Variation of Phenolic Acid Compounds in the Iranian Germplasm of Boraginaceae, a Chemotaxonomy Approach

Document Type : Research Paper

Authors

1 Department of Biology, Faculty of Basic Sciences, Azarbaijan Shahid Madani University, Tabriz, Iran

2 Department of Chemistry, Faculty of Basic Sciences, Azarbaijan Shahid Madani University, Tabriz, Iran

3 Faculty of Life Sciences & Biotechnology, Shahid Beheshti University, Tehran, Iran

Abstract

In this study, phenolic acid compositions in fourteen taxa of Boraginaceae were analyzed by HPLC-UV to obtain informative chromatographic data. In general, 9 phenolic acid compounds were identified in different studied taxa. m-coumaric acid (1.80-1962.09 mg/kg), salicylic acid (13.22-867.35 mg/kg), ferulic acid (0.00-661.69 mg/kg), and p-coumaric acid (12.10-392.48 mg/kg) were characterized as the main compounds of the studied taxa. The results indicated that m-coumaric acid was the main phenolic acid in H. rigidium, M. sylvatica, and solnathus stamineus. Furthermore, salicylic acid was the main phenolic acids of M. sylvatica and N. caspica. Also, the highest amounts of ferulic acid and p-coumaric acid were detected in M. sylvatica and Heliotropium europaeum, respectively. The qualitative and quantitative evaluation of these compounds was used for the characterization of the taxa and for revealing their phytochemical similarity and differentiation. Hierarchical cluster analysis showed that the studied taxa were classified into two main clusters (I and II) based on main phenolic acid compounds. Cluster I included H. rigidum, S. stamineus, and L. microcarpaa, and the rest studied taxa grouped in cluster II. The chemotaxonomic significance of the isolated compounds was discussed.

