Glycosides of the Neurotoxin Tutin in Toxic Honeys Are from Coriaria arborea Phloem Sap, Not Insect Metabolism
Some honeys contain the neurotoxin tutin (1) plus hyenanchin (2), 2-(β-d-glucopyranosyl)tutin (3), and 2-[6′-(α-d-glucopyranosyl)-β-d-glucopyranosyl]tutin (4). These honeys are made by bees collecting honeydew from passionvine hoppers feeding on the sap of tutu plants (Coriaria spp.). We report a...
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Veröffentlicht in: | Journal of natural products (Washington, D.C.) D.C.), 2018-04, Vol.81 (4), p.1116-1120 |
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creator | Watkins, Oliver C Joyce, Nigel I Gould, Nick Perry, Nigel B |
description | Some honeys contain the neurotoxin tutin (1) plus hyenanchin (2), 2-(β-d-glucopyranosyl)tutin (3), and 2-[6′-(α-d-glucopyranosyl)-β-d-glucopyranosyl]tutin (4). These honeys are made by bees collecting honeydew from passionvine hoppers feeding on the sap of tutu plants (Coriaria spp.). We report a LC-MS study showing that all these picrotoxanes are of plant, not insect, origin. Hyenanchin was barely detectable and the diglucoside was not detectable in C. arborea leaves, but tutu phloem sap contained all four compounds at concentrations up to the highest found in honeydew. It is proposed that the diglucoside may function as a transport form of tutin, analogous to sucrose transport in phloem. |
doi_str_mv | 10.1021/acs.jnatprod.8b00120 |
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These honeys are made by bees collecting honeydew from passionvine hoppers feeding on the sap of tutu plants (Coriaria spp.). We report a LC-MS study showing that all these picrotoxanes are of plant, not insect, origin. Hyenanchin was barely detectable and the diglucoside was not detectable in C. arborea leaves, but tutu phloem sap contained all four compounds at concentrations up to the highest found in honeydew. It is proposed that the diglucoside may function as a transport form of tutin, analogous to sucrose transport in phloem.</description><identifier>ISSN: 0163-3864</identifier><identifier>EISSN: 1520-6025</identifier><identifier>DOI: 10.1021/acs.jnatprod.8b00120</identifier><identifier>PMID: 29504746</identifier><language>eng</language><publisher>United States: American Chemical Society and American Society of Pharmacognosy</publisher><ispartof>Journal of natural products (Washington, D.C.), 2018-04, Vol.81 (4), p.1116-1120</ispartof><lds50>peer_reviewed</lds50><woscitedreferencessubscribed>false</woscitedreferencessubscribed><citedby>FETCH-LOGICAL-a348t-bedbc21a07ae2361fff17a60e31e562e7757468d2cb11b8eecfb107653e9645b3</citedby><cites>FETCH-LOGICAL-a348t-bedbc21a07ae2361fff17a60e31e562e7757468d2cb11b8eecfb107653e9645b3</cites><orcidid>0000-0002-1451-4841 ; 0000-0003-0209-316X ; 0000-0003-3196-3945</orcidid></display><links><openurl>$$Topenurl_article</openurl><openurlfulltext>$$Topenurlfull_article</openurlfulltext><thumbnail>$$Tsyndetics_thumb_exl</thumbnail><linktopdf>$$Uhttps://pubs.acs.org/doi/pdf/10.1021/acs.jnatprod.8b00120$$EPDF$$P50$$Gacs$$H</linktopdf><linktohtml>$$Uhttps://pubs.acs.org/doi/10.1021/acs.jnatprod.8b00120$$EHTML$$P50$$Gacs$$H</linktohtml><link.rule.ids>314,777,781,2752,27057,27905,27906,56719,56769</link.rule.ids><backlink>$$Uhttps://www.ncbi.nlm.nih.gov/pubmed/29504746$$D View this record in MEDLINE/PubMed$$Hfree_for_read</backlink></links><search><creatorcontrib>Watkins, Oliver C</creatorcontrib><creatorcontrib>Joyce, Nigel I</creatorcontrib><creatorcontrib>Gould, Nick</creatorcontrib><creatorcontrib>Perry, Nigel B</creatorcontrib><title>Glycosides of the Neurotoxin Tutin in Toxic Honeys Are from Coriaria arborea Phloem Sap, Not Insect Metabolism</title><title>Journal of natural products (Washington, D.C.)</title><addtitle>J. Nat. Prod</addtitle><description>Some honeys contain the neurotoxin tutin (1) plus hyenanchin (2), 2-(β-d-glucopyranosyl)tutin (3), and 2-[6′-(α-d-glucopyranosyl)-β-d-glucopyranosyl]tutin (4). These honeys are made by bees collecting honeydew from passionvine hoppers feeding on the sap of tutu plants (Coriaria spp.). We report a LC-MS study showing that all these picrotoxanes are of plant, not insect, origin. Hyenanchin was barely detectable and the diglucoside was not detectable in C. arborea leaves, but tutu phloem sap contained all four compounds at concentrations up to the highest found in honeydew. 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Nat. Prod</addtitle><date>2018-04-27</date><risdate>2018</risdate><volume>81</volume><issue>4</issue><spage>1116</spage><epage>1120</epage><pages>1116-1120</pages><issn>0163-3864</issn><eissn>1520-6025</eissn><abstract>Some honeys contain the neurotoxin tutin (1) plus hyenanchin (2), 2-(β-d-glucopyranosyl)tutin (3), and 2-[6′-(α-d-glucopyranosyl)-β-d-glucopyranosyl]tutin (4). These honeys are made by bees collecting honeydew from passionvine hoppers feeding on the sap of tutu plants (Coriaria spp.). We report a LC-MS study showing that all these picrotoxanes are of plant, not insect, origin. Hyenanchin was barely detectable and the diglucoside was not detectable in C. arborea leaves, but tutu phloem sap contained all four compounds at concentrations up to the highest found in honeydew. 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title | Glycosides of the Neurotoxin Tutin in Toxic Honeys Are from Coriaria arborea Phloem Sap, Not Insect Metabolism |
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