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Evaluation of the Enzyme Inhibitory and Antioxidant Activities of Entada spiralis Stem Bark and Isolation of the Active Constituents.
Molecules. 2019 Mar 13; 24(6)M

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'-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'-dihydroxy-3,7,3'-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 IC50 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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Authors+Show Affiliations

Roheem FO
Department of Pharmaceutical Chemistry, International Islamic University Malaysia, Bandar Indera Mahkota, 25200 Kuantan, Pahang D.M., Malaysia. bukolami_fatty@yahoo.com.
Mat Soad SZ
Department of Pharmaceutical Chemistry, International Islamic University Malaysia, Bandar Indera Mahkota, 25200 Kuantan, Pahang D.M., Malaysia. dszaiton@iium.edu.my.
Ahmed QU
Department of Pharmaceutical Chemistry, International Islamic University Malaysia, Bandar Indera Mahkota, 25200 Kuantan, Pahang D.M., Malaysia. quahmed@iium.edu.my.
Ali Shah SA
Atta-ur-Rahman Institute for Natural Products Discovery (AuRIns), Universiti Teknologi MARA, Bandar Puncak Alam, 42300 Selangor Darul Ehsan, Malaysia. benzene301@yahoo.com. Faculty of Pharmacy, Universiti Teknologi MARA, Puncak Alam Campus, 42300 Bandar Puncak Alam, Selangor D.E., Malaysia. benzene301@yahoo.com.
Latip J
School of Chemical Sciences and Food Technology, Faculty of Science and Technology, Universiti Kebangsaan Malaysia, 43600 Bandar Baru Bangi, Selangor, Malaysia. jalifah@ukm.edu.my.
Zakaria ZA
Department of Biomedical Science, Faculty of Medicine and Health Sciences, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia. zaz@upm.edu.my. Halal Institute Research Institute, Universiti Putra Malaysia, 43400 Serdang, Selangor, Malaysia. zaz@upm.edu.my.

MeSH

AntioxidantsChemical FractionationEnzyme InhibitorsFabaceaeFlavonoidsGlycoside Hydrolase InhibitorsMolecular StructurePhytochemicalsPlant BarkPlant StemsPlants, Medicinalalpha-Amylases

Pub Type(s)

Journal Article

Language

eng

PubMed ID

30871172

Citation

Roheem, Fatimah Opeyemi, et al. "Evaluation of the Enzyme Inhibitory and Antioxidant Activities of Entada Spiralis Stem Bark and Isolation of the Active Constituents." Molecules (Basel, Switzerland), vol. 24, no. 6, 2019.
Roheem FO, Mat Soad SZ, Ahmed QU, et al. Evaluation of the Enzyme Inhibitory and Antioxidant Activities of Entada spiralis Stem Bark and Isolation of the Active Constituents. Molecules. 2019;24(6).
Roheem, F. O., Mat Soad, S. Z., Ahmed, Q. U., Ali Shah, S. A., Latip, J., & Zakaria, Z. A. (2019). Evaluation of the Enzyme Inhibitory and Antioxidant Activities of Entada spiralis Stem Bark and Isolation of the Active Constituents. Molecules (Basel, Switzerland), 24(6). https://doi.org/10.3390/molecules24061006
Roheem FO, et al. Evaluation of the Enzyme Inhibitory and Antioxidant Activities of Entada Spiralis Stem Bark and Isolation of the Active Constituents. Molecules. 2019 Mar 13;24(6) PubMed PMID: 30871172.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Evaluation of the Enzyme Inhibitory and Antioxidant Activities of Entada spiralis Stem Bark and Isolation of the Active Constituents. AU - Roheem,Fatimah Opeyemi, AU - Mat Soad,Siti Zaiton, AU - Ahmed,Qamar Uddin, AU - Ali Shah,Syed Adnan, AU - Latip,Jalifah, AU - Zakaria,Zainul Amiruddin, Y1 - 2019/03/13/ PY - 2018/10/31/received PY - 2018/11/29/revised PY - 2018/11/30/accepted PY - 2019/3/16/entrez PY - 2019/3/16/pubmed PY - 2019/6/30/medline KW - 2,2-diphenyl-1-picrylhydrazyl assay KW - 2,2′-azinobis(-3-ethylbenzothiazine-6-sulfonic acid) assay KW - Entada spiralis KW - active principles KW - α-amylase KW - α-glucosidase KW - β-carotene assay JF - Molecules (Basel, Switzerland) JO - Molecules VL - 24 IS - 6 N2 - 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'-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'-dihydroxy-3,7,3'-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 IC50 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. SN - 1420-3049 UR - https://www.unboundmedicine.com/medline/citation/30871172/Evaluation_of_the_Enzyme_Inhibitory_and_Antioxidant_Activities_of_Entada_spiralis_Stem_Bark_and_Isolation_of_the_Active_Constituents_ DB - PRIME DP - Unbound Medicine ER -