New natural products from the epicuticular wax of Dianthus cruentus Griseb. (Caryophyllaceae)

Abstract

Detailed GC and GC-MS analysis of a diethyl ether washings of fresh flowers of Dianthus cruentus Griseb. (Caryophyllaceae) enabled the identification of 153 constituents. The major identified compounds were long-chain n-alkanes - pentacosane (5.0 %), heptacosane (19.5 %) and nonacosane (6.5 %). Detailed analyses, in combination with synthesis and chemical transformations (transesterification and synthesis of dimethyl disulfide adducts), led to the identification of a homologous series of n-, iso- and anteiso- long-chain esters (n-hexyl alkanoates and alkyl benzoates) and long-chain (Z)- and (E)-alkenes (C23–C35) with several different double bond positions. Fifty five of these constituents (eight hexyl esters, two benzoates and forty five alkenes) represented new natural products in Plantae (10 new compounds in general). The identified metabolites appear to be chemotaxonomic markers of Dianthus spp.