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Phlobaphene

February 15, 2024

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[1] (tanner's red).[2] The name phlobaphen come from the Greek roots φλoιὀς (phloios) meaning bark and βαφή (baphe) meaning dye.[3][4]

Phlobaphene is the red pigment present in the pericarp of certain maize varieties

No biological activities have currently been reported for phlobaphenes.[5] Phlobaphenes from hawthorn fruits (Fructus Crataegi) may have a specific action on the coronary circulation[citation needed]. They are converted into humins in soils.[6]

Naturally formed phlobaphenes edit

Natural phlobaphenes are the common bark, pericarp, cob glume 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.[7]

In bark, phlobaphenes accumulate in the phellem layer of cork cambium, part of the suberin mixture.[8]

Occurrences edit

 
Cinchona officinalis bark

Many cinchona barks contain a particular tannin, cinchotannic acid, which by oxidation rapidly yields a dark-coloured phlobaphene[9] called red cinchonic,[10] cinchono-fulvic acid or cinchona red.[11]

They are common in redwoods barks like Sequoia sempervirens[12] or in oak barks where the chief constituent, quercitannic acid, a molecule also present in quercitron, 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.[13]

 
The common tormentil (Potentilla erecta)


Phlobaphenes can be extracted from the root of the common tormentil (Potentilla erecta) as tormentil red.

 
Kola nut

Phlobaphens can be found in the kola nut (where they are called kola red),[14] chocolate liquor (called cocoa red)[15] or in the red skins or testa of the peanut.[16] They are also reported in the fruits of the genus Crataegus (Fructus Crataegi)or can be extracted from hop flowers.[17]

 
Copious flow of kino from a wound near the base of the trunk of a Corymbia calophylla (marri)

The chief constituent of kino is kinotannic acid, of which it contains 70 to 80 per cent. It also contains kino red, a phlobaphene produced from kinotannic acid by oxidation.[18]

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,[19] maize[20] or sorghum.[21]

Biosynthesis edit

In maize, phlobaphenes are synthesized in the flavonoids synthetic pathway[22] from polymerisation of flavan-4-ols[23] by the expression of maize pericarp color1 (p1) gene[24] which encodes an R2R3 myb-like transcriptional activator[25] of the A1 gene encoding for the dihydroflavonol 4-reductase (reducing dihydroflavonols into flavan-4-ols)[26] while another gene (Suppressor of Pericarp Pigmentation 1 or SPP1) acts as a suppressor.[27] 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.[24] 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.[28]

In the sorghum, the corresponding yellow seed 1 gene (y1)[29] 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.[30]

Chemically formed phlobaphenes edit

It is a dark-colored resin-like substance made of water-insoluble, alcohol-soluble polymers.[31]

Phlobaphens can be formed under action of acids or heating of condensed tannins or of the fraction of tannins called phlobatannins. Water containing soda can be used for the conversion of hop tannins into phlobaphens.[32] When heated with hydrochloric acid, tannins in cocoa solids yield a glucose and a phlobaphene.[33]

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.[34]

The use of synthetic tannin neradol D can help solubilize phlobaphene in tanning solutions.[35]

