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Title: Octulosonic acid derivatives from roman chamomile (Chamaemelum Nobile) with activities against inflammation and metabolic disorder

Author
item ZHAO, JIANPING - University Of Mississippi
item KHAN, SHABANA - University Of Mississippi
item WANG, MEI - University Of Mississippi
item VASQUEZ, YELKAIRA - University Of Mississippi
item YANG, MIN HYE - University Of Mississippi
item AVULA, BHARATHI - University Of Mississippi
item YAN-HONG, WANG - University Of Mississippi
item AVONTO, CRISTINA - University Of Mississippi
item SMILLIE, TROY - University Of Mississippi
item KHAN, IKHLAS - University Of Mississippi

Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: 12/1/2013
Publication Date: 1/28/2014
Citation: Zhao, J., Khan, S.I., Wang, M., Vasquez, Y., Yang, M., Avula, B., Yan-Hong, W., Avonto, C., Smillie, T.J., Khan, I.A. 2014. Octulosonic acid derivatives from roman chamomile (Chamaemelum Nobile) with activities against inflammation and metabolic disorder. Journal of Natural Products. 77:509-515.

Interpretive Summary: Six novel octulosonic acid derivatives were isolated from the flower-heads of Roman chamomile (Chamaemelum nobile (L.) Allioni). Their structures were elucidated by means of 1D and 2D NMR, HRESIMS, UV and FTIR analyses. The biological activity of the isolated compounds was evaluated towards multiple targets related to inflammation and metabolic disorder, Similar to the action of NSAIDs, all the six compounds increased NAG-1 activity 2 - 3 fold. They also decreased cellular oxidative stress by inhibiting ROS generation. None of the compounds showed significant inhibitions against iNOS or NF-kB. The compounds seem to affect multiple pathways related to inflammation and metabolic disorder.

Technical Abstract: Chamaemelum nobile (L.) Allioni, with the common name Roman chamomile, is widely cultivated in all parts of Europe, northern Africa, North American and southwest Asia. Roman chamomile is listed by the Council of Europe as a natural source of food flavoring. The flowering tops of the plant are used to make teas, liquid extracts, capsules, or tablets sold as dietary supplements. Traditionally, the plant has been used internally or externally as a household medicine for the treatment of a variety of health disorders, such as dyspepsia, nausea, rheumatic pain, eczema, wounds, hemorrhoids, and neuralgia. In our effort to profile the characteristic secondary metabolites in Roman chamomile, six new caffeoyl derivatives possessing a rare-class octulosonic acid skeleton were isolated and identified from the flower-heads of C. nobile. The anti-inflammatory activity of isolated compounds was tested through a series of cellular assays targeting NAG-1 (NSAIDs activated gene-1), NF-'B, iNOS, ROS, PPARa, PPAR', and LXR which are related to metabolic disorders (diabetes and cardiovascular) and inflammatory processes. Similar to the action of NSAIDs, all the six compounds (1 - 6) increased NAG-1 activity 2 - 3 fold. They also decreased cellular oxidative stress by inhibiting ROS generation. Compounds 3, 5 and 6 activated PPAR-alpha 1.6 - 2.1 fold, while PPARa was activated 1.4 fold by compounds 5 and 6 only. None of the compounds showed significant inhibitions against iNOS or NF-kB. The compounds seem to affect multiple pathways related to inflammation and metabolic disorder. This is the first report of the isolation of octulosonic acid derivatives from the flower-heads of Roman chamomile. Roman chamomile has been used for centuries as a dietary supplement to treat inflammatory disorders. Presence of these octulosonic acid derivatives seems to contribute to the anti-inflammatory and hypoglycemic properties of Roman chamomile. The compounds seem to affect multiple pathways related to inflammation and metabolic disorder.