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conferenceseries
.com
Volume 7
Pharmaceutical Regulatory Affairs: Open Access
ISSN: 2167-7689
Pharma Europe 2018
May 07-09, 2018
May 07-09, 2018 | Frankfurt, Germany
15
th
Annual European Pharma Congress
Caffeic acid-derived polyether from medicinal plants: Structure and biological activity
Vakhtang Barbakadze
Tbilisi State Medical University, Georgia
A
newseriesof linear andregular3-arylglycericacid-derivedpolyether, namely, poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)
ethylene] or poly[3-(3,4-dihydroxyphenyl)glyceric acid] (PDPGA) was isolated and identified in the water-soluble, high-
molecular weight fractions obtained from extracts of different species of Comfrey.
Symphytum asperum, S. caucasicum, S.
officinale, S. grandiflorum
and
Bugloss Anchusa italica
. According to data of 13C, 1H NMR, APT, 2D 1H/13C HSQC, 1D NOE
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. This compound is a first representative of a new class of natural polyethers. Then
the racemic monomer 2,3-dihydroxy-3-(3,4-dihydroxyphenyl)propionic acid (DDPPA) and its virtually pure enantiomers
(+)-(2R,3S)-2,3-dihydroxy-3-(3,4-dihydroxyphenyl)propionic acid and (-)-(2S,3R)-2,3-dihydroxy-3-(3,4-dihydroxyphenyl)
propionic acid were synthesized for the first time via Sharpless asymmetric dihydroxylation of trans-caffeic acid derivatives
using a potassiumosmate catalyst, a stoichiometric oxidant N-methylmorpholine-N-oxide and enantiocomplementary catalysts
cinchona alkaloid derivatives (DHQ)2-PHAL and (DHQD)2-PHA as chiral auxiliaries. It is well known that epoxides are
valuable synthons in organic synthesis and have been introduced into pharmaceutical applications, such as in the synthesis of
antitumor drugs. Subsequently, the building block for the production of derivatives of PDPGA, methyl 3-(3,4-dimethoxyphenyl)
glycidate was synthesized based on the Darzen reaction or by oxidation with oxone in order to produce future derivatives of
synthetic analogue of natural polymers through ring-opening polymerization of 2,3-disubstituted oxirane. PDPGA is endowed
with intriguing pharmacological properties as anticomplementary, antioxidant, anti-inflammatory, burn and wound healing
and anticancer properties. PDPGA and DPGA exerted anticancer activity
in vitro
and
in vivo
against human prostate cancer
(PCA) cells. However, 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 applications.
v_barbakadze@hotmail.comPharmaceut Reg Affairs 2018, Volume 7
DOI: 10.4172/2167-7689-C1-031