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Phlobaphenes (or phlobaphens, CAS No.:71663-19-9) 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 (tanner's red). The name ''phlobaphen'' come from the Greek roots φλoιὀς (''phloios'') meaning
bark Bark may refer to: * Bark (botany), an outer layer of a woody plant such as a tree or stick * Bark (sound), a vocalization of some animals (which is commonly the dog) Places * Bark, Germany * Bark, Warmian-Masurian Voivodeship, Poland Arts, ...
and βαφή (''baphe'') meaning
dye A dye is a colored substance that chemically bonds to the substrate to which it is being applied. This distinguishes dyes from pigments which do not chemically bind to the material they color. Dye is generally applied in an aqueous solution an ...
. No biological activities have currently been reported for phlobaphenes.Phlobaphene on Dr. Duke's Phytochemical and Ethnobotanical Databases
/ref> Phlobaphenes from
hawthorn Hawthorn or Hawthorns may refer to: Plants * '' Crataegus'' (hawthorn), a large genus of shrubs and trees in the family Rosaceae * ''Rhaphiolepis'' (hawthorn), a genus of about 15 species of evergreen shrubs and small trees in the family Rosace ...
fruits (''Fructus Crataegi'') may have a specific action on the
coronary circulation Coronary circulation is the circulation of blood in the blood vessels that supply the heart muscle (myocardium). Coronary arteries supply oxygenated blood to the heart muscle. Cardiac veins then drain away the blood after it has been deoxygenat ...
. They are converted into humins in soils.


Naturally formed phlobaphenes

Natural phlobaphenes are the common
bark Bark may refer to: * Bark (botany), an outer layer of a woody plant such as a tree or stick * Bark (sound), a vocalization of some animals (which is commonly the dog) Places * Bark, Germany * Bark, Warmian-Masurian Voivodeship, Poland Arts, ...
, pericarp, cob
glume In botany, a glume is a bract (leaf-like structure) below a spikelet in the inflorescence (flower cluster) of grasses (Poaceae) or the flowers of sedges (Cyperaceae). There are two other types of bracts in the spikelets of grasses: the lemma and ...
and seed coat (''testa'') pigments. They have not been found in flowers, unless the brown and black pigments in the involucrum of certain compositae are found to be of the phlobaphene type. In bark, phlobaphenes accumulate in the phellem layer of cork cambium, part of the suberin mixture.


Occurrences

Many
cinchona ''Cinchona'' (pronounced or ) is a genus of flowering plants in the family Rubiaceae containing at least 23 species of trees and shrubs. All are native to the Tropical Andes, tropical Andean forests of western South America. A few species are ...
barks contain a particular tannin,
cinchotannic acid Cinchotannic acid is a tannin contained in many cinchona barks, which by oxidation rapidly yields a dark-coloured phlobaphen Phlobaphenes (or phlobaphens, CAS No.:71663-19-9) are reddish, alcohol-soluble and water-insoluble phenolic substances. Th ...
, which by oxidation rapidly yields a dark-coloured phlobaphene called ''red cinchonic'', ''cinchono-fulvic acid'' or ''cinchona red''. They are common in
redwood Sequoioideae, popularly known as redwoods, is a subfamily of coniferous trees within the family Family (from la, familia) is a Social group, group of people related either by consanguinity (by recognized birth) or Affinity (law), affini ...
s barks like '' Sequoia sempervirens'' or in oak barks where the chief constituent,
quercitannic acid Quercitannic acid is one of the two forms of tannic acid found in oak bark and leaves. The other form is called gallotannic acid and is found in oak galls. The quercitannic acid molecule is also present in quercitron, a yellow dye obtained from th ...
, a molecule also present in
quercitron Quercitron is a yellow natural dye obtained from the bark of the Eastern Black Oak (''Quercus velutina''), a forest tree indigenous in North America. It was formerly called Dutch pink, English pink, or Italian pink. The name is a shortened fo ...
, is an unstable substance, having a tendency to give off water to form anhydrides (phlobaphenes), one of which is called ''oak-red'' (C28H22O11). '' Cuscuta europaea'' L., the European dodder, is reported to contain 30,000 ppm in the root.
Phlobaphenes can be extracted from the root of the
common tormentil ''Potentilla erecta'' (syn. ''Tormentilla erecta'', ''Potentilla laeta'', ''Potentilla tormentilla'', known as the (common) tormentil, septfoil or erect cinquefoil ) is a herbaceous perennial plant belonging to the rose family (Rosaceae). Descri ...
(''Potentilla erecta'') as ''tormentil red''. Phlobaphens can be found in the
kola nut The term kola nut usually refers to the seeds of certain species of plant of the genus ''Cola'', placed formerly in the cocoa family Sterculiaceae and now usually subsumed in the mallow family Malvaceae (as subfamily Sterculioideae). These cola ...
(where they are called kola red), chocolate liquor (called cocoa red) or in the red skins or testa of the peanut. They are also reported in the fruits of the genus ''
Crataegus ''Crataegus'' (), commonly called hawthorn, quickthorn, thornapple, Voss, E. G. 1985. ''Michigan Flora: A guide to the identification and occurrence of the native and naturalized seed-plants of the state. Part II: Dicots (Saururaceae–Cornacea ...
'' (''Fructus Crataegi'')or can be extracted from
hop A hop is a type of jump. Hop or hops may also refer to: Arts and entertainment * ''Hop'' (film), a 2011 film * Hop! Channel, an Israeli TV channel * ''House of Payne'', or ''HOP'', an American sitcom * Lindy Hop, a swing dance of the 1920s and ...
flowers. The chief constituent of
kino Kino may refer to: Arts, entertainment and media Broadcasters * KINO, a radio station in Arizona, U.S. * Kino FM (98.0 FM – Moscow), a Russian music radio station * KinoTV, now Ruutu+ Leffat ja Sarjat, a Finnish TV channel Fictional entities ...
is
kinotannic acid Kinotannic acid is the chief constituent of the kino gum, of which it contains 70 to 80 per cent. Kino also contains kino red, a phlobaphene produced from kinotannic acid by oxidation. It is closely related to the tannin from catechu ( or ...
, of which it contains 70 to 80 per cent. It also contains kino red, a phlobaphene produced from kinotannic acid by oxidation. Phlobaphenes are not present in the model plant ''Arabidopsis thaliana'' but can be studied as the pigment responsible for the red color in some monocot cereals, including wheat, maize or
sorghum ''Sorghum'' () is a genus of about 25 species of flowering plants in the grass family (Poaceae). Some of these species are grown as cereals for human consumption and some in pastures for animals. One species is grown for grain, while many othe ...
.


