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

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...

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Published in:Journal of natural products (Washington, D.C.) D.C.), 1998-09, Vol.61 (9), p.1090-1095
Main Authors: Kashiwada, Yoshiki, Wang, Hui-Kang, Nagao, Tsuneatsu, Kitanaka, Susumu, Yasuda, Ichiro, Fujioka, Toshihiro, Yamagishi, Takashi, Cosentino, L. Mark, Kozuka, Mutsuo, Okabe, Hikaru, Ikeshiro, Yasumasa, Hu, Chang-Qi, Yeh, Eric, Lee, Kuo-Hsiung
Format: Article
Language:English
Subjects:
Anti-HIV Agents - chemistry
Anti-HIV Agents - isolation & purification
Anti-HIV Agents - pharmacology
Biological and medical sciences
Cell Line
General pharmacology
Humans
Medical sciences
Oleanolic Acid - analogs & derivatives
Oleanolic Acid - chemistry
Oleanolic Acid - isolation & purification
Oleanolic Acid - pharmacology
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
Plants, Medicinal - chemistry
Triterpenes - chemistry
Triterpenes - isolation & purification
Triterpenes - pharmacology
Viral Plaque Assay
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Summary: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 μg/mL, and inhibited H9 cell growth with an IC50 value of 21.8 μg/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 μg/mL, T. I. 16.6). Although ursolic acid did show anti-HIV activity (EC50 2.0 μg/mL), it was slightly toxic (IC50 6.5 μg/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 1β-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 μg/mL and a T. I. value of 22 400.
ISSN:0163-3864
1520-6025
DOI:10.1021/np9800710