References edit

  1. ^ Foo, L. Yeap; Karchesy, Joseph J. (1989), "Chemical Nature of Phlobaphenes", Chemistry and Significance of Condensed Tannins, p. 109, doi:10.1007/978-1-4684-7511-1_6, ISBN 978-1-4684-7513-5
  2. ^ Richard W. Hemingway; Peter Edward Laks; Susan J. Branham (1992). Plant polyphenols: synthesis, properties, significance. ISBN 978-0-306-44252-0.
  3. ^ Römpp CD 2006, Georg Thieme Verlag 2006
  4. ^ Etti, C. (1883). "Zur Geschichte der Eichenrindegerbsäuren". Monatshefte für Chemie. 4: 512–530. doi:10.1007/BF01517990. S2CID 105109992.
  5. ^ Phlobaphene on Dr. Duke's Phytochemical and Ethnobotanical Databases
  6. ^ A Manual of pharmacology and its applications to therapeutics and toxicology by Torald Sollmann, M. D.
  7. ^ Paech, K (1955). "Colour Development in Flowers". Annual Review of Plant Physiology. 6: 273–298. doi:10.1146/annurev.pp.06.060155.001421.
  8. ^ Duke, James A (2000-11-10). Handbook of Nuts: Herbal Reference Library. ISBN 978-0-8493-3637-9. Par James A. Duke
  9. ^ Cinchona Bark (Cortex Cinchonae). Part 3
  10. ^ Cinchonaceae on chestofbooks.com
  11. ^ Quinine on www.1902encyclopedia.com
  12. ^ Buchanan, M. A.; Lewis, H. F.; Kurth, E. F. (1944). "Chemical Nature of Redwood Tannin and Phlobaphene". Industrial & Engineering Chemistry. 36 (10): 907–910. doi:10.1021/ie50418a008.
  13. ^ Hager's Handbuch der Pharmazeutischen Praxis, List, P.H. and Horhammer, L., Vols. 2–6, Springer-Verlag, Berlin, 1969–1979
  14. ^ "Herbal Medicine Materia Medica: Kola".
  15. ^ Blyth, Alexander Wynter; Wynter Blyth, Meredith (1903). Foods: Their composition and analysis. C. Griffin & Co., Ltd. p. 236.
  16. ^ Stansbury, Mack F.; Field, Elsie T.; Guthrie, John D. (1950). "The tannin and related pigments in the red skins (Testa) of peanut kernels". Journal of the American Oil Chemists' Society. 27 (8): 317. doi:10.1007/BF02649320. S2CID 95107923.
  17. ^ The Principles Of Hop-Analysis, Cech G. O.
  18. ^ Kino on www.henriettesherbal.com
  19. ^ Himi, Eiko; Noda, Kazuhiko (2005). "Red grain colour gene (R) of wheat is a Myb-type transcription factor". Euphytica. 143 (3): 239. doi:10.1007/s10681-005-7854-4. S2CID 26883288.
  20. ^ Phlobaphene biosynthesis in maize
  21. ^ Phlobaphene on trophort.com 2012-03-01 at the Wayback Machine
  22. ^ Himi, E; Mares, DJ; Yanagisawa, A; Noda, K (2002). "Effect of grain colour gene (R) on grain dormancy and sensitivity of the embryo to abscisic acid (ABA) in wheat". Journal of Experimental Botany. 53 (374): 1569–1574. doi:10.1093/jxb/erf005. PMID 12096095.
  23. ^ Winkel-Shirley, B. (2001). "Flavonoid Biosynthesis. A Colorful Model for Genetics, Biochemistry, Cell Biology, and Biotechnology". Plant Physiology. 126 (2): 485–493. doi:10.1104/pp.126.2.485. PMC 1540115. PMID 11402179.
  24. ^ a b Braess, CH; Cocciolone, SM; Bushman, S; Sangar, V; McMullen, MD; Peterson, T (1976). "Is Igls worth a journey? Report on the 19th International Congress on General Medicine of the SIMG in Igls/Innsbruck, September 22–27, 1975". Zeitschrift für Allgemeinmedizin. 52 (8): 432–433. PMID 1266355.
  25. ^ Structural And Transcriptional Analysis Of The Complex P1-wr Cluster In Maize. Wolfgang Goettel, Joachim Messing. Plant & Animal Genomes XVI Conference 2012-02-18 at the Wayback Machine
  26. ^ Dong, X.; Braun, EL; Grotewold, E (2001). "Functional Conservation of Plant Secondary Metabolic Enzymes Revealed by Complementation of Arabidopsis Flavonoid Mutants with Maize Genes". Plant Physiology. 127 (1): 46–57. doi:10.1104/pp.127.1.46. PMC 117961. PMID 11553733.
  27. ^ Lee E.A; Harper V (2002). "Suppressor of Pericarp Pigmentation 1 (SPP1), a novel gene involved in phlobaphene accumulation in maize (Zea mays L.) pericarps". Maydica. 47 (1): 51–58. INIST 13772300.
  28. ^ Grotewold, Erich; Drummond, Bruce J.; Bowen, Ben; Peterson, Thomas (1994). "The myb-homologous P gene controls phlobaphene pigmentation in maize floral organs by directly activating a flavonoid biosynthetic gene subset". Cell. 76 (3): 543–553. doi:10.1016/0092-8674(94)90117-1. PMID 8313474. S2CID 42197232.
  29. ^ Boddu, Jayanand; Svabek, Catherine; Ibraheem, Farag; Jones, A. Daniel; Chopra, Surinder (2005). "Characterization of a deletion allele of a sorghum Myb gene yellow seed1 showing loss of 3-deoxyflavonoids". Plant Science. 169 (3): 542. doi:10.1016/j.plantsci.2005.05.007. INIST 16983977.
  30. ^ Boddu, Jayanand; Jiang, Cizhong; Sangar, Vineet; Olson, Terry; Peterson, Thomas; Chopra, Surinder (2006). "Comparative Structural and Functional Characterization of Sorghum and Maize Duplications Containing Orthologous Myb Transcription Regulators of 3-Deoxyflavonoid Biosynthesis". Plant Molecular Biology. 60 (2): 185–199. doi:10.1007/s11103-005-3568-1. PMID 16429259. S2CID 23841582.
  31. ^ Dihydroquercetin dimers by oxidative coupling reactions. Gonzalez-Laredo, Ruben F., Malan, Johannes C.S., Chen, Jie, Todd, Jim, Karchesy, Joseph J. 2nd International Electronic Conference on Synthetic Organic Chemistry (ECSOC-2), September 1–30, 1998
  32. ^ Dingler's Polytech. Journ., C. Etti, 1878, p. 354.
  33. ^ Warden C. J. H., Pharm. Jour., [3], xviii. 985
  34. ^ Sealy-Fisher, V. J.; Pizzi, A. (1992). "Increased pine tannins extraction and wood adhesives development by phlobaphenes minimization". Holz Als Roh- und Werkstoff. 50 (5): 212. doi:10.1007/BF02663290. S2CID 6585979.
  35. ^ Georg Grasser (March 2007). Synthetic Tannins. ISBN 978-1-4067-7301-9.

