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Previously undescribed antioxidative O-heterocyclic angiotensin converting enzyme inhibitors from the intertidal seaweed Sargassum wightii as potential antihypertensives

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Relation http://eprints.cmfri.org.in/12991/
https://www.sciencedirect.com/science/article/pii/S0963996918305738?via%3Dihub
https://doi.org/10.1016/j.foodres.2018.07.035
 
Title Previously undescribed antioxidative O-heterocyclic angiotensin converting
enzyme inhibitors from the intertidal seaweed Sargassum wightii as potential
antihypertensives
 
Creator Anusree, M
Chakraborty, Kajal
 
Subject Bioactive compound
Seaweed
 
Description Four previously undescribed antioxidative O-heterocyclic analogues, characterized as 3″-isopropyl-3c-{3b-[(2-
oxo-3,4-dihydro-2H-chromen-3-yl) methyl] butyl}-2″-butenyl-3′-hydroxy-2′-(2′b-methoxy-2′-oxoethyl)-3′, 4′-
dihydro-2H-pyran-4′-carboxylate (1), 2c-methylbutyl-6-[6c-(benzoyloxy)propyl]-6-methyl-tetrahydro-2Hpyran-
2-carboxylate (2), 6-{6b-[3′-(5′a-methyl propyl)-3′, 4′-dihydro-2H-pyran-6′-yl] ethyl}-tetrahydro-2Hpyran-
2-one (3) and 7-(7c-methylpentyl)-hexahydro-2H-chromen-2-one (4) were isolated from the ethylacetate:
methanol fraction of the brown seaweed Sargassum wightii. Nuclear magnetic resonance and mass spectroscopic
experiments unambiguously attributed their structural identities. Antihypertensive activities of the studied
compounds were determined in terms of their angiotensin converting enzyme (ACE) inhibitory potential.
The 2H-pyranylcarboxylate derivative (1) displayed comparable activity (IC50 0.08 mg/mL) with standard antihypertensive
agent captopril (IC50 0.07 mg/mL). The O-heterocyclic derivatives bearing 2H-pyran-4′-carboxylate
(1) and 2H-pyran-2-carboxylate (2) frameworks showed significantly greater (p < 0.05) 1, 1-diphenyl-2-
picryl-hydrazil radical quenching potential {IC50 (1) 0.34 and IC50 (2) 0.45 mg/mL} compared to the standard
antioxidant α-tocopherol (IC50 0.63 mg/mL). Structure-activity relationship analyses demonstrated that the
electronic and lipophilic descriptors might significantly contribute towards the target bioactivities of 2H-pyranylcarboxylates
(1 and 2). Molecular docking simulations were carried out for ACE inhibition, and the binding
energy obtained for the compounds (~7.04–8.48 kcal/mol) demonstrated their potential enzyme-ligand interactions.
The potential of hitherto undescribed O-heterocyclic derivatives as natural antioxidant and antihypertensive
functional food supplements and their utilization as therapeutic leads in the antihypertensive
management were described in the present study.
 
Date 2018
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/12991/1/Kajal%20Chakraborty_2018_Food%20Research%20International_Previously%20undescribed%20antioxidative%20O-heterocyclic%20angiotensin%20converting%20enzyme%20inhibitors%20from%20seaweed.pdf
Anusree, M and Chakraborty, Kajal (2018) Previously undescribed antioxidative O-heterocyclic angiotensin converting enzyme inhibitors from the intertidal seaweed Sargassum wightii as potential antihypertensives. Food Research International, 113. pp. 474-486. ISSN 0963-9969