Anti-inflammatory polyoxygenated furanocembranoids, salmacembranes A–B from the sea urchin Salmacis bicolor attenuate pro-inflammatory cyclooxygenases and lipoxygenase

Francis, Prima and Chakraborty, Kajal (2020) Anti-inflammatory polyoxygenated furanocembranoids, salmacembranes A–B from the sea urchin Salmacis bicolor attenuate pro-inflammatory cyclooxygenases and lipoxygenase. Medicinal Chemistry Research, 29. pp. 2066-2076.

[img] Text
Medicinal Chemistry Research_2020_Kajal Chakraborty_Anti-inflammatory polyoxygenated furanocembranoids.pdf
Restricted to Registered users only

Download (1MB) | Request a copy
Official URL: https://link.springer.com/article/10.1007%2Fs00044...
Related URLs:

    Abstract

    Two undescribed polyoxygenated furanocembranoid derivatives, methyl 15-(9-hydroxy-8-methoxy-2,12-dimethyl-15-oxa-bicyclo [10.2.1]pentadeca-2,4,6,11-tetraen-3-yl)propanoate (salmacembrane A) and 1-(16-methyl-2,16-dihydrofuran)-8-methoxy-12- methyl-20-oxabicyclo[10.2.1]pentadeca-2,4,6,11-tetraen-9-ol (salmacembrane B), were isolated from the organic extract of sea urchin Salmacis bicolor (family Temnopleuridae) by extensive chromatographic purification. Their structures were elucidated using detailed spectroscopic evidence. Salmacembrane A displayed significantly greater attenuation property against pro-inflammatory cyclooxygenase-2 (IC50 1.71 mM) than that exhibited by salmacembrane B (IC50 1.99 mM). Salmacembrane A could potentially inhibit 5-lipoxygenase (IC50 1.87 mM) and its activity was significantly greater than that exhibited by anti-inflammatory agent ibuprofen (IC50 4.50mM, p < 0.05). The greater selectivity index (anti-cyclooxygense-2/anti-cyclooxygense-1) of salmacembrane A (1.06) than ibuprofen (0.43) further supported higher selectivity toward pro-inflammatory isoenzyme cyclooxygenase-2. Salmacembrane A displayed higher antioxidant properties against 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) and 2,2- diphenyl-1-picrylhydrazyl (IC50 1.57 and 1.65mM, respectively) than those exhibited by salmacembrane B (IC50 > 1.85mM). In addition, these antioxidant activities were comparable to the standard α-tocopherol (IC50 DPPH 1.51 mM, IC50 ABTS+ 1.70mM p < 0.05). The higher electronic parameters obtained from structure–activity relationship analysis along with greater binding affinities of salmacembrane A at the active site of cyclooxygenase-2 ascribed its potential anti-inflammatory activity.

    Item Type: Article
    Uncontrolled Keywords: Sea urchin; Salmacis bicolor; Salmacembranes; Polyoxygenated furanocembranoids; Anti-inflammatory activity; Selectivity index
    Subjects: Biochemistry > Bioactive compounds
    Biochemistry
    Echinoderms
    Echinoderms > sea Urchin
    Divisions: CMFRI-Kochi > Marine Biotechnology
    Subject Area > CMFRI > CMFRI-Kochi > Marine Biotechnology
    CMFRI-Kochi > Marine Biotechnology
    Subject Area > CMFRI-Kochi > Marine Biotechnology
    Depositing User: Arun Surendran
    Date Deposited: 13 Oct 2020 04:53
    Last Modified: 13 Oct 2020 04:53
    URI: http://eprints.cmfri.org.in/id/eprint/14687

    Actions (login required)

    View Item View Item