240-7.
• 19. Dharmananda S. Platycodon and other Chinese herbs with triterpene glycosides. http://www. itmonline.org/arts/latyg.htm 2000.
• 20. Huan VD, Yamamura S, Ohtani K, Kasai R, Yamasaki K, Nham NT et al. Oleanane saponins from Polyscias fiuticosa. Phytochemistry 1998; 47(3):451-7.
• 21. Agarwal SK, Rastogi R. Triterpenoid saponins and their genins. Phytochemistry 1974; 13(12):2623-45.
• 22. Marquina S, Maldonado N, Garduno-Ramirez EA, Villarreal ML, Navarro V, Bye R et al. Bioactive oleanolic acid saponins and other constituents from the roots of Viguiera decurrens. Phytochemistry 2001; 56(1 ):93-7.
• 23. Chen W, Wu WW, Sticher O, Nanz D. Leonticins A-C, three octasaccharide saponins from Leontice kianganensis. J Nat Prod 1996; 59(8):722-8.
• 24. Gafner F, Msonthi DJ, Hostettman K. Molluscicidal saponins from Talinum tenissinum. Helv Chim Arta 1985; 68(5):555-9.
• 25. Miyakoshi M, Shirasuna K, Hirai Y, Shingu K, Isoda S, Shoji J et al. Triterpenoid saponins of Acanthopanax nipponicus leaves. J Nat Prod 1999; 62(3):445-8.
• 26. Bahuguna RP.Jangwan JS, Sakakibara T. Clemontanoside-A, a bisglycoside from Clematis montana. Phytochemistry 1989; 28(9):2511-13.
• 27. Siddiqui BS, Sultana I, Begum S. Triterpenoidal constituents from Eucalyptus camaldulensis var. obtusa leaves. Phytochemistry 2000; 54(8):861-5.
• 28. Ye WC, Zhang QW, Liu X, Che CT, Zhao SH. Oleanane saponins from Gymnema sylvestre. Phytochemistry 2000; 53(8):893-9.
• 29. Elias R, Meo MD, Vidal-Ollivier E, Laget M, Baiansard G, Dumenil G. Antimutagenic activity of some saponins isolated from Calendulla officinalis L., C. arvensis and Hederá helix L. Mutagenesis 1990; 5(4):327-31.
• 30. Martinet A, Ndjoko K, Terreaux C, Marston A, Hostettmann K, Schutz Y. NMR and LC-MSN characterisation of two minor saponins from Ilex paraguariensis. Phytochem Anal 2001 ; 12( 1 ).48-52
• 31. Strzelecka H, Kowalski J. Encyklopedia zielarstwa i ziołolecznictwa. Warszawa: PWN, 2000:44, 65, 68, 189, 314, 329, 374, 511, 525, 536, 577, 594.
• 32. Fumiko A, Yamauchi T, Nagano T, Kinjo J, Okabe H, Higo H et al. Ursolic acid as a trypanocidal constituent in rosemary. Biol Pharm Bull 2002; 25(11): 1485-7.
• 33. Cai L, Wu CD. Compounds from Syzygium aromaticum possessing growth inhibitory activity against oral pathogens. J Nat Prod 1996; 59(10):987-90.
• 34. Ismaili H, Tortora S, Sosa S, Fkih-Tetouani S, Ilidrissi A, Della Loggia R et al. Topical anti- inflammmatory activity of Thymus willdenowii. J Pharm Pharmacol 2001; 53(12):1645-52.
• 35. Wollenweber E, Wieland A, Hass K. Epicuticular waxes and flavonol aglycones of the european mistletoe, Viscum album L. Z Naturforsh [C]2000; 55(5-6):314-7.
• 36. Kasprzyk Z, Wojciechowski Z, Kuczewska-Jankowska A. The glycosides of triterpenic acid from Helianthus annus L. Flowers. Bull Acad Polon Sei 1966; 14(11-12):747-9.
• 37. Bisset RG, Wichtl M. Herbal drugs and phytopharmaceuticals. Boca Raton: CRC Press, 2001:167,446.
• 38. Woldemichael GM, Singh MP, Maiese WM, Timmermann BN. Constituents of bacterial extract of Caesalpinia paraguariensis Burk. Z Naturforsch [C] 2003; 58(l-2):70-5.
• 39. Lemmich E, Cornett C, Furu P, Jorstian C, Knudse DA, Oisen CE et al. Molluscicidal saponins from Catunaregam nilotica. Phytochemistry 1995; 39(1):63-8.
• 40. Bedir E, Kirmizipekmez H, Stitcher O, Cal D. Triterpene saponins from the fruits of Hedera helix. Phytochemistry 2000; 53(8):905-9.
• 41. Matsuda H, Li Y, Murakami T, Matsumara J, YamaharaJ, Yoshikawa M. Antidiabetic principles of natural medicines. 111. Structure-related inhibitory activity and action mode of oleanolic acid glycosides on hypoglycemic activity. Chem Pharm Bull 1998; 46(9): 1399-403.
• 42. Parkhurst PM, Thomas WD, Skinner WA. Molluscicidal saponins of Phytolacca dodecanra: Oleanoglycotoxin-A. Phytochemistry 1973; 12(6): 1437-42.
• 43. Wolbis M, Olszewska M, Wesołowski WJ. Triterpenes and sterols in flowers and leaves of Prunus spinosa L. (Rosaceae). Acta Pol Pharm 2001; 58(6):459-62.
• 44. Dubois M, Benze S, Wagner H. New biologically active triterpene saponins from Randia dumetorum. Planta Med 1990; 56(5):451-5.
• 45. Kanchanapoom T, Kasai R, Yamasaki K. Acetylated triterpene saponins from the Thai medicinal plant, Sapindus emarginatus. Chem Pharm Bull 2001; 49(9):1195-7.
• 46. Dini I, Schettino O, Simioli T, Dini A. Studies on the constituents of Chenopodium quinoa seeds: isolation and characterization of new triterpene saponins. J Agrie Food Chem 2001; 49(2):741-6.
• 47. Tiwari KP, Singh RB. Rivularinin, a new saponin from Anemone rivularis. Phytochemistry 1978; 17(11): 1991-4.
• 48. Kamel MS, Mohamed KM, Hassanean HA, Ohtani K, Kasai R, Yamasaki K. Acylated favonoid glycosides from Bassia muricata. Phytochemistry 2001;57(8). 1259-62
• 49. De Tommasi N, Conti C, Stein ML, Pizza C. Structure and in vitro antiviral activity of «-¡terpenoid saponins from Calendula arvensis. Planta Med 1991 ;57(3).250-3
• 50. Tripathi RP, Tiwari KP. Geniculatin, a «¡terpenoid saponin from Euphorbia geniculata.j Nat Prod 1980; 19(16).2163-9
• 51. Miyase T, Melek FR, El-Gindi OD, Abdel-Khalik SM, Haggag MY, Hila! SH. Saponins from Fagonia arabica. Phytochemistry 1996;41(4).1175-9