Biosynthesis of Cyanogenic Glycosides in Butterflies and Moths: Incorporation of Valine and Isoleucine into Linamarin and Lotaustralin by Zygaena and Heliconius Species (Lepidoptera)
نویسندگان
چکیده
Cyanogenic Glycosides, Linamarin, Lotaustralin, Biosynthesis, Lepidoptera C -13 NMR data for linamarin and lotaustralin, obtained after feeding of either Zygaena Jilipendulae or Heliconius melpomone (Lepidoptera) with C-13 enriched valine and isoleucine respectively, indicate that intact units of amino acid with loss of the carboxyl group are incorporated during the biosynthesis of these cyanogenic glycosides.
منابع مشابه
Spatial separation of the cyanogenic β-glucosidase ZfBGD2 and cyanogenic glucosides in the haemolymph of Zygaena larvae facilitates cyanide release
Low molecular weight compounds are typically used by insects and plants for defence against predators. They are often stored as inactive β-glucosides and kept separate from activating β-glucosidases. When the two components are mixed, the β-glucosides are hydrolysed releasing toxic aglucones. Cyanogenic plants contain cyanogenic glucosides and release hydrogen cyanide due to such a well-charact...
متن کاملChemical Defense Balanced by Sequestration and De Novo Biosynthesis in a Lepidopteran Specialist
The evolution of sequestration (uptake and accumulation) relative to de novo biosynthesis of chemical defense compounds is poorly understood, as is the interplay between these two strategies. The Burnet moth Zygaena filipendulae (Lepidoptera) and its food-plant Lotus corniculatus (Fabaceae) poses an exemplary case study of these questions, as Z. filipendulae belongs to the only insect family kn...
متن کاملCyanogenic and non-cyanogenic glycosides from Manihot esculenta.
In addition to lotaustralin and linamarin, a novel cyanogenic glycoside, 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)-2-met hylbutanenitrile , two novel non-cyanogenic glycosides, (2S)-((6-O-(beta-D-apiofuranosyl)-beta-D- glucopyranosyl)oxy)butane and 2-((6-O-(beta-D-apiofuranosyl)-beta-D-glucopyranosyl)oxy)propane, and a simple non-cyanogenic glycoside, ethyl beta-D-glucopyranosid...
متن کاملGenetic screening identifies cyanogenesis-deficient mutants of Lotus japonicus and reveals enzymatic specificity in hydroxynitrile glucoside metabolism.
Cyanogenesis, the release of hydrogen cyanide from damaged plant tissues, involves the enzymatic degradation of amino acid-derived cyanogenic glucosides (alpha-hydroxynitrile glucosides) by specific beta-glucosidases. Release of cyanide functions as a defense mechanism against generalist herbivores. We developed a high-throughput screening method and used it to identify cyanogenesis deficient (...
متن کاملBiosynthesis of the cyanogenic glucosides linamarin and lotaustralin in cassava: isolation, biochemical characterization, and expression pattern of CYP71E7, the oxime-metabolizing cytochrome P450 enzyme.
Cassava (Manihot esculenta) is a eudicotyledonous plant that produces the valine- and isoleucine-derived cyanogenic glucosides linamarin and lotaustralin with the corresponding oximes and cyanohydrins as key intermediates. CYP79 enzymes catalyzing amino acid-to-oxime conversion in cyanogenic glucoside biosynthesis are known from several plants including cassava. The enzyme system converting oxi...
متن کامل