Guaiane sesquiterpenes from seaweed Ulva fasciata Delile and their antibacterial properties

Chakraborty, Kajal and Lipton, A P and Paulraj, R and Chakraborty, Rekha D (2010) Guaiane sesquiterpenes from seaweed Ulva fasciata Delile and their antibacterial properties. European Journal of Medicinal Chemistry, 45. pp. 2237-2244.

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    Two new guaiane sesquiterpene derivatives, guai-2-en-10a-ol (1) and guai-2-en-10a-methanol (2), were chromatographically purified as major constituents of the CHCl3/CH3OH (1:1, v/v) soluble fraction of Ulva fasciata. Acetylation of 2 furnished guai-2-en-10a-methyl methanoate (3) with acetyl group at C11 position. The structures of the compounds were elucidated using one and two-dimensional NMR and mass spectrometric analysis. Compounds 2 and 3 exhibited significant inhibition to the growth of Vibrio parahaemolyticus with minimum inhibitory concentrations of 25 and 35 mg/mL, respectively. The electronegative C10 acetyl group with high polarisability (7.02� 10�24 cm3) in 3 appeared to withdraw electron cloud from substituted cycloheptyl ring and (R)-3-methylcyclohept-1-ene moiety, thus acting as the nucleophilic center of the molecule resulting in high bioactivity.

    Item Type: Article
    Uncontrolled Keywords: Ulva fasciata Delile; Guaiane sesquiterpenoides; Antibacterial activity; Minimum inhibitory concentration
    Subjects: Biochemistry > Bioactive compounds
    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: 12 May 2016 05:30
    Last Modified: 10 Jul 2017 10:52

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