Biosynthesis of acridone alkaloids formation of rutacridone by cell‐free extracts of Ruta graveolens cell suspension cultures

Abstract

Microsomes prepared either by ultracentrifugation or MgC12 precipitation from cultured Ruta graveolens cells catalyze the condensation of 1,3-dihydroxy-N-methylacridone and isopentenylpyrophosphate or dimethylallylpyrophosphate. In the presence of NADPH and oxygen rutacridone was identified as reaction product. By omission of NADPH glycocitrine-II is accumulated. The results suggest that at first a prenylated acridone is formed which in turn is cyclized giving the dihydrofuran part of rutacridone.

Specific accumulation and revised structures of acridone alkaloid glucosides in the tips of transformed roots of Ruta graveolens

“…Many of these compounds are physiologically active and therefore of pharmacological interest. The high level of secondary compounds in Ruta plants encouraged several groups to establish in vitro cell and root cultures (Reinhard et al, 1968;Kuzovkina et al, 1971Kuzovkina et al, , 1979Ramawat et al, 1985) in order to investigate biosynthetic pathways (Baumert et al, 1982;Maier et al, 1990) and key enzymes (Kuzovkina et al, 1987;Baumert et al, 1994). The intense autofluorescence of some compounds from Ruta allows them to be easily localized in the tissue (Versar-Petri et al, 1976;Zobel and Brown, 1989).…”

Quinoline, quinazoline, and acridone alkaloids

“…Three of the four alkaloids found in Gulipea bract eat^,^ (7), (8), and (9), were previously known as synthetic compounds ; and although the authors claim that this is the first report of their isolation from a natural source, 2-pentylquinoline (8) has in fact previously been isolated from Galipea oficinalis.20 The fourth alkaloid, (lo), also occurs in Galipea longzflora together with four other new alkaloids (1 1 >-( 14) and six known alkaloids (see Table 1). lo Two of the latter, cusparine (15) and 4-methoxy- (49) Skimmianine *4-Ethoxycarbonylquinolin-2-one ( 1 8) *5,7-Dimethoxy-4-(4-methoxyphenyl)quinolin-2-one (1 9) *8-Hydroxy-5,7-dimethoxy-4-(4-methoxyphenyl)quinolin-2-one (20) 2-pentylquinoline (1 6), were also found during earlier examinations of G. oficinalis.20 The alkaloids of G. bracteata inhibited the growth of lettuce seedlings, while compounds (8), (9), and especially (10) showed molluscicidal activity against Biomphalaria glabrata, an aquatic snail involved in the transmission of schistosomiasis. While the properties of the G. longzflora alkaloids were not examined, the investigation was undertaken in view of the traditional use of extracts of this plant in treating parasitic infestations.…”