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First report of bioactive sterols from the muricid gastropod Chicoreus ramosus

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Relation http://eprints.cmfri.org.in/13014/
https://www.sciencedirect.com/science/article/pii/S0039128X18301260
https://doi.org/10.1016/j.steroids.2018.07.003
 
Title First report of bioactive sterols from the muricid gastropod Chicoreus
ramosus
 
Creator Salas, Soumya
Chakraborty, Kajal
 
Subject New record
Bioactive compounds
Biochemistry
Gastropods
 
Description Two unusual △5 sterols with unprecedented skeletons were isolated from the organic extract of muricid gastropod
Chicoreus ramosus collected off the Gulf of Mannar Coast. This is the first report of isolation of bioactive
sterols endowed with anti-inflammatory potentials from this species. The compounds were characterized as (5Z)-
24a-homo-cholesta-5,24a1(24a2) dien-3β-ol (1) and 27(25→23)-abeo-(5Z)-3β-hydroxy-24-isopropyl cholesteno-
26,23-lactone (2) by the interpretation of a series of spectroscopic techniques involving two-dimensional
nuclear magnetic resonance and mass spectral data. The compound 1 is unusual in that it has an ethylene
attachment stemming from the additional methylene group at the 24a position of the steroid side chain, whereas
compound 2 has a unique side chain bearing a γ-valerolactone ring. The △5 sterol bearing ethylene group (1)
displayed comparatively better antidiabetic activity as characterized by inhibitory effects towards α-amylase and
α-glucosidase enzymes (IC50 1.97mM and 1.78 mM, respectively), whereas the cholestenolactone analogue (2)
manifested higher anti-inflammatory activity (IC50 1.42 mM) as determined by in vitro 5-lipoxygenase inhibitory
potential. Structure-activity correlation study showed that the biological activities of the studied sterols were
directly related to their electronic properties. The homosterol (1) exhibiting improved antidiabetic properties
showed higher lipophilic character coupled with lesser steric restrictions.
 
Publisher Elsevier
 
Date 2018
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/13014/1/Kajal%20Chakraborty_2018_Steroids_First%20report%20of%20bioactive%20sterols%20from%20the%20muricid%20gastropod%20Chicoreus%20ramosus.pdf
Salas, Soumya and Chakraborty, Kajal (2018) First report of bioactive sterols from the muricid gastropod Chicoreus ramosus. Steroids, 137. pp. 57-63.