Antioxidative 2 H ‐chromenyls attenuate pro‐inflammatory 5‐lipoxygenase and carbolytic enzymes: Prospective bioactive agents from Babylonidae gastropod mollusk Babylonia spirata

Abstract

Oxygenated heterocycles are emerging as valuable pharmacophores involved in the prophylaxis and treatment of several diseases elicited by the reactive oxygen species. Bioassay‐led chromatographic fractionation of the organic extract of the gastropod mollusk Babylonia spirata (family Babylonidae) yielded two unprecedented 2H‐chromenyl derivatives characterized as 2‐(butyryloxy)‐5‐hydroxy‐hexahydro‐2H‐chromene‐3‐methyl carboxylate (1) and (3‐hydroxy‐hexahydro‐2H‐chromen‐2‐yl)methyl pentanoate (2). The chromenyl derivative (1) registered significantly greater attenuation potential against pro‐inflammatory 5‐lipoxygenase (IC50 ~ 2.02 mM) than those exhibited by the compound (2) (IC50 2.76 mM) and the non‐steroidal anti‐inflammatory drug ibuprofen (IC50 4.36 mM, p < .05). The compound (1) exhibited comparable antioxidant activity (IC50 1.47–1.72 mM) with standard antioxidative agent α‐tocopherol (IC50 1.4–1.7 mM). Inhibitory potential of chromenyl derivative (1) toward α‐glucosidase (IC50 1.18 mM) and α‐amylase (IC50 0.92 mM) was greater than those displayed by 2 (IC50 1.16–1.56 mM). Structure–activity relationships revealed that bioactivities of the compounds were determined by the electronic factors and hydrophilic–lipophilic balance. Practical applications The marine gastropod Babylonia spirata is one of the prominent edible gastropod species harvested from the coastlines along the southwestern region of the Indian peninsula. Two 2H‐chromenyl derivatives were isolated to homogeneity from the organic extract of the marine buccinid gastropod B. spirata by the bioactivity‐guided chromatographic fractionation and were found to possess potential antioxidant and attenuation properties against pro‐inflammatory 5‐lipoxygenase and carbolytic enzymes. The attenuation properties of the 2H‐chromenyls against pro‐inflammatory 5‐lipoxygenase showed that 2H‐chromenyl analogs possessed significantly greater anti‐inflammatory potential than the non‐steroidal anti‐inflammatory drug ibuprofen. In particular, the chromenyl derivative bearing 2H‐chromene‐3‐methyl carboxylate framework might constitute a prospective biogenic constituent in functional food and pharmaceutical applications for use against oxidative agents, including inflammation and hyperglycemic pathologies.

High-value compounds from the molluscs of marine and estuarine ecosystems as prospective functional food ingredients: An overview

“…A polysaccharide, namely glycosaminoglycan-xylopyranan from B. spirata was reported to attenuate pro-inflammatory 5-lipoxygenase ( Chakraborty, Krishnan, & Joy, 2019 ). Anti-inflammatory 2 H ‐chromenyl derivatives were isolated from the organic extract of B. spirata ( Chakraborty & Salas, 2020 ). A polygalactosamino-glucopyranosyl fucopyranose isolated from C .…”

Oxaspiro Indiculides from Old Woman Octopus Cistopus indicus as Dual Inhibitors of Inducible Cyclooxygenase and Lipoxygenase

“…The base peak at m/z 84 (i) corresponds to 3,4‐dihydropyran ( Figure S12–S13 ). The absorption peaks displayed in the FT‐IR spectrum at 1123, 1045 cm −1 correspond to ethereal linkages (C−O−C), and those at 1628 cm −1 are indicative of stretching vibration of olefinic (−C=C−) moiety [21] . Chemical‐ionization mass spectrum (CI‐MS) displayed a peak at m/z 421.2 corresponding to the [M+1] peak ( Figure S14 ).…”

“…[12,18,19] The connectivity of furanone containing 13-methoxy- [20] The relative conformation of protons in the stereogenic centers was allocated by NOESY (nuclear overhauser effect) correlations alongside molecular mechanics MM2 studies ( The absorption peaks displayed in the FT-IR spectrum at 1123, 1045 cm À 1 correspond to ethereal linkages (CÀ OÀ C), and those at 1628 cm À 1 are indicative of stretching vibration of olefinic (À C=CÀ ) moiety. [21] Chemical-ionization mass spectrum (CI-MS) displayed a peak at m/z 421.2 corresponding to the [M + 1] peak (Figure S14). The purity of the compound was analyzed using an HPLC chromatogram (Figure S15) and UV spectrum recorded a peak at 305 nm (Figure S16).…”