title: Sesquiterpenoid glycosides from glandular trichomes of the wild tomato relative Solanum habrochaites.
abstract: Profiles of terpenoid glycoside metabolites in glandular trichomes of Solanum habrochaites LA1777 leaves were generated using ultrahigh performance liquid chromatography/time-of-flight mass spectrometry with multiplexing of non-selective collision-induced dissociation (CID). Profiling data suggested a diverse group of 52 sesquiterpenoid glycosides, and fragment ions observed in both non-selective CID mass spectra and true tandem mass spectrometry (MS/MS) product ion spectra documented variation in extent of glycosylation and the presence of malonate or acetate esters. Up to 10 isomers were detected for some metabolites. Malonate and acetate esters of three sesquiterpene diol glucosides and one unmodified diglucoside were purified using reversed phase semipreparative HPLC and analyzed and identified using 1D and 2D NMR and mass spectrometry. All four of the isolated products were glucosides of campheranane-2,12-diol.
authors: Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
authors: E A Prabodha
authors: EA
authors: Ekanayaka
authors: Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA.
authors: Chao
authors: C
authors: Li
authors: Department of Chemistry, Michigan State University, East Lansing, MI 48824, USA; Department of Biochemistry and Molecular Biology, Michigan State University, East Lansing, MI 48824, USA. Electronic address: jonesar4@msu.edu.
authors: A Daniel
authors: AD
authors: Jones
mesh_terms: D006027:Glycosides / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D008968:Molecular Conformation; D012639:Seeds / Q000737:chemistry / Q000378:metabolism; D012717:Sesquiterpenes / Q000737:chemistry / Q000302:isolation & purification* / Q000378:metabolism; D032322:Solanum / Q000737:chemistry* / Q000378:metabolism; D064201:Trichomes / Q000737:chemistry* / Q000378:metabolism
chemical_list: D006027:Glycosides; D012717:Sesquiterpenes
keywords: CJPUZYHTTDRUHK-SIEUFYATSA-N; Campherenane-2,12-diol; Glandular trichomes; Malonate esters; Metabolomics; NMR spectroscopy; NUHBBNIHNIYJFM-ARYWSNPOSA-N; Natural products; ONZKIHDQZHGVBA-DSMBRBAFSA-N; Plant defense compounds; Sesquiterpenoid glycosides; Solanaceae; Solanum habrochaites; Ultrahigh performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS); Wild tomato; ZGRDRXDPBUJPBW-NWRPPJOHSA-N