From liverworts

Toyota, M., Koyama, H., Mizutani, M. and Asakawa, Y. 1996. (-)-enr-Spathulenol isolated from liverworts is an artefact. Phytochemistry 41 1347-1350. 

Lignans of another type, dicarboxylic acid lignans (p-hydroxycinnamate dimers), were isolated from liverworts (Hepaticopsida) and some vascular plants [11, 64]. Little is known about the biosynthesis of this class of lignans, but a feeding experiment demonstrated the conversion of caffeic acid to optically pure epiphyllic acid in a liyerwoTt Lophocolea heterophylla (Fig. 12.9) [65]. 

Asakawa Y, Toyota M, Tori M, Hashimoto T (2000) Chemical Structures of Macrocyclic Bis(bibenzyls) Isolated from Liverworts (Hepaticae). Spectroscopy 14 149... 

Bringmann G, Miihlbacher J, Reichert M, Dreyer M, Kolz J, Speicher A (2004) Stereochemistry of Isoplagiochin C, a Macrocyclic Bisbibenzyl from Liverworts. J Am Chem Soc 126 9283... 

An optically active dicarboxylic acid lignan (caffeic acid dimer), named epiphyllic acid was isolated from liverwort as well as its derivatives, which do not belong to any typical lignan-producing subgroups. They also occur in some vascular plants, even as a triterpene ester of epiphyllic acid in Rhoipte-lea chiliantha [37]. The conversion of caffeic acid to epiphyllic acid was demonstrated by Tazaki et al. [38]. However, little is known about the biosynthesis of this type of lignan in vascular plants yet. 

A continuing investigation of the sesquiterpenoids from liverworts (Plagiochila species) has revealed the presence of more seco-aromadendrane compounds, namely plagiochilines A (652), B (653), C (654), D (655), E (656), and F (657). Plagiochilide (658) has been found in the Swiss species of P. asplenioides but not in the French version. The presumed precursor of these compounds, (-)-bicyclogermacrene (659), has also been identified in the extracts... 

Halogenated natural products are mainly known from marine organisms, fungi and higher plants. The halogenated structures isolated from liverworts should, of course, have chemotaxonomical significance. 

Some new pinguisane sesquiterpenoids have been isolated from liverwort species. These include dehydropinguisanin (820), dehydropinguisenol (821), and pinguisenal... 

The colonization of the land by plants began in the Ordovician, based on an age of c.475 Ma for the earliest known fossil spores, which appear to have derived from liverwort-like plants (Wellman et al. 2003). By this time there was a well developed ozone (03) layer providing protection against harmful UV radiation. Aquatic plants are supported by the density of water, do not require protection from desiccation and have their nutrient requirements delivered to all parts by the water they inhabit. Like aquatic plants, bryophytes do not have a vascular system, and so are restricted to areas of plentiful water supply. In order to spread across the continents in... 

Structure, biological activities, and total syntheses of macrocyclic ethers with two bisbibenzyl fragments from liverworts 00YGK654. 

The considerable number of monofiinctional MGL-compounds (28% of all STL in the database) probably reflects the capability of the MGL to render the compounds sufficiently reactive to yield quite an effective chemical protection. It should be mentioned at this point that the MGL structure can be considered a primitive character in terms of evolution, since it occurs already in STLs isolated from liverworts, e.g. the frullanolides [4], It may thus be speculated that compounds possessing this structure element have represented the starting point in the evolution of the biosynthetic pathways leading to more complex alkylants. 

Under similar conditions, but with the ketone present in slightly greater amounts than the base, enolate equilibration causes the thermodynamic enolate to predominate. This procedure was used in the first step of a laboratory synthesis of gymnomitrol, a natural product isolated from liverwort. 

Harinantenaina, L., D.N. Quang, T. Nishizawa et al., 2007. Bioactive compounds from liverworts Inhibition of lipopolysaccharide-induced inducible NOS mRNA in RAW 264.7 cells by herbertenoids and cuparenoids. Phvtomedicine. 14 486-491. 

Schwartner C, Michel C, Stettmaier K, Wagner H, Bors W (1996) Marchantins and related polyphenols from liverwort physico-chemical studies of their radical-scavenging properties. 

Harinantenaina L, Quang DN, Takeshi N, Hashimoto T, Kohchi C, Soma G-I, Asakawa Y (2005) Bis(bibenzyls) from liverworts inhibit lipopolysaccharide-induced inducible NOS in RAW 264.7 cells a study of structure - activity relationships and molecular mechanism. 

In recent years many bicyclogermacrane and aromadendrane derivatives have been obtained from liverworts and marine organisms (13, 89 vol. 12). 

Benesova, V., I. Benes, H. M. Chau, and V. Herout Diterpenoids from Liverworts. Collect. Czech. Chem. Comm. 40, 658 (1975). 

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