On the Absolute Configuration of Matricin

Abstract

The assignment of the absolute configuration of matricin rests on indirect evidence. On the basis of synthetic, NMR and CD studies with its decomposition product, chamazulene carboxylic acid, we were able to firmly establish the accepted 3S,3aR,4S,9R,9aS,9bS configuration of matricin.

Artarborol, a nor-Caryophyllane Sesquiterpene Alcohol from Artemisia arborescens. Stereostructure Assignment through Concurrence of NMR Data and Computational Analysis

“…A. arborescens is a prolific producer of bitter sesquiterpene lactones but interest in this plant has so far mainly focused on its essential oil, a major source of chamazulene and a potent antiherpetic agent . In the frame of a research project aimed at investigating the molecular basis for the taste properties of sesquiterpene lactones, we have recently undertaken the chemical investigation of a Sardinian chemotype of A. arborescens that was identified as a good source of the bitter guaianolides arborescin ( 1 ) 2 and matricin ( 2 ) …”

Natural sesquiterpenoids

“…308 The configurations of the alcohols obtained from dihydro-O-acetylisophoto-α-santonic lactone have been revised, 363 whilst the absolute configuration of matricin has been confirmed. 364 The microbiological transformation of dehydrocostuslactone with different fungi has been investigated. 84 Syntheses of a guaiana-4,11-dien-3-one and of hydrocolorenone have been reported.…”

Stereostructure Assignment of Medium-Sized Rings through an NMR−Computational Combined Approach. Application to the New Germacranes Ketopelenolides C and D

“…Ketopelenolides C ( 2 ) and D ( 3 ) were obtained from the great mugwort ( Artemisia arborescens L., Asteraceae, tribe Anthemidae), an evergreen shrub endemic to the Mediterranean area that presents several features to justify a systematic study of its secondary metabolites. Indeed, the essential oil of A. arborescens has the highest amount of chamazulene of any essential oil known (up to 40%), and the plant is a prolific producer of bitter sesquiterpene lactones, two of which, the guaianolides arborescin ( 4 ) and matricin ( 5 ) (Chart ), are currently used as starting material for our ongoing studies on the mechanism of bitter taste …”