Sucrose Esters from the Fruits of Physalis nicandroides var. attenuata

Abstract

Three 2,3,1',3'-tetraacyl- and two 2,3,3'-triacylsucroses, nicandroses A-E (1-5), were isolated from the fruits of Physalis nicandroides var. attenuata. The acyl groups in these new compounds were identified as decanoyl, isobutyryl, 2-methylbutanoyl, and acetyl. The structures of 1-5 were determined on the basis of NMR and MS analyses.

Functionally Divergent Alleles and Duplicated Loci Encoding an Acyltransferase Contribute to Acylsugar Metabolite Diversity in Solanum Trichomes

“…The products can be stored, emitted as volatiles, or secreted to the plant surface where they participate in several aspects of plant physiology and ecology such as insect herbivory (Simmons and Gurr, 2005;Weinhold and Baldwin, 2011), pathogen attack (Shepherd et al, 2005), and attraction of pollinators (Werker, 2000). The glandular trichomes of many species in the nightshade family (Solanaceae), including Solanum pennellii, potato (Solanum berthaultii), tobacco (Nicotiana tabacum), petunia (Petunia hybrida), Physalis nicandroides, and Datura metel, produce and secrete sugar polyesters known as acylsugars (Fobes et al, 1985;Severson et al, 1985;King et al, 1986Ohya et al, 1996;Maldonado et al, 2006). Characterized acylsugars are comprised of a sugar backbone, either glucose or sucrose, to which multiple short to medium chain length branched or straight aliphatic acids are esterified ( Figure 1).…”

Solanaceae specialized metabolism in a non-model plant: trichome acylinositol biosynthesis

“…Phylogenetic analysis of acylsugar-producing species point to sucrose as the ASAT ancestral acyl acceptor – it is the sugar acceptor in earlier diverging lineages leading to S. sinuata and P. axillaris (Moghe et al, 2017; Nadakuduti et al, 2017). Further, acylsucrose-accumulating species are present throughout the Solanaceae family (Burke et al, 1987; King and Calhoun, 1988; Matsuzaki et al, 1991; Maldonado et al, 2006; Ghosh et al, 2014; Liu et al, 2017; Moghe et al, 2017), whereas reported acylinositol accumulators are S. quitoense and S. lanceolatum ( Fig. 1 ) (Herrera-Salgado et al, 2005).…”

“…The acyl chains are branched or straight and are proposed to be derived from amino acid or fatty acid metabolism, respectively (Walters and Steffens, 1990; Kroumova and Wagner, 2009; Ning et al, 2015). Acylsugar cores from Solanaceae species are primarily sucrose or sometimes glucose (King et al, 1986; King and Calhoun, 1988; Maldonado et al, 2006; Ghosh et al, 2014; Liu et al, 2017; Moghe et al, 2017; Leong et al, 2019). Solanum lanceolatum is a published exception, accumulating acylated disaccharide cores that contain myo -inositol bound to glucose or xylose (Herrera-Salgado et al, 2005).…”

Characterization of novel regulators for heat stress tolerance in tomato from Indian sub-continent

“…We selected 4 previously uncharacterized ERFs family that act as natural chemicals against pests like whiteflies and spider mites 4 8 5 (Alba et al, 2009;Liedl et al, 1995). Acylsugars are produced in the tip cell of the 4 8 6 long glandular secreting trichomes using ASAT enzymes that catalyse sequential 4 8 7 addition of specific acyl chains to the sucrose molecule using acyl CoA donors 4 8 8 (Schilmiller et al, 2008;Maldonado et al, 2006). Solyc09g014280 and Figure S11) are reported to be enriched in the glandular trichomes in (Supplementary Figure S12) showed severe drooping of leaves upon recovery after 4 9 7 being exposed to HS in comparison to vector-control plants ( Figure 4A).…”