Antibacterial activity of naringin derivatives against pathogenic strains

Abstract

Aims: To study the antimicrobial activity of naringin (NAR), a flavonoid extracted from citrus industry waste, and NAR derivatives [naringenin (NGE), prunin and alkyl prunin esters] against pathogenic bacteria such as L. monocytogenes, E. coli O157:H7 and S. aureus. The relationship between the structure of the chemical compounds and their antagonistic effect was also analysed. Methods and Results: The agar dilution technique and direct contact assaying were applied. NGE, prunin and NAR showed no antimicrobial activity at a concentration of 0·25 mmol l−1. Similarly, fatty acids with a chain length between C2 and C18 showed no antimicrobial activity at the same concentration. However, prunin‐6″‐O‐acyl esters presented high antibacterial activity, mainly against Gram‐positive strains. This activity increased with increasing chain length (up to 10–12 carbon atoms). Alkyl prunin esters with 10–12 carbon atoms diminished viability of L. monocytogenes by about 3 log orders and S. aureus by 6 log orders after 2 h of contact at 37°C and at a concentration of 0·25 mmol l−1. The compounds examined were not effective against any of the Gram‐negative strains assayed, even at the highest concentration. Conclusions: Addition of sugars to the aglycone did not enhance its antimicrobial activity. Attachment of a saturated aliphatic chain with 10–12 carbon atoms to the A ring of the flavonoid (or to sugars attached to this ring), seems to be the most promising modification. In conclusion, alkyl prunin esters with a chain length of C10–C12 have promising features as antimicrobial agents because of their high antilisterial and antistaphylococcal activity. Significance and Impact of the Study: This study shows that it is possible to obtain NAR derivatives with important antimicrobial activity, especially against Gram‐positive pathogenic bacteria. It also provides guidelines on the structural modifications in similar molecules to enhance the antimicrobial activity.

Additive antibacterial activity of naringenin and antibiotic combinations against multidrug resistant Staphylococcus aureus

“…In fact, data demonstrate that an increase in chain length (10-12 carbon atoms) and modifying its structure increased the antibacterial activities. This shows that the structure of naringenin is important for interaction with the antibiotics in combination studies (Celiz et al, 2011;Lee et al, 2013). Synergy studies of natural products and antibiotics are increasing in order to assess their combination effects (Olajuyigbe and Afolayan, 2013).…”

“…It contains two benzene rings linked together with a heterocyclic pyrone ring (a class of cyclic compounds) (Tripoli et al, 2007). It is believed to possess antibacterial (Celiz et al, 2011), antioxidant, anticancer anti-inflammatory and immunomodulatory properties (Goldwasser et al, 2011;Khachatoorian et al, 2012;Lee et al, 2013). The purpose of this study was to evaluate the antibacterial activities of naringenin on its own, as well as assess the combinatory antibacterial effects of naringenin and antibiotics against methicillinsensitive and methicillin-resistant strains of S. aureus (i.e.…”

Ameliorative effect of naringin against doxorubicin-induced acute cardiac toxicity in rats

“…Naringin (NR) is a bioflavonoid found in grapefruits and other citrus species (Figure 1). It has been shown to exhibit various pharmacological and therapeutic properties, e.g., antimicrobial (Céliz et al, 2011), antimutagenic (Jagetia et al, 2007), anticancer (Li et al, 2013), anti-inflammatory, cholesterol-lowering, and antioxidant effects (Jeon et al, 2002). Few studies have reported the cardioprotective effect of NR against isoproterenol (ISO)-induced myocardium infarction (MI) in rats (Rajadurai & Prince, 2006;Rajadurai et al, 2007).…”

Polyphenolic content and bactericidal effect of Mexican Citrus limetta and Citrus reticulata

“…Citrus flavonoids, in particular, are recognized as antioxidants (Procházková et al 2011;Yu et al 2014;Asikin et al 2015), antifungals (Buer et al 2010), antimicrobials (Vikram et al 2010;Cushnie and Lamb 2011;Céliz et al 2011), and even accelerating wound and disease healing (Neves et al Neves et al 2010;Arab and Liebeskind 2010;Codoñer-Franch and Valls-Bellés 2010;Wang et al 2014). In plants, flavonoids appear to play defensive roles against pathogens, including bacteria, fungi and viruses; these are generally found in glycosylated forms in plants, and the sugar moiety is an important factor determining their bioavailability (Agati et al 2012).…”