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Chromene derivatives with manifold structural framework and pharmacological properties were ubiquitous in the mollusks of marine origin. A previously undescribed 1H-benzochromenone was isolated through bioassay-guided chromatographic purification of the organic extract of the marine gastropod mollusk Chicoreus ramosus. The compound was characterised as 6-(2′,2′-dimethyl)-3′-en-1′-yl-1′-oxy)-3-hydroxy-1H-benzo[c]chromene-2(10aH)-one based on integrated spectroscopic analysis. The antioxidant studies by employing the stable free radicals reported that the antioxidant activity (IC50 1.4–1.6 mM) was comparable to α-tocopherol (IC50 1.4–1.7 mM). The attenuating potential of the studied compound against pro-inflammatory 5-lipoxygenase (IC50 2.12 mM) was significantly greater than that exhibited by anti-inflammatory drug ibuprofen (IC50 4.4 mM), whereas its inhibitory properties against carbolytic α-amylase (IC50 ∼0.72 mM) was comparable with that displayed by acarbose (IC50 0.43 mM). The present study recognised the potential of 1H-benzochromenone derivative isolated from C. ramosus as important pharmaceutical lead with anti-diabetic and anti-inflammatory potentials to reduce the risk of hyperglycaemia and inflammatory pathologies. [ABSTRACT FROM AUTHOR]

The chemical analyses of ethyl acetate-methanol (EtOAc-MeOH) extract of muricid gastropod mollusk, Chicoreus ramosus from the southeastern coast of Indian peninsular led to the identification of unprecedented cembrane-type diterpenoid, which was characterized as (3E, 6E, 10E)-8a-butoxy-17(15→14), 20(12→11)-bis-abeo-cembra-3,6,10,14(17),15-pentaene (1). The structure of the studied cembrane was unambiguously assigned through the extensive spectroscopic experimentations. The antioxidant potentials of the bis-abeo cembrane as determined by in vitro 2,2-diphenyl-1-picrylhydrazyl and 2,2'-azino-bis-3-ethylbenzothiozoline-6-sulfonic acid diammonium salt radical quenching potentials were greater (IC50 < 0.40 mg/mL) related to α-tocopherol (IC50 > 0.60 mg/mL). The pro-inflammatory anti-5-lipoxygenase potential of studied cembrane was higher (IC50 < 0.80 mg/mL) related to those demonstrated by ibuprofen and sodium salicylate (IC50 > 0.90 mg/mL). [ABSTRACT FROM AUTHOR]

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. [ABSTRACT FROM AUTHOR]

A previously undescribed xylated glycosaminoglycan characterized as β‐D‐Xylop(1 → 3)‐(⋯ → 4)‐GlcpA(1 → 3)‐GlcpNAc(1 → ⋯) was purified from the buccinid gastropod Babylonia spirata and was evaluated for pharmacological properties using different in vitro models. The glycosaminoglycan‐xylopyranan displayed prospective free radical quenching activities (IC50 < 0.7 mg/ml), whereas it exhibited potentially greater attenuation against the inductive proinflammatory enzyme 5‐lipoxygenase (5‐LOX, IC50 0.36 mg/ml) than the synthetic nonsteroidal anti‐inflammatory drug aspirin (0.42). Gel permeation chromatography analysis specified the average molecular mass of the purified polysaccharide to be 231.88 kDa. The linkage sites, anomeric configuration, and the sequence of sugar residues of the purified xylated glycosaminoglycan were attributed by the inter‐residue correlation obtained via two‐dimensional nuclear resonance spectroscopic techniques. The results specified that the studied compound was composed of GlcpA(1 → 3)‐GlcpNAc (1 → ⋯) disaccharide repeating unit in the glycosaminoglycan backbone, with the xylose residues branching as C‐3 substituents of the GlcpA.. Practical applications: The edible marine buccinid mollusk Babylonia spirata is a gastropod species of economic significance in the coastal regions of peninsular India. A previously unreported xylated glycosaminoglycan with a β‐D‐Xylop(1 → 3)‐(⋯ → 4)‐GlcpA(1 → 3)‐GlcpNAc(1 → ⋯) framework was isolated to homogenity and was found to possess potential antioxidant and 5‐lipoxygenase attenuation activities. The isolated metabolite might be anticipated as potential naturally‐derived bioactive constituent in functional food and pharmaceutical applications. [ABSTRACT FROM AUTHOR]

