Journal of Advances in Environmental Health Research

Journal of Advances in Environmental Health Research

Isolation and characterization of p-Coumaric acid from Diospyros melanoxylon medicinal plant endemic to Western Ghats, India

Document Type : Original Article

Authors
Anil Kumar K M 1, 2
Pallavi S 1, 2
H.P. Shivaraju 1
1 Department of Water and Health, JSS Academy of Higher Education and Research, Mysore, India-570015
2 Center for Water, Food and Energy, GREENS trust, Harikaranahalli, Dombaranahalli Post, Turuvekere Taluka, Tumkur District, Karnataka, India-572215
10.22102/jaehr.2019.195537.1138
Abstract
Diospyros melanoxylon has been traditionally for the treatment of fistula, relieving arthritis, and skin care. The bark extracts of the plant have been investigated in terms of phytochemical and pharmacological potential, while the leaf extract has been untapped. The present study aimed to evaluate the methanol extract of D. melanoxylon (DMM) in terms of the antibacterial (P<0.05), antioxidant (1.2-1.6-fold) and anti-inflammatory potential (IC50: 80 µg/ml). DMM exhibited effective antibacterial, antioxidant, and anti-inflammatory activities at significantly higher levels than the standards. In addition, the HR-LCMS analysis of MBI revealed the presence of a few active compounds, which belonged to the class of phenolic acids and flavonoids at greater concentrations than other phytochemicals (n>20). The activity-guided repeated fractionation of the methanol extract using silica gel column chromatography yielded a single compound, which exhibited remarkable antioxidant activity. The physicochemical and spectroscopic analyses (UV, IR, 1 H NMR, 13 C NMR, and MS) indicated that the bioactive isolated compound was p-coumaric acid, the effect of which was on par with the standard antioxidant, antibacterial, and anti-inflammatory drugs. Conversely, the effects of the extract on these pharmacological attributes enhanced, confirming that the better activity observed in the study was mainly due to the synergistic effects exerted by various compounds in the extract. In-silico studies have also confirmed the potential of the compound in these effective antibacterial properties. Therefore, the D. melanoxylon extract is a strong therapeutic agent with pharmacological potential.
Keywords
Phenolic acids
p-Coumaric acid
Methanol extract
Free radicals
Anti-inflammatory
  1. Roxburgh W. Flora Indica (Eds Carey W and WallichN). Serampore. 2: 1820–1824
  2. Wallinofer B. The biology and systematics of Ebenaceae: A review. Ann Naturlist Mus Wien 2001; 103(2): 485−512.
  3. Rathore JS. Diospyros melanoxylon, a bread-winner tree of India. Econ Bot 1972; 26(4): 333–339.
  4. Palaparthi S. Pharmacological Profile of Diospyros melanoxylon Methanolic Extract. J Pharmacogn Nat Prod 2019: 5: 157.
  5. RathS K, Mohapatra N, Dubey D, PandaS K, Thatoi HN, Dutta SK. Antimicrobial activity of Diospyros melanoxylon bark from Similipal Biosphere Reserve, Orissa, India. Afr J Biotechnol 2009; 8 (9): 1924-1928.
  6. El-Seedi HR, El-Said AM, Khalifa SA, Göransson U, Bohlin L, Borg-Karlson AK, et al. Biosynthesis, natural sources, dietary intake, pharmacokinetic properties, and biological activities of hydroxycinnamicacids. J Agric Food Chem 2012: 60:10877–10895.
  7. Pragasam SJ, Venkatesan V, Rasool M. Immunomodulatory and anti-inflammatory effect of p-coumaric acid, a common dietary polyphenol on experimental inflammation in rats. Inflammation 2013; 36: 169–176.
  8. Torres y Torres J L, P.N Rosazza J. Microbial transformations of p-coumaric acid by Bacillus megaterium and Curvularia lunata. J Nat Prod 2001; 64: 1408-14.
  9. Lou Z, Wang H, Rao S, Sun J, Ma C, Li J. p-Coumaric acid kills bacteria through dual damage mechanisms. Food Control 2012;25(2): 550–554.
  10. Harborne A J. Phytochemical methods: A guide to modern techniques of plant analysis. Chapman and Hall Ltd, London, Springer Netherlands 1998..
  11. Kujala TS, Loponen JM, Klika KD, Pihlaja K. Phenolic andbetacyanins in red beetroot (Beta vulgaris) root: Distribution and effects of coldstorage on the content of total phenolics and three individual compounds. J Agric Food Chem 2000; 48: 5338–5342.
  12. Ordonez AAL, Gomez JD, Vattuone MA&Isla MI. Antioxidantactivities of Sechiumedule (Jacq.) Swart extracts. Food Chem 2006; 97: 452–458.
