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 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.
Fujioka
T
T
Natural Products Laboratory, Division of Medicinal Chemistry, University of North Carolina, Chapel Hill 27599.
Kashiwada
Y
Y
Kilkuskie
R E
RE
Cosentino
L M
LM
Ballas
L M
LM
Jiang
J B
JB
Janzen
W P
WP
Chen
I S
IS
Lee
K H
KH
D000998:Antiviral Agents / Q000302:isolation & purification* / Q000494:pharmacology; D002478:Cells, Cultured; D015497:HIV-1 / Q000187:drug effects* / Q000502:physiology; D006801:Humans; D008214:Lymphocytes / Q000382:microbiology; D053978:Pentacyclic Triterpenes; D010946:Plants, Medicinal / Q000737:chemistry*; D011493:Protein Kinase C / Q000037:antagonists & inhibitors; D014315:Triterpenes / Q000302:isolation & purification* / Q000494:pharmacology; D014779:Virus Replication / Q000187:drug effects; D000094062:Betulinic Acid
D000998:Antiviral Agents; D053978:Pentacyclic Triterpenes; D014315:Triterpenes; C087107:platanic acid; D011493:Protein Kinase C; D000094062:Betulinic Acid