First report of a lactonic disecosteroid from the buccinid gastropod Babylonia spirata

Chakraborty, Kajal and Joy, Minju and Salas, Soumya (2019) First report of a lactonic disecosteroid from the buccinid gastropod Babylonia spirata. Steroids, 143. pp. 41-48.

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Kajal Chakraborty_2019_Steroids_First report of a lactonic disecosteroid from the buccinid gastropod Babylonia spirata.pdf

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    Abstract

    A lactonic steroid with an unprecedented 1, 10: 8, 9-disecoergostane framework was identified from the ethyl acetate-methanol extract of buccinid gastropod mollusk, Babylonia spirata collected from the southwestern coast of Indian peninsular region. The compound was characterized as 1, 10: 8, 9-disecoergosta-8-en-A-homo-6a-oxa-1-one by exhaustive spectroscopic methods including two-dimensional nuclear magnetic resonance and mass spectroscopic investigations. The disecosteroid displayed moderate carbolytic enzyme inhibition activity as distinguished by its inhibitive effects against α-amylase and α-glucosidase (IC50 0.40 and 0.54 mg/mL, respectively). The anti-inflammatory (5-lipoxidase inhibitory) activity of the titled secondary metabolite was found to be superior (IC50 < 0.85 mg/mL) than the commercial anti-inflammatory drug (ibuprofen IC50 > 0.85 mg/mL). However, significantly greater antioxidant property was recorded for the studied disecosteroid as evaluated by in vitro 2, 2-diphenyl-1-picrylhydrazyl radical inhibition potential (IC50 0.30 mg/mL) than that of standard, α-tocopherol (IC50 > 0.50 mg/mL). The in silico molecular docking studies were conducted to explain the anti-5-lipoxidase and anti-α-amylase properties of the isolated compound. The molecular binding interactions of the ligands with the pro-inflammatory 5-lipoxidase and the carbolytic enzyme α-amylase, demonstrated that their binding energies/docking scores were positively associated with their in vitro bioactivies. A plausible pathway for the biosynthetic origin of lactonic disecosteroid in B. spirata was proposed from an ergosterol precursor. Structure-activity correlation study demonstrated that the biological activities of the disecosteroid were directly proportional to their electronic properties allied with lesser steric restrictions.

    Item Type: Article
    Uncontrolled Keywords: 5-Lipoxidase; Anti-inflammatory; Babylonia spirata; Carbolytic enzyme inhibition activity; Lactonic disecosteroid; Molecular binding
    Subjects: CMFRI Departments > CMFRI-Kochi > Marine Biotechnology
    CMFRI > CMFRI-Kochi > Marine Biotechnology
    CMFRI-Kochi > Marine Biotechnology
    CMFRI-Kochi > Marine Biotechnology

    Biochemistry > Bioprospecting
    Biochemistry > Bioactive compounds
    Molluscan Fisheries > Gastropods
    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: 26 Dec 2018 09:48
    Last Modified: 26 Dec 2018 09:48
    URI: http://eprints.cmfri.org.in/id/eprint/13277

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