Chemotypes and Biomarkers of Seven Species of New Caledonian Liverworts from the Bazzanioideae Subfamily

Abstract

Volatile components of seven species of the Bazzanioideae sub-family (Lepidoziaceae) native to New Caledonia, including three endemic species (Bazzania marginata, Acromastigum caledonicum and A. tenax), were analyzed by GC-FID-MS in order to index these plants to known or new chemotypes. Detected volatile constituents in studied species were constituted mainly by sesquiterpene, as well as diterpene compounds. All so-established compositions cannot successfully index some of them to known chemotypes but afforded the discovery of new chemotypes such as cuparane/fusicoccane. The major component of B. francana was isolated and characterized as a new zierane-type sesquiterpene called ziera-12(13),10(14)-dien-5-ol (23). In addition, qualitative intraspecies variations of chemical composition were very important particularly for B. francana which possessed three clearly defined different compositions. We report here also the first phytochemical investigation of Acromastigum species. Moreover, crude diethyl ether extract of B. vitatta afforded a new bis(bibenzyl) called vittatin (51), for which a putative biosynthesis was suggested.

Phytocannabinoids: Origins and Biosynthesis

“…Liverworts (Marchantiophyta; also called 'hepatics') are prolific producers of compounds with a bibenzyl backbone, such as lunularic acid and vittatin [15]. Cannabinoids with a bibenzyl structure have been isolated from Radula perrottetii Gottsche ex Steph., R. marginata Taylor ex Gottsche, and R. laxiramea Steph.…”

Bis-bibenzyls, Bibenzyls, and Terpenoids in 33 Genera of the Marchantiophyta (Liverworts): Structures, Synthesis, and Bioactivity

“…The genera Bazzania and Lepidozia are found in Japan, east and northern Asia, and Europe and contain about 223 and 26 species, respectively. Species belonging to both of these genera are rich sources of various sesquiterpenoids of the aristolane, aromadendrane, barbatane, bazzanane, calamenane, chamigrane, cuparane, drimane, eudesmane, myltaylane, and lepidozane types. ,, Bazzania species are divided mainly into two chemotypes, namely, the albicanyl-caffeate-cuparene and calamenane types …”

“…In New Caledonia, 20 Bazzania species or varieties including 12 endemic taxa are known. Bazzania vitatta produces a characteristic bis-bibenzyl named vitattin ( 100 ), which might be biosynthesized by biaryl meta–meta coupling at the aromatic ring between two lunularic acid ( 127 ) units at the A-ring (see below) …”

Improving the Antioxidant Properties of Calophyllum inophyllum Seed Oil from French Polynesia: Development and Biological Applications of Resinous Ethanol-Soluble Extracts

“…However, despite its great potential interest, major drawbacks of using TO as a raw material for therapeutic and cosmetic applications arise both from a very high lipophilicity and the weak amount of potentially bioactive compounds contained in the minor soluble phase [ 17 ]. This latter issue could be solved by ethanol extraction, a process that would allow recovering the largest amount of TO metabolites.…”