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

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Relation http://eprints.cmfri.org.in/15291/
https://www.tandfonline.com/doi/full/10.1080/14786419.2021.1938041
 
Title Cistobislactone, an undescribed variant of 14-membered
bislactonic macrodiolide, from old-lady octopus Cistopus
indicus (family Octopodidae) attenuates inflammatory
lipoxygenase
 
Creator Shilpa, K P
Chakraborty, Kajal
 
Subject Biochemistry
Fish Biotechnology
 
Description 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 macrodio-lide cistobislactone, which was characterized as 12-(4’-ethyl-6’-
methoxy-3’-methyl-hex-1-enyl)-5,11-dihydroxy-6-methyl-1,7-dioxa-cyclotetradeca-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 ibupro-fen (IC50 4.61 mM, p < 0.05). Superior antioxidant properties of cis-tobislactone against the oxidants (IC50 -1.8 mM) also reinforced
its promising anti-inflammatory activity. Higher electronic proper-ties (topological polar surface area of 102.3) and balanced hydro-phobicity (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 cistobislac-tone with the aminoacyl residues of 5-lipoxygenase could further
recognize its anti-inflammatory potential.
 
Publisher Taylor and Francis
 
Date 2021
 
Type Article
NonPeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/15291/1/Natural%20Product%20Research_2021_Chakraborty%20Kajal_Cistopus%20indicus.pdf
Shilpa, K P and Chakraborty, Kajal (2021) Cistobislactone, an undescribed variant of 14-membered bislactonic macrodiolide, from old-lady octopus Cistopus indicus (family Octopodidae) attenuates inflammatory lipoxygenase. Natural Product Research. pp. 1-11.