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

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.

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    Abstract

    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.

    Item Type: Article
    Uncontrolled Keywords: Sargassum wightii; Sargassaceae; Brown seaweed; Fridooleanene triterpenoids; Labdane diterpenoids; Antioxidant activity; Protein tyrosine phosphatase-1B inhibitors; Anti-diabetic activity
    Subjects: Fish Biotechnology > Bioactive compound
    Algae > Seaweed
    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: 14 Sep 2017 09:48
    Last Modified: 14 Sep 2017 09:48
    URI: http://eprints.cmfri.org.in/id/eprint/12155

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