Bioactive 12-oleanene triterpene and secotriterpene acids from Maytenus undata.
The aerial parts of Maytenus undata yielded four new 12-oleanene and 3,4-seco-12-oleanene triterpene acids, namely, 3-oxo-11alpha-methoxyolean-12-ene-30-oic acid (1), 3-oxo-11alpha-hydroxyolean-12-ene-30-oic acid (2), 3-oxo-olean-9(11), 12-diene-30-oic acid (3), and 3,4-seco-olean-4(23),12-diene-3, 29-dioic acid (20-epi-koetjapic acid) (5), together with the known 3, 11-dioxoolean-12-ene-30-oic acid (3-oxo-18beta-glycyrrhetinic acid) (4), koetjapic acid (6), and the 12-oleanene artifact 3-oxo-11alpha-ethoxyolean-12-ene-30-oic acid (7). Koetjapic acid (6) inhibited the growth of Staphylococcus aureus, methicillin-resistant S. aureus, and Pseudomonas aeruginosa, with an MIC range of 3.125-6.25 microg/mL. The new 3,4-secotriterpene acid 20-epi-koetjapic acid (5) potently inhibited rat neonatal brain microglia phorbol ester-stimulated thromboxane B(2) (IC(50) = 0.5 microM) and superoxide anion (IC(50) = 1.9 microM) generation.
Muhammad
I
I
Medicinal, Aromatic and Poisonous Plants Research Center (MAPPRC) and Department of Pharmacognosy, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia.
El Sayed
K A
KA
Mossa
J S
JS
Al-Said
M S
MS
El-Feraly
F S
FS
Clark
A M
AM
Hufford
C D
CD
Oh
S
S
Mayer
A M
AM
D000900:Anti-Bacterial Agents / Q000302:isolation & purification / Q000494:pharmacology; D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000302:isolation & purification / Q000494:pharmacology; D001419:Bacteria / Q000187:drug effects; D002478:Cells, Cultured; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D010946:Plants, Medicinal / Q000737:chemistry*; D012529:Saudi Arabia; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013237:Stereoisomerism; D014315:Triterpenes / Q000302:isolation & purification* / Q000494:pharmacology
D000900:Anti-Bacterial Agents; D000894:Anti-Inflammatory Agents, Non-Steroidal; D014315:Triterpenes