Thirteen costus-sensitive patients were patch tested with 38 sesquiterpene lactones of five different classes over a two-year period. Cross-reacting agents fell into two chemical categories: (1) those that resembled the primary sensitizer, and (2) those belonging to different skeletal classes. An exocyclic methylene group conjugated to a gamma-lactone was present in both chemicals that cross-reacted and those that did not. The difference between these two groups is that cross-reacting chemicals are not highly substituted, tending to be lipophilic, while those giving negative responses all are highly substituted at the C-8/C-6 position. This functional group may hinder binding of exocyclic methylene with skin protein or the actual antigenic site with an immune receptor cell.

Download full-text PDF

Source
http://dx.doi.org/10.1001/archderm.116.1.59DOI Listing

Publication Analysis

Top Keywords

exocyclic methylene
8
highly substituted
8
sesquiterpene lactone
4
lactone dermatitis
4
dermatitis cross-sensitivity
4
cross-sensitivity costus-sensitized
4
costus-sensitized patients
4
patients thirteen
4
thirteen costus-sensitive
4
costus-sensitive patients
4

Similar Publications

Reactivity of Anomalous Aziridines for Versatile Access to High Fsp Amine Chemical Space.

Acc Chem Res

January 2025

Department of Chemistry, University of Wisconsin, 1101 University Avenue, Madison, Wisconsin 53706, United States.

ConspectusThe manipulation of strained rings is a powerful strategy for accessing the valuable chemical frameworks present in natural products and active pharmaceutical ingredients. Aziridines, the smallest N-containing heterocycles, have long served as building blocks for constructing more complex amine-containing scaffolds. Traditionally, the reactivity of typical aziridines has been focused on ring-opening by nucleophiles or the formation of 1,3-dipoles.

View Article and Find Full Text PDF

Spiro-meroterpenoids, Syzygioblanes D-H, Isolated from Indonesian Medicinal Plant .

J Nat Prod

December 2024

School of Pharmaceutical Sciences, College of Medical, Pharmaceutical and Health Sciences, Kanazawa University, Kanazawa 920-1192, Japan.

Syzygioblanes A-C (-), isolated from the Indonesian traditional herbal medicine (), are meroterpenoids with a spiro ring formed through a [4 + 2] cycloaddition of the flavanone desmethoxymatteucinol with cyclic sesquiterpenoids. Our ongoing phytochemical investigation of resulted in the isolation of five additional spiro-meroterpenoids, syzygioblanes D-H (-), which are hybrids of the same flavanone with eudesmane/cadinane-type sesquiterpenoids. A possible biosynthetic pathway involves enzymatic dearomative hydroxylation of desmethoxymatteucinol followed by [4 + 2] cyclization of the resulting diene with a cyclic sesquiterpene containing an exocyclic methylene to form the unique spiro ring in the syzygioblane molecule.

View Article and Find Full Text PDF

(Dimethylamino)methylene hydantoins as building blocks in the synthesis of oxoaplysinopsins and parabanic acids with antifungal activity.

Org Biomol Chem

October 2024

Departamento de Química Orgánica, Escuela Nacional de Ciencias Biológicas, Instituto Politécnico Nacional, Prolongación de Carpio y Plan de Ayala S/N, 11340 Mexico City, Mexico.

A short, efficient, and stereoselective methodology is described for the synthesis of 5-((dimethylamino)methylene)hydantoins and their conversion into oxoaplysinopsins and parabanic acids. A highly convergent one-pot, two-step reaction between methyl -arylglycinates, isocyanates, and DMFDMA under microwave irradiation provided the corresponding (dimethylamino)methylene hydantoins as a single -stereoisomer in high overall yields. The synthesis of ()-1-(1-phenylethyl) chiral hydantoins, which undergo a stereoselective addition of acetic anhydride, aza-heterocycles, and amines, received special attention.

View Article and Find Full Text PDF

A facile copper-catalyzed [3 + 2] cycloaddition of -2,2,2-trifluoroethylisatin ketimines with various electron-deficient alkenes to access structurally polyfunctionalized spiro-pyrrolidine-oxindole motifs has been developed. Under the catalytic system, the -2,2,2-trifluoroethylisatin ketimines could be utilized to react with a series of exocyclic alkenes, including 2-acylamino acrylates, 3-methylene-β-lactams, and sterically hindered cycloalkenes represented by cyclobutenone, to obtain a variety of densely functionalized spiro-pyrrolidine frameworks bearing an α-amino acid ester, β-lactam, and cyclobutanone, respectively, in generally good yields with excellent diastereo- and enantioselectivities.

View Article and Find Full Text PDF

Nitroxides are stable organic radicals with exceptionally long lifetimes, which render them uniquely suitable as observable probes or polarising agents for spectroscopic investigation of biomolecular structure and dynamics. Radical-based probes for biological applications are ideally characterized by both robustness towards reductive degradation and beneficial electron spin relaxation parameters. These properties are largely influenced by the molecular structure of the nitroxide scaffold, and also by the conformations it prefers to adopt.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!