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PM · Lens · Antioxidant, Anti-inflammatory and Cytotoxic Activity of Schinus terebinthifolia Fruit and Isolation of a New Immunomodulatory Polyphenolic Compound

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Article · Volume 19, Issue 1 · pp. 13–22

Antioxidant, Anti-inflammatory and Cytotoxic Activity of Schinus terebinthifolia Fruit and Isolation of a New Immunomodulatory Polyphenolic Compound

Aljawharah Alqathama1, Mohamed I. S. Abdelhady2,3, Mohsen S. Al-Omar4,5, Mohamed F. Barghash6, Aliaa I. Shallan7

  1. 1Department of Pharmacognosy, College of Pharmacy, Umm Al-Qura University, Makkah, Saudi Arabia.
  2. 2Pharmacognosy Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt.
  3. 3College of Pharmacy, Umm Al-Qura University, Makkah, Saudi Arabia.
  4. 4Department of Medicinal Chemistry & Pharmacognosy, College of Pharmacy, Qassim University, Buraydah, Saudi Arabia.
  5. 5Department of Medicinal Chemistry & Pharmacognosy, Faculty of Pharmacy, Jordan University of Science & Technology, Irbid, Jordan.
  6. 6Biochemistry Department, Genetic Engineering and Biotechnology Research Division, National Research Center, Dokki, Giza, Egypt.
  7. 7Analytical Chemistry Department, Faculty of Pharmacy, Helwan University, Cairo, Egypt.

Abstract

Background: The fruit of Schinus terebinthifolia Raddi is used in ethnomedicine for the treatment of different ailments.Materials and Methods: We studied the phytochemical profile of S. terebinthifolia fruit and evaluated its properties, including its antioxidant, anti-inflammatory, analgesic, cytotoxic and antimicrobial activity.Results: Phytochemical investigation of S. terebinthifolia fruit showed an estimated total phenolic content of 67 mg of gallic acid equivalent (GAE)/g, with respect to gallic acid, while the flavonoid content was 26 mg of quercetin equivalent (QE)/g, in terms of quercetin. Bioassay fractionation of methanolic extract of the fruit resulted in the isolation of a new molecule for the first time from this natural source: 4′,methoxy-6-vinyl-7-O-rhamnosyl-dihydromyricetin or 4′,methoxy-6-vinyl-7-O- rhamnosyl-ampelopsin (Compound 8). Seven other phenolic compounds were isolated, such as (1) gallic acid; (2) afzelin; (3) quercetin 3-O-β-D-glucopyranoside; (4) genistein 7-O-α-l-rhamnopyranoside; (5) ellagic acid; (6) kaempferol and (7) quercetin. The new compound was ascertained using UV, NMR and MS spectra and acid hydrolysis analysis. Significant antioxidant, cytotoxic, anti-inflammatory, analgesic and antimicrobial properties were observed in the alcohol extract, as well as proliferation inhibition in MCF-7 human cancer cell lines. Its activity in elevating glutathione levels in diabetic rats could be due to its anti-inflammatory and immunomodulatory properties.Conclusion: The new compound shows immunomodulatory effects that can be utilized to augment host responses, which is important in both cancer and infectious diseases and thus worth further pharmacological investigation.

Keywords: Schinus terebinthifolia; f lavonoid glycosides; antioxidant; anti-inflammatory; analgesic; immunomodulatory; antimicrobial; cytotoxic

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