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

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Relation https://eprints.cmfri.org.in/13277/
https://linkinghub.elsevier.com/retrieve/pii/S0039128X18302265
https://doi.org/10.1016/j.steroids.2018.12.004
 
Title First report of a lactonic disecosteroid from the buccinid gastropod Babylonia spirata
 
Creator Chakraborty, Kajal
Joy, Minju
Salas, Soumya
 
Subject Bioprospecting
New record
Bioactive compounds
Gastropods
 
Description 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.
 
Publisher Elsevier
 
Date 2019
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier https://eprints.cmfri.org.in/13277/1/Kajal%20Chakraborty_2019_Steroids_First%20report%20of%20a%20lactonic%20disecosteroid%20from%20the%20buccinid%20gastropod%20Babylonia%20spirata.pdf
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.