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

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.

Formulation of Creams Containing Active Fraction of Cassia fistula L. Barks and its Antibacterial Activity against Propionibacterium acnes and Pseudomonas aeruginosa

“…Positive results were dicided when the well showing no growth of bacteria (visually observed as clear solution), and it was determined as the MIC. 21 Based on Table 6, it can be concluded that MIC of the active fraction of Cassia fistula's bark against Propionibacterium acnes was 175 ppm, while that against Pseudomonas aeruginosa was 400 ppm.…”

Microencapsulation of Macaranga gigantea Leaf Extracts: Production and Characterization

“…This polymer can prevent the release of drugs in saliva at pH 6.8 -7.4, on the other hand it will dissolve directly in stomach fluid at pH 1.0 -1.5. [26][27][28][29] Ethyl cellulose (EC) is a partly O-ethylated cellulose ether derivative. It is available in a variety of grades, which differ in viscosity, usually hydrophobic in nature and widely used in the biomedical and pharmaceutical industries.…”

“…The effectiveness of the solvent evaporation method to produce microspheres depends on the successful entrapment of the active agent within the particles, and thus, this process is most successful with drugs which are either insoluble or poorly soluble in the aqueous medium which comprises the continuous phase. [27][28][29][30][31][32] There are different methods to prepare microparticles by solvent evaporation method. The choice of the method that will give rise to an efficient drug encapsulation depends on the hydrophilicity or the hydrophobicity of drug.…”

Antifungal Activity of Neolignan Derivatives from Eusideroxylon zwageri Against Pathogenic Fungus Microsporum gypseum

“…These effects were interconnected with secondary metabolites contained within. [1][2][3] There are four big metabolites group produced by Eusideroxylon zwageri. They are alkaloid, steroid, terpenoid and phenolic compounds.…”

“…Microsporum gypseum is a fungus that causes skin diseases in humans. 3 Parts of human body that are often moist can easily be infected by pathogenic fungi. One of the most infectious pathogenic fungi is Microsporum gypseum which causes ringworm.…”