Enzymatic Synthesis and Antimicrobial Activity of Oligomer Analogues of Medicinal Biopolymers from Comfrey and Other Species of the Boraginaceae Family
Maia Merlani,
Dieter M. Scheibel,
Vakhtang Barbakadze,
Lali Gogilashvili,
Lela Amiranashvili,
Athina Geronikaki,
Valentina Catania,
Domenico Schillaci,
Giuseppe Gallo,
Ivan Gitsov
Affiliations
Maia Merlani
Kutateladze Institute of Pharmacochemistry, Tbilisi State Medical University, 36 P.Sarajishvili Street, 0159 Tbilisi, Georgia
Dieter M. Scheibel
Department of Chemistry, College of Environmental Science and Forestry, State University of New York, 1 Forestry Drive, Syracuse, NY 13210, USA
Vakhtang Barbakadze
Kutateladze Institute of Pharmacochemistry, Tbilisi State Medical University, 36 P.Sarajishvili Street, 0159 Tbilisi, Georgia
Lali Gogilashvili
Kutateladze Institute of Pharmacochemistry, Tbilisi State Medical University, 36 P.Sarajishvili Street, 0159 Tbilisi, Georgia
Lela Amiranashvili
Kutateladze Institute of Pharmacochemistry, Tbilisi State Medical University, 36 P.Sarajishvili Street, 0159 Tbilisi, Georgia
Athina Geronikaki
School of Pharmacy, Aristotle University, 54124 Thessaloniki, Greece
Valentina Catania
Laboratory of Microbiology and Biologic Assays, Department of Biological, Chemical and Pharmaceutical Sciences and Technologies, University of Palermo, 32 Via Archirafi, 90123 Palermo, Italy
Domenico Schillaci
Laboratory of Microbiology and Biologic Assays, Department of Biological, Chemical and Pharmaceutical Sciences and Technologies, University of Palermo, 32 Via Archirafi, 90123 Palermo, Italy
Giuseppe Gallo
Laboratory of Molecular Microbiology and Biotechnology, Department of Biological, Chemical and Pharmaceutical Sciences and Technologies, University of Palermo, Viale delle Scienze, ed. 16, 90128 Palermo, Italy
Ivan Gitsov
Department of Chemistry, College of Environmental Science and Forestry, State University of New York, 1 Forestry Drive, Syracuse, NY 13210, USA
This study reports the first enzymatic synthesis leading to several oligomer analogues of poly[3-(3,4-dihydroxyphenyl)glyceric acid]. This biopolymer, extracted from plants of the Boraginaceae family has shown a wide spectrum of pharmacological properties, including antimicrobial activity. Enzymatic ring opening polymerization of 2-methoxycarbonyl-3-(3,4-dibenzyloxyphenyl)oxirane (MDBPO) using lipase from Candida rugosa leads to formation of poly[2-methoxycarbonyl-3-(3,4-dibenzyloxyphenyl)oxirane] (PMDBPO), with a degree of polymerization up to 5. Catalytic debenzylation of PMDBPO using H2 on Pd/C yields poly[2-methoxycarbonyl-3-(3,4-dihydroxyphenyl)oxirane] (PMDHPO) without loss in molecular mass. Antibacterial assessment of natural polyethers from different species of Boraginaceae family Symhytum asperum, S. caucasicum,S. grandiflorum, Anchusa italica, Cynoglossum officinale, and synthetic polymers, poly[2-methoxycarbonyl-3-(3,4-dimethoxyphenyl)oxirane (PMDMPO) and PMDHPO, reveals that only the synthetic analogue produced in this study (PMDHPO) exhibits a promising antimicrobial activity against pathogenic strains S.aureus ATCC 25923 and E.coli ATCC 25922 the minimum inhibitory concentration (MIC) being 100 µg/mL.