Biosynthesis

In maize, phlobaphenes are synthesized in the flavonoids synthetic pathway from polymerisation of flavan-4-ols by the expression of maize pericarp color1 (p1) gene which encodes an R2R3 myb-like transcriptional activator of the A1 gene encoding for the dihydroflavonol 4-reductase (reducing dihydroflavonols into flavan-4-ols) while another gene (Suppressor of Pericarp Pigmentation 1 or SPP1) acts as a suppressor. The p1 gene encodes an Myb-homologous transcriptional activator of genes required for biosynthesis of red phlobaphene pigments, while the P1-wr allele specifies colorless kernel pericarp and red cobs, and unstable factor for orange1 (Ufo1) modifies P1-wr expression to confer pigmentation in kernel pericarp, as well as vegetative tissues, which normally do not accumulate significant amounts of phlobaphene pigments. The maize P gene encodes a Myb homolog that recognizes the sequence CCT/AACC, in sharp contrast with the C/TAACGG bound by vertebrate Myb proteins. In the sorghum, the corresponding yellow seed 1 gene (y1) also encodes a R2R3 type of Myb domain protein that regulates the expression of chalcone synthase, chalcone isomerase and dihydroflavonol reductase genes required for the biosynthesis of
3-deoxyflavonoids The flavan-4-ols (3-deoxyflavonoids) are flavone-derived alcohols and a family of flavonoids. Flavan-4-ols are colorless precursor compounds that polymerize to form red phlobaphene pigments. They can be found in the sorghum. Glycosides (abacopterin ...
.


Chemically formed phlobaphenes

It is a dark-colored resin-like substance made of water-insoluble, alcohol-soluble polymers. Phlobaphens can be formed under action of acids or heating of
condensed tannin Condensed tannins (proanthocyanidins, polyflavonoid tannins, catechol-type tannins, pyrocatecollic type tannins, non-hydrolyzable tannins or flavolans) are polymers formed by the condensation of flavans. They do not contain sugar residues. They ...
s or of the fraction of tannins called ''phlobatannins''. Water containing soda can be used for the conversion of
hop A hop is a type of jump. Hop or hops may also refer to: Arts and entertainment * ''Hop'' (film), a 2011 film * Hop! Channel, an Israeli TV channel * ''House of Payne'', or ''HOP'', an American sitcom * Lindy Hop, a swing dance of the 1920s and ...
tannins into phlobaphens. When heated with hydrochloric acid, tannins in cocoa solids yield a glucose and a phlobaphene. Ordinary or warm soluble quebracho (also known as insoluble quebracho) is the natural extract obtained directly from the quebracho wood. This type of extract is rich in condensed tannins of natural high molecular weight (phlobaphenes), which are not easily soluble. Its use is therefore limited to small additions during sole leather tannage carried out in hot liquors (temperature above 35 °C) to improve the yield and the water-proofness of the leather. The cold soluble extracts are obtained by subjecting the ordinary extract to a sulfiting process which transforms the phlobaphenes into completely soluble tannins. The cold soluble quebracho extracts are the most universally known and used types. The main properties of these extracts are: a very rapid penetration, a high tannin content and a relatively low percentage of non-tannins. The rather low acid and medium salt content characterise them as mild tanning extracts (low astringency). Phlobaphenes formation (tannins condensation and precipitation) can be minimized in using strong nucleophiles, such as phloroglucinol, ''m''-phenylenediamine and urea, during pine tannins extraction. The use of synthetic tannin
neradol Leather is a strong, flexible and durable material obtained from the tanning, or chemical treatment, of animal skins and hides to prevent decay. The most common leathers come from cattle, sheep, goats, equine animals, buffalo, pigs and hogs, ...
D can help solubilize phlobaphene in tanning solutions.


References


External links


Phlobaphene on www.liberherbarum.com
{{Condensed tannin Tannins Plant dyes