Evaluation of the enzyme inhibitory and antioxidant activities of entada spiralis stem bark and isolation of the active constituents

Fatimah Opeyemi Roheem, Siti Zaiton Mat Soad, Qamar Uddin Ahmed, Syed Adnan Ali Shah, Jalifah Latip, Zainul Amiruddin Zakaria

Research output: Contribution to journalArticle

Abstract

Digestive enzymes and free radical inhibitors are used to prevent complications resulting from diabetes. Entada spiralis (family Leguminosae), which is a well-known medicinal plant in herbal medicine due to its various traditional and medicinal applications, was studied. Crude extracts were successively obtained from the stem bark using petroleum ether, chloroform and methanol as extracting solvents. The antioxidant activity of all the extracts, fractions and isolated compounds were estimated using 2,2-diphenyl-1-picrylhydrazyl (DPPH), β-carotene and 2,2 0 -azinobis(-3-ethylbenzothiazine-6-sulfonic acid) (ABTS) assays, while digestive enzymes inhibitory activity was assessed using α-amylase and α-glucosidase inhibitory methods. Structure elucidation of pure compounds was achieved through different spectroscopic analysis methods. Fractionation and purification of the most active methanol extract resulted in the isolation of a ferulic ester namely; (E)-hexyl 3-(4-hydroxy-3-methoxyphenyl) acrylate (FEQ-2) together with five known phenolic constituents, identified as kaempferol (FEQ-3), 5,4 0 -dihydroxy-3,7,3 0 -trimethoxyflavone (FEQ-2), gallic acid (FEQ-5), (+)-catechin (FEQ-7) and (−)-epicatechin (FEQ-8). FEQ-5 exhibited the strongest antioxidant and enzyme inhibitory activities followed by FEQ-3 and FEQ-4. FEQ-2 also displayed potent free radical scavenging activity with IC 50 values of 13.79 ± 2.13 (DPPH) and 4.69 ± 1.25 (ABTS) µg/mL, respectively. All other compounds were found active either against free radicals or digestive enzymes.

Original languageEnglish
Article number1006
JournalMolecules
Volume24
Issue number6
DOIs
Publication statusPublished - 1 Jan 2019

Fingerprint

antioxidants
stems
free radicals
Free Radicals
enzymes
isolation
enzyme activity
Catechin
Antioxidants
Enzyme activity
Methanol
evaluation
Enzymes
methyl alcohol
Glucosidases
carotene
Gallic Acid
Spectroscopic analysis
Sulfonic Acids
sulfonic acid

Keywords

  • 2,2-diphenyl-1-picrylhydrazyl assay
  • 2 -azinobis(-3-ethylbenzothiazine-6-sulfonic acid) assay
  • active principles
  • EF-carotene assay
  • Entada spiralis
  • VT-amylase
  • VT-glucosidase

ASJC Scopus subject areas

  • Analytical Chemistry
  • Chemistry (miscellaneous)
  • Molecular Medicine
  • Pharmaceutical Science
  • Drug Discovery
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Evaluation of the enzyme inhibitory and antioxidant activities of entada spiralis stem bark and isolation of the active constituents. / Roheem, Fatimah Opeyemi; Soad, Siti Zaiton Mat; Ahmed, Qamar Uddin; Shah, Syed Adnan Ali; Latip, Jalifah; Zakaria, Zainul Amiruddin.

In: Molecules, Vol. 24, No. 6, 1006, 01.01.2019.

Research output: Contribution to journalArticle

Roheem, Fatimah Opeyemi ; Soad, Siti Zaiton Mat ; Ahmed, Qamar Uddin ; Shah, Syed Adnan Ali ; Latip, Jalifah ; Zakaria, Zainul Amiruddin. / Evaluation of the enzyme inhibitory and antioxidant activities of entada spiralis stem bark and isolation of the active constituents. In: Molecules. 2019 ; Vol. 24, No. 6.
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abstract = "Digestive enzymes and free radical inhibitors are used to prevent complications resulting from diabetes. Entada spiralis (family Leguminosae), which is a well-known medicinal plant in herbal medicine due to its various traditional and medicinal applications, was studied. Crude extracts were successively obtained from the stem bark using petroleum ether, chloroform and methanol as extracting solvents. The antioxidant activity of all the extracts, fractions and isolated compounds were estimated using 2,2-diphenyl-1-picrylhydrazyl (DPPH), β-carotene and 2,2 0 -azinobis(-3-ethylbenzothiazine-6-sulfonic acid) (ABTS) assays, while digestive enzymes inhibitory activity was assessed using α-amylase and α-glucosidase inhibitory methods. Structure elucidation of pure compounds was achieved through different spectroscopic analysis methods. Fractionation and purification of the most active methanol extract resulted in the isolation of a ferulic ester namely; (E)-hexyl 3-(4-hydroxy-3-methoxyphenyl) acrylate (FEQ-2) together with five known phenolic constituents, identified as kaempferol (FEQ-3), 5,4 0 -dihydroxy-3,7,3 0 -trimethoxyflavone (FEQ-2), gallic acid (FEQ-5), (+)-catechin (FEQ-7) and (−)-epicatechin (FEQ-8). FEQ-5 exhibited the strongest antioxidant and enzyme inhibitory activities followed by FEQ-3 and FEQ-4. FEQ-2 also displayed potent free radical scavenging activity with IC 50 values of 13.79 ± 2.13 (DPPH) and 4.69 ± 1.25 (ABTS) µg/mL, respectively. All other compounds were found active either against free radicals or digestive enzymes.",
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