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Prolonged exposure of human dermal fibroblasts (HDF) to ultraviolet (UV) radiation triggers the production of reactive oxygen species by upregulating the expression of matrix metalloproteinases (MMPs), causing type-I collagen degradation and photoaging. A sulfated (1 → 3)/(1 → 4) mannogalactan exopolysaccharide (BVP-2) characterized as [→3)-α-Galp-{(1 → 4)-α-6-O-SO 3 -Manp}-(1 → 3)-α-6-O-SO 3 -Galp-(1→] was isolated from seaweed-associated heterotrophic bacterium Bacillus velezensis MTCC13097. Whole genome analysis of B. velezensis MTCC13097 (Accession number JAKYLL000000000) revealed saccharine biosynthetic gene clusters for exopolysaccharide production. BVP-2 administered cells showed noteworthy reduction in mitochondrial superoxide (∼85 %, p < 0.05) and ROS production (62 %) than those exhibited by UV-A irradiated HDF cells. Oxidative imbalance in HDF cells (after UV-A exposure) was recovered with BVP-2 treatment by significantly downregulating nitric oxide (NO) production (98.6 μM/mL, 1.9-fold) and DNA damage (⁓67 %) in comparison with UV-A induced cells (191.8 μM/mL and 98.7 %, respectively). UV-irradiated HDF cells showed a ∼30-50 % downregulation in the expression of MMPs (1, 2, and 9) following treatment with BVP-2. Considerable amount of sulfation (18 %) along with (1 → 3)/(1 → 4) glycosidic linkages in BVP-2 could be pivotal factors for down-regulation of the intracellular MMP-1, which was further supported by molecular docking and structure-activity studies. The (1 → 3)/(1 → 4)-linked bacterial exopolysaccharide (BVP-2) might be used as prospective natural lead to attenuate and mitigate UV-A-induced photoaging., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024. Published by Elsevier B.V.)

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.

Angiotensin-I-converting enzyme (ACE) is considered as a major drug target for the treatment of hypertension as it catalyses the production of vasoconstrictor angiotensin II from angiotensin I. ACE inhibitor agents are an effective therapeutic strategy to control high blood pressure. Unprecedented polyether macrolides, marginolide A and B were isolated from the crude extract of marine octopus, Amphioctopus marginatus via bioassay-directed sequential chromatographic fractionation. Marginolide A displayed considerably greater ACE attenuation potential (IC 50 0.58 mM) than that exhibited by marginolide B (IC 50 0.72 mM). Higher antioxidant properties of marginolide A against the oxidant species (IC 50 ∼ 1 mM) also supported its potential ACE inhibitory activity. Higher polar characteristics along with acceptable hydrophobic-hydrophilic equilibrium (partition coefficient of octanol-water, log P ow 2-4) revealed the potential anti-hypertensive activities of marginolides. This study recognized the anti-hypertensive properties of marginolides as promising pharmaceutical leads.

Three Δ 5 steroid analogues, marginoids A-C were purified from the organic extract of marine veined octopus Amphioctopus marginatus (Taki, 1964) (family Octopodidae) distributed on the Asian and Mediterranean coasts. Their structures were elucidated as (5Z)-3β-acetoxy-cholesta-5-en-25-ethylene-22β-hydroxy-23,26-lactone (marginoid A), (5Z, 25Z)-3β-yl-(1'-(E)-3'-hydroxy-4'-methyl-hex-5'-enoate)-22-oxo-26-furanyl-cholesta-5,25-diene (marginoid B), and (5Z)-3β-yl-(7'-methoxypropan-8'-yl)-tetrahydro-2H-pyran-2-one-cholesta-5,24-dien (marginoid C) based on extensive spectroscopic experiments. Marginoid B with hydroxyl-methyl-hexanoate at the C-3 position in conjunction with the heterocyclic furanyl ring displayed superior anti-hyperglycemic properties as acknowledged by its promising serine protease dipeptidyl peptidase-4 attenuation potential (IC 50 3.49 µM) displaying comparable activity with the standard DPP-4 inhibitor (DPP-4i) diprotin A (IC 50 4.53 µM). The anti-hyperglycemic properties were corroborated by the promising antioxidant activities (IC 50  ∼ 0.8-1.0 mM) of these Δ 5 steroids, marginoids A-C. Sizeably greater electronic properties, balanced hydrophobic-lipophilic properties (log P OW 6.4-8.3), and comparatively lower steric factors were directly proportional to their bioactive properties. Molecular simulation studies in the binding sites of DPP-4 and lesser binding energy (-12.17 kcal/mol) and inhibition constant (Ki 1.20 nM) of marginoid B could be correlated with anti-hyperglycemic properties. Promising bioactivities of marginoid B isolated from A. marginatus are anticipated for nutraceutical applications against hyperglycemia., Competing Interests: Declaration of Competing Interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2022 Elsevier Inc. All rights reserved.)