The muricid gastropod, Chicoreus ramosus, is a nutrient‐enriched food source available along the coastal peninsular of the Indian subcontinent. This study was aimed at bioactivity‐directed chromatographic fractionation of the organic extract of C. ramosus to isolate an unprecedented drimane‐type sesquiterpenoid Ramosane, characterized as 3‐hydroxy‐7,9b‐dimethyl‐5‐methylene‐8‐pentyl‐octahydro‐1H‐cyclopenta[a]naphthalen‐9(2H)‐one. The compound possessed potential antioxidant activities {2, 2′‐diphenyl‐1‐picryl hydrazyl (DPPH) and 2,2′‐azino‐bis(3‐ethylbenzothiazoline‐6‐sulfonic acid (ABTS) radical scavenging activities of IC50 1.42 mM and 1.72 mM, respectively} and was proportionate with those (IC50 1.39 and 1.69 mM, respectively) exhibited by α‐tocopherol. The studied sesquiterpenoid exhibited potential attenuation property countering the pro‐inflammatory 5‐lipoxygenase (IC50 ~ 4 mM), and its activity was analogous with that exhibited by the anti‐inflammatory ibuprofen (IC50 4.36 mM), whereas its carbolytic α‐amylase activity (IC50 0.96 mM) was commensurate with that displayed by acarbose (IC50 0.43 mM). The isolated metabolite might anticipate as potential naturally derived bioactive constituent in functional food and pharmaceutical applications. Practical applications: The edible marine muricid gastropod C. ramosus is a prominently available gastropod species of commercial significance in the coastal regions of Indian Peninsula. An unprecedented drimane‐type sesquiterpenoid Ramosane was isolated through the bioactivity‐directed chromatographic fractionation of the organic extract of muricidae C. ramosus displaying potential anti‐inflammatory and anti‐diabetic properties. The present study apprehended the prospective of drimane‐type sesquiterpenoid derivative Ramosane purified from C. ramosus as a naturally derived pharmacophore with anti‐diabetic and anti‐inflammatory potential for utilization in functional food and pharmaceutical formulations to minimize the likelihood of inflammation and hyperglycemic pathologies. [ABSTRACT FROM AUTHOR]

Chromene derivatives with manifold structural framework and pharmacological properties were ubiquitous in the mollusks of marine origin. A previously undescribed 1 H -benzochromenone was isolated through bioassay-guided chromatographic purification of the organic extract of the marine gastropod mollusk Chicoreus ramosus . The compound was characterised as 6-(2',2'-dimethyl)-3'-en-1'-yl-1'-oxy)-3-hydroxy-1 H -benzo[c]chromene-2(10a H )-one based on integrated spectroscopic analysis. The antioxidant studies by employing the stable free radicals reported that the antioxidant activity (IC 50 1.4-1.6 mM) was comparable to α -tocopherol (IC 50 1.4-1.7 mM). The attenuating potential of the studied compound against pro-inflammatory 5-lipoxygenase (IC 50 2.12 mM) was significantly greater than that exhibited by anti-inflammatory drug ibuprofen (IC 50 4.4 mM), whereas its inhibitory properties against carbolytic α -amylase (IC 50 ∼0.72 mM) was comparable with that displayed by acarbose (IC 50 0.43 mM). The present study recognised the potential of 1 H -benzochromenone derivative isolated from C. ramosus as important pharmaceutical lead with anti-diabetic and anti-inflammatory potentials to reduce the risk of hyperglycaemia and inflammatory pathologies.