Cistobislactone, an undescribed variant of 14-membered bislactonic macrodiolide, from old-lady octopus Cistopus indicus (family Octopodidae) attenuates inflammatory lipoxygenase

Silpa, K P and Chakraborty, Kajal (2022) Cistobislactone, an undescribed variant of 14-membered bislactonic macrodiolide, from old-lady octopus Cistopus indicus (family Octopodidae) attenuates inflammatory lipoxygenase. Natural Product Research, 36 (12). pp. 3002-3012. ISSN 1478-6427 (Online)

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    Abstract

    Chemical evaluation of specialised metabolites from the old-lady marine octopus Cistopus indicus (family Octopodidae) led to the isolation of an undescribed 14-membered bislactonic macrodiolide cistobislactone, which was characterized as 12-(4'-ethyl-6'-methoxy-3'-methyl-hex-1-enyl)-5,11-dihydroxy-6-methyl-1,7-dioxacyclotetradeca-3,9-diene-2,8-dione. Cistobislactone exhibited noticeably greater inhibitory potential against 5-lipoxygenase (IC50 2.06 mM) compared to standard anti-inflammatory agent ibuprofen (IC50 4.61 mM, p < 0.05). Superior antioxidant properties of cistobislactone against the oxidants (IC50 ∼1.8 mM) also reinforced its promising anti-inflammatory activity. Higher electronic properties (topological polar surface area of 102.3) and balanced hydrophobicity (logarithm of octanol-water coefficient ∼3) could recognize its higher interaction at the enzyme active site resulting in an effective attenuation of 5-lipoxygenase and efficient inter-membrane permeability. Comparatively lesser binding energy (-6.5 kcal mol−1) and docking score (-7.5 kcal mol−1) of cistobislactone with the aminoacyl residues of 5-lipoxygenase could further recognize its anti-inflammatory potential.

    Item Type: Article
    Uncontrolled Keywords: Old-lady octopus Cistopus indicus; Octopodidae; bislactonic macrodiolide; cistobislactone; inflammatory 5-lipoxygenase
    Subjects: Biochemistry
    Molluscan Fisheries > Cephalopods
    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: 22 Jun 2022 06:14
    Last Modified: 22 Jun 2022 06:14
    URI: http://eprints.cmfri.org.in/id/eprint/16001

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