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

• Published in: Molecules (Basel, Switzerland) Switzerland), 2019-03, Vol.24 (6), p.1078
• Main Authors: Bittner Fialová, Silvia, Kello, Martin, Čoma, Matúš, Slobodníková, Lívia, Drobná, Eva, Holková, Ivana, Garajová, Mária, Mrva, Martin, Zachar, Vlastimil, Lukáč, Miloš
• Format: Article
• Language: English
• Subjects: Acanthamoeba - drug effects; Alzheimer's disease; anti-Acanthamoeba activity; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; Anti-Infective Agents - chemistry; Anti-Infective Agents - pharmacology; antibacterial; anticancer; antifungal; Antifungal Agents - chemistry; Antifungal Agents - pharmacology; Antiinfectives and antibacterials; Antimicrobial activity; Antimicrobial agents; Antiprotozoal Agents - chemistry; Antiprotozoal Agents - pharmacology; Antitumor activity; Bacteria; Breast cancer; Cell cycle; Cinnamates - chemistry; Cinnamates - pharmacology; Colorectal cancer; Depsides - chemistry; Depsides - pharmacology; Fungicides; Gram-negative bacteria; HCT116 Cells; Humans; Inflammation; Lung cancer; Metastasis; Microbial Sensitivity Tests; MRSA; Organophosphorus Compounds - chemistry; Organophosphorus Compounds - pharmacology; quaternary phosphonium salts; Rosmarinic Acid; Salts; Scavenging; Skin cancer
• ISSN: 1420-3049; 1420-3049
• DOI: 10.3390/molecules24061078

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 IC 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 and a greater than eight-fold increase of activity against 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.