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This study characterized the functional properties of ethyl acetate-methanol (EA-MeOH) and chloroform extracts of the muricid gastropod Chicoreus ramosus and buccinid Babylonia spirata. The EA-MeOH extract of B. spirata was a potent quencher of radical cation (IC90 < 1 mg/mL), whereas that of C. ramosus held greater anti–inflammatory potential (IC90 5-lipoxygenase inhibition 1.74 mg/mL) than the buccinid gastropod. The EA-MeOH extract of C. ramosus displayed potent antidiabetic activities as deduced by its attenuation properties against carbolytic enzymes α-amylase and α-glycosidase (IC90 1.06 and 2.25 mg/mL, respectively) than those exhibited by B. spirata (IC90 2.32 and 4.50 mg/mL, respectively). The spectroscopic dereplication studies to determine probable chemical groups in the solvent extracts of the studied gastropods revealed the presence of functionalities, which might augment the electronic properties of the bioactive principles present within the extract, thereby enhancing their activity. Thus, the present study recognized that marine gastropods C. ramosus and B. spirata have potential functional implications against oxidative stress-induced diseases, such as diabetes and inflammation. This research supports further investigation of these previously uncharacterized marine gastropod species to isolate potential bioactive leads for use against various biological targets and to develop functional food formulations. [ABSTRACT FROM AUTHOR]

Graphical abstract Highlights • First report of lactonic disecosteroid was isolated from Babylonia spirata. • Disecosteroid possessed potential anti-inflammatory and anti-carbolytic activities. • Bioactive potencies of disecosteroid was dictated by polarizability factors. • Molecular docking showed ligand-receptor interaction in 5-lipoxidase and α -amylase. • Putative biosynthetic pathway of disecosteroid validated structural attributions. Abstract A lactonic steroid with an unprecedented 1, 10: 8, 9-disecoergostane framework was identified from the ethyl acetate-methanol extract of buccinid gastropod mollusk, Babylonia spirata collected from the southwestern coast of Indian peninsular region. The compound was characterized as 1, 10: 8, 9-disecoergosta-8-en- A - homo -6a-oxa-1-one by exhaustive spectroscopic methods including two-dimensional nuclear magnetic resonance and mass spectroscopic investigations. The disecosteroid displayed moderate carbolytic enzyme inhibition activity as distinguished by its inhibitive effects against α -amylase and α -glucosidase (IC 50 0.40 and 0.54 mg/mL, respectively). The anti-inflammatory (5-lipoxidase inhibitory) activity of the titled secondary metabolite was found to be superior (IC 50 < 0.85 mg/mL) than the commercial anti-inflammatory drug (ibuprofen IC 50 > 0.85 mg/mL). However, significantly greater antioxidant property was recorded for the studied disecosteroid as evaluated by in vitro 2, 2-diphenyl-1-picrylhydrazyl radical inhibition potential (IC 50 0.30 mg/mL) than that of standard, α -tocopherol (IC 50 > 0.50 mg/mL). The in silico molecular docking studies were conducted to explain the anti-5-lipoxidase and anti- α -amylase properties of the isolated compound. The molecular binding interactions of the ligands with the pro-inflammatory 5-lipoxidase and the carbolytic enzyme α -amylase, demonstrated that their binding energies/docking scores were positively associated with their in vitro bioactivities. A plausible pathway for the biosynthetic origin of lactonic disecosteroid in B. spirata was proposed from an ergosterol precursor. Structure-activity correlation study demonstrated that the biological activities of the disecosteroid were directly proportional to their electronic properties allied with lesser steric restrictions. [ABSTRACT FROM AUTHOR]