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(+)-epi-Epoformin, a Phytotoxic Fungal Cyclohexenepoxide: Structure Activity Relationships
- Source :
- Molecules, Volume 23, Issue 7, Molecules, Vol 23, Iss 7, p 1529 (2018)
- Publication Year :
- 2018
- Publisher :
- Multidisciplinary Digital Publishing Institute, 2018.
-
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.
- Subjects :
- epi-epoformin
etiolated wheat coleoptile bioassay
Pharmaceutical Science
Epoxide
phytotoxicity
010402 general chemistry
Diplodia quercivora
01 natural sciences
Analytical Chemistry
lcsh:QD241-441
chemistry.chemical_compound
lcsh:Organic chemistry
oak
Drug Discovery
cyclohexeneoxide
Structure–activity relationship
Bioassay
Physical and Theoretical Chemistry
organic_chemistry
Allelopathy
Natural product
010405 organic chemistry
Chemistry
Drug Discovery3003 Pharmaceutical Science
Organic Chemistry
0104 chemical sciences
Coleoptile
Biochemistry
Chemistry (miscellaneous)
Etiolation
allelopathy
Molecular Medicine
Phytotoxicity
SAR
Subjects
Details
- Language :
- English
- ISSN :
- 14203049
- Database :
- OpenAIRE
- Journal :
- Molecules
- Accession number :
- edsair.doi.dedup.....d2a2d8aef8b2866d6c375b410f66fffd
- Full Text :
- https://doi.org/10.3390/molecules23071529