title: Metabolite profiling of sesquiterpene lactones from Lactuca species. Major latex components are novel oxalate and sulfate conjugates of lactucin and its derivatives.
abstract: Wounding leaves or stems of Lactuca species releases a milky latex onto the plant surface. We have examined the constituents of latex from Lactuca sativa (lettuce) cv. Diana. The major components were shown to be novel 15-oxalyl and 8-sulfate conjugates of the guaianolide sesquiterpene lactones, lactucin, deoxylactucin, and lactucopicrin. The oxalates were unstable, reverting to the parent sesquiterpene lactone on hydrolysis. Oxalyl derivatives have been reported rarely from natural sources. The sulfates were stable and are the first reported sesquiterpene sulfates from plants. Unusual tannins based on 4-hydroxyphenylacetyl conjugates of glucose were also identified. Significant qualitative and quantitative variation was found in sesquiterpene lactone profiles in different lettuce varieties and in other Lactuca spp. The proportions of each conjugate in latex also changed depending on the stage of plant development. A similar profile was found in chicory, in which oxalyl conjugates were identified, but the 8-sulfate conjugates were notably absent. The presence of the constitutive sesquiterpene lactones was not correlated with resistance to pathogens but may have a significant bearing on the molecular basis of the bitter taste of lettuce and related species. The induced sesquiterpene lactone phytoalexin, lettucenin A, was found in the Lactuca spp. but not in chicory.
authors.affiliation: Department of Biological Sciences, Wye College, University of London, Ashford, Kent, TN25 5AH, United Kingdom.
authors.forename: R A
authors.initials: RA
authors.lastname: Sessa
authors.forename: M H
authors.initials: MH
authors.lastname: Bennett
authors.forename: M J
authors.initials: MJ
authors.lastname: Lewis
authors.forename: J W
authors.initials: JW
authors.lastname: Mansfield
authors.forename: M H
authors.initials: MH
authors.lastname: Beale
mesh_terms: D002851:Chromatography, High Pressure Liquid; D007783:Lactones / Q000378:metabolism*; D007840:Latex; D018545:Lactuca / Q000254:growth & development / Q000378:metabolism*; D010070:Oxalates / Q000378:metabolism; D012717:Sesquiterpenes / Q000378:metabolism*; D013431:Sulfates / Q000378:metabolism
chemical_list: D007783:Lactones; D007840:Latex; D010070:Oxalates; D012717:Sesquiterpenes; D013431:Sulfates