Identification of a compound isolated from German chamomile (Matricaria chamomilla) with dermal sensitization potential
- National Center for Natural Products Research, Research Institute of Pharmaceutical Sciences, School of Pharmacy, The University of Mississippi, MS 38677 (United States)
- The Center for Food Safety and Applied Nutrition, US Food and Drug Administration, College Park, MD 20740 (United States)
German chamomile is one of the most popular herbal ingredients used in cosmetics and personal care products. Allergic skin reactions following topical application of German chamomile have been occasionally reported, although it is not fully understood which of the chemical constituents is responsible for this adverse effect. In the present work, three candidate sensitizers were isolated from German chamomile based on activity-guided fractionation of chamomile extracts tested using the in vitro KeratinoSens™ assay. The compounds were identified as the polyacetylene tonghaosu (1), and both trans- and cis-glucomethoxycinnamic acids (2 and 3). These three compounds were classified as non- to weakly reactive using in chemico methods; however, aged tonghaosu was found to be more reactive when compared to freshly isolated tonghaosu. The polyacetylene (1) constituent was determined to be chemically unstable, generating a small electrophilic spirolactone, 1,6-dioxaspiro[4.4]non-3-en-2-one (4), upon aging. This small lactone (4) was strongly reactive in both in chemico HTS- and NMR-DCYA methods and further confirmed as a potential skin sensitizer by Local Lymph Node Assay (LLNA). - Highlights: • Fractions of German chamomile tested positive in the KeratinoSens™ assay. • Three compounds containing structural alerts were isolated and tested with in chemico methods. • The polyacetylene tonghaosu was found to be unstable and categorized as potential pre-hapten. • A degradation product of tonghaosu tested as positive dermal sensitizer in animal studies.
- OSTI ID:
- 22690929
- Journal Information:
- Toxicology and Applied Pharmacology, Journal Name: Toxicology and Applied Pharmacology Vol. 318; ISSN TXAPA9; ISSN 0041-008X
- Country of Publication:
- United States
- Language:
- English
Similar Records
The pilosebaceous unit—a phthalate-induced pathway to skin sensitization
Draft genome sequence of Paenbacillus polymyxa strain Mc5Re-14, an antagonistic root endophyte of Matricaria chamomilla