Anti-inflammatory scalarane-type sesterterpenes, erectascalaranes A–B, from the marine sponge Hyrtios erectus attenuate pro-inflammatory cyclooxygenase-2 and 5-lipoxygenase

Francis, Prima and Chakraborty, Kajal (2021) Anti-inflammatory scalarane-type sesterterpenes, erectascalaranes A–B, from the marine sponge Hyrtios erectus attenuate pro-inflammatory cyclooxygenase-2 and 5-lipoxygenase. Medicinal Chemistry Research, 30. pp. 886-896.

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    Abstract

    Chemical investigation of demosponge Hyrtios erectus (family Thorectidae) resulted in the identification of two scalarane-type sesterterpenes, erectascalaranes A–B, which were characterized as 3-((but-35-enyloxy)methyl)-icosahydro-11-hydroxy-4,4,8,10,13-pentamethyl-20-oxochryseno[2,1-c]furan-12-yl acetate (erectascalarane A) and 3-((but-35-enyloxy)methyl)-hexadecahydro-11-hydroxy-4,4,8,10,13-pentamethylchryseno[2,1-c]furan-20(5bH)-one (erectascalarane B) using detailed spectroscopic experiments. Erectascalarane A exhibited significantly greater attenuation property against pro-inflammatory cyclooxygenase-2 (IC50 0.80 mM) than that displayed by erectascalarane B (IC50 ~ 1 mM). Erectascalarane A was found to be a potential inhibitor against 5-lipoxygenase (IC50 1.21 mM), and its activity was significantly higher than that displayed by standard anti-inflammatory agent ibuprofen (IC50 4.50 mM, p < 0.05). Greater anti-inflammatory selectivity index of erectascalarane A (1.15) than ibuprofen (0.43) also accounted for greater selectivity of the former against cyclooxygenase-2. Erectascalarane A also exhibited significantly greater antioxidant activities against oxidants (IC50 ~ 0.8 mM) than the standard α-tocopherol (IC50 > 1.5 mM). Lesser docking parameters obtained for erectascalarane A at the active site of COX-2 and greater electronic factors acquired from structure–activity analyses (topological polar surface area 82.06) were also in agreement with greater anti-inflammatory activity. Lesser steric bulk and greater electronic properties combined with lower binding energy with cyclooxygenase-2 further reinforced the significant anti-inflammatory potential of erectascalarane A.

    Item Type: Article
    Uncontrolled Keywords: Demospongiae; Hyrtios erectus; Erectascalaranes A–B; Scalarane-type sesterterpenes; Anti-inflammatory activity
    Subjects: Biochemistry > Bioprospecting
    Biochemistry > Bioactive compounds
    Biochemistry
    Algae > Seaweed
    Marine Ecosystems > Sponges
    Marine Ecosystems
    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: 19 Mar 2021 06:32
    Last Modified: 19 Mar 2021 06:32
    URI: http://eprints.cmfri.org.in/id/eprint/15024

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