Keywords

References

  1. Granica S., Zidorn C. Phenolic compounds from aerial parts as chemosystematic markers in the Scorzonerinae (Asteraceae). Biochem Syst Ecol. 2015;58:102-113.
  2. Lemma B., Grehl C., Zech M., Mekonnen B., Zech W., Nemomissa S., Bekele T., Glaser B. Phenolic compounds as unambiguous chemical markers for the identification of keystone plant species in the bale mountains, Ethiopia. Plants. 2019;8(7):228.
  3. Li L., He L., Su X., Amu H., Li J., Zhang Z. Chemotaxonomy of Aster species from the Qinghai‐Tibetan Plateau based on metabolomics. Phytochem Anal. 2022;33(1):23-39.
  4. Singh R. Chemotaxonomy: a tool for plant classification. J Med Plant. 2016;4(2):90-93.
  5. Gottschling M., Hilger H.H., Wolf M., Diane N. Secondary structure of the ITS1 transcript and its application in a reconstruction of the phylogeny of Boraginales. Plant Biol. 2001;3:629-636.
  6. Cheynier V., Comte G., Davies K.M., Lattanzio V., Martens S. Plant phenolics: Recent advances on their biosynthesis, genetics and ecophysiology. Plant Physiol Biochem. 2013;72:1-20.
  7. Giada M.L.R. Food phenolic compounds: main classes, sources and their antioxidant power. Oxidative stress and chronic degenerative diseases-A role for antioxidants. InTech. 2013;2013:87-112.
  8. Heleno S.A., Martins A., Queiroz M.J.R.P., Ferreira I.C.F.R. Bioactivity of phenolic acids: metabolites versus parent compounds: a review. Food Chem. 2015;173:501-513.
  9. Williamson G. The role of polyphenols in modern nutrition. Nut Bulletin. 2017; 42:226-235.
  10. Gomes C.A., Girão da Cruz T., Andrade J.L., Milhazes N., Borges F., Marques M.P. Anticancer activity of phenolic acids of natural or synthetic origin: a structure− activity study. J Med Chem. 2003;46(25):5395-5401.
  11. Saxena M., Saxena J., Pradhan A. Flavonoids and phenolic acids as antioxidants in plants and human health. Int J Pharm Sci Rev Res. 2012;16:130-134.
  12. Su X., Zhang J., Wang H., Xu J., He J., Liu L., Zhang T., Chen R., Kang J. Phenolic acid profiling, antioxidant, and anti-inflammatory activities, and miRNA regulation in the polyphenols of 16 blueberry samples from China. Molecules. 2017;22(2):312.
  13. Wu Y.H., Zhang B.Y., Qiu L.P., Guan R.F., Ye ZH., Yu X.P. Structure properties and mechanisms of action of naturally originated phenolic acids and their derivatives against human viral infections. Cur Med Chem. 2017;24(38):4279-302.
  14. Dresler S., Szymczak G., Wójcik M. Comparison of some secondary metabolite content in the seventeen species of the Boraginaceae family. Pharm Boil. 2017;55(1):691-695.
  15. Watanabe M., Miyashita T., Devkota H.P. Phenolic compounds and ecdysteroids of Diplazium esculentum (Retz.) Sw. (Athyriaceae) from Japan and their chemotaxonomic significance. Biochem Syst Ecol. 2021;94:104211.
  16. Riedl H. Boraginaceae in Rechinger, K.H., Flora Iranica, 1967;no.48.-Graz.
  17. Hazrati S., Ebadi M.T., Mollaei S., Khurizadeh S. Evaluation of volatile and phenolic compounds, and antioxidant activity of different parts of Ferulago angulata (schlecht.) Boiss. Ind Crop Prod. 2019;140:111589.
  18. Mollaei S., Hazrati S., Lotfizadeh V., Dastan D., Asgharian P. Phytochemical variation and biological activities of Zosima absinthifolia during various stages of growth. Inter J Food Prop. 2020;23(1):1556-1567.
  19. Vinayagam R., Jayachandran M., Xu B. Antidiabetic Effects of Simple Phenolic Acids: A Comprehensive Review. Phyther Res. 2016;30:184-199.
  20. Kumar N., Goel N. Phenolic acids: Natural versatile molecules with promising therapeutic applications. Biotechnol Rep. 2019;24:e00370.
  21. Park J., Gim S.Y., Jeon J.Y., Kim M.J., Choi H.K., Lee J. Chemical profiles and antioxidant properties of roasted rice hull extracts in bulk oil and oil-in-water emulsion. Food Chem. 2019;272:242-250.
  22. Pieczykolan A., Pietrzak W., Gawlik-Dziki U., Nowak R. Antioxidant, Anti-Inflammatory, and Anti-Diabetic Activity of Phenolic Acids Fractions Obtained from Aerva lanata (L.) Juss. Molecules 2012.26(12):3486.
  23. Bogucka-Kocka A., Zidorn C., Kasprzycka M., Szymczak G., Szewczyk K. Phenolic acid content, antioxidant and cytotoxic activities of four Kalanchoë species. Saudi J Boil Sci. 2018;25(4):622-630.
  24. Bentham G., Hooker J.D. Genera plantarum. 2(2). Londini [London]: Reeve. 1876.
  25. Nazaire M., Hufford L. A broad phylogenetic analysis of Boraginaceae: Implications for the relationships of Mertensia. Syst Bot. 2012;37:758-783.
  26. Refulio-Rodríguez N.F., Olmstead R.G. Phylogeny of Lamiidae. Amer J Bot. 2014;101:287-299.
  27. Weigend M., Luebert F., Gottschling M., Couvreur T.L., Hilger H.H., Miller J.S. From capsules to nutlets-phylogenetic relationships in the B oraginales. Cladistics 2014;30(5):508-18.
  28. Chacón J., Luebert F., Hilger H.H., Ovchinnikova S., Selvi F., Cecchi L., Weigend M. The borage family (Boraginaceae s. str.): A revised infrafamilial classification based on new phylogenetic evidence, with emphasis on the placement of some enigmatic genera. Taxon 2016;65(3):523-546.
  29. Nakiboglu M. The classification of the Salvia L. (Labiatae) species distributed in west Anatolia according to phenolic compounds. Turkish J Bot. 2002;26:103-108
  30. Mika V., Kuban V., Keljdus B., Odstrcilova V., Nerusil P. Phenolic compounds as chemical markers of low taxonomic levels in the Family Poaceae. Plant Soil Envir. 2005;51:506-512.
  31. Hamad M.S., Kabbashi A.S., Madani I.A. Chemtaxonomic Relationship of Roots Phenolic Compounds for Selected Species of Four Families Recently Grouped in Brassicales by APGIII. World 2017;2(4):140-144.
Journal of Medicinal plants and By-Products
Volume 13, Issue 1
March 2024
Pages 171-177

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