Record Details

Non-sulfated steroidal glycosides cistoindosides from marine ‘old woman octopus’ Cistopus indicus attenuate pro-inflammatory lipoxygenase

CMFRI Repository

View Archive Info
 
 
Field Value
 
Relation http://eprints.cmfri.org.in/16034/
https://www.tandfonline.com/doi/abs/10.1080/14786419.2022.2095634?journalCode=gnpl20
https://doi.org/10.1080/14786419.2022.2095634
 
Title Non-sulfated steroidal glycosides cistoindosides from
marine ‘old woman octopus’ Cistopus indicus attenuate
pro-inflammatory lipoxygenase
 
Creator Shilpa, K P
Chakraborty, Kajal
 
Subject Bioactive compounds
Biochemical composition
Cephalopods
 
Description Two non-sulfated steroidal glycosides, cistoindosides A-B were isolated from organic extract of the marine ‘old woman octopus’ Cistopus indicus (family Octopodidae). Their structures were characterized as 3β-acteoxy-23β-hydroxy-cholesta-9-ene-β-D-xylopyranoside (cistoindoside A) and 22,23-epoxy-3β-hydroxy-cholesta-5-ene-β-D-4'-O-acetoxy-xylopyranoside (cistoindoside B). Cistoindoside B, glycosylated with β-D-4'-O-acetoxy-xylopyranoside in conjunction with epoxy moieties displayed superior anti-inflammatory properties as acknowledged by its promising 5-lipoxygenase attenuation potential (IC50 2.11 µM) than the 5-lipoxygenase inhibitor drug zileuton (IC50 3.76 µM). The anti-inflammatory properties were corroborated by the promising antioxidant activities (IC50 ∼ 1.0–1.5 mM) of these steroid glycosides. Sizeably greater electronic properties, balanced hydrophobic-lipophilic properties (log POW ∼ 4.0) and comparatively lower steric factors were directly proportional to their bioactivities. Molecular simulation studies in the active sites of 5-lipoxygenase displaying lesser binding energies and inhibition constant (Ki) of cistoindoside B could be correlated with anti-inflammatory properties. Cistoindosides could be projected for their utilization as potential bioactive leads in functional food and pharmaceutical applications.
 
Publisher Taylor and Francis
 
Date 2022
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/16034/1/Natural%20Product%20Research_2022_Kajal%20Chakraborty.pdf
Shilpa, K P and Chakraborty, Kajal (2022) Non-sulfated steroidal glycosides cistoindosides from marine ‘old woman octopus’ Cistopus indicus attenuate pro-inflammatory lipoxygenase. Natural Product Research. pp. 1-12.