Dihydrostilbenoids (bibenzyls) are natural phenols formed from the dihydrostilbene (bibenzyl) backbone.
Dihydrostilbenoids (bibenzyls) are natural phenols formed from the dihydrostilbene (bibenzyl) backbone.
Dihydro-resveratrol is a natural phenol with a bibenzyl structure found in wine. [1] It is also a metabolite of trans-resveratrol formed in the intestine by the hydrogenation of the double bond by microflora. [2]
Combretastatin and combretastatin B-1 are two dihydrostilbenoids found in Combretum caffrum, an African tree.
Isonotholaenic acid is another dihydrostilbenoid found in the Andean fern Argyrochosma nivea . [3]
Bibenzyls (3,4'-dihydroxy-5,5'-dimethoxybibenzyl, 3,3'-dihydroxy-5-methoxybibenzyl (batatasin III)) can be found in the orchid Bulbophyllum vaginatum . [4]
Bis(bibenzyls) [5] and macrocyclic bis(benzyls) [6] can be found in bryophytes, such as the compounds plagiochin E, 13,13'-O-isoproylidenericcardin D, riccardin H, marchantin E, neomarchantin A, marchantin A and marchantin B in the Chinese liverwort Marchantia polymorpha . [7] Prenylated bibenzyls can be isolated from the New Zealand liverwort Marsupidium epiphytum [8] or from Radula kojana . [9]
One unique class of stilbenoid derivative was first isolated from Scorzonera humilis . They were named the tyrolobibenzyls after Tyrol in the eastern Alps, where the plant was collected. [10]
The Marchantiophyta are a division of non-vascular land plants commonly referred to as hepatics or liverworts. Like mosses and hornworts, they have a gametophyte-dominant life cycle, in which cells of the plant carry only a single set of genetic information.
An antheridium is a haploid structure or organ producing and containing male gametes. The plural form is antheridia, and a structure containing one or more antheridia is called an androecium. Androecium is also the collective term for the stamens of flowering plants.
Marchantiales is an order of thallose liverworts that includes species like Marchantia polymorpha, a widespread plant often found beside rivers, and Lunularia cruciata, a common and often troublesome weed in moist, temperate gardens and greenhouses.
Cavicularin is a natural phenolic secondary metabolite isolated from the liverwort Cavicularia densa. This macrocycle is unusual because it was the first compound isolated from nature displaying optical activity solely due to the presence of planar chirality and axial chirality. The specific rotation for (+)-cavicularin is +168.2°. It is also a very strained molecule. The para-substituted phenol ring is bent about 15° out of planarity, adopting a somewhat boat-like geometry. This type of angle strain in aromatic compounds is normally reserved for synthetic cyclophanes.
Phenanthrenoids are chemical compounds formed with a phenanthrene backbone. These compounds occur naturally in plants, although they can also be synthesized.
MicroRNA (miRNA) precursor miR156 is a family of plant non-coding RNA. This microRNA has now been predicted or experimentally confirmed in a range of plant species. Animal miRNAs are transcribed as ~70 nucleotide precursors and subsequently processed by the Dicer enzyme to give a ~22 nucleotide product. miR156 functions in the induction of flowering by suppressing the transcripts of SQUAMOSA-PROMOTER BINDING LIKE (SPL) transcription factors gene family. It was suggested that the loading into ARGONAUTE1 and ARGONAUTE5 is required for miR156 functionality in Arabidopsis thaliana. In plants the precursor sequences may be longer, and the carpel factory (caf) enzyme appears to be involved in processing. In this case the mature sequence comes from the 5' arm of the precursor, and both Arabidopsis thaliana and rice genomes contain a number of related miRNA precursors which give rise to almost identical mature sequences. The extents of the hairpin precursors are not generally known and are estimated based on hairpin prediction. The products are thought to have regulatory roles through complementarity to mRNA.
Perrottetinene is a naturally occurring cannabinoid compound found in liverworts from the genus Radula native to Japan, New Zealand and Costa Rica, namely Radula perrottetii, Radula marginata and Radula laxiramea, along with a number of similar compounds. Its chemical structure closely resembles that of THC, the main active component of marijuana but with a cis rather than trans conformation and a bibenzyl tailchain instead of pentyl. The absolute configuration of perrottetinene was established in 2008 by an enantioselective total synthesis.
Maxillaria densa, the crowded maxillaria, is a species of orchid ranging from Mexico south to Nicaragua.
Marchantia polymorpha is a species of large thalloid liverwort in the class Marchantiopsida. M. polymorpha is highly variable in appearance and contains several subspecies. This species is dioicous, having separate male and female plants. M. polymorpha has a wide distribution and is found worldwide. Common names include common liverwort or umbrella liverwort.
Bibenzyl is the organic compound with the formula (C6H5CH2)2. It can be viewed as a derivative of ethane in which one phenyl group is bonded to each carbon atom. It is a colorless solid.
Riccardin C is a macrocyclic bis(bibenzyl). It is a secondary metabolite isolated from the Siberian cowslip subspecies Primula veris subsp. macrocalyx, in Reboulia hemisphaerica and in the Chinese liverwort Plagiochasma intermedium.
Reboulia hemisphaerica, the hemisphaeric liverwort or small mushroom-headed liverwort, is the only species of liverwort in the genus Reboulia.
Dihydro-resveratrol is a dihydrostilbenoid found in wine. It is also a metabolite of trans-resveratrol formed in the intestine by the hydrogenation of the double bond by microflora. It is also a non-cannabinoid estrogenic compound found in cannabis.
Marsupidium epiphytum is a liverwort species in the genus Marsupidium from the New Zealand.
Lunularic acid is a dihydrostilbenoid found in the liverwort Lunularia cruciata and in the roots of Hydrangea macrophylla.
Isoscutellarein is a flavone found in Cupuaçu and in the liverwort Marchantia berteroana.
Marchantia berteroana is a liverwort species in the genus Marchantia.
Radula perrottetii is a species of plant in genus Radula, a genus of liverworts. It is endemic in Japan. It contains the small molecule perrottetinene a cannabinoid and other metabolites of scientific interest including marchantin A.
The oil bodies of liverworts, occasionally dubbed “complex” for distinction, are unique organelles exclusive to the Marchantiophyta. They are markedly different from the oil bodies found in algae and other plants in that they are membrane-bound, and are not associated with food storage. The organelles are variable and present in an estimated 90% of liverwort species, often proving taxonomically relevant. As a whole, the formation and function of the organelles are poorly understood. Complex oil bodies are recognized as sites of isoprenoid biosynthesis and essential oil accumulation, and have been implicated with anti-herbivory, desiccation tolerance, and photo-protection.
Monoclea forsteri is one of the two species in the thallose liverwort family Monocleaceae. It is dioicous with the capsule dehiscing with a single longitudinal slit. Endemic and widely distributed throughout New Zealand, it is also the country's largest thalloid liverwort. Hooker described the species in 1820. The holotype is in the British Museum.
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