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Previously undescribed fridooleanenes and oxygenated labdanes from the brown seaweed Sargassum wightii and their protein tyrosine phosphatase-1B inhibitory activity

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Relation http://eprints.cmfri.org.in/12155/
http://www.sciencedirect.com/science/article/pii/S0031942217302868
 
Title Previously undescribed fridooleanenes and oxygenated labdanes from the brown seaweed Sargassum wightii and their protein tyrosine phosphatase-1B inhibitory activity
 
Creator Anusree, M
Chakraborty, Kajal
 
Subject Bioactive compound
Seaweed
 
Description Previously undescribed fridooleanene triterpenoids 2a-hydroxy-(28,29)-frido-olean-12(13), 21(22)-dien-
20-propyl-21-hex-40(Z)-enoate, 2a-hydroxy-(28,29)-frido-olean-12(13), 21(22)-dien-20-prop-2(E)-en-
21-butanoate and oxygenated labdane diterpenoids 2a-hydroxy-8(17), (12E), 14-labdatriene, 3b, 6b, 13atri
hydroxy 8(17), 12E, 14-labdatriene were purified from the ethyl acetate-methanol and dichloromethane
fractions of the air-dried thalli of Sargassum wightii (Sargassaceae), a brown seaweed collected
from the Gulf-of-Mannar of Penninsular India. Inhibitory potential of D12 oleanenes towards protein
tyrosine phosphatase-1B, the critical regulator of insulin-receptor activity were found to be significantly
greater (IC50 0.1 � 10�2 and 0.09 � 10�2 mg/mL, respectively) than the standard sodium metavanadate
(IC50 0.31 � 10�2 mg/mL). Fridooleanene triterpenoids displayed greater antioxidant activities (IC50DPPH
0.16e0.18 mg/mL) than the commercially available antioxidants, butylated hydroxytoluene and atocopherol
(IC50DPPH 0.25 and 0.63 mg/mL, respectively). In general, the oxygenated labdane diterpenoids
displayed significantly lesser antioxidant and tyrosine phosphatase-1B inhibitory properties than those
exhibited by the fridooleanenes. Bioactivities of the titled compounds were primarily determined by the
electronic and lipophilic parameters and not by the steric descriptors. Molecular docking simulations and
kinetic studies were employed to describe the tyrosine phosphatase-1B inhibitory mechanism. The
previously undescribed fridooleanene triterpenoids might be used as potential anti-hyperglycaemic
pharmacophore leads to reduce the risk of elevated postprandial glucose levels.
 
Date 2017
 
Type Article
PeerReviewed
 
Format text
 
Language en
 
Identifier http://eprints.cmfri.org.in/12155/1/Phytochemistry_2017-144-Anusree_Kajal%20Chakraborty_Previously%20undescribed%20fridooleanenes%20and%20oxygenated%20labdanes%20from%20the%20brown%20seaweed.pdf
Anusree, M and Chakraborty, Kajal (2017) Previously undescribed fridooleanenes and oxygenated labdanes from the brown seaweed Sargassum wightii and their protein tyrosine phosphatase-1B inhibitory activity. Phytochemistry, 144. pp. 19-32.