Triumfettamide and Triumfettoside Ic, Two Ceramides and Other Secondary Metabolites from the Stems of Wild Triumfetta cordifolia A. Rich. (Tiliaceae)

• Published in: Helvetica chimica acta 2008-07, Vol.91 (7), p.1326-1335
• Main Authors: Pergaud Sandjo, Louis, Hannewald, Paul, Yemloul, Mehdi, Kirsch, Gilbert, Tchaleu Ngadjui, Bonaventure
• Format: Article
• Language: English
• Subjects: Ceramides; Metabolites; Triumfetta cardifolia; Triumfettamide; Triumfettoside Ic
• ISSN: 0018-019X; 1522-2675
• DOI: 10.1002/hlca.200890144

Two new ceramides, triumfettamide (1) and triumfettoside Ic (2), characterized as (2R,6Z)‐2‐hydroxy‐N‐[(2S,3S,4R)‐1,3,4‐trihydroxyhexacosan‐2‐yl]heptadec‐6‐enamide and (2R)‐N‐{(1S,2R,3E,6Z, 9Z,12Z,15Z)‐1‐[(β‐D‐glucopyranosyloxy)methyl]‐2‐hydroxyheneicosa‐3,6,9,12,15‐pentaen‐1‐yl}‐2‐hydroxytetradecanamide, respectively, were isolated from the stems of Triumfetta cordifolia A. Rich. besides eight known secondary metabolites identified as heptadecanoic acid, β‐sitosterol glucopyranoside, friedelin, lupeol, betulin, maslinic acid, 2‐hydroxyoleanolic acid and the mixture of stigmasterol and β‐sitosterol. Their structures were determined on the basis of spectroscopic methods as well as HR‐MALDI‐FT‐ICR‐MS analysis, chemical transformation, and by comparison of their physical and spectral data with those reported in the literature and with authentic specimens for some known compounds. Five pentacyclic triterpenoids, friedelin, lupeol, betulin, maslinic acid, and 2‐hydroxyoleanolic acid, have been isolated from Triumfetta genus for the first time.