Semi-synthesis of new antimicrobial esters from the natural oleanolic and maslinic acids

• Published in: Food chemistry 2015-09, Vol.183, p.8-17
• Main Authors: Chouaïb, Karim, Hichri, Fayçal, Nguir, Asma, Daami-Remadi, Majda, Elie, Nicolas, Touboul, David, Ben Jannet, Hichem, Hamza, M’hamed Ali
• Format: Article
• Language: English
• Subjects: Anti-Infective Agents - chemical synthesis; Anti-Infective Agents - chemistry; Antibacterial activity; Antifungal activity; Chemical Sciences; Esters - chemical synthesis; Esters - chemistry; Maslinic acid; Olea europaea; Oleanolic acid; Oleanolic Acid - chemical synthesis; Oleanolic Acid - chemistry; Pentacyclic triterpenoids esters; Triterpenes - chemical synthesis; Triterpenes - chemistry
• ISSN: 0308-8146; 1873-7072
• DOI: 10.1016/j.foodchem.2015.03.018

[Display omitted] •New procedure was used for the selective isolation of OA and MA from pomace olive.•Synthesis of a series of new triterpenic acid esters (1a–j, 2a–o).•Compounds having sulfur and chlorine atoms exhibited interesting antibacterial activities.•Sulfur triterpenoid derivatives 1a and 2a have displayed good antifungal activity.•Compound 2f was the most active against Aspergillus niger (IZ=19mm). In this article, we report an effective procedure for the selective isolation of oleanolic acid 1 and maslinic acid 2 (3.4 and 8.5mg/g DW, respectively) from pomace olive (Olea europaea L.) using an ultrasonic bath, and the synthesis of a series of new triterpenic acid esters. The compounds were characterized by their spectral data and were evaluated for their antimicrobial activity. Among the compounds tested, those having sulfur and chlorine atoms were found to be antibacterial. They showed activity against two Gram-positive bacteria Staphylococcus aureus and Enterococcus faecalis and two Gram-negative bacteria Escherichia coli and Pseudomonas aeruginosa (MICs within a range of 5–25μg/mL). The fungus Penicillium italicum was found to be the most sensitive to both sulfur derivatives: (3β)-3-((thiophene-2-carbonyl)oxy)-olean-12-en-28-oic acid (1a) (IZ=22mm) and (2α,3β-2,3-bis((thiophene-2-carbonyl)oxy)olean-12-en-28-oic acid (2a) (IZ=24mm).