Structure characterization of plant biomacromolecule as prospective therapeutic agent

2^nd International Conference and Exhibition on Polymer Chemistry

November 15-17, 2017 | San Antonio, USA

Vakhtang Barbakadze

Tbilisi State Medical University, Georgia

Posters & Accepted Abstracts: J Material Sci Eng

Abstract :

Plant biomacromolecule, namely poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene] or poly[3-(3,4-dihydroxyphenyl)glyceric acid] (PDPGA) was detected in high-molecular fractions obtained from water extracts of different species of Boraginaceae family. According to data of 13C, 1H NMR, 2D 1H/13C HSQC and 2D DOSY experiments, the polyoxyethylene chain is the backbone of the polymer molecule. 3,4-Dihydroxyphenyl and carboxyl groups are regular substituents at two carbon atoms in the chain. The repeating unit of this regular polymer is 3-(3,4-dihydroxyphenyl)glyceric acid residue. Most of the carboxylic groups of PDPGA from Anchusa italica and Symphytum grandiflorum unlike the polymer of S. asperum, S. caucasicum and S. officinale are methylated. The 2D DOSY experiment gave the similar diffusion coefficient for the methylated and non-methylated signals of PDPGA. This would imply a similar molecular weight for methylated and non-methylated polymers. Then basic monomeric moiety of this polymer, 3-(3,4-dihydroxyphenyl)glyceric acid (DPGA) was synthesized via Sharpless asymmetric dihydroxylation of trans-caffeic acid derivatives using an osmium catalyst. Besides, the building block for the production of derivatives of PDPGA, methyl 3-(3,4-dimethoxyphenyl)glycidate was synthesized in order to produce, in future, derivatives of synthetic analogue of natural polymer through ring-opening polymerization of 2,3-disubstituted oxirane. PDPGA is endowed with intriguing pharmacological properties as anti-complementary, antioxidant, anti-inflammatory, burn and wound healing and anticancer properties. S. caucasicum PDPGA and DPGA exerted anti-cancer efficacy in vitro and in vivo. However, our results showed that anticancer efficacy of PDPGA is more effective compared to its synthetic monomer. Overall, this study identifies S. caucasicum PDPGA as a potent agent against prostate cancer without any toxicity and supports its clinical application.