The plant kingdom is prolific at synthesizing an enormous array of bioactive metabolites, but the genes, enzymes, and pathways leading to their biosyntheses often remain unknown. Our current research aims to discover biosynthetic pathways leading to accumulation of specialized metabolites in hair-like epidermal cells called trichomes in tomato and its relatives. Trichomes present a complex chemical arsenal including glucose or sucrose polyesters of 2-5 short- to medium-chain fatty acids, profiled using LC/time-of-flight MS and multiplexed collision-induced dissociation (CID). However, genetic variants within the genus Solanum showed evidence for multiple acylsugar forms that suggest selective acylation chemistry. Substructural redundancy makes purification and characterization of acylsugars challenging. A thorough understanding and proper interpretation of complex 2D NMR spectra (COSY, HMBC and HSQC) of such compounds has provided clear evidence for position-selective acylation of sucroses, and has yielded complete structures for more than 20 distinct acylsucrose forms in trichomes from Solanum species.

Selective acyl substitutions of trichome-derived acylsugars from tomato and its wild relatives

245th National Meeting (2013)

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