Two rare antioxidant and anti-inflammatory oleanenes from loop root Asiatic mangrove Rhizophora mucronata

Chakraborty, Kajal and Raola, Vamshi Krishna (2017) Two rare antioxidant and anti-inflammatory oleanenes from loop root Asiatic mangrove Rhizophora mucronata. Phytochemistry, 135. pp. 160-168.

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    Abstract

    Two oleanenes, olean-18(19)-en-3b-yl-(3,6-dimethyl-3E,6Z-dienoate) and (13a)-27-frido-olean-14(15)- en-(17a)-furanyl-3b-ol representing a class of rare natural pentacyclic triterpenoids were isolated from the chloroform extract of Asiatic mangrove, Rhizophora mucronata Lam. (Family: Rhizophoraceae). The furanyl oleanene exhibited significantly greater antioxidative activities (IC50 0.73e0.76 mg/mL), than prenylated oleanene (IC50 0.84e0.96 mg/mL) (P < 0.05). No significant differences in anti-5-lipoxygenase activities of these compounds with the synthetic drug ibuprofen was discernable (IC50 0.8e0.9 mg/mL), whilst furanyl oleanene demonstrated significantly greater anti-cyclooxygenase-2 (IC50 0.84 mg/mL) and anti-5-lipoxygenase activities (IC50 0.78 mg/mL) over prenylated oleanene (IC50 > 0.90 mg/mL). These compounds exhibited lesser activity against cyclooxygenase-1 than cyclooxygenase-2 isoform, and therefore, their selectivity indices remained significantly greater (anti-cyclooxygenase-1IC50/anti-cyclooxygenase- 2IC50 > 1) than the aspirin (0.02) and ibuprofen (0.44). The lipophilic and steric molecular descriptors were found to occupy a prominent role in determining the bioactivities of the compounds. These previously undescribed oleanenes might serve as potential antioxidative and anti-inflammatory lead molecules in medicinal formulations and food industries.

    Item Type: Article
    Uncontrolled Keywords: Rhizophora mucronata Lam.; Rhizophoraceae; Olean-18(19)-en-3β-yl (3, 6-dimethyl-3, 6-dienoate); (13α) 27-Frido-olean-14(15)-en-(17α)-furanyl-3β-ol; Antioxidative; Cyclooxygenase-2; 5-Lipoxygenase; Structure activity relationship analysis
    Subjects: Biochemistry > Bioactive compounds
    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: 13 May 2016 09:11
    Last Modified: 13 Feb 2017 09:58
    URI: http://eprints.cmfri.org.in/id/eprint/10791

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