title: Two rare antioxidant and anti-inflammatory oleanenes from loop root Asiatic mangrove Rhizophora mucronata.
abstract: Two oleanenes, olean-18(19)-en-3β-yl-(3,6-dimethyl-3E,6Z-dienoate) and (13α)-27-frido-olean-14(15)-en-(17α)-furanyl-3β-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 (IC500.73-0.76 mg/mL), than prenylated oleanene (IC500.84-0.96 mg/mL) (P < 0.05). No significant differences in anti-5-lipoxygenase activities of these compounds with the synthetic drug ibuprofen was discernable (IC500.8-0.9 mg/mL), whilst furanyl oleanene demonstrated significantly greater anti-cyclooxygenase-2 (IC500.84 mg/mL) and anti-5-lipoxygenase activities (IC500.78 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.
authors.affiliation: Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P.B. No. 1603, Cochin, India. Electronic address: kajal_cmfri@yahoo.com.
authors.forename: Kajal
authors.initials: K
authors.lastname: Chakraborty
authors.affiliation: Marine Bioprospecting Section of Marine Biotechnology Division, Central Marine Fisheries Research Institute, Ernakulam North, P.B. No. 1603, Cochin, India.
authors.forename: Vamshi Krishna
authors.initials: VK
authors.lastname: Raola
mesh_terms: D000893:Anti-Inflammatory Agents / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D000975:Antioxidants / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D016861:Cyclooxygenase Inhibitors / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D024301:Plant Bark / Q000737:chemistry; D018517:Plant Roots / Q000737:chemistry*; D043982:Rhizophoraceae / Q000737:chemistry*
chemical_list: D000893:Anti-Inflammatory Agents; D000975:Antioxidants; D016861:Cyclooxygenase Inhibitors
keywords: (13α) 27-Frido-olean-14(15)-en-(17α)-furanyl-3β-ol; 5-Lipoxygenase; Antioxidative; Cyclooxygenase-2; Olean-18(19)-en-3β-yl (3, 6-dimethyl-3, 6-dienoate); Rhizophora mucronata Lam.; Rhizophoraceae; Structure activity relationship analysis