O-prenylated acridone alkaloids from the stems of Balsamocitrus paniculata (Rutaceae).
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.
Department of Chemistry, University of Douala, Faculty of Science, Douala, Cameroon.
Emmanuel Ngeufa
EN
Happi
Alain François
AF
Waffo
Jean Duplex
JD
Wansi
Bonaventure Tchaleu
BT
Ngadjui
Norbert
N
Sewald
D000166:Acridines / Q000737:chemistry; D054831:Acridones; D000470:Alkaloids / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000890:Anti-Infective Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D006801:Humans; D020128:Inhibitory Concentration 50; D008297:Male; D013058:Mass Spectrometry; D016488:Medicine, African Traditional; D015394:Molecular Structure; D010936:Plant Extracts / Q000737:chemistry*; D018547:Plant Stems / Q000737:chemistry; D054876:Prenylation; D027821:Rutaceae / Q000737:chemistry*
D000166:Acridines; D054831:Acridones; D000470:Alkaloids; D000890:Anti-Infective Agents; D010936:Plant Extracts; C041300:acridone