O-prenylated acridone alkaloids from the stems of Balsamocitrus paniculata (Rutaceae).

Abstract

Two new O-prenylated acridone alkaloids, balsacridone A (1) and B (2), together with eighteen known compounds were isolated from the methanol extract from the stems of Balsamocitrus paniculata, a Cameroonian medicinal plant. The structures of all compounds were determined by comprehensive analyses of their 1D and 2D NMR, mass spectral (EI and ESI) data, and chemical reactions. N-methyl-6-methoxybenzoxazolinone (16) was isolated for the first time from a natural source while compounds 13, 14, and 15 for the first time from this genus. Pure compounds were tested for their activity against bacteria, fungi, and plant pathogen oomycetes, using the paper disk agar diffusion assay. The agar diffusion test delivered low to missing antimicrobial activities, corresponding to MICs > 1 mg/mL. However, compounds 1-15 exhibited a strong suppressive effect on phagocytosis response upon activation with serum opsonized zymosan in the range of IC50 = 0.5-7.2 μM, and the acridone alkaloids (1-5), N-trans-p-coumaroyltyramine (13), and N-trans-pcoumaroyloctopamine (14) displayed weak cytotoxic activity against the human Caucasian prostate adenocarcinoma cell line PC-3, with IC₅₀ values ranging from 69.8 to 99.0 μM.

• Authors: Emmanuel Ngeufa Happi, Alain François Waffo, Jean Duplex Wansi, Bonaventure Tchaleu Ngadjui, Norbert Sewald
• Journal: Planta medica (Planta Med) Vol. 77 Issue 9 Pg. 934-8 (Jun 2011) ISSN: 1439-0221 [Electronic] Germany
• PMID: 21243586 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)
• Copyright: © Georg Thieme Verlag KG Stuttgart · New York.

Chemical References

• Acridines
• Acridones
• Alkaloids
• Anti-Infective Agents
• Plant Extracts
• acridone

Topics

• Acridines (chemistry)
• Acridones
• Alkaloids (chemistry, isolation & purification, pharmacology)
• Anti-Infective Agents (chemistry, isolation & purification, pharmacology)
• Cell Line, Tumor
• Cell Survival (drug effects)
• Humans
• Inhibitory Concentration 50
• Male
• Mass Spectrometry
• Medicine, African Traditional
• Molecular Structure
• Plant Extracts (chemistry)
• Plant Stems (chemistry)
• Prenylation
• Rutaceae (chemistry)