ANTI-OXIDANT AND ANTI-INFLAMMATORY POTENTIAL OF SECONDARY METABOLITES FROM Daphne mucronata ROYLE AND THEIR FIRST-PRINCIPLES INVESTIGATIONS

ABSTRACT Ten coumarin class of compounds, including new fused coumarinolignoids namely, mucronin-C ( 1 ) were isolated from the methanol extract from whole plant of Daphne mucronata Royle. The structures of mucronin-C ( 1 ) and its configurations were determined by chemical and spectroscopic methods...

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Autores principales:	Imran,Muhammad, Irfan,Ahmad, Hussain,Sajjad, Assiri,Mohammed A., Uddin,Jalal, Hussain,Ajaz, Khalid,Noreen, Al-Sehemi,Abdullah G.
Lenguaje:	English
Publicado:	Sociedad Chilena de Química 2021
Materias:	Daphne mucronata Royle mucronin-C antioxidant activity anti-inflammatory activity density functional theory
Acceso en línea:	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072021000305300
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spelling	oai:scielo:S0717-970720210003053002021-10-14ANTI-OXIDANT AND ANTI-INFLAMMATORY POTENTIAL OF SECONDARY METABOLITES FROM Daphne mucronata ROYLE AND THEIR FIRST-PRINCIPLES INVESTIGATIONSImran,MuhammadIrfan,AhmadHussain,SajjadAssiri,Mohammed A.Uddin,JalalHussain,AjazKhalid,NoreenAl-Sehemi,Abdullah G. Daphne mucronata Royle mucronin-C antioxidant activity anti-inflammatory activity density functional theory ABSTRACT Ten coumarin class of compounds, including new fused coumarinolignoids namely, mucronin-C ( 1 ) were isolated from the methanol extract from whole plant of Daphne mucronata Royle. The structures of mucronin-C ( 1 ) and its configurations were determined by chemical and spectroscopic methods including 1DNMR, 2D-NMR and HR-FAB-MS. The isolated compounds 1 - 10 were evaluated for in-vitro biological activities. The anti-inflammatory (lipoxygenase) activities of compound 1, 4, 8, 9 and 10 (IC50 = 21.7, 23.7, 25.1, 27.3 and 26.0 μg/mL, respectively) were higher compared with standard Quercetin (IC50 = 22.5 μg/mL). The antioxidant property of coumarin as evaluated by DPPH scavenging bioassay was significantly greater in compounds 1-5, 9 and 10 (IC50 = 0.7, 0.8, 1.9, 2.3, 2.8, 0.5 and 2.1 μg/mL respectively) as standard Trolox (IC50 = 0.3 μg/mL). The density functional descriptors in the progress of quantitative structure-activity relationship (QSAR) are significant to analyze the reactive sites and antioxidant ability of compounds. We have explored the reactive sites and radical scavenging activity of studied coumarin derivatives by shedding light on electron affinity, ionization potential, molecular electrostatic potential, frontier molecular orbitals and molecular descriptors analysis. First-principles calculations about one-electron transfer mechanism revealed that smaller ionization potential value of Compounds 1-5, 9 and 10 are leading to superior antioxidant activity, which is in good agreement with the experimental data.info:eu-repo/semantics/openAccessSociedad Chilena de QuímicaJournal of the Chilean Chemical Society v.66 n.3 20212021-09-01text/htmlhttp://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072021000305300en10.4067/S0717-97072021000305300
institution	Scielo Chile
collection	Scielo Chile
language	English
topic	Daphne mucronata Royle mucronin-C antioxidant activity anti-inflammatory activity density functional theory
