New Furoacridone Alkaloids from Tissue Culture ofRuta graveolens

Abstract

Two new furacridone alkaloids have been obtained from tissue culture of RUTA GRAVEOLENS by DCCC of a crude dichloromethane extract and subsequent CC and TLC. On the basis of spectroscopic data their structures have been determined to be 1-hydroxyrutacridone epoxide ( 3) and its intramolecular substitution product ( 5, rutagravin); a third furoacridone has been identified as gravacridonol ( 4).

Algicidal and antifungal compounds from the roots of Ruta graveolens and synthesis of their analogs

“…The results of the bioassay indicated that 2 was 100· less active than 1 against O. perornata (Table 1). Both compound 2 and its possible biosynthetic precursor 1 have been previously isolated from R. graveolens Reisch et al, 1976;Baumert et al, 1987;Nahrstedt et al, 1981Nahrstedt et al, , 1985. Rutacridone (3), a possible biosynthetic precursor of compound 2, was isolated from the same extract and had no activity in this bioassay.…”

Naturstoffchemie, 174. Mitt. [1]: Oxidation von Acronycin mit Kaliumpermanganat

“…Hierbei gilt besonderes Interesse den Epoxiden von Acronycin (1) und Rutacridon, sowie den entsprechenden Folgeprodukten nach Hydrolyse. In unserer Arbeitsgruppe [3], [4], [5], [6] ftihrten umfangreiche Oxidationsversuche unter anderem zu dem aus Ruta graveolens isolierten Naturstoff Rutagravin [7], sowie zu einem potentiellen Naturstoff Dihydrohallacridon [8], vermutlich eine biosynthetische Vorstufe von Hallacridon [9]. Die Synthese von Dihydrohallacridon und Rutagravin erfolgte durch Oxidation von Rutacridon mit Kaliumpermanganat [4].…”

Secondary metabolites produced by callus cultures of various Ruta species

“…After preparative HPLC the mass spectrum showed the following peaks at m/z 323 (M +) 306, 294, 292, 278, 265, 241. The 2H NMR spectrum was fully in accord with that of gravacridonol [7,12]. Especially informative are the two two-proton signals at 5.3 and 4.3 ppm showing the presence of a hydroxymethylethenyl group.…”