6533b82dfe1ef96bd1291fdd

RESEARCH PRODUCT

Enzymatic Synthesis and Antimicrobial Activity of Oligomer Analogues of Medicinal Biopolymers from Comfrey and Other Species of the Boraginaceae Family

Maia MerlaniDieter M. ScheibelVakhtang BarbakadzeLali GogilashviliLela AmiranashviliAthina GeronikakiValentina CataniaDomenico SchillaciGiuseppe GalloIvan Gitsov

subject

RS1-441Poly[3-(34-dihydroxyphenyl)glyceric acid]Pharmacy and materia medicapoly[3-(34-dihydroxyphenyl)glyceric acid]; enzymatic polymerization; lipase; antimicrobial activity; Boraginaceae familyBoraginaceae familyPharmaceutical ScienceLipaseAntimicrobial activityArticleEnzymatic polymerization

description

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.

yearjournalcountryeditionlanguage
2022-01-04
10.3390/pharmaceutics14010115http://hdl.handle.net/10447/531068