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Current Organocatalysis

Author(s): Muhaimin Muhaimin*, Syamsurizal Syamsurizal, Madyawati Latief, Rahmi Iskandar , Anis Yohana Chaerunisaa and Didin Mujahidin

DOI: 10.2174/2213337206666190730144041

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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

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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.

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