Volume 8 ; Issue 1 ; in Month : Jan-June (2024) Article No : 178
Oladimeji OH, Nkwachukwu CM, Opara CM, et al.

Abstract

Background: Caffeic acid is a poly-phenolic compound which can be obtained from natural sources such as coffee, turmeric, oregano, mushrooms, vegetables and fruits amongst many others. This acid and a number of its synthesized derivatives have shown different activities such as anti-diabetic, antiviral, anti-inflammatory, anti-aging, cardio-protective potentialities, antioxidant and antimicrobial amongst others. This necessitated the present study. Objectives: Increasing concerns about the debilitating effects of free radical species have become a source of worry to man hence the attention of the scientific world. These chemical species routinely wrought damages in human cells, tissues and organs resulting in a host of diverse patho-physiological and neurodegenerative conditions. Furthermore, the growing resistance to antibiotics and antifungal drugs has encouraged the search for lead compound(s) with the aim of chemically modifying the molecular structure(s) of compounds/drugs/chemicals or synthesizing derivatives from different reactions involving them. The search for novel and pharmacologically active derivatives with the aim of reducing the effects or out-right termination of these conditions led to the choice of caffeic acid. Methodology: The pro-drug, caffeic acid was subjected to different synthetic procedures such as esterification, acetylation and reduction. The melting points, refractive indices and optical rotations of the acid and derivatives were obtained. The antioxidant activity (IC50) of caffeic acid and synthesized products was determined using the DPPH (2, 2-diphenyl-1-picrylhydrazyl hydrate) test. A comparison of the obtained antioxidant activities was done to determine if any improvements could be noticed in the derivatives. The agar-in-hole method was adopted for screening caffeic acid and the synthesized compounds against Staphylococcus aureus, Escherichia coli and Candida albicans for antibacterial and antifungal activities respectively. Results: The identities of the derivatives have been revealed to be ethyl caffeate (CE), acetyl caffeate (CA) and 1-(3,4-dihydroxy phenyl)-2-propen-3-ol (3,4-benzenediol-2-propen-3-ol) (CR), a novel aryl substituted alkenol assigned the trivial nomenclature of (Ladimejol) respectively using a combination of physico-chemical determinations and IR spectral technique. Caffeic acid, (CE), and (CA) demonstrated significant antioxidant activity (IC50) of 0.22, 0.19 and 0.16 µg/mL respectively which compare favourably with 0.18 µg/mL obtained with Vitamin C (a standard antioxidant drug). The acetyl derivative gave a comparably remarkable antioxidant activity than Vitamin C. However, the antioxidant activity of (CR) (Ladimejol) could not be regressed in this study. The antibacterial and antifungal activities elicited by both caffeic acid and obtained derivatives were concentration-dependent. Furthermore, the acetyl derivative (CA) was distinctly more bacteriostatic than the other two synthesized products against the test bacteria and was also hugely anti-candidal. In addition this derivative elicited higher activities than even caffeic acid. The reduced product (CR) (Ladimejol) recorded no growths in the screening for both antibacterial and antifungal activities. Conclusion: The results from this study indicate that the synthesized novel aryl substituted alkenol, 1-(3,4-dihydroxy phenyl)-2-propen-3-ol (3,4-benzenediol-2-propen-3-ol) (CR) (Ladimejol) did not show any potentialities for antioxidant, antibacterial and antifungal activities. However, the acetyl caffeate (CA) demonstrated significant antioxidant, antibacterial and antifungal activities. Hence, acetyl caffeate could be considered as a lead candidate compound in the search for newer and more efficacious antioxidant and antimicrobial agents in more expanded structural activity relationship studies (SARS), drug design development and formulation studies.

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