Dimeric and esterified sesquiterpenes from the liverwort Chiastocaulon caledonicum

Abstract

This is the first chemical investigation of Chiastocaulon caledonicum, an endemic liverwort from New Caledonia. We herein present the isolation of thirteen compounds including seven undescribed sesquiterpenoids, namely four barbatane- and three myltaylane-type sesquiterpenes. The structures of these compounds were elucidated based on the interpretation of their chemical and spectroscopic/spectrometric data. Chiastocaulins A and B are the first examples of dimers based on two myltaylane units. The chemotaxonomic importance and the biosynthesis of the chiastocaulin structure are discussed. Terpenoid dimers formed via a Diels-Alder cyclization are thought to be specific to the Plagiochilaceae family.

Keywords: Chemotaxonomy; Chiastocaulin; Chiastocaulon caledonicum; Diels-Alder cyclization; Plagiochilaceae; Sesquiterpene; bis(bibenzyls).