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United States Department of Agriculture

Agricultural Research Service

Research Project: DISCOVERY AND DEVELOPMENT OF NATURAL PRODUCTS FOR PHARMACEUTICAL AND AGROCHEMICAL APPLICATIONS

Location: Natural Products Utilization Research

Title: Hydroxylated bisabolol oxides: evidence for secondary oxidative metabolism in Matricaria chamomilla

Authors
item Avonto, Cristian -
item Wang, Mei -
item Chittiboyina, Amar -
item Avula, Bharathi -
item Zhao, Jianping -
item Khan, Ikhlas -

Submitted to: Journal of Natural Products
Publication Type: Peer Reviewed Journal
Publication Acceptance Date: August 1, 2013
Publication Date: September 26, 2013
Citation: Avonto, C., Wang, M., Chittiboyina, A.G., Avula, B., Zhao, J., Khan, I.A. 2013. Hydroxylated bisabolol oxides: evidence for secondary oxidative metabolism in Matricaria chamomilla. Journal of Natural Products. 76:1848-1853.

Interpretive Summary: The presented GC-assisted fractionation approach successfully enabled us in the identification of bisabolol oxide derivatives never isolated previously. These compounds were found to be biosynthetically related and could be useful for the further studies about chamomile biosynthetic pathways. In addition to identification of novel compounds, this rationale might serve as an easy and robust tool for rapid identification of minor compounds from dietary supplements originated from German chamomile.

Technical Abstract: German chamomile (Matricaria recutita L.) is one of the most popular medicinal plants used in Western medicine. Among the various phytochemicals present in essential oils of German chamomile, bisabolol and its oxidative metabolites are considered as marker compounds for distinguishing different chemotypes. These compounds play a significant role in the biosynthesis of various terpenoids. They are also influential in the aroma of essential oils and the therapeutic properties (anti-inflammatory,antibacterial, insecticidal and antiulcer) of chamomile as well. In order to find other possible bisabolol derivatives as marker compounds for authentication of German chamomile in botanical and commercial products, an in-depth investigation using a GC-assisted fractionation was performed on apolar fractions. As a result of this approach, for the first time, three new hydroxyl derivative of bisabolol oxides A and B)and one known seco-bisabolol compound have been isolated from M. recutita. Plausible biosynthetic pathways are also presented.

Last Modified: 12/20/2014
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