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Unreported polyether macrocyclic lactone with antioxidative and anti-lipoxygenase activities from the Babylonidae gastropod mollusc Babylonia spirata

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Relation https://eprints.cmfri.org.in/13242/
https://link.springer.com/article/10.1007%2Fs00044-018-2248-z
https://doi.org/10.1007/s00044-018-2248-z
 
Title Unreported polyether macrocyclic lactone with antioxidative and
anti-lipoxygenase activities from the Babylonidae gastropod mollusc
Babylonia spirata
 
Creator Salas, Soumya
Chakraborty, Kajal
 
Subject Bioactive compounds
Biochemistry
Gastropods
 
Description A 16-member polyether macrocyclic lactone, with previously unreported framework was isolated as a result of the bioassay guided chromatographic fractionation of the ethyl acetate-methanol extract of the Babylonidae Babylonia spirata collected from the southwestern coast of Indian peninsular. The compound was characterized as 10, 14-dihydroxy-4-(1′-propyl-1′(Z)-hexen-1′-yl)-7, 12-dioxapentadecanolide based on extensive spectral data analysis. The antioxidant activities evaluated by in vitro free radical scavenging capacities reported that the studied compound possessed greater activity (IC50 0.058–0.065 × 10−2 M) than the commercial standards, butylated hydroxy anisole, butylated hydroxyl toluene and α-tocopherol (IC50 0.118–0.189 × 10−2 M). The compound was found to possess greater anti-inflammatory potentials as recognized by its lower IC50 value for the 5-lipoxygenase inhibition assay (0.073 × 10−2 M) than the non steroidal anti-inflammatory drugs aspirin (0.211 × 10−2 M) and ibuprofen (0.436 × 10−2 M). Structure-activity studies showed that bioactivities of the polyether macrocyclic lactone were directed by electronic and lipophilic descriptors. The lipophilic parameter of octanol-water partition coefficient (log Pow) of the studied compound recorded a value as low as 2.76 when judged against commercial antioxidant α-tocopherol (log Pow 9.98), and was recognized as a primary physico-chemical descriptor dictating the antioxidant characteristics of the isolated polyether macrocyclic lactone, whereas the electronic parameters appeared to contribute towards its anti-inflammatory activity. This is the first report of the occurrence of macrocyclic lactone featuring a dioxapentadecanolide framework possessing potential antioxidative and anti-inflammatory activities, and therefore, anticipated as a potential naturally-derived antioxidative and anti-inflammatory constituent in functional food and pharmaceutical applications.
 
Date 2018
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier https://eprints.cmfri.org.in/13242/1/Kajal%20Chakraborty_2018_Medicinal%20Chemistry%20Research_Unreported%20polyether%20macrocyclic%20lactone%20from%20Babylonia%20spirata.pdf
Salas, Soumya and Chakraborty, Kajal (2018) Unreported polyether macrocyclic lactone with antioxidative and anti-lipoxygenase activities from the Babylonidae gastropod mollusc Babylonia spirata. Medicinal Chemistry Research, 27 (11-12). pp. 2446-2453.