External links edit

  • Phlobaphene on www.liberherbarum.com

February 15, 2024
phlobaphene, phlobaphens, 71663, reddish, alcohol, soluble, water, insoluble, phenolic, substances, they, extracted, from, plants, result, from, treatment, tannin, extracts, with, mineral, acids, tanner, name, phlobaphen, come, from, greek, roots, φλoιὀς, phlo. 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 1 tanner s red 2 The name phlobaphen come from the Greek roots floiὀs phloios meaning bark and bafh baphe meaning dye 3 4 Phlobaphene is the red pigment present in the pericarp of certain maize varietiesNo biological activities have currently been reported for phlobaphenes 5 Phlobaphenes from hawthorn fruits Fructus Crataegi may have a specific action on the coronary circulation citation needed They are converted into humins in soils 6 Contents 1 Naturally formed phlobaphenes 1 1 Occurrences 1 2 Biosynthesis 2 Chemically formed phlobaphenes 3 References 4 External linksNaturally formed phlobaphenes editNatural phlobaphenes are the common bark pericarp cob glume 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 7 In bark phlobaphenes accumulate in the phellem layer of cork cambium part of the suberin mixture 8 Occurrences edit nbsp Cinchona officinalis barkMany cinchona barks contain a particular tannin cinchotannic acid which by oxidation rapidly yields a dark coloured phlobaphene 9 called red cinchonic 10 cinchono fulvic acid or cinchona red 11 They are common in redwoods barks like Sequoia sempervirens 12 or in oak barks where the chief constituent quercitannic acid a molecule also present in quercitron 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 13 nbsp The common tormentil Potentilla erecta Phlobaphenes can be extracted from the root of the common tormentil Potentilla erecta as tormentil red nbsp Kola nutPhlobaphens can be found in the kola nut where they are called kola red 14 chocolate liquor called cocoa red 15 or in the red skins or testa of the peanut 16 They are also reported in the fruits of the genus Crataegus Fructus Crataegi or can be extracted from hop flowers 17 nbsp Copious flow of kino from a wound near the base of the trunk of a Corymbia calophylla marri The chief constituent of kino is kinotannic acid of which it contains 70 to 80 per cent It also contains kino red a phlobaphene produced from kinotannic acid by oxidation 18 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 19 maize 20 or sorghum 21 Biosynthesis edit In maize phlobaphenes are synthesized in the flavonoids synthetic pathway 22 from polymerisation of flavan 4 ols 23 by the expression of maize pericarp color1 p1 gene 24 which encodes an R2R3 myb like transcriptional activator 25 of the A1 gene encoding for the dihydroflavonol 4 reductase reducing dihydroflavonols into flavan 4 ols 26 while another gene Suppressor of Pericarp Pigmentation 1 or SPP1 acts as a suppressor 27 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 24 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 28 In the sorghum the corresponding yellow seed 1 gene y1 29 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 30 Chemically formed phlobaphenes editIt is a dark colored resin like substance made of water insoluble alcohol soluble polymers 31 Phlobaphens can be formed under action of acids or heating of condensed tannins or of the fraction of tannins called phlobatannins Water containing soda can be used for the conversion of hop tannins into phlobaphens 32 When heated with hydrochloric acid tannins in cocoa solids yield a glucose and a phlobaphene 33 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 34 The use of synthetic tannin neradol D can help solubilize phlobaphene in tanning solutions 35 References edit Foo L Yeap Karchesy Joseph J 1989 Chemical Nature of Phlobaphenes Chemistry and Significance of Condensed Tannins p 109 doi 10 1007 978 1 