Planta Med 2011; 77(13): 1559-1561
DOI: 10.1055/s-0030-1270850
Natural Product Chemistry
Letters
© Georg Thieme Verlag KG Stuttgart · New York

Simple Indole Alkaloids from the Neotropical Rutaceous Tree Raputia simulans

Konstantina Vougogiannopoulou1 , Nikolas Fokialakis1 , Nektarios Aligiannis1 , Charles Cantrell2 , Alexios-Leandros Skaltsounis1
  • 1Department of Pharmacognosy and Natural Product Chemistry, Faculty of Pharmacy, University of Athens, Athens, Greece
  • 2Natural Products Utilization Research Unit, USDA/ARS, National Centre for Natural Products Research, University, MS, USA
Further Information

Publication History

received December 9, 2010 revised February 2, 2011

accepted February 4, 2011

Publication Date:
07 March 2011 (online)

Abstract

The genus Raputia Aubl. comprises 10 neotropical species of the family Rutaceae belonging to the subtribe Cuspariinae. We report herein the investigation of the dichloromethane extract of the stem bark of R. simulans, which has led to the isolation of indole type alkaloids. The isolation procedure was performed by fast centrifugal partition chromatography (FCPC) and adsorption chromatography and afforded 11 isolates: indole-5-carbaldehyde (1), 7-prenylindole (2), 5-prenylindole (3), verticillatine B (4), 5-(but-3′-en-2′-one)indole (5), 5-(2′-methylbut-3′-en-1′-ol)indole (6), 5-[methyl-4′-(2′-methyl-4-oxobutanoate)]indole (7), 5-[4-(methyl)furan-2-yl]indole (8), 5-[4-(methoxymethyl)furan-2-yl]indole (9), 5-[5′-(3-methylfuran-2′(5′H)-one)]indole (10), and 5-(4′-methyl-2′,5′-dihydrofuran-2′-yl)indole (11). Metabolites 511 were isolated for the first time and bear uncommon substituents on position 5 of the indole moiety.

References

  • 1 Aublet J B C F. Histoire des plantes de la Guiane Françoise, Vol. 2. P. F. Didot jeune; London and Paris 1800
  • 2 Kallunki J A. An emended description of and new combinations in Raputia (Cuspariinae, Rutaceae).  Brittonia. 1990;  42 175-177
  • 3 Kallunki J A. Revision of Raputia Abl. (Cuspariinae, Rutaceae).  Brittonia. 1994;  46 279-295
  • 4 Vougogiannopoulou K, Fokialakis N, Aligiannis N, Cantrell C, Skaltsounis A L. The raputindoles: novel cyclopentyl bisindole alkaloids from Raputia simulans.  Org Lett. 2010;  12 1908-1911
  • 5 Bakhtiar A, Gleye J, Moulis C, Fouraste I. C-glycosyl flavones from Raputia paraensis.  Phytochemistry. 1991;  30 3840-3841
  • 6 de Souza J P I, Arruda A C, Muñoz G D, Arruda M S P, Müller A H. Prenylated flavones from Neoraputia paraensis.  Phytochemistry. 1999;  52 1705-1709
  • 7 Arruda A C, Vieira P C, Fernandes J B, da Silva M F D G F, Francisco R H P, Rodrigues A M G D, Lechat J R. Two pyrano flavones from Neorapuia alba.  Phytochemistry. 1991;  30 3157-3159
  • 8 Passador E A P, da Silva M F D G F, Fo E R, Fernandes J B, Vieira P C, Pirani J R. A pyrano chalcone and a flavanone from Neoraputia magnifica.  Phytochemistry. 1997;  45 1533-1537
  • 9 Nunya M H H, Makangara J J, Jonker S J. Prenylindoles from Tanzanian Monodora and Isolona species.  Nat Prod Res. 2004;  18 253-258
  • 10 Delle Monache F, Delle Monache G, Souza M A M, Cavalcanti M S, Chiappeta A. Isopentenylindole derivatives and other components of Esenbeckia leiocarpa.  Gazz Chim Ital. 1989;  119 435-439
  • 11 Achenbach H, Renner C. Constituents of West African medicinal plants XVIII: The annonidines – a new class of prenylated bisindole alkaloids from Annonidium mannii.  Heterocycles. 1985;  23 2075-2081
  • 12 Moreira V F, Oliveira R R, Mathias L, Braz-Filho R, Vieira I J C. New chemical constituents from Borreria verticillata (Rubiaceae).  Helv Chim Acta. 2010;  93 1751-1757
  • 13 Boyle J, Fenwick A E, Gethin D M, McCuscer C F. Preparation of imidazobenzazepin-2(1H)-ones as beta 2 adrenoceptor agonists. US Patent 103130. 2008
  • 14 Wu Y, Suehiro M, Kitajima M, Matsuzaki T, Hashimoto S, Nagaoka M, Zhang R, Takayama H. Rhazinilam and quebrachamine derivatives from Yunnan Kopsia arborea.  J Nat Prod. 2009;  72 204-209
  • 15 Kinoshita T, Tatara S, Ho F, Sankawa U. 3-prenylindoles from Murraya paninculata and their biogenetic significance.  Phytochemistry. 1989;  28 147-151

Prof. Alexios-Leandros Skaltsounis

Department of Pharmacognosy and Natural Product Chemistry
Faculty of Pharmacy
University of Athens

Panepistimiopolis Zografou

15771 Athens

Greece

Phone: +30 21 07 27 45 98

Fax: +30 21 07 27 45 94

Email: skaltsounis@pharm.uoa.gr