Flavan

Last updated
Flavan
Flavan acsv.svg
Names
IUPAC name
Flavan
Systematic IUPAC name
2-Phenyl-3,4-dihydro-2H-1-benzopyran
Identifiers
3D model (JSmol)
383899
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.007.079 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 207-786-6
PubChem CID
  • InChI=1S/C15H14O/c1-2-6-12(7-3-1)15-11-10-13-8-4-5-9-14(13)16-15/h1-9,15H,10-11H2
    Key: QOLIPNRNLBQTAU-UHFFFAOYSA-N
  • C1CC2=CC=CC=C2OC1C1=CC=CC=C1
Properties
C15H14O
Molar mass 210.27 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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The flavans are benzopyran derivatives that use the 2-phenyl-3,4-dihydro-2H-chromene skeleton. They may be found in plants. These compounds include the flavan-3-ols, flavan-4-ols and flavan-3,4-diols (leucoanthocyanidin).

A C-glycosidic flavan can be isolated from cocoa liquor. [1]

Casuarina glauca is an actinorhizal plant producing root nitrogen-fixing nodules infested by Frankia . There is a regular pattern of cell layers containing flavans. [2]

Related Research Articles

<span class="mw-page-title-main">Leghemoglobin</span> Phytoglobin

Leghemoglobin is an oxygen-carrying phytoglobin found in the nitrogen-fixing root nodules of leguminous plants. It is produced by these plants in response to the roots being colonized by nitrogen-fixing bacteria, termed rhizobia, as part of the symbiotic interaction between plant and bacterium: roots not colonized by Rhizobium do not synthesise leghemoglobin. Leghemoglobin has close chemical and structural similarities to hemoglobin, and, like hemoglobin, is red in colour. It was originally thought that the heme prosthetic group for plant leghemoglobin was provided by the bacterial symbiont within symbiotic root nodules. However, subsequent work shows that the plant host strongly expresses heme biosynthesis genes within nodules, and that activation of those genes correlates with leghemoglobin gene expression in developing nodules.

<span class="mw-page-title-main">Rhizobia</span> Nitrogen fixing soil bacteria

Rhizobia are diazotrophic bacteria that fix nitrogen after becoming established inside the root nodules of legumes (Fabaceae). To express genes for nitrogen fixation, rhizobia require a plant host; they cannot independently fix nitrogen. In general, they are gram negative, motile, non-sporulating rods.

<span class="mw-page-title-main">Flavonoid</span> Class of plant and fungus secondary metabolites

Flavonoids are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans.

<span class="mw-page-title-main">Flavan-3-ol</span> Category of polyphenol compound

Flavan-3-ols are a subgroup of flavonoids. They are derivatives of flavans that possess a 2-phenyl-3,4-dihydro-2H-chromen-3-ol skeleton. Flavan-3-ols are structurally diverse and include a range of compounds, such as catechin, epicatechin gallate, epigallocatechin, epigallocatechin gallate, proanthocyanidins, theaflavins, thearubigins. They play a part in plant defense and are present in the majority of plants.

<span class="mw-page-title-main">Casuarinaceae</span> Family of plants

The Casuarinaceae are a family of dicotyledonous flowering plants placed in the order Fagales, consisting of four genera and 91 species of trees and shrubs native to eastern Africa, Australia, Southeast Asia, Malesia, Papuasia, and the Pacific Islands. At one time, all species were placed in the genus Casuarina. Lawrence Alexander Sidney Johnson separated out many of those species and renamed them into the new genera of Gymnostoma in 1980 and 1982, Allocasuarina in 1982, and Ceuthostoma in 1988, with some additional formal descriptions of new species in each other genus. At the time, it was somewhat controversial. The monophyly of these genera was later supported in a 2003 phylogenetic study of the family. In the Wettstein system, this family was the only one placed in the order Verticillatae. Likewise, in the Engler, Cronquist, and Kubitzki systems, the Casuarinaceae were the only family placed in the order Casuarinales.

<i>Dryas</i> (plant) Genus of flowering plants

Dryas is a genus of perennial cushion-forming evergreen dwarf shrubs in the family Rosaceae, native to the arctic and alpine regions of Europe, Asia and North America. The genus is named after the dryads, the tree nymphs of ancient Greek mythology. The classification of Dryas within the Rosaceae has been unclear. The genus was formerly placed in the subfamily Rosoideae, but is now placed in subfamily Dryadoideae.

Diazotrophs are bacteria and archaea that fix gaseous nitrogen in the atmosphere into a more usable form such as ammonia.

<span class="mw-page-title-main">Root nodule</span> Plant part

Root nodules are found on the roots of plants, primarily legumes, that form a symbiosis with nitrogen-fixing bacteria. Under nitrogen-limiting conditions, capable plants form a symbiotic relationship with a host-specific strain of bacteria known as rhizobia. This process has evolved multiple times within the legumes, as well as in other species found within the Rosid clade. Legume crops include beans, peas, and soybeans.

