O-Prenylated Acridone Alkaloids from the Stems of Balsamocitrus paniculata (Rutaceae)

Emmanuel Ngeufa Happi; Alain François Kamdem Waffo; Jean Duplex Wansi; Bonaventure Tchaleu Ngadjui; Norbert Sewald

doi:10.1055/s-0030-1250692

Planta Medica, Table of Contents

Planta Med 2011; 77(9): 934-938
DOI: 10.1055/s-0030-1250692

Natural Product Chemistry

Original Papers
© Georg Thieme Verlag KG Stuttgart · New York

O-Prenylated Acridone Alkaloids from the Stems of Balsamocitrus paniculata (Rutaceae)

Emmanuel Ngeufa Happi¹ , Alain François Kamdem Waffo¹ , Jean Duplex Wansi¹ ^, ² , Bonaventure Tchaleu Ngadjui³ , Norbert Sewald²

¹Department of Chemistry, University of Douala, Faculty of Science, Douala, Cameroon
²Organic and Bioorganic Chemistry, Department of Chemistry, Bielefeld University, Bielefeld, Germany
³Department of Organic Chemistry, University of Yaounde I, Faculty of Science, Yaounde, Cameroon

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-p-coumaroyloctopamine (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.

Key words

Balsamocitrus paniculata - Rutaceae - acridone - antimicrobial - oxidative burst inhibition - cytotoxic activities

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Jean Duplex Wansi

Faculty of Science, Department of Chemistry
University of Douala

P. O. Box 24157

Douala

Cameroon

Phone: +23 7 74 72 54 25

Fax: +23 7 33 40 75 69

Email: jdwansi@yahoo.fr