Derivatization of Rosmarinic Acid Enhances its in vitro Antitumor, Antimicrobial and Antiprotozoal Properties

Abstract

On its own, rosmarinic acid possesses multiple biological activities such as anti-inflammatory, antimicrobial, cardioprotective and antitumor properties, and these are the consequence of its ROS scavenging and inhibitory effect on inflammation. In this study, two quaternary phosphonium salts of rosmarinic acid were prepared for the purpose of increasing its penetration into biological systems with the aim of improving its antimicrobial, antifungal, antiprotozoal and antitumor activity. The synthetized molecules, the triphenylphosphonium and tricyclohexylphosphonium salts of rosmarinic acid, exhibited significantly stronger inhibitory effects on the growth of HCT116 cells with IC50 values of 7.28 or 8.13 μM in comparison to the initial substance, rosmarinic acid (>300 μM). For the synthesized derivatives, we detected a greater than three-fold increase of activity against Acanthamoeba quina, and a greater than eight-fold increase of activity against A. lugdunensis in comparison to rosmarinic acid. Furthermore, we recorded significantly higher antimicrobial activity of the synthetized derivatives when compared to rosmarinic acid itself. Both synthetized quaternary phosphonium salts of rosmarinic acid appear to be promising antitumor and antimicrobial agents, as well as impressive molecules for further research.

Polyphenol Profile and Antimicrobial and Cytotoxic Activities of Natural Mentha × piperita and Mentha longifolia Populations in Northern Saudi Arabia

“…Cryptochlorogenic acid was moderately effective against fungi, but rosmarinic acid was the weakest. Previous studies reported moderate-to-low antimicrobial activities for rosmarinic acid [86,87] and naringin [88], and high antibacterial activities have been reported for chlorogenic acid (cryptochlorogenic acid derivatives) from Mammillaria extracts [4,89]. Chlorogenic acid displayed fungicidal activities against other pathogenic fungi such as Fusarium solani, Sclerotinia sclerotiorum, and Botrytis cinerea [90], and caffeic acid showed strong antibacterial and antifungal activities against several bacterial strains [2].…”

Phytochemical Screening and Acanthamoebic Activity of Shoots from in Vitro Cultures and in Vivo Plants of Eryngium alpinum L.—The Endangered and Protected Species

“…As stated by Mahboob et al [34], the acanthamoebicidal effect of Lonicera japonica flower, which evoked a significant reduction of trophozoite viability, depends mostly on the major compound form the extract, that is chlorogenic acid. According to Bittner Fialová, rosmarinic acid and its derivates appeared to be promising anti-Acanthamoeba agents with the EC 50 values between 5.6 ± 0.3 mM and 19.1 ± 0.4 mM [35]. The biological study of the Passiflora spp.…”

Antimicrobial and Antioxidant Properties of Four Lycopus Taxa and an Interaction Study of Their Major Compounds

“…However, we have not evaluated the interaction of the individual secondary metabolites contained in the Lycopus infusions with the cell walls of the mentioned microbes. Concerning the antibacterial activity of the examined Lycopus infusions, we suggest that it could be bound to the presence of RA, which even in solo has excellent antimicrobial activity [27][28][29][30].…”