4684 7511 1 6 ISBN 978 1 4684 7513 5 Richard W Hemingway Peter Edward Laks Susan J Branham 1992 Plant polyphenols synthesis properties significance ISBN 978 0 306 44252 0 Rompp CD 2006 Georg Thieme Verlag 2006 Etti C 1883 Zur Geschichte der Eichenrindegerbsauren Monatshefte fur Chemie 4 512 530 doi 10 1007 BF01517990 S2CID 105109992 Phlobaphene on Dr Duke s Phytochemical and Ethnobotanical Databases A Manual of pharmacology and its applications to therapeutics and toxicology by Torald Sollmann M D Paech K 1955 Colour Development in Flowers Annual Review of Plant Physiology 6 273 298 doi 10 1146 annurev pp 06 060155 001421 Duke James A 2000 11 10 Handbook of Nuts Herbal Reference Library ISBN 978 0 8493 3637 9 Par James A Duke Cinchona Bark Cortex Cinchonae Part 3 Cinchonaceae on chestofbooks com Quinine on www 1902encyclopedia com Buchanan M A Lewis H F Kurth E F 1944 Chemical Nature of Redwood Tannin and Phlobaphene Industrial amp Engineering Chemistry 36 10 907 910 doi 10 1021 ie50418a008 Hager s Handbuch der Pharmazeutischen Praxis List P H and Horhammer L Vols 2 6 Springer Verlag Berlin 1969 1979 Herbal Medicine Materia Medica Kola Blyth Alexander Wynter Wynter Blyth Meredith 1903 Foods Their composition and analysis C Griffin amp Co Ltd p 236 Stansbury Mack F Field Elsie T Guthrie John D 1950 The tannin and related pigments in the red skins Testa of peanut kernels Journal of the American Oil Chemists Society 27 8 317 doi 10 1007 BF02649320 S2CID 95107923 The Principles Of Hop Analysis Cech G O Kino on www henriettesherbal com Himi Eiko Noda Kazuhiko 2005 Red grain colour gene R of wheat is a Myb type transcription factor Euphytica 143 3 239 doi 10 1007 s10681 005 7854 4 S2CID 26883288 Phlobaphene biosynthesis in maize Phlobaphene on trophort com Archived 2012 03 01 at the Wayback Machine Himi E Mares DJ Yanagisawa A Noda K 2002 Effect of grain colour gene R on grain dormancy and sensitivity of the embryo to abscisic acid ABA in wheat Journal of Experimental Botany 53 374 1569 1574 doi 10 1093 jxb erf005 PMID 12096095 Winkel Shirley B 2001 Flavonoid Biosynthesis A Colorful Model for Genetics Biochemistry Cell Biology and Biotechnology Plant Physiology 126 2 485 493 doi 10 1104 pp 126 2 485 PMC 1540115 PMID 11402179 a b Braess CH Cocciolone SM Bushman S Sangar V McMullen MD Peterson T 1976 Is Igls worth a journey Report on the 19th International Congress on General Medicine of the SIMG in Igls Innsbruck September 22 27 1975 Zeitschrift fur Allgemeinmedizin 52 8 432 433 PMID 1266355 Structural And Transcriptional Analysis Of The Complex P1 wr Cluster In Maize Wolfgang Goettel Joachim Messing Plant amp Animal Genomes XVI Conference Archived 2012 02 18 at the Wayback Machine Dong X Braun EL Grotewold E 2001 Functional Conservation of Plant Secondary Metabolic Enzymes Revealed by Complementation of Arabidopsis Flavonoid Mutants with Maize Genes Plant Physiology 127 1 46 57 doi 10 1104 pp 127 1 46 PMC 117961 PMID 11553733 Lee E A Harper V 2002 Suppressor of Pericarp Pigmentation 1 SPP1 a novel gene involved in phlobaphene accumulation in maize Zea mays L pericarps Maydica 47 1 51 58 INIST 13772300 Grotewold Erich Drummond Bruce J Bowen Ben Peterson Thomas 1994 The myb homologous P gene controls phlobaphene pigmentation in maize floral organs by directly activating a flavonoid biosynthetic gene subset Cell 76 3 543 553 doi 10 1016 0092 8674 94 90117 1 PMID 8313474 S2CID 42197232 Boddu Jayanand Svabek Catherine Ibraheem Farag Jones A Daniel Chopra Surinder 2005 Characterization of a deletion allele of a sorghum Myb gene yellow seed1 showing loss of 3 deoxyflavonoids Plant Science 169 3 542 doi 10 1016 j plantsci 2005 05 007 INIST 16983977 Boddu Jayanand Jiang Cizhong Sangar Vineet Olson Terry Peterson Thomas Chopra Surinder 2006 Comparative Structural and Functional Characterization of Sorghum and Maize Duplications Containing