Cephalopod cuttlefish, Sepia pharaonis, has been considered as a commercially important resource, which is widely regarded as nutritious food in the southwest of Indian and Mediterranean coasts. Chemical analysis of the crude extract of S. pharaonis resulted in the isolation of an undescribed 2H-benzochromenone, pharachromenone, which was characterized as methyl-2″-(7-hydroxy-4-(5'-methylpent-5'-en-1'-yl-oxy-methyl)-2-oxo-2H-benzo[h]chromen-5-yl-methyl)-butanoate by mass and nuclear magnetic resonance spectral experiments. Pharachromenone revealed effective biopotency against 5-lipoxygenase (IC 50 1.85 mM) and cyclooxygenase-2 (IC 50 0.52 mM) than that displayed by nonsteroidal anti-inflammatory drug ibuprofen (IC 50 4.36 mM, p < .05). Promising antioxidant property for pharachromenone (IC 50 1.42-1.61 mM) compared with those exhibited by antioxidative agents butylated hydroxyl anisole (BHA) and α-tocopherol (IC 50 1.40-1.90 mM) could conceivably validate its dual inhibition potential against 5-lipoxygenase and cyclooxygenase-2. Greater electronic parameters, lesser steric bulkiness, along with acceptable lipophilic-hydrophobic balance significantly contributed toward its promising anti-inflammatory activities. Molecular docking studies showing significantly greater inhibition constant (Ki) 8.24 nM and binding energy (-11.03 kcal/mol) of pharachromenone than the standard ibuprofen (Ki 4.65 μM, binding energy -7.27 kcal/mol) at the binding site of 5-lipoxygenase recognized its noncompetitive binding, which could describe the promising anti-inflammatory potential. Pharachromenone could be developed as a functional food component against oxidative stress-related inflammatory disorders. PRACTICAL APPLICATIONS: The cuttlefish Sepia pharaonis (family Sepiidae) comprises a major share in the global fishery sector due to its culinary delicacy and nutritionally valued high-quality meat. Furthermore, cephalopod mollusks are gaining pharmaceutical acceptance as resources to derive bioactive compounds with therapeutic significance. Bioassay-guided chromatographic fractionation of crude extract of S. pharaonis could result in the isolation of a 2H-benzochromenone derivative, pharachromenone exhibiting potent antioxidant and anti-inflammatory properties. This study recognized the therapeutic potential of a marine cuttlefish-originated food constituent against inflammatory conditions, and could be anticipated as a high-value functional food lead to minimize oxidative stress-related inflammatory disorders., (© 2022 Wiley Periodicals LLC.)

Biochemical investigation of crude solvent extract of pharaoh cuttlefish Sepia pharaonis (family Sepiidae) led to the isolation of two undescribed disecolactonic ergosteroids, pharaonoids A-B. The compounds were characterized as 11β-acteoxy-7α-hydroxy-19-Nor-1,10:9,10-disecoergosta-3-ene-6 1 -oxa-1-one (pharaonoid A) and 11β-hydroxy-19-Nor-1,10:9,10-disecoergosta-3-ene-6 1 -oxa-1-one (pharaonoid B) in conjunction with spectroscopic analysis encompassing one and two-dimensional nuclear magnetic resonance and mass spectrometric analyses. Pharaonoid A, bearing an acetoxy and hydroxyl groups, respectively at C-11 and C-7 positions exhibited considerably greater inhibition potential against carbohydrate hydrolysing enzymes α-amylase (IC 50 1.14 mM) and α-glucosidase (IC 50 1.23 mM) than those displayed by pharaonoid B (IC 50 1.49/1.38 mM), and was proportionate with those exhibited by standard drug acarbose (IC 50 0.60 and 0.40 mM, respectively), thereby recognizing the anti-hyperglycemic potential of pharaonoid A. Promising anti-oxidant property for pharaonoid A (IC 50  ∼ 1 mM) could conceivably corroborate its attenuation potential against carbohydrate digestive enzymes. Greater electronic parameters along with optimum lipophilic-hydrophobic balance of pharaonoid A were directly corroborated to the anti-carbolytic properties occurring via transcellular mechanism. Greater binding energies (-9.50 kcal mol -1 ) and inhibition constant (Ki 48.21 nM) at the active site of α-amylase enzyme were displayed by pharaonoid A than those exhibited by its B analogue. Promising bioactive properties of the disecolactonic steroids isolated from the marine pharaoh cuttlefish are anticipated to be utilized as functional food components and potential nutraceuticals against oxidative stress and hyperglycemic disorders., (Copyright © 2022 Elsevier Inc. All rights reserved.)

