Contrasting Dihydronaphthoquinone Patterns in Closely Related Drosera (Sundew) Species Enable Taxonomic Distinction and Identification.

Dihydronaphthoquinones are described as constituents of sundews ( Drosera ), Venus flytraps ( Dionaea ), and dewy pines ( Drosophyllum ) for the first time. As in the corresponding naphthoquinones, these reduced derivatives may occur in two regio-isomeric series distinguished by the relative position of a methyl group (at position 2 or 7 in the naphthalene skeleton), depending on the taxon. Species producing plumbagin (2-methyljuglone, 1 ) do commonly contain the corresponding dihydroplumbagin ( 5 ), while species containing ramentaceone (7-methyljuglone, 2 ) also contain dihydroramentaceone (7-methyl-β-dihydrojuglone, 6 ). So far, only few species containing plumbagin ( 1 ) and dihydroplumbagin ( 5 ) additionally form dihydroramentaceone ( 6 ) but not ramentaceone ( 2 ). Thus, subtle but constant differences in the chemism of closely related and morphologically similar species reliably define and distinguish taxa within D . sect. Arachnopus , which is taken to exemplify their chemotaxonomic utility. The joint presence of quinones and hydroquinones allows observations and predictions on the chemical structures and the reactions of these intriguing natural products.