5,7-dihydroxy-2-(3-hydroxy-4, 5-dimethoxy-phenyl)-chromen-4-one-a flavone from Bruguiera gymnorrhiza displaying anti-inflammatory properties.
OBJECTIVE
Bruguiera gymnorrhiza (BRG) (L.) Lamk (Rhizophoraceae), a mangrove species, is widely distributed in the Pacific region, eastern Africa, Indian subcontinent, and subtropical Australia. The leaves of this plant are traditionally used for treating burns and inflammatory lesions. This study isolates the bioactive compound from the methanol extract of BRG leaves and evaluates the possible mechanisms of anti-inflammatory activity involved.


METHODS
Bioassay-guided fractionation of BRG was performed to identify the bioactive fraction (displaying inhibition of cyclooxygenase 2 [COX2] - 5-lipoxygenase (5-LOX) activities and tumor necrosis factor-alpha (TNF-α) production at the tested concentrations of 100 and 10 μg/ml). The fractionation was performed by solvent extraction and preparative high-performance liquid chromatography. The bioactive compound was characterized by ultraviolet-visible, liquid chromatography-mass spectrometry and nuclear magnetic resonance spectroscopy. The antioxidant potential was evaluated by electron spin resonance spectrum of 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical at 250 μM. The effect of the compound was also studied on TNF-α converting enzyme and nuclear factor kappa B (NF-κB) activities at the concentrations 100, 10 and 1 μg/ml.


RESULTS
Bioassay-guided purification of BRG revealed the presence of a flavone (5,7-dihydroxy-2- [3-hydroxy-4,5-dimethoxy-phenyl]-chromen-4-one) of molecular weight 330Da. It demonstrated more than 80% inhibition against COX2, 5-LOX activities and TNF-α production at 100 μg/ml. It also displayed 40% inhibition against DPPH radical at the tested concentration along with 23.1% inhibition of NF-κB activity at 100 μg/ml.


CONCLUSIONS
The isolated methoxy-flavone may play a predominant role in the anti-inflammatory properties displayed by BRG leaves. Such activity may involve multiple mechanisms, namely (a) modulation of oxidative stress (b) inhibition of arachidonic acid metabolism and (c) downregulation of pro-inflammatory cytokines probably through NF-κB inhibition.
Demaceutical Technology, Jadavpur University, Salt Lake, Kolkata, West Bengal, India; TCG Life Sciences Ltd., Salt Lake, Kolkata, West Bengal, India.
Rajib
R
Barik
Demaceutical Technology, Jadavpur University, Salt Lake, Kolkata, West Bengal, India.
Ratul
R
Sarkar
Demaceutical Technology, Jadavpur University, Salt Lake, Kolkata, West Bengal, India.
Prova
P
Biswas
Demaceutical Technology, Jadavpur University, Salt Lake, Kolkata, West Bengal, India; TCG Life Sciences Ltd., Salt Lake, Kolkata, West Bengal, India.
Rammohan
R
Bera
TCG Life Sciences Ltd., Salt Lake, Kolkata, West Bengal, India.
Soma
S
Sharma
TCG Life Sciences Ltd., Salt Lake, Kolkata, West Bengal, India.
Suvadeep
S
Nath
Demaceutical Technology, Jadavpur University, Salt Lake, Kolkata, West Bengal, India.
Sanmoy
S
Karmakar
Demaceutical Technology, Jadavpur University, Salt Lake, Kolkata, West Bengal, India.
Tuhinadri
T
Sen
D000893:Anti-Inflammatory Agents / Q000494:pharmacology*; D001094:Arachidonate 5-Lipoxygenase / Q000378:metabolism; D015232:Dinoprostone / Q000096:biosynthesis; D047309:Flavones / Q000494:pharmacology*; D006801:Humans; D043982:Rhizophoraceae / Q000737:chemistry*; D014409:Tumor Necrosis Factor-alpha / Q000096:biosynthesis
D000893:Anti-Inflammatory Agents; D047309:Flavones; D014409:Tumor Necrosis Factor-alpha; D001094:Arachidonate 5-Lipoxygenase; D015232:Dinoprostone
5-lipoxygenase; cyclooxygenase; cytokine; flavone; nuclear factor kappa B; transactivation assay