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Molecules 2018, 23(7), 1529; https://doi.org/10.3390/molecules23071529

(+)-epi-Epoformin, a Phytotoxic Fungal Cyclohexenepoxide: Structure Activity Relationships

1
Allelopathy Group, Department of Organic Chemistry, School of Science, Institute of Biomolecules (INBIO), University of Cádiz, C/República Saharaui 7, 11510 Puerto Real, Cádiz, Spain
2
Department of Chemical Sciences, University of Naples “Federico II”, Complesso Universitario Monte S. Angelo, Via Cintia 4, 80126 Napoli, Italy
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Received: 7 June 2018 / Revised: 20 June 2018 / Accepted: 20 June 2018 / Published: 25 June 2018
(This article belongs to the Special Issue Structure-Activity Relationship of Natural Products 2018)
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Abstract

(+)-epi-Epoformin (1), is a fungal cyclohexene epoxide isolated together with diplopimarane and sphaeropsidins A and C, a nor-ent-pimarane and two pimaranes, from the culture filtrates of Diplodia quercivora, a fungal pathogen for cork oak in Sardinia, Italy. Compound 1 possesses a plethora of biological activities, including antifungal, zootoxic and phytotoxic activity. The last activity and the peculiar structural feature of 1 suggested to carry out a structure activity relationship study, preparing eight key hemisynthetic derivatives and the phytotoxicity was assayed. The complete spectroscopic characterization and the activity in the etiolated wheat coleoptile bioassay of all the compounds is reported. Most of the compounds inhibited growth and some of them had comparable or higher activity than the natural product and the reference herbicide Logran. As regards the structure-activity relationship, the carbonyl proved to be essential for their activity of 1, as well as the conjugated double bond, while the epoxide could be altered with no significant loss. View Full-Text
Keywords: Diplodia quercivora; oak; epi-epoformin; cyclohexeneoxide; etiolated wheat coleoptile bioassay; phytotoxicity; allelopathy; SAR Diplodia quercivora; oak; epi-epoformin; cyclohexeneoxide; etiolated wheat coleoptile bioassay; phytotoxicity; allelopathy; SAR
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited (CC BY 4.0).

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Cala, A.; Masi, M.; Cimmino, A.; Molinillo, J.M.G.; Macias, F.A.; Evidente, A. (+)-epi-Epoformin, a Phytotoxic Fungal Cyclohexenepoxide: Structure Activity Relationships. Molecules 2018, 23, 1529.

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