spellingShingle	Daphne mucronata Royle mucronin-C antioxidant activity anti-inflammatory activity density functional theory Imran,Muhammad Irfan,Ahmad Hussain,Sajjad Assiri,Mohammed A. Uddin,Jalal Hussain,Ajaz Khalid,Noreen Al-Sehemi,Abdullah G. ANTI-OXIDANT AND ANTI-INFLAMMATORY POTENTIAL OF SECONDARY METABOLITES FROM Daphne mucronata ROYLE AND THEIR FIRST-PRINCIPLES INVESTIGATIONS
description	ABSTRACT Ten coumarin class of compounds, including new fused coumarinolignoids namely, mucronin-C ( 1 ) were isolated from the methanol extract from whole plant of Daphne mucronata Royle. The structures of mucronin-C ( 1 ) and its configurations were determined by chemical and spectroscopic methods including 1DNMR, 2D-NMR and HR-FAB-MS. The isolated compounds 1 - 10 were evaluated for in-vitro biological activities. The anti-inflammatory (lipoxygenase) activities of compound 1, 4, 8, 9 and 10 (IC50 = 21.7, 23.7, 25.1, 27.3 and 26.0 μg/mL, respectively) were higher compared with standard Quercetin (IC50 = 22.5 μg/mL). The antioxidant property of coumarin as evaluated by DPPH scavenging bioassay was significantly greater in compounds 1-5, 9 and 10 (IC50 = 0.7, 0.8, 1.9, 2.3, 2.8, 0.5 and 2.1 μg/mL respectively) as standard Trolox (IC50 = 0.3 μg/mL). The density functional descriptors in the progress of quantitative structure-activity relationship (QSAR) are significant to analyze the reactive sites and antioxidant ability of compounds. We have explored the reactive sites and radical scavenging activity of studied coumarin derivatives by shedding light on electron affinity, ionization potential, molecular electrostatic potential, frontier molecular orbitals and molecular descriptors analysis. First-principles calculations about one-electron transfer mechanism revealed that smaller ionization potential value of Compounds 1-5, 9 and 10 are leading to superior antioxidant activity, which is in good agreement with the experimental data.
author	Imran,Muhammad Irfan,Ahmad Hussain,Sajjad Assiri,Mohammed A. Uddin,Jalal Hussain,Ajaz Khalid,Noreen Al-Sehemi,Abdullah G.
author_facet	Imran,Muhammad Irfan,Ahmad Hussain,Sajjad Assiri,Mohammed A. Uddin,Jalal Hussain,Ajaz Khalid,Noreen Al-Sehemi,Abdullah G.
author_sort	Imran,Muhammad
title	ANTI-OXIDANT AND ANTI-INFLAMMATORY POTENTIAL OF SECONDARY METABOLITES FROM Daphne mucronata ROYLE AND THEIR FIRST-PRINCIPLES INVESTIGATIONS
title_short	ANTI-OXIDANT AND ANTI-INFLAMMATORY POTENTIAL OF SECONDARY METABOLITES FROM Daphne mucronata ROYLE AND THEIR FIRST-PRINCIPLES INVESTIGATIONS
title_full	ANTI-OXIDANT AND ANTI-INFLAMMATORY POTENTIAL OF SECONDARY METABOLITES FROM Daphne mucronata ROYLE AND THEIR FIRST-PRINCIPLES INVESTIGATIONS
title_fullStr	ANTI-OXIDANT AND ANTI-INFLAMMATORY POTENTIAL OF SECONDARY METABOLITES FROM Daphne mucronata ROYLE AND THEIR FIRST-PRINCIPLES INVESTIGATIONS
title_full_unstemmed	ANTI-OXIDANT AND ANTI-INFLAMMATORY POTENTIAL OF SECONDARY METABOLITES FROM Daphne mucronata ROYLE AND THEIR FIRST-PRINCIPLES INVESTIGATIONS
title_sort	anti-oxidant and anti-inflammatory potential of secondary metabolites from daphne mucronata royle and their first-principles investigations
publisher	Sociedad Chilena de Química
publishDate	2021
url	http://www.scielo.cl/scielo.php?script=sci_arttext&pid=S0717-97072021000305300
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ANTI-OXIDANT AND ANTI-INFLAMMATORY POTENTIAL OF SECONDARY METABOLITES FROM Daphne mucronata ROYLE AND THEIR FIRST-PRINCIPLES INVESTIGATIONS

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