Anti-AIDS Agents, 11. Betulinic Acid and Platanic Acid as Anti-HIV Principles from Syzigium claviflorum, and the Anti-HIV Activity of Structurally Related Triterpenoids

Betulinic acid [1] and platanic acid [2], isolated from the leaves of Syzigium claviforum, were found to be inhibitors of HIV replication in H9 lymphocyte cells. Evaluation of anti-HIV activity with eight derivatives of 1 revealed that dihydrobetulinic acid [3] was also a potent inhibitor of HIV rep...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 1994-02, Vol.57 (2), p.243-247
Main Authors: Fujioka, Toshihiro, Kashiwada, Yoshiki, Kilkuskie, Robert E, Cosentino, L. Mark, Ballas, Lawrence M, Jiang, Jack B, Janzen, William P, Chen, Ih-Sheng, Lee, Kuo-Hsiung
Format: Article
Language:English
Subjects:
ACQUIRED IMMUNE DEFICIENCY SYNDROME
AIDS/HIV
ANTIVIRAL
ANTIVIRAL AGENTS
Antiviral Agents - isolation & purification
Antiviral Agents - pharmacology
Cells, Cultured
DEFICIENCE IMMUNOLOGIQUE
DEFICIENCIA INMUNOLOGICA
DERIVATIVES
DRUG PLANTS
ENZYME INHIBITORS
EUGENIA
FEUILLE
HIV-1 - drug effects
HIV-1 - physiology
HOJAS
human immunodeficiency virus
Humans
IMMUNOLOGICAL DEFICIENCY
INHIBIDORES DE ENZIMAS
INHIBITEUR D'ENZYME
LEAVES
Lymphocytes - microbiology
MEDICINAL PLANTS
PLANTAS MEDICINALES
PLANTE MEDICINALE
Plants, Medicinal - chemistry
PROTEIN KINASE
Protein Kinase C - antagonists & inhibitors
PROTEINA QUINASA
PROTEINE KINASE
SYZYGIUM
TAIWAN
Triterpenes - isolation & purification
Triterpenes - pharmacology
TRITERPENOIDE
TRITERPENOIDOS
TRITERPENOIDS
VIRICIDAS
Virus Replication - drug effects
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Summary:Betulinic acid [1] and platanic acid [2], isolated from the leaves of Syzigium claviforum, were found to be inhibitors of HIV replication in H9 lymphocyte cells. Evaluation of anti-HIV activity with eight derivatives of 1 revealed that dihydrobetulinic acid [3] was also a potent inhibitor of HIV replication. The C-3 hydroxy group and C-17 carboxylic acid group, as well as the C-19 substituents, contribute to enhanced anti-HIV activity. The inhibitory activity of these compounds against protein kinase C (PKC) was also examined, since a correlation between anti-HIV and anti-PKC activities has been suggested. However, there was no apparent correlation between anti-HIV activity and the inhibition of PKC among these compounds.
ISSN:0163-3864
1520-6025
DOI:10.1021/np50104a008