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Synthesis of 7,3'-Epoxy-8,4'-Oxyneolignane-1’-Carboxylic Acid from Natural Eusiderin A and its Activity Against Trichophyton mentagrophytes

[ Vol. 7 , Issue. 1 ]

Author(s):

Muhaimin Muhaimin*, Syamsurizal Syamsurizal, Madyawati Latief, Rahmi Iskandar , Anis Yohana Chaerunisaa and Didin Mujahidin   Pages 44 - 54 ( 11 )

Abstract:


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.

Keywords:

Antifungal, eusiderin A, 7, 3’-epoxy-8, 4’-oxyneolignane-1’-carboxylic acid, oxidation, Trichophyton mentagrophytes.

Affiliation:

Department of Chemistry Education, Faculty of Education, University of Jambi, Jambi, Department of Chemistry Education, Faculty of Education, University of Jambi, Jambi, Department of Chemistry, Faculty of Science and Technology, University of Jambi, Jambi, Department of Chemistry, Faculty of Science and Technology, University of Jambi, Jambi, Faculty of Pharmacy, Padjadjaran University, Bandung, Department of Chemistry, Faculty of Mathematics and Natural Sciences, Bandung Institute of Technology, Bandung

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