Naphthoquinone Glucosides ofDrosera giganteafromin vitroCultures

Abstract

From the shoots of Drosera gigantea propagated under in vitro culture, the rare naphthoquinone glucosides droserone (3,5-dihydroxy-2-methyl-1,4-naphthoquinone) and hydroxydroserone (3,5,8-trihydroxy-2-methyl-1,4-napthoquinone) 5-O-beta-glucosides, together with the free naphthoquinones droserone, hydroxydroserone and plumbagin were isolated. The structures of the glucosides and hydroxydroserone were studied by 2D NMR techniques. The glucosides appear to be responsible for the brown-red (maroon) colour of this plant. Of the other naphthoquinones typical for the family Droseraceae only hydroplumbagin glucoside could be detected, whereas the presence of 7-methyljuglone and rossoliside (= 7-methylhydrojuglone glucoside) was excluded.

Separation and Identification of 1,2,4-Trihydroxynaphthalene-1-O-glucoside in Impatiens glandulifera Royle

“…Naphthoquinones from Drosera rotundifolia L. are used in respiratory difficulties [12]. In experiments on tobacco BY-2 cells naphthoquinones play a role in the cell death [13]. 2-Methoxy-1,4-naphthoquinone has strong in vitro anticancer activity against HepG2 cells, experiments that were performed with extracts from Impatients balsamina L. [14].…”

Cytotoxic Quinones from the Roots of Aloe dawei

“…Six additional known naphthoquinones 2 – 7 were also isolated from the extract. They were spectroscopically identified as ancistroquinone C ( 2 ), previously isolated from stress-induced cell culture of Ancistrocladus abbreviates [9]; 5,8-dihydroxy-3-methoxy-2-methyl-1,4-naphthoquinone ( 3 ), recently reported from the roots of Aloe secundiflora [13], malvone A ( 4 ) [9,14], droserone ( 5 ) [15,16,17], droserone-5-methyl ether ( 6 ) [18] and hydroxydroserone ( 7 ) [19,20,21].…”

Induced production of antifungal naphthoquinones in the pitchers of the carnivorous plant Nepenthes khasiana

“…2). Droserone was identified in several plant families, for example, Plumbaginaceae (Dinda et al , 1995), Nepenthaceae (Likhitwitayawuid et al , 1998), Droseraceae (Kreher et al , 1990; Budzianowski, 2000), and Dioncophyllaceae (Bringmann et al , 2000) and was shown to exert antimalarial (Likhitwitayawuid et al , 1998) and pesticidal activities (Bringmann et al , 1993; Bringmann and Feineis, 2001). Me-droserone is rare in nature and was only identified in Diospyros melanoxylon Roxb.…”

“…Naphthoquinones, considered to be potential antifungal drugs, are produced by many plants that belong to the Caryophyllales families (Rischer et al , 2002), including Nepenthaceae (Bringmann et al , 2000; Aung et al , 2002; Rischer et al , 2002), Droseraceae (Didry et al , 1998; Budzianowski, 2000), Plumbaginaceae (de Paiva et al , 2003), Drosophyllaceae (Bringmann et al , 1998), and Ebenaceae (Dzoyem et al , 2007). Naphthoquinones are synthesized by the shikimate and acetate–malonate (polyketide) pathways (Babula et al , 2009).…”

“…Several plumbagin derivatives have been examined to identify products exerting plumbagin-like fungicidal activity but lower toxicity (Sankaram et al , 1975; Ogihara et al , 1997; Likhitwitayawuid et al , 1998; Hazra et al , 2002; Tandon et al , 2004, Ganapaty et al , 2006). Droserone, the oxygenated derivative of plumbagin, is synthesized in a variety of Nepenthales species (Bringmann et al , 2000; Budzianowski, 2000). It lacks immunostimulating activity (Kreher et al , 1988), but exhibits anti-malarial and possibly pesticidal activity (Bringmann et al , 1993; Bringmann and Feineis, 2001).…”