<i>Frankia</i> Genus of bacteria

Frankia is a genus of nitrogen-fixing bacteria that live in symbiosis with actinorhizal plants, similar to the Rhizobium bacteria found in the root nodules of legumes in the family Fabaceae. Frankia also initiate the forming of root nodules.

<span class="mw-page-title-main">Mimosine</span> Chemical compound

Mimosine or leucenol is a toxic non-protein amino acid chemically similar to tyrosine. It occurs in some Mimosa spp. and all members of the closely related genus Leucaena.

<i>Chamaebatia</i> Genus of evergreen shrubs in the rose family

Chamaebatia, also known as mountain misery, is a genus of two species of aromatic evergreen shrubs endemic to California. Its English common name derives from early settlers' experience with the plant's dense tangle and sticky, strong-smelling resin. They are actinorhizal, non-legumes capable of nitrogen fixation through symbiosis with the actinobacterium, Frankia.

In enzymology, a dihydrokaempferol 4-reductase (EC 1.1.1.219) is an enzyme that catalyzes the chemical reaction

<span class="mw-page-title-main">MYB (gene)</span> Protein-coding gene in the species Homo sapiens

Myb genes are part of a large gene family of transcription factors found in animals and plants. In humans, it includes Myb proto-oncogene like 1 and Myb-related protein B in addition to MYB proper. Members of the extended SANT/Myb family also include the SANT domain and other similar all-helical homeobox-like domains.

Actinorhizal plants are a group of angiosperms characterized by their ability to form a symbiosis with the nitrogen fixing actinomycetota Frankia. This association leads to the formation of nitrogen-fixing root nodules.

<i>Casuarina glauca</i> Species of tree

Casuarina glauca, commonly known as swamp she-oak, swamp buloke, swamp she-oak, marsh sheoak, grey she-oak, grey she-oak, native pine, or guman by the Gadigal people, is a species of flowering plant that is endemic to eastern Australia. It is a dioecious tree that often forms root suckers and has fissured and scaly bark, spreading or drooping branchlets, the leaves reduced to scales in whorls of 12 to 20, the fruit 9–18 mm (0.35–0.71 in) long containing winged seeds (samaras) 3.5–5.0 mm (0.14–0.20 in) long.

<i>Trevoa</i> Family of shrubs and trees

Trevoa is a genus of actinorhizal plants; these dicotyledon flora are trees or small shrubs. The genus was first proposed by Miers in 1825, but was not fully described until 1830 by Sir William Jackson Hooker. Genus members are notable for their ability to fix nitrogen. Species of this genus are generally found in the near coastal forests and arid shrubland of South America. Some species are localized in the mountains of central Chile; for example, the species Trevoa trinervis occurs in the La Campana National Park and other proximate areas of central Chile.

<span class="mw-page-title-main">Dryadoideae</span> Subfamily of flowering plants

The subfamily Dryadoideae consists of four genera in the family Rosaceae, all of which contain representative species with root nodules that host the nitrogen-fixing bacterium Frankia. They are subshrubs, shrubs, or small trees with a base chromosome number of 9, whose fruits are either an achene or an aggregate of achenes.

<span class="mw-page-title-main">Phlobaphene</span>

Phlobaphenes are reddish, alcohol-soluble and water-insoluble phenolic substances. They can be extracted from plants, or be the result from treatment of tannin extracts with mineral acids. The name phlobaphen come from the Greek roots φλoιὀς (phloios) meaning bark and βαφή (baphe) meaning dye.

<span class="mw-page-title-main">Condensed tannin</span> Polymers formed by the condensation of flavans.

Condensed tannins are polymers formed by the condensation of flavans. They do not contain sugar residues.

<i>Frankia alni</i> Species of bacterium

Frankia alni is a Gram-positive species of actinomycete filamentous bacterium that lives in symbiosis with actinorhizal plants in the genus Alnus. It is a nitrogen-fixing bacterium and forms nodules on the roots of alder trees.

References

  1. Proanthocyanidin glycosides and related polyphenols from cacao liquor and their antioxidant effects. Tsutomu Hatano, Haruka Miyatake, Midori Natsume, Naomi Osakabe, Toshio Takizawa, Hideyuki Ito and Takashi Yoshida, Phytochemistry, April 2002, Volume 59, Issue 7, Pages 749–758, doi : 10.1016/S0031-9422(02)00051-1
  2. Laplaze, L.; Gherbi, H.; Frutz, T.; Pawlowski, K.; Franche, C.; Macheix, J. J.; Auguy, F.; Bogusz, D.; Duhoux, E. (2002). "Flavan-Containing Cells Delimit Frankia Infected Compartments in Casuarina glauca Nodules". Nitrogen Fixation: From Molecules to Crop Productivity. Current Plant Science and Biotechnology in Agriculture. Vol. 38. p. 455. doi:10.1007/0-306-47615-0_254. ISBN   0-7923-6233-0.