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

Abstract

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 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 (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.

Graphical Abstract

Keywords:

• Marine octopus Cistopus indicus
• Octopodidae
• steroidal glycosides
• cistoindosides A-B
• inflammatory 5-lipoxygenase

Funding and acknowledgements

The authors gratefully acknowledge the funding by the Indian Council of Agricultural Research (ICAR, New Delhi, India) under Central Marine Fisheries Research Institute (ICAR-CMFRI) project “Characterisation and evaluation of bioactive compounds from marine organisms for use against different diseases” (MBT/HM/SUB/23). The authors thank the Director, Indian Council of Agricultural Research-Central Marine Fisheries Research Institute (ICAR-CMFRI), and Head, Marine Biotechnology Division, ICAR-CMFRI for facilitating the research. The authors are thankful to the Chairman, Department of Chemistry, Mangalore University (Karnataka State, India) for providing with guidance and necessary support. S.K.P. gratefully acknowledges the Indian Council of Agricultural Research for financial support.

Disclosure statement

No potential conflicts of interest were reported by the authors.

Data availability

Chromatographic and spectroscopic spectral data are included as supplementary information.

Additional information

Funding

The authors gratefully acknowledge the funding by the Indian Council of Agricultural Research (ICAR, New Delhi, India) under Central Marine Fisheries Research Institute (ICAR-CMFRI) project “Characterisation and evaluation of bioactive compounds from marine organisms for use against different diseases” (MBT/HM/SUB/23). The authors thank the Director, Indian Council of Agricultural Research-Central Marine Fisheries Research Institute (ICAR-CMFRI), and Head, Marine Biotechnology Division, ICAR-CMFRI for facilitating the research. The authors are thankful to the Chairman, Department of Chemistry, Mangalore University (Karnataka State, India) for providing with guidance and necessary support. S.K.P. gratefully acknowledges the Indian Council of Agricultural Research for financial support.