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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 3 β -acteoxy-23 β -hydroxy-cholesta-9-ene- β -D-xylopyranoside (cistoindoside A) and 22,23-epoxy-3 β -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 (IC 50  2.11 µM) than the 5-lipoxygenase inhibitor drug zileuton (IC 50  3.76 µM). The anti-inflammatory properties were corroborated by the promising antioxidant activities (IC 50  ∼ 1.0–1.5 mM) of these steroid glycosides. Sizeably greater electronic properties, balanced hydrophobic-lipophilic properties (log P OW  ∼ 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 (K i ) 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.

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