Preprint Article Version 1 Preserved in Portico This version is not peer-reviewed

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

Antonio Cala
,
Marco Masi
ORCID logo ,
Alessio Cimmino
ORCID logo ,
José M.G. Molinillo
ORCID logo ,
Francisco A. Macías
* ORCID logo ,
Antonio Evidente
Version 1 : Received: 7 June 2018 / Approved: 8 June 2018 / Online: 8 June 2018 (13:15:11 CEST)

A peer-reviewed article of this Preprint also exists.

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. 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.

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 their 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.

Keywords

Diplodia quercivora; oak; epi-epoformin; cyclohexeneoxide; etiolated wheat coleoptile bioassay; phytotoxicity; allelopathy; SAR

Subject

Chemistry and Materials Science, Organic Chemistry

Copyright: 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.

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