Highly oxygenated isoprenylated cyclohexanoids from the fungus Parastagonospora nodorum SN15

Amr El-Demerdash; Grégory Genta-Jouve; Margot Bärenstrauch; Caroline Kunz; Emmanuel Baudouin; Soizic Prado

doi:10.1016/j.phytochem.2019.112056

Highly oxygenated isoprenylated cyclohexanoids from the fungus Parastagonospora nodorum SN15

Phytochemistry. 2019 Oct:166:112056. doi: 10.1016/j.phytochem.2019.112056. Epub 2019 Jul 11.

Authors

Amr El-Demerdash¹, Grégory Genta-Jouve², Margot Bärenstrauch³, Caroline Kunz⁴, Emmanuel Baudouin⁵, Soizic Prado⁶

Affiliations

¹ Muséum National d'Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes, UMR 7245, CP 54, 57 Rue Cuvier, 75005, Paris, France; Organic Chemistry Division, Chemistry Department, Faculty of Science, Mansoura University, Mansoura, 35516, Egypt.
² Muséum National d'Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes, UMR 7245, CP 54, 57 Rue Cuvier, 75005, Paris, France; Université Paris Descartes, Laboratoire de Chimie-Toxicologie Analytique et Cellulaire (C-TAC), UMR CNRS 8638, COMETE, 4 Avenue de l'Observatoire, 75006, Paris, France.
³ Muséum National d'Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes, UMR 7245, CP 54, 57 Rue Cuvier, 75005, Paris, France.
⁴ Muséum National d'Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes, UMR 7245, CP 54, 57 Rue Cuvier, 75005, Paris, France; Sorbonne Université, Faculté des Sciences et Ingénierie, UFR 927, F-75005, Paris, France.
⁵ Sorbonne Université, CNRS, Laboratoire de Biologie du Développement, Institut de Biologie Paris Seine (LBD-IBPS), Paris, F-75005, France.
⁶ Muséum National d'Histoire Naturelle, Unité Molécules de Communication et Adaptation des Micro-organismes, UMR 7245, CP 54, 57 Rue Cuvier, 75005, Paris, France. Electronic address: sprado@mnhn.fr.

PMID: 31302342
DOI: 10.1016/j.phytochem.2019.112056

Abstract

The chemical investigation of the wheat plant pathogen Parastagonospora nodorum SN15 led to the purification of seven highly oxygenated acetylenic cyclohexanoids named stagonosporynes A-G. Their structures were determined on the basis of extensive NMR and the relative and absolute configurations by an array of computational methods including simulation of NOESY spectrum and electronic circular dichroism (ECD). All compounds were evaluated for their herbicidal activity and stagonosporyne G displayed the most significant herbicidal activity.

MeSH terms

Ascomycota / chemistry*
Cyclohexanols / chemistry*
Models, Molecular
Molecular Conformation
Oxygen / chemistry*
Prenylation*

Substances

Cyclohexanols
Oxygen