Toward the control of Leptosphaeria maculans: design, syntheses, biological activity, and metabolism of potential detoxification inhibitors of the crucifer phytoalexin brassinin

Bioorganic & Medicinal Chemistry
M Soledade C Pedras, Mukund Jha

Abstract

Brassinin (1), a crucial plant defense produced by crucifers, is detoxified by the phytopathogenic fungus Leptosphaeria maculans (Phoma lingam) to indole-3-carboxaldehyde using a putative brassinin oxidase. Potential inhibitors of brassinin detoxification were designed by replacement of its dithiocarbamate group (toxophore) with carbamate, dithiocarbonate, urea, thiourea, sulfamide, sulfonamide, dithiocarbazate, amide, and ester functional groups. In addition, the indolyl moiety was substituted for naphthalenyl and phenyl. The syntheses and chemical characterization of these potential detoxification inhibitors, along with their antifungal and cytotoxic activity, as well as screening using cultures of L. maculans are reported. Overall, three types of interaction were observed in cultures of L. maculans co-incubated with the potential inhibitors and brassinin: (1) a decrease on the rate of brassinin detoxification due to the strong inhibitory activity of the compound on fungal growth, (2) a decrease on the rate of brassinin detoxification due to the inhibitory activity of the compound on the putative brassinin oxidase, and (3) a low to no detectable effect on the rate of brassinin detoxification. A noticeable decrease in the rate...Continue Reading

Citations

Dec 18, 2013·Chemical Reviews·William Spillane, Jean-Baptiste Malaubier
Jul 25, 2012·Journal of Agricultural and Food Chemistry·M Soledade C Pedras, Vijay K Sarma-Mamillapalle
Jan 1, 2008·Acta Crystallographica. Section E, Structure Reports Online·Radia BouaslaCarole Barbey
Jan 1, 2008·Acta Crystallographica. Section E, Structure Reports Online·Muhammad Nadeem ArshadMuhammad Zia-Ur-Rehman
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Muhammad Nadeem ArshadMuhammad Shafiq
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Muhammad ShafiqImtiaz Ahmad
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Irfana MariamIslam Ullah Khan
Jan 1, 2009·Acta Crystallographica. Section E, Structure Reports Online·Islam Ullah KhanMuhammad Shafiq
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online· Aziz-Ur-RehmanIslam Ullah Khan
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online· Aziz-Ur-RehmanIslam Ullah Khan
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online· Aziz-Ur-RehmanIslam Ullah Khan
Jan 1, 2010·Acta Crystallographica. Section E, Structure Reports Online·Sidra Muzaffar MirzaMuhammad Shafiq
Apr 28, 2011·Acta Crystallographica. Section E, Structure Reports Online· Aziz-Ur-RehmanIslam Ullah Khan
Jul 15, 2011·Acta Crystallographica. Section E, Structure Reports Online·Najat AbbassiHafid Zouihri
Aug 13, 2011·Acta Crystallographica. Section E, Structure Reports Online·Najat AbbassiHafid Zouihri
Nov 18, 2011·Acta Crystallographica. Section E, Structure Reports Online·Rui-Bin Hou, Dong-Feng Li
Dec 27, 2011·Acta Crystallographica. Section E, Structure Reports Online·Najat AbbassiHafid Zouihri
Dec 27, 2011·Acta Crystallographica. Section E, Structure Reports Online·Najat AbbassiHafid Zouihri
Sep 11, 2007·Chemical & Pharmaceutical Bulletin·Nobuko MibuKunihiro Sumoto
Jun 2, 2009·Chemical & Pharmaceutical Bulletin·Chennan RamalinganYoung-Woo Kwak
Sep 22, 2015·Nature Chemical Biology·Andrew P Klein, Elizabeth S Sattely
Aug 15, 2017·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·M Soledade C PedrasVijay K Sarma-Mamillapalle
Oct 13, 2006·Organic & Biomolecular Chemistry·M Soledade C Pedras, Mojmír Suchý
Apr 3, 2008·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·M Soledade C Pedras
May 17, 2012·Acta Crystallographica. Section E, Structure Reports Online·Najat AbbassiHafid Zouihri
Nov 26, 2015·Acta Crystallographica. Section E, Crystallographic Communications·Wayland E NolandKenneth J Tritch

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