Background:
Eusiderin A is a neolignan derivate, which makes up the majority of the secondary
metabolite of Eusideroxylon zwageri. It has been reported as a potent biopesticide and antifungal
agent. Previous studies on the oxidation of terminal methylene of the allylic chain in Eusiderin A
have been able to produce primary alcohol, pinacol, and an aldehyde which demonstrated strong
activity against plant pathogenic fungi, therefore activity against dermal fungi needs to be studied.
Objective:
The current study aims to improve the hydrophilicity of Eusiderin A via oxidation of the
allylic chain in order to derive a potent antifungal property.
Methods:
Transformation of Eusiderin A has been achieved by using the Wacker Oxidation Method in
combination with the α-Hydroxylation-Ketone Method to produce 7,3’-epoxy-8,4’-oxyneolignane-1’-
carboxylic acid. The structure of the 7,3’-epoxy-8,4’-oxyneolignane-1’-carboxylic acid was identified
from spectroscopy data. The in vitro antifungal activity study was performed using the paper disc
diffusion method against Trichophyton mentagrophytes.
Results:
New molecule of natural Eusiderin A through the oxidation of the allylic chain to increase the
hydrophilicity of Eusiderin A has been designed. Based on the observed UV, IR, 1H and 13C-NMR,
and MS spectra, it can be stated that the 7,3’-epoxy-8,4’-oxyneolignane-1’-carboxylic acid has been
formed. At a concentration of 50 ppm, this compound showed antifungal activity against Trichophyton
mentagrophytes.
Conclusion:
It can be concluded that the 7,3’-epoxy-8,4’-oxyneolignane-1’-carboxylic acid is a potent
antifungal agent as it is able to inhibit the Trichophyton mentagrophytes colonies growth.