Alkaloids from Spathelia excelsa: Their chemosystematic significance

• Published in: Phytochemistry (Oxford) 2005-07, Vol.66 (13), p.1560-1566
• Main Authors: Lima, M. da Paz, Rosas, Lisandra Vieira, da Silva, M. Fátima das G.F., Ferreira, A. Gilberto, Fernandes, João B., Vieira, Paulo C.
• Format: Article
• Language: English
• Subjects: 2-alkyl-4(1 H)-quinolones; Alkaloids - chemistry; Alkaloids - isolation & purification; Biological and medical sciences; Chemical constitution; Chemosystematics; Fundamental and applied biological sciences. Psychology; Magnetic Resonance Spectroscopy; Magnoliopsida - chemistry; Plant cytology, morphology, systematics, chorology and evolution; Plant Extracts - chemistry; Plant Extracts - isolation & purification; Plant Leaves - chemistry; Plant physiology and development; Rutaceae; Spathelia excelsa; Spectrometry, Mass, Electrospray Ionization; Spermatophyta; Systematics (diagnosis, chromosome numbers)
• ISSN: 0031-9422; 1873-3700
• DOI: 10.1016/j.phytochem.2005.05.019

Spathelia excelsa afforded six new alkaloids 2-(12-oxo-tridecanyl)-3-methoxy-4-quinolone, 2-(10′-hydroxy-10′-methyldodecanyl)-3-methoxy-4-quinolone, 2-(11′-hydroxy-11′-methyldodecanyl)-3-methoxy-4-quinolone, 2-(12′-hydroxytridecanyl)-3-methoxy-4-quinolone, 7-hydroxy-2-(3′-hydroxy-3′-methylbutyl)-4-quinolone, 6-hydroxy-2-(3′-hydroxy-3′-methylbutyl)-4-quinolone. The data provide firm support for removing Spathelioideae to or within the Dictyolomatoideae. The methanol extract from the leaves of Spathelia excelsa yielded six alkaloids: 2-(12-oxo-tridecanyl)-3-methoxy-4-quinolone, 2-(10-hydroxy-10-methyldodecanyl)-3-methoxy-4-quinolone, 2-(11-hydroxy-11-methyldodecanyl)-3-methoxy-4-quinolone, 2-(12-hydroxytridecanyl)-3-methoxy-4-quinolone, 7-hydroxy-2-(3-hydroxy-3-methylbutyl)-4-quinolone and 6-hydroxy-2-(3-hydroxy-3-methylbutyl)-4-quinolone, in addition to the known 3- O-β- d-glucopiranosylsitosterol and (−)-epicatechin. The 2-alkyl-4(1 H)-quinolones in S. excelsa display strong similarities with those in Dictyolomatoideae, which contains several 2-alkyl-4-quinolones. The data reported herein thus provide firm support for placing Spathelioideae close to or within the Dictyolomatoideae.