Octulosonic Acid Derivatives from Roman Chamomile (Chamaemelum nobile) with Activities against Inflammation and Metabolic Disorder

• Published in: Journal of natural products (Washington, D.C.) D.C.), 2014-03, Vol.77 (3), p.509-515
• Main Authors: Zhao, Jianping, Khan, Shabana I, Wang, Mei, Vasquez, Yelkaira, Yang, Min Hye, Avula, Bharathi, Wang, Yan-Hong, Avonto, Cristina, Smillie, Troy J, Khan, Ikhlas A
• Format: Article
• Language: English
• Subjects: Anti-Inflammatory Agents, Non-Steroidal - chemistry; Anti-Inflammatory Agents, Non-Steroidal - isolation & purification; Anti-Inflammatory Agents, Non-Steroidal - pharmacology; Chamaemelum - chemistry; Flowers - chemistry; Hypoglycemic Agents - pharmacology; Mississippi; Molecular Structure; NF-kappa B - metabolism; Nitric Oxide Synthase Type II - drug effects; Nuclear Magnetic Resonance, Biomolecular; Oxidative Stress - drug effects; PPAR alpha - metabolism; PPAR gamma - metabolism; Sugar Acids - chemistry; Sugar Acids - isolation & purification; Sugar Acids - pharmacology
• ISSN: 0163-3864; 1520-6025
• DOI: 10.1021/np400780n

Six new octulosonic acid derivatives (1–6) were isolated from the flower heads of Roman chamomile (Chamaemelum nobile). Their structures were elucidated by means of spectroscopic interpretation. The biological activity of the isolated compounds was evaluated toward multiple targets related to inflammation and metabolic disorder such as NAG-1, NF-κB, iNOS, ROS, PPARα, PPARγ, and LXR. 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 PPARγ 1.6–2.1-fold, while PPARα was activated 1.4-fold by compounds 5 and 6 only. None of the compounds showed significant activity against iNOS or NF-κB. This is the first report of biological activity of octulosonic acid derivatives toward multiple pathways related to inflammation and metabolic disorder. The reported anti-inflammatory, hypoglycemic, antiedemic, and antioxidant activities of Roman chamomile could be partly explained as due to the presence of these constituents.