Planta Med 2009; 75(5): 517-521
DOI: 10.1055/s-0029-1185327
Natural Product Chemistry
Original Paper
© Georg Thieme Verlag KG Stuttgart · New York

Amides from the Stem Bark of Fagara macrophylla

Jean Duplex Wansi1 , 2 , Sarah Onyenibe Nwozo3 , Luc Meva'a Mbaze1 , Krishna Prasad Devkota2 , Suzye Mireille Donkwe Moladje4 , Z. Tanee Fomum4 , 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 Biochemistry, Faculty of Basic Medical Sciences, College of Medicine, University of Ibadan, Ibadan, Nigeria
  • 4Department of Organic Chemistry, University of Yaoundé I, Faculty of Science, Yaoundé, Cameroon
Further Information

Publication History

received August 15, 2008 revised Nov. 24, 2008

accepted Dec. 8, 2008

Publication Date:
20 February 2009 (online)

Abstract

Five new amide alkaloids, N-(4-hydroxyphenethyl)octacosanamide (1), N-(4-hydroxyphenethyl)hexacosanamide (2), N-(4-hydroxyphenethyl)decanamide (3), N-vanilloyltyramine (4), and N-[O-docosanoylvanilloyl]tyramine (5), were isolated from Fagara macrophylla, together with 15 known compounds. Their structures were established by using spectroscopic techniques, chemical reactions, and comparison with previously known analogues. A cytotoxicity assay was performed with the isolates, in which compounds 4, 8, and 9 were found to possess moderate to weak activity, with IC50 values of 30.5, 11.5, and 13.5 µg/mL, respectively.

References

  • 1 Irvine F R. Woody plants of Ghana. With special reference to their uses. London; Oxford University Press 1961
  • 2 Zirihi G N, Mambu L, Guédé-Guina F, Bodo B, Grellier P. In vitro antiplasmodial activity and cytotoxicity of 33 West African plants used for treatment of malaria.  J Ethnopharmacol. 2005;  98 281-285
  • 3 Sandberg F, Premila P I, Hesham R ES. A Swedish collection of medicinal plants from Cameroon.  J Ethnopharmacol. 2005;  102 336-343
  • 4 Torto F G, Mensah I A. Alkaloids of Fagara macrophylla.  Phytochemistry. 1970;  9 911-914
  • 5 Tringali C, Spatafora C, Cali V, Simmonds M SJ. Antifeedant constituents from Fagara macrophylla.  Fitoterapia. 2001;  72 538-543
  • 6 Keawpradub N, Amooqyaye E E, Burke P J, Houghton P J. Cytotoxic activity of indole alkaloids from Alstonia macrophylla.  Planta Med. 1999;  65 311-315
  • 7 Mbaze L M, Poumale H MP, Wansi J D, Lado J A, Shamsun N K, Iqbal C, Ngadjui T B, Laatsch H. α-Glucosidase inhibitory pentacyclic triterpenes from the stem bark of Fagara tessmannii (Rutaceae).  Phytochemistry. 2007;  68 591-595
  • 8 Ezugwu C, Erdal B, Chuck D, Khan I A, Okunji C O, Schuster M B, Iwu M M. Indoloquinazoline alkaloids from Araliopsis tabouensis.  Helv Chim Acta. 2003;  86 2914-2918
  • 9 Wu Y C, Chang G Y, Ko F N, Teng C M. Bioactive constituents from the stems of Annona montana.  Planta Med. 1995;  61 146-149
  • 10 Atta-ur-Rahman, Bhatti M K, Akhtar F, Choudhary M I. Alkaloids of Fumaria indica.  Phytochemistry. 1992;  31 2869-2872
  • 11 Wandji J, Tillequin F, Mulholland D A, Wansi J D, Fomum T Z, Fuendjiep V, Libot F, Tsabang N. Fatty acid esters of triterpenoids and steroid glycosides from Gambeya africana.  Planta Med. 2002;  68 822-826
  • 12 Ouattara B, Angenot L, Guissou P, Fondu P, Dubois J, Frédérich M, Jansen O, Heugen J-C, Wauters J-N, Tits M. LC/MS/NMR analysis of isomeric divanilloylquinic acids from the root barks of Fagara zanthoxyloides Lam.  Phytochemistry. 2004;  65 1145-1151
  • 13 Messmer W M, Tin-Wa M, Fong H H, Bevelle C, Farnsworth N R, Abraham D J, Trojanek J. Fagaronine, a new tumor inhibitor isolated from Fagara zanthoxyloides Lam. (Rutaceae).  J Pharm Sci. 1972;  61 1858-1859
  • 14 Comoe L, Kouamouo J, Jeannesson P, Desoize B, Dufour R, Yapo E A, Jardilliers J C. Cytotoxic effects of Fagara zanthoxyloïdes Lam. (Rutaceae) root extracts on human erythroleukemia K562 cell line.  Ann Pharm Fr. 1987;  45 79-86
  • 15 Wall M E, Wani M C, Taylor H. Plant antitumor agent. Isolation, structure, and structure activity relationships of alkaloids from Fagara macrophylla.  J Nat Prod. 1987;  50 1095-1099

Dr. Jean Duplex Wansi

Department of Chemistry
University of Douala
Faculty of Science

P. O. Box 24 157

Douala

Cameroon

Phone: + 23 7 77 81 77 31

Email: jdwansi@yahoo.fr