Betulinic acid

Article number:

7500633

CAS No.:

472-15-1

Formula:

C30H48O3

Chemical description:

Betulinic acid is isolated from Platanus acerifolia. Its pharmacological properties are anti-malarial, anti-protozoal, anti-HIV, anti-inflammatory, anthelmintic, proapoptotic.

Synonyms:

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysene-3a-carboxylic acid; 3ß-Hydroxy-lup-20(29)-en-28-säure, 3-beta-Hydroxy-20(29)-lupaene-28-oic acid; Betulic acid; Mairin

Molecular weight:

456,71 g/mol

Betulinic acid induces a novel cell death pathway that depends on cardiolipin modification. Potze L, Di Franco S, Grandela C, Pras-Raves ML, Picavet DI, van Veen HA, van Lenthe H, Mullauer FB, van der Wel NN, Luyf A, van Kampen AH, Kemp S, Everts V, Kessler JH, Vaz FM, Medema JP. Oncogene. 2015 Apr 20. doi: 10.1038/onc.2015.102. [Epub ahead of print] *** Sequential treatment with betulinic acid followed by 5-fluorouracil shows synergistic cytotoxic activity in ovarian cancer cells. Wang YJ, Liu JB, Dou YC. Int J Clin Exp Pathol. 2015 Jan 1;8(1):252-9. eCollection 2015. *** Betulinic acid attenuates renal oxidative stress and inflammation in experimental model of murine polymicrobial sepsis. Lingaraju MC, Pathak NN, Begum J, Balaganur V, Ramachandra HD, Bhat RA, Ram M, Singh V, Kandasamy K, Kumar D, Kumar D, Tandan SK. Eur J Pharm Sci. 2015 Apr 5;70:12-21. doi: 10.1016/j.ejps.2015.01.001. Epub 2015 Jan 10. *** Characterization and in vitro studies of the anticancer effect of oxidized carbon nanotubes functionalized with betulinic acid. Tan JM, Karthivashan G, Arulselvan P, Fakurazi S, Hussein MZ.Drug Des Devel Ther. 2014 Nov 20;8:2333-43. doi: 10.2147/DDDT.S70650. eCollection 2014. *** Investigation of antimalarial activity, cytotoxicity and action mechanism of piperazine derivatives of betulinic acid. Silva GN, Schuck DC, Cruz LN, Moraes MS, Nakabashi M, Gosmann G, Garcia CR, Gnoatto SC.Trop Med Int Health. 2015 Jan;20(1):29-39. doi: 10.1111/tmi.12395. Epub 2014 Oct 13. *** Betulinic acid negates oxidative lung injury in surgical sepsis model. Lingaraju MC, Pathak NN, Begum J, Balaganur V, Bhat RA, Ram M, Kumar D, Kumar D, Tandan SK.J Surg Res. 2015 Feb;193(2):856-67. doi: 10.1016/j.jss.2014.09.008. Epub 2014 Sep 10. *** Potent anti-inflammatory activity of betulinic acid treatment in a model of lethal endotoxemia. Costa JF, Barbosa-Filho JM, Maia GL, Guimarães ET, Meira CS, Ribeiro-dos-Santos R, de Carvalho LC, Soares MB.Int Immunopharmacol. 2014 Dec;23(2):469-74. doi: 10.1016/j.intimp.2014.09.021. Epub 2014 Oct 1.

Plant:

occurs mainly in the bark of many different plant species, especially in the bark of trees belonging to the families of the sycamore, birch and ebony, e.g. with approx. 2.5 % in the bark of sycamore trees (Plantanus acerifolia) and to a small percentage in the dried bark sap of birch trees.

  • In laboratory tests, it has an inhibitory effect on melanoma cells (by initiating the cell death program) and HI viruses (by inhibiting reverse transcriptase).
  • It is the starting material for advanced AIDS drugs such as Bevirimat, which is currently undergoing clinical trials.
  • Efficacy of betulinic acid against dermatophytes and plasmodia indicates the original utility of the substance against fungal and plasmodial infestations of the plant

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Betulinic acid

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