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An anti-inflammatory salmachroman from the sea urchin Salmacis bicolor: a prospective duel inhibitor of cyclooxygenase-2 and 5-lipoxygenase.
Nat Prod Res. 2020 Jun 22 [Online ahead of print]NP

Abstract

An isochroman derived polyketide, salmachroman characterized as methyl 153(11-(10-hydroxy-12-oxo-6-pent-63-en-61-yl)isochroman-10-yl)-13-oxotetrahydrofuran-15-yl was isolated from the organic extract of the Echinodermata sea urchin Salmacis bicolor (family Temnopleuridae) through chromatographic fractionation. The structure of the compound was identified by detailed spectroscopic techniques. Salmachroman demonstrated significant duel inhibition potential against pro-inflammatory enzymes, cyclooxygense-2 (IC50 1.29 mM) and 5-lipoxygenase (IC50 1.39 mM). The compound exhibited significantly greater anti-inflammatory selectivity index (1.03) than that displayed by the anti-inflammatory agent ibuprofen (0.43). The isochroman analogue exhibited greater antioxidant activities against 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (IC50 1.19 mM) and 2,2-diphenyl-1-picrylhydrazyl (IC50 1.24 mM) than the standard antioxidative agent α-tocopherol (IC50 > 1.50 mM). The binding properties of the compound with the active site of cyclooxygense-2 and 5-lipoxygenase enzymes, combined with its higher electronic parameters as attributed by the structure-activity relationship accounted for its significant anti-inflammatory properties.

Authors+Show Affiliations

Central Marine Fisheries Research Institute, Cochin, India. Department of Chemistry, Mangalore University, Mangalagangothri, Karnataka, India.Central Marine Fisheries Research Institute, Cochin, India.

Pub Type(s)

Journal Article

Language

eng

PubMed ID

32571101

Citation

Francis, Prima, and Kajal Chakraborty. "An Anti-inflammatory Salmachroman From the Sea Urchin Salmacis Bicolor: a Prospective Duel Inhibitor of Cyclooxygenase-2 and 5-lipoxygenase." Natural Product Research, 2020, pp. 1-10.
Francis P, Chakraborty K. An anti-inflammatory salmachroman from the sea urchin Salmacis bicolor: a prospective duel inhibitor of cyclooxygenase-2 and 5-lipoxygenase. Nat Prod Res. 2020.
Francis, P., & Chakraborty, K. (2020). An anti-inflammatory salmachroman from the sea urchin Salmacis bicolor: a prospective duel inhibitor of cyclooxygenase-2 and 5-lipoxygenase. Natural Product Research, 1-10. https://doi.org/10.1080/14786419.2020.1781115
Francis P, Chakraborty K. An Anti-inflammatory Salmachroman From the Sea Urchin Salmacis Bicolor: a Prospective Duel Inhibitor of Cyclooxygenase-2 and 5-lipoxygenase. Nat Prod Res. 2020 Jun 22;1-10. PubMed PMID: 32571101.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - An anti-inflammatory salmachroman from the sea urchin Salmacis bicolor: a prospective duel inhibitor of cyclooxygenase-2 and 5-lipoxygenase. AU - Francis,Prima, AU - Chakraborty,Kajal, Y1 - 2020/06/22/ PY - 2020/6/24/entrez KW - Salmacis bicolor KW - Temnopleuridae KW - anti-inflammatory and antioxidant activity KW - isochroman derived polyketide KW - salmachroman KW - selectivity index SP - 1 EP - 10 JF - Natural product research JO - Nat. Prod. Res. N2 - An isochroman derived polyketide, salmachroman characterized as methyl 153(11-(10-hydroxy-12-oxo-6-pent-63-en-61-yl)isochroman-10-yl)-13-oxotetrahydrofuran-15-yl was isolated from the organic extract of the Echinodermata sea urchin Salmacis bicolor (family Temnopleuridae) through chromatographic fractionation. The structure of the compound was identified by detailed spectroscopic techniques. Salmachroman demonstrated significant duel inhibition potential against pro-inflammatory enzymes, cyclooxygense-2 (IC50 1.29 mM) and 5-lipoxygenase (IC50 1.39 mM). The compound exhibited significantly greater anti-inflammatory selectivity index (1.03) than that displayed by the anti-inflammatory agent ibuprofen (0.43). The isochroman analogue exhibited greater antioxidant activities against 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) (IC50 1.19 mM) and 2,2-diphenyl-1-picrylhydrazyl (IC50 1.24 mM) than the standard antioxidative agent α-tocopherol (IC50 > 1.50 mM). The binding properties of the compound with the active site of cyclooxygense-2 and 5-lipoxygenase enzymes, combined with its higher electronic parameters as attributed by the structure-activity relationship accounted for its significant anti-inflammatory properties. SN - 1478-6427 UR - https://www.unboundmedicine.com/medline/citation/32571101/An_anti-inflammatory_salmachroman_from_the_sea_urchin_Salmacis_bicolor:_a_prospective_duel_inhibitor_of_cyclooxygenase-2_and_5-lipoxygenase L2 - http://www.tandfonline.com/doi/full/10.1080/14786419.2020.1781115 DB - PRIME DP - Unbound Medicine ER -
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