  13. Sun BS, Ricardo-da-Silva JM, Spranger I. Quantification of catechins and proanthocyanidins in several Portuguese grapevine varieties and red wines. Ciencia T ecVitiv 2001; 16:23–34.
  14. Nurhanani R, Rasyidah R, Sarni MJ, Azlina AA. Radical scavenging and reducingproperties of extracts of cashew shoots (Anacardiumoccidentale). Food Chem 2008; 111: 38–44.
  15. Ramith Ramu, Prithvi S Shirahatti, Farhan Zameer, Dhananjaya B Lakkapa, MN Nagendra. Evaluation of Banana (Musa sp. var. Nanjangud Rasa bale) flower and pseudostem extracts on antimicrobial, cytotoxicity and thrombolytic activities. Int J Pharm Pharm Sci 2015; 7 (1): 136-140.
  16. Mizushima Y, Kobayashi M. Interaction of anti-inflammatory drugs withserumpreoteins, especially with some biologically active proteins. J Pharm Pharmacol 1968;20(3):169–73.
  17. Rabia Naz, Hafsa Ayub, Sajid Nawaz, Zia Ul Islam, Tayyaba Yasmin, AsghariBano, et al. Antimicrobial activity, toxicity and anti-inflammatorypotential of methanolicextracts of four ethnomedicinalplantspecies from Punjab, Pakistan. BMC Complement Altern Med 2017; 17(1): 302.
  18. Oyedepo OO, Femurewa AJ. Anti-protease and membrane stabilizingactivities of extracts of Fagrazanthoxiloides, OlaxsubscorpioidesandTetrapleuratetraptera. Int J Pharmcogn 1995; 33: 65–9.
  19. Katsuko Inamatsu. Isolation of P-coumaric acid and sterols from rice straw compost. Soil Sci Plant Nutr 1968:14(2): 62-67.
  20. Elgizawy H, Hussein M A. Isolation, Structure Elucidation of Ferulic and Coumaric acids from Fortunella japonica Swingle leaves and their Structure Antioxidant activity relationship. Free Radic Antioxidant 2017; 7(1): 23-30.
  21. Feng Guo, Shuoyang Zhang, Xiuying Yan, Yuhan Dan, Jian Wang, YunliZhao, et al. Bioassay-guided isolation of antioxidant and a-glucosidase inhibitory constituentsfrom stem of Vignaangularis. Bioorganic Chem 2019; 87: 312-320.
  22. Zhao Y, Chen MS, Zhao ZG, Yu SJ. The antibiotic activity and mechanisms of sugarcane (Saccharumofficinarum L.) bagasse extract against food-borne pathogens. Food Chem 2015; 185:112–118.
  23. Pereira JA, Oliveira I, Sousa A, Valentao P, Andrade PB, Ferreira ICFR. et al. Walnut (Juglansregia L.) leaves: phenolic compounds, antibacterial activity and antioxidant potential of different cultivars. Food Chem Toxicol 2007; 45(11):2287–2295.
  24. Madikizela B, Aderogba MA, Finnie JF, Van Staden J. Isolation and characterization of antimicrobial compounds from Terminalia phanerophlebia Engl. & Diels leaf extracts. J Ethnopharmacol 2014; 156:228–234.
  25. Tawata S, Taira S, Kobamoto N, Zhu J, Ishihara M, Toyama S. Synthesis and antifungal activity of cinnamic acid esters. Biosci Biotechnol Biochem 1996; 60(5):909–910.
  26. Rice Evans CA, Miller NJ, Paganga G. Structure-antioxidant activity relationships of flavonoids and phenolic acids. Free Radical Biol Med 1996; 20(7):933-56.
  27. PuF, Ren XL, Zhang XP. Phenolic compounds and antioxidant activity in fruits of six Diospyros kaki genotypes. Eur Food Res Technol 2013; 237(16): 923–932.
  28. Casselst BK, Asencio M, Conget P, Speisky H, Videla LA, Lissi EA. Structure-antioxidative activity relationships in benzylisoquinoline alkaloids. Pharmacol Res 1995; 31(2): 103–107.
  29. Yin WQ, Duan SQ, Zhang Y, Zeng L, Song XM. Antioxidant activities of different solvents extracts and alkaloids of Uncariarhynchophylla (Miq.) Jacks. J Guangxi Normal University 2010; 28(1): 31–34.
  30. Al Rashid MH, P.v.p DB, Majumder S, Mandal V, Pal M, Mandal SC, et al. Antioxidant and anticancer activity of extract and fractions obtained from Diospyros Melanoxylon Roxb. leaves and correlation with their polyphenolic profiles. Int J Pharm Pharm Sci 2018; 10(11): 6-16.
  31. Hmar BZ, Mishra S, Pradhan RC. Physico-Chemical, mechanical and antioxidant properties of Kendu (Diospyros Melanoxylon Roxb.). Curr Res Nutr Food Sci 2017; 5 (3):214-222.
  32. Bhuvana P, Anuradha V, Syed Ali M, Suganya V, Sangeetha P. Drug standardization and invitro anti-inflammatory and antibacterial activity of Chlorella vulgaris. Int J Pharm Biol Sci 2018; 8 (1): 103-110.
  33. Bigoniya P, Rana AC. Protective Effect of Wrightiatinctoria Bark Triterpenoid 342 Fraction on Carbon Tetrachloride Induced Acute Rat Liver Toxicity. Iran J Pharm Ther 2010; 9(2): 55-62.
Journal of Advances in Environmental Health Research
Volume 7, Issue 4
Autumn 2019
Pages 269-282