Biologically Active Poly[3-(3,4-Dihydroxyphenyl)Glyceric Acid] from Borago officinalis (Boraginaceae)

Authors

  • Teona Kekeishvili Tbilisi State Medical University I. Kutateladze Institute of Pharmacochemistry
  • Maia Merlani Tbilisi State Medical University I. Kutateladze Institute of Pharmacochemistry
  • Lela Amiranashvili Tbilisi State Medical University I. Kutateladze Institute of Pharmacochemistry
  • Lali Gogilashvili Tbilisi State Medical University I. Kutateladze Institute of Pharmacochemistry
  • Vakhtang Barbakadze Tbilisi State Medical University I. Kutateladze Institute of Pharmacochemistry https://orcid.org/0000-0002-8716-909X

DOI:

https://doi.org/10.52340/csw.2022.05.930

Keywords:

Caffeic acid-derived polyether, poly[3-(3,4-dihydroxyphenyl)glyceric acid], poly[oxy-1-carboxy-2-(3,4-dihydroxyphenyl)ethylene], Borago officinalis, Boraginaceae

Abstract

A high-molecular water-soluble preparation from stems of Borago officinalis (Boraginaceae family) was isolated. According to data from UV, IR, 1H, 13C NMR, gCOSY and 2D heteronuclear 1H/13C gHSQCED experiments, the main chemical constituent of this water-soluble high-molecular preparation from stems of Borago officinalis (HMP-BS) was found to be a biologically active caffeic acid-derived polymer, namely poly[oxy-1-carboxy-2-(3,4-dihydroxy­phenyl)­ethylene] also referred to as poly[3-(3,4-dihydroxyphenyl)glyceric acid] (PDPGA). PDPGA was previously detected in high-molecular preparations of Symphytum asperum, S. caucasicum, S. officinale, Anchusa italica and Cynoglossum officinale. The detection of this compound in different genera of the Boraginaceae family is interesting as this unusual caffeic acid-derived polymer could be consider a chemotaxonomic marker among Boraginaceae plants. Thus, PDPGA is interesting due to the importance of its chemotaxonomic significance, the potential biomedical applications of the Boraginaceae plants and the chemical importance of PDPGA. The presence of poly[3-(3,4-dihydroxy­phenyl)­glyceric acid] in multiple Boraginaceae species expands the resources of raw materials for this biologically active polymer.

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...

References

Barbakadze V., Kemertelidze E., Targamadze I., Mulkijanyan K., Shashkov A.S., Usov A. I. (2005) Poly[3-(3,4-dihydroxyphenyl)glyceric acid], a new biologically active polymer from Symphytum asperum Lepech. and S.caucasicum Bieb. (Boraginaceae). Molecules, 10, 9: 1135-1144. https://doi.org/10.3390/10091135

Barbakadze V., van den Berg A.J.J., Beukelman C.J., Kemmink J., Quarles van Ufford H.C. (2009) Poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Symphytum officinale roots and its biological activity. Chem. Nat. Compds., 45, 1: 6-10. https://doi.org/10.1007/s10600-009-9221-5

Barbakadze V., Gogilashvili L., Amiranashvili L., Merlani M., Mulkijanyan K., Churadze M., Salgado A., Chankvetadze B. (2010) Poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Anchusa italica roots. Nat. Prod. Commun., 5, 7: 1091-1095. https://doi.org/10.1177/1934578X1000500722

Gokadze S., Gogilashvili L., Amiranashvili L., Barbakadze V., Merlani M., Bakuridze A., Salgado A., Chankvetadze B. (2017) Investigation of water-soluble high molecular preparation of Symphytum grandiflorum DC (Boraginaceae). Bull. Georg. Natl. Acad. Sci., 11, 1:115-121. http://science.org.ge/bnas/vol-11-2.html

Gogilashvili L., Amiranashvili L., Merlani M., Salgado A., Chankvetadze B., Barbakadze V. (2020) Poly[3-(3,4-Dihydroxyphenyl)Glyceric Acid] from Cynoglossum officinale L. (Boraginaceae). Bull. Georg. Natl. Acad. Sci., 14, 1: 108-113. http://science.org.ge/bnas/vol-14-1.html

Barthomeuf C.M., Debiton E., Barbakadze V., Kemertelidze E.P. (2001) Evaluation of the dietetic and therapeutic potential of a high molecular weight hydroxicinnamate-derived polymer from Symphytum asperum Lepech. Regarding its antioxidant, antilipoperoxidant, antiinflammatory, and cytotoxic properties. J. Agric. Food Chem., 49, 8: 3942-3946. https://doi.org/10.1021/jf010189d

Barbakadze V., Kemertelidze E.P., Mulkijanyan K.G., van den Berg A.J.J., Beukelman C.J., van den Worm E., Quarles van Ufford H.C., Usov A.I. (2007) Poly[3-(3,4-dihydroxyphenyl)glyceric acid] from Symphytum officinale roots and its biological activity. Pharm. Chem. J., 41, 1: 14-16. http://dx.doi.org/10.1007/s11094-007-0040-3

Shrotriya S., Deep G., Ramasamy K., Raina K., Barbakadze V., Merlani M., Gogilashvili L., Amiranashvili L., Mulkijanyan K., Papadopoulos K., Agarwal C., Agarwal R. (2012) Poly[3-(3, 4-dihydroxyphenyl) glyceric] acid from comfrey exerts anti-cancer efficacy against human prostate cancer via targeting androgen receptor, cell cycle arrest and apoptosis. Carcinogenesis, 33, 8: 1572–1580. https://doi.org/10.1093/carcin/bgs202

Downloads

Published

2022-05-18

How to Cite

Teona Kekeishvili, Maia Merlani, Lela Amiranashvili, Lali Gogilashvili, & Vakhtang Barbakadze. (2022). Biologically Active Poly[3-(3,4-Dihydroxyphenyl)Glyceric Acid] from Borago officinalis (Boraginaceae). COLLECTION OF SCIENTIFIC WORKS OF TBILISI STATE MEDICAL UNIVERSITY, 55. https://doi.org/10.52340/csw.2022.05.930