Anti-AIDS Agents. 30. Anti-HIV Activity of Oleanolic Acid, Pomolic Acid, and Structurally Related Triterpenoids

Abstract

Oleanolic acid (1) was identified as an anti-HIV principle from several plants, including Rosa woodsii (leaves), Prosopis glandulosa (leaves and twigs), Phoradendron juniperinum (whole plant), Syzygium claviflorum (leaves), Hyptis capitata (whole plant), and Ternstromia gymnanthera (aerial part). It inhibited HIV-1 replication in acutely infected H9 cells with an EC50 value of 1.7 microg/mL, and inhibited H9 cell growth with an IC50 value of 21.8 microg/mL [therapeutic index (T. I.) 12.8]. Pomolic acid, isolated from R. woodsii and H. capitata, was also identified as an anti-HIV agent (EC50 1.4 microg/mL, T. I. 16.6). Although ursolic acid did show anti-HIV activity (EC50 2.0 microg/mL), it was slightly toxic (IC50 6.5 microg/mL, T. I. 3.3). A new triterpene (11) was also isolated from the CHCl3-soluble fraction of R. woodsii, though it showed no anti-HIV activity. The structure of 11 was determined to be 1beta-hydroxy-2-oxopomolic acid by spectral examination. Based on these results, we examined the anti-HIV activity of oleanolic acid- or pomolic acid-related triterpenes isolated from several plants. In addition, we previously demonstrated that derivatives of betulinic acid, isolated from the leaves of S. claviflorum as an anti-HIV principle, exhibited extremely potent anti-HIV activity. Accordingly, we prepared derivatives of oleanolic acid and evaluated their anti-HIV activity. Among the oleanolic acid derivatives, 18 demonstrated most potent anti-HIV activity, with an EC50 value of 0. 0005 microg/mL and a T. I. value of 22 400.

Antibacterial activity of oleanolic and ursolic acids and their derivatives

“…OA, UA and their derivatives efficiently inhibit the development of several viruses including HIV. The mechanism of their antiviral activity is already partially resolved, which should permit the therapeutic use of these compounds in the near future [16][17][18][19][20].…”

Extended longevity ofDrosophila melanogasterby water and ethanol extracts ofStachys lavandulifolia

“…Both oleonolic acid and ursolic acid, which are rather similar because of the closeness of their chemical structures, have many important pharmacological effects. The literature includes numerous data on anti-inflammatory (Safayhi & Sailer, 1997), antitumor (Ovesna et al, 2004), anti-HIV (Kashiwada et al, 1998), antimicrobial (Mallavadhani et al, 2004. ), antifungal (Rocha et al, 2004), hypoglycemic (Perez et al, 1998) and antihyperlipidemic (Ma, 1982) properties.…”

Simultaneous Quantification of Bioactive Triterpene acids (Ursolic acid and Oleanolic acid) in Different Extracts of Eucalyptus globulus (L) by HPTLC Method

“…promising compounds for the development of new multi-targeting bioactive agents [5][6][7][8] For example, oleanolic and ursolic acids show significant antiinflammatory, [9][10][11][12][13][14][15][16] anticancer, 17 Anti-Platelet Aggregation, [18][19] Anti-HIV/AIDS, [20][21] Anti-Mycobaterium Tuberculosis, [22][23][24][25][26][27] anti-proliferative 28 and hepatoprotective [29][30][31] properties in laboratory animals.…”