Download PDF
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
Further Information

Publication History

received Sept. 26, 2010 revised Dec. 9, 2010

accepted Dec. 11, 2010

Publication Date:
17 January 2011 (online)

Also available at
   Permissions and Reprints

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

References

  • 1 Engler A H G. Die Pflanzenwelt Afrikas, Vol. 3 (1). Leipzig; Verlag W. Engelmann 1915: 761
    Search in Google Scholar
  • 2 Asase A, Oteng-Yeboah A A, Odamtten G T, Simmonds M S J. Ethnobotanical study of some Ghanaian anti-malarial plants.  J Ethnopharmacol. 2005;  99 273-279
    CrossrefPubMedSearch in Google Scholar
  • 3 Igoli J O, Ogaji O G, Tor-Igoli N P. Traditional medicine practice amongst the Igede people of Nigeria.  Afr J Trad CAM. 2005;  2 134-152
    PubMedSearch in Google Scholar
  • 4 Tsassi V B, Hidayat H, Meffo B Y, Kouam S F, Dongo E, Schulz B, Green I R, Krohn K. Antimicrobial coumarins from the stem bark of Afraegle paniculata.  Nat Prod Commun. 2010;  5 559-561
    PubMedSearch in Google Scholar
  • 5 Maskey R P, Asolkar R N, Kapaun E, Wagner-Döbler I, Laatsch H. Phytotoxic arylethylamides from limnic bacteria using a screening with microalgae.  J Antibiot. 2002;  55 643-649
    CrossrefPubMedSearch in Google Scholar
  • 6 Clinical and Laboratory Standards Institute/NCCLS .Performance standards for antimicroblial susceptibility testing: 19th edition. CLSI/NCCLS M 100-S18. Wayne; Clinical and Laboratory Standards Institute 2008
    Search in Google Scholar
  • 7 Helfand S L, Werkmeister J, Roder J C. Chemiluminescence response of human natural killer cells. The relationship between target cell binding, chemiluminescence, and cytolysis.  J Exp Med. 1982;  156 492-505
    CrossrefPubMedSearch in Google Scholar
  • 8 Zhao Q, Chen Q, Hao X J, Han J, Zuo Y G, Zuo C, Xu G L. Cytotoxicity of laddane-type diterpenoids from Hedychium fonestii.  Chem Pharm Bull. 2008;  56 210-212
    CrossrefPubMedSearch in Google Scholar
  • 9 Negi N, Jinguji Y, Ushijima K, Ikeda S, Takemura Y, Ju-ichi M, Wu T-S, Ito C, Furukawa H. Two new dimeric acridone alkaloids from Glycosmis citrifolia.  Chem Pharm Bull. 2004;  52 362-364
    CrossrefPubMedSearch in Google Scholar
  • 10 Brader G, Bacher M, Greger H, Hofer O. Pyranoquinolones and acridones from Vepris bilocularis.  Phytochemistry. 1996;  42 881-884
    CrossrefPubMedSearch in Google Scholar
  • 11 Wu T-S, Kuoh C-S, Furukawa H. Acrdone alkaloids. VI. The constituents of Citrus depressa. Isolation and structure elucidation of new acridone alkaloids from Citrus genus.  Chem Pharm Bull. 1983;  31 895-900
    CrossrefPubMedSearch in Google Scholar
  • 12 Weniger B, Um B-H, Valentin A, Estrada A, Lobstein A, Anton R, Maillé M, Sauvin M. Bioactive acridone alkaloids from Swinglea glutinosa.  J Nat Prod. 2001;  64 1221-1223
    CrossrefPubMedSearch in Google Scholar
  • 13 Mbaze L M, Lobe S J, Wansi J D, Kamdem W A F, Dongo E, Ngando M T, Sewald N. Acridone alkaloids and coumarins from the stem bark of Citropsis articulata.  Z Naturforsch. 2010;  65b 525-527
    PubMedSearch in Google Scholar
  • 14 Wansi J D, Djouaka B L J, Happi N E, Devkota K P, Lenta N B, Mesaik M A, Choudhary M I, Fomum Z T, Sewald N. Bioactive phenylethanoids and coumarins from Basalmocitrus cameroonensis.  Z Naturforsch. 2009;  64b 452-458
    PubMedSearch in Google Scholar
  • 15 Duan C-L, Jiang Y, Jiang Y, Lin C-R, Liu J-X, Tu P-F. Liposoluble chemical constituents from the fibrous roots of the Ophiopogon japonicas.  J China Pharm Sci. 2009;  18 236-239
    PubMedSearch in Google Scholar
  • 16 Chen C-M, Chen M-T. 6-Methoxybenzoxazolinone and triterpenoids from roots of Scoparia dulcis.  Phytochemistry. 1976;  15 1997-1999
    CrossrefPubMedSearch in Google Scholar
  • 17 Marikkar J M N, Lai O M, Ghazali H M, Chen Man Y B. Compositional and thermal analysis of RBD palm oil adulterated with lipase-catalysed interesterified lard.  Food Chem. 2002;  76 249-258
    CrossrefPubMedSearch in Google Scholar
  • 18 Wansi J D, Nwozo O S, Mbaze L M, Devkota K P, Donkwe S M M, Fomum Z T, Sewald N. Amides from the stem bark of Fagara macrophylla.  Planta Med. 2009;  75 517-521
    Thieme ConnectPubMedSearch in Google Scholar
  • 19 Wu T-S, Furukawa H. Acridone alkaloids. VII. Constituents of Citrus sinensis Osbeck var. brasiliensis Tanaka. Isolation and characterization of three new acridone alkaloids, and a new coumarin.  Chem Pharm Bull. 1983;  31 901-906
    CrossrefPubMedSearch in Google Scholar
  • 20 Wu T-S, Kuoh C-S, Furukawa H. Acridone alkaloids and a coumarin from Citrus grandis.  Phytochemistry. 1983;  22 1493-1497
    CrossrefPubMedSearch in Google Scholar

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