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Polymer Congress 2018
Polymer Sciences
ISSN: 2471-9935
Page 85
June 04-05, 2018
London, UK
4
th
Edition of International Conference on
Polymer Science and
Technology
W
ithin the field of pharmacologically active biopolymers
the area of stable polyethers seems rather attractive.
The high-molecular fractions from the several species of
two genera Symphytum and Anchusa were isolated by
ultrafiltration of water-soluble crude polysaccharides on the
membrane filter with cut-off value of 1000 kDa. According to
IR, 13C and 1H NMR, 1D NOE, 2D heteronuclear 1H/13C HSQC
and 2D DOSY experiments the main structural element of
these preparations was found to be a new regular polymeric
molecule. The polyoxyethylene chain is the backbone of this
biopolymer. 3,4-Dihydroxyphenyl and carboxyl groups are
regular substituents at two carbon atoms in the chain. The
repeating unit of this regular caffeic acid-derived polyether,
is 3-(3,4-dihydroxyphenyl)glyceric acid residue. Thus, the
structure of natural polymer under study was found to be
poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene] or poly[3-
(3,4-dihydroxyphenyl)glyceric acid] (PDPGA). Such caffeic
acid-derived biopolymer to our knowledge has not been known
and has been identified for the first time. This compound
represents a new class of natural polyethers. Then the racemic
monomer and its pure enantiomers (+)-(2R,3S)-2,3-dihydroxy-
3-(3,4-dihydroxy-phenyl)-propionic acid [(2R,3S)-DDPPA] and
(-)-(2S,3R)-2,3-dihydroxy-3-(3,4-dihydroxy-phenyl) propionic
acid [(2S,3R)-DDPPA] were synthesized for the first time via
sharpless asymmetric dihydroxylation of trans-caffeic acid
derivatives using an osmium catalyst and (DHQ)2-PHAL and
(DHQD)2-PHAL as chiral auxiliaries. PDPGA is endowed with
intriguing pharmacological activities as anticomplementary,
antioxidant, anti-inflammatory, burn and wound healing and
anticancer properties. PDPGA and its synthetic monomer
exerted anticancer activity in vitro and in vivo against
androgen-dependent and -independent human prostate cancer
(PCA) cells via targeting androgen receptor, cell cycle arrest
and apoptosis without any toxicity, together with a strong
decrease in prostate specific antigen level in plasma. However,
our results showed that anticancer efficacy of PDPGA is more
effective compared to its synthetic monomer. Overall, this
study identifies PDPGA as a potent agent against PCA without
any toxicity and supports its clinical application.
v_barbakadze@hotmail.comA new class of caffeic acid-derived biopolyether from medicinal
plants its synthetic basic monomeric moiety and their
anticancer efficacy
V Barbakadze
1,2
1
Tbilisi State Medical University, Georgia
2
I G Kutateladze Institute of Pharmacochemistry, Georgia
Polym Sci 2018, Volume 4
DOI: 10.4172/2471-9935-C2-012