First report of antioxidative 2H-chromenyl derivatives from the intertidal red seaweed Gracilaria salicornia as potential anti-inflammatory agents

Antony, Tima and Chakraborty, Kajal (2020) First report of antioxidative 2H-chromenyl derivatives from the intertidal red seaweed Gracilaria salicornia as potential anti-inflammatory agents. Natural Product Research, 34 (24). pp. 3470-3482. ISSN 1478-6427 (Online)

[img] Text
Natural Product Research_2020_Kajal Chakraborty_Gracilaria salicornia.pdf
Restricted to Registered users only

Download (1MB) | Request a copy | Please mail the copy request to cmfrilibrary@gmail.com
Official URL: https://www.tandfonline.com/doi/full/10.1080/14786...
Related URLs:

Abstract

Phytochemical investigation on biologically active compounds of an intertidal red seaweed Gracilaria salicornia (family Gracilariaceae) guided to the separation of two previously undisclosed 2H-chromenyl derivatives. The compounds were characterised as 40-[100-[7-hydroxy-2,8-dimethyl-6-(pentyloxy)- 2H-chromen-2-yl]ethyl]-30,40-dimethyl-cyclohexanone (1) and 30-[100-(8-hydroxy-5-methoxy-2,6,7-trimethyl-2H-chromen- 2-yl)ethyl]-30-methyl-20-methylene cyclohexyl butyrate (2) by extensive spectroscopic experiments. The studied metabolites recorded prospective bioactivities against 5-lipoxygenase (IC50<2.50mM), whereas their selectivity indices were significantly greater (�1) than ibuprofen (0.89) (p<0.05), which attributed higher anti-inflammatory selectivity of 2Hchromenyl compounds against inducible cyclooxygenase-2 than its constitutive pro-inflammatory isoform of cyclooxygenase- 1. The radical scavenging potential of 2 against oxidants, 2,2-diphenyl-1-picrylhydrazyl and 2,20-azino-bis-3 ethylbenzothiozoline-6-sulfonic acid were higher (IC50< 1.35mM) than standard antioxidant, a-tocopherol (IC50 1.42- 1.79mM). The greater hydrogen bond interactions and binding affinity of 2 (�7.35 kcal mol�1) bearing 2H-chromenyl ethyl-30-methyl-40-methylenecyclohexyl butyrate moiety with 5-lipoxygenase, along with higher electronic properties and permissible hydrophobic-hydrophilic balance, manifested towards its greater anti-inflammatory activity than 1.

Item Type: Article
Uncontrolled Keywords: Gracilaria salicornia; Gracilariaceae; 2Hchromenyl derivatives; antioxidant; antiinflammatory; proinflammatory cyclooxygenase and lipoxygenase
Subjects: CMFRI Departments > CMFRI-Kochi > Marine Biotechnology
CMFRI > CMFRI-Kochi > Marine Biotechnology
CMFRI-Kochi > Marine Biotechnology
CMFRI-Kochi > Marine Biotechnology

Biochemistry > Bioprospecting
Biochemistry
Algae > Seaweed
Divisions: CMFRI-Kochi > Marine Biotechnology
Subject Area > CMFRI > CMFRI-Kochi > Marine Biotechnology
CMFRI-Kochi > Marine Biotechnology
Subject Area > CMFRI-Kochi > Marine Biotechnology
Depositing User: Arun Surendran
Date Deposited: 08 Dec 2020 04:45
Last Modified: 05 Jan 2021 11:03
URI: http://eprints.cmfri.org.in/id/eprint/14744

Actions (login required)

View Item View Item