Increased prevalence of microbial resistance and development of drug-resistant pathogens have triggered an urge among researchers to discover potential antimicrobial compounds, particularly from the marine habitat. The present study highlights the cultivable diversity and bioactivities of heterotrophic bacteria associated with marine macroalgae of southeast Indian coastal region. Culture-dependent isolation method resulted in 40 isolates, in which greater part of the isolates represented Gammaproteobacteria (62%) followed by that comprised of the phylum Firmicutes. One of the most active strains isolated from a macroalga, Laurencia papillosa, was characterized based on the integrated phenotypic and genotypic analysis as Bacillus velezensis MBTDLP1 MTCC 13048, with an inhibition zone of about 35 mm against methicillin-resistant Staphylococcus aureus (MRSA), was selected for bioprospecting studies. Type-I pks gene (MT394492) of 700 bp could be amplified from the heterotrophic B. velezensis. The bacterium exhibited siderophore production and possessed genes implicated in the biosynthesis of siderophore type of metabolites exhibiting 99% similarity with other GenBank sequences in BLAST search. B. velezensis exhibited promising anti-infective properties against methicillin-resistant Staphylococcus aureus (minimum inhibitory concentration 15 µg/mL), and the activities were positively correlated (r 2  > 0.9) with iron-chelating activities. Chemical investigation of the organic extract of B. velezensis MBTDLP1 characterized a macrocyclic polyketide exhibiting prospective antibacterial potential against methicillin-resistant S. aureus (MIC 0.38 µg/mL), than that exhibited by positive control chloramphenicol (6.25 µg/mL). Significant antibacterial activity against drug-resistant bacteria combined with the presence of genes coding for bioactive secondary metabolites revealed that this marine symbiotic bacterium could be used against emerging antibiotic resistance., (© 2021. The Author(s), under exclusive licence to Springer-Verlag GmbH Germany, part of Springer Nature.)

Marine pharaoh cuttlefish Sepia pharaonis (family Sepiidae) is regarded as an economically important class of cephalopod in the coastal Mediterranean and Asian regions. Bioassay-guided chromatographic purification of solvent extract of S. pharaonis led to the identification of a trans-decalin based spirolactone, spiropharanone, which was characterized as 1-hydroxy-7-(4'-methoxy-3-methylbut-2-enyl)-3,9,15-trimethyl-8-oxo-octahydro-5H-spiro[furan-8,9-naphtho]-8-yl-acetate by spectroscopic techniques. Spiropharanone exhibited significantly greater anti-inflammatory activity by attenuating pro-inflammatory 5-lipoxygenase (IC 50 1.02 mM) than the non-steroidal drug ibuprofen (IC 50 4.61 mM, p ≤ .05). Superior antioxidant properties of spiropharanone against free radicals (EC 50 ~1.20 mM) and other oxidants (hydroxyl [EC 50 0.97 mM] and superoxide [EC 50 1.47 mM] scavenging) also reinforced its promising anti-inflammatory activity. The studied spiropharanone also exhibited significant attenuation toward insulin secretion regulating enzyme dipeptidyl peptidase-4 (IC 50 0.92 mM) recognizing its anti-hyperglycemic potential. Significantly higher electronic properties (topological polar surface area ~100) combined with balanced hydrophilic-lipophilic properties (partition coefficient of logarithmic octanol-water ~3) and lesser docking parameters of spiropharanone demonstrated that the compound could be utilized as an important bioactive lead against oxidative stress, inflammation, and hyperglycemic-related ailments. PRACTICAL APPLICATIONS: Nutritionally rich edible marine pharaoh cuttlefish Sepia pharaonis occupies a prominent place among seafood fisheries owing to the presence of bioactive nutrients and functional food ingredients. These marine cuttlefish are widely distributed along the Asian and Mediterranean coasts, and consumed as culinary delicacy for decades. An undescribed trans-decalin spirolactone, spiropharanone was isolated from the organic extract of S. pharaonis based on bioactivity-assisted sequential chromatographic fractionation. Spiropharanone displayed promising antioxidant potential along with attenuation properties against inducible pro-inflammatory 5-lipoxygenase and insulin secretion regulating enzyme dipeptidyl peptidase-4. This study established the ameliorating potential of a naturally derived marine food constituent against inflammatory and diabetic ailments, and thus anticipated as functional food lead in pharmaceutical formulations towards inflammation and maintaining glucose homeostasis., (© 2021 Wiley Periodicals LLC.)