Biogenic guaianolide-type sesquiterpene lactones with antioxidative and anti-inflammatory properties from natural mangrove hybrid Rhizophora annamalayana

Raola, Vamshi Krishna and Chakraborty, Kajal (2017) Biogenic guaianolide-type sesquiterpene lactones with antioxidative and anti-inflammatory properties from natural mangrove hybrid Rhizophora annamalayana. Natural Product Research. pp. 1-11. ISSN 1478-6427 (Online)

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    Abstract

    Previously undescribed guaianolide-type sesquiterpene lactones were isolated from the chloroform fraction of the natural hybrid mangrove Rhizophora annamalayana, and were characterised as (Z)-3α,4,5,6-tetrahydro-5α-isobutyl-2β-(methoxymethyl)-7-methyl-3H-cyclohepta[b]carbolactone (1) and (7Z)-isopentyl 3α,4,5,6,7,8-hexahydro-2β-((E)-11-methylbut-10-enyl)-1-oxo-2H-cyclohepta[b]furan-6-carboxylate (2). Compound 2 displayed greater antioxidative activities {1, 1-diphenyl-2-picrylhydrazyl (DPPH) and 2, 2'-azino-bis-3 ethylbenzothiozoline-6-sulphonic acid diammonium salt (ABTS), IC50 0.65 and 0.62 mg/mL, respectively)} compared to 1 (IC50 0.83 and 1.14 mg/mL, respectively) (p < 0.05). Compound 2 recorded no significant difference in DPPH. scavenging activities (IC50 0.65 mg/mL) compared to α-tocopherol (IC50 0.63 mg/mL). Pro-inflammatory 5-lipoxygenase inhibitory activity of 2 was found to be comparable (IC50 0.98 mg/mL) to that displayed by synthetic anti-inflammatory drug ibuprofen (IC50 0.93 mg/mL). Compound 2 showed significantly greater selectivity index (anti-cyclooxygenase-1/anti-cyclooxygenase-2 = 2.15) than non-steroidal anti-inflammatory ibuprofen (<0.5) (p < 0.05), and therefore, might be used as selective cyclooxygenase-2 inhibitor. The hitherto undescribed guaianolide lactones might be used as potential anti-inflammatory and antioxidative pharmacophore leads.

    Item Type: Article
    Uncontrolled Keywords: Natural mangrove hybrid; Rhizophora annamalayana; anti-inflammatory; anti-inflammatory selectivity index; antioxidative; guaianolide-type sesquiterpene lactones
    Subjects: Fish Biotechnology > Bioactive compound
    Marine Ecosystems > Mangroves
    Fish Biotechnology
    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: 24 Aug 2011 11:03
    Last Modified: 17 Apr 2017 05:58
    URI: http://eprints.cmfri.org.in/id/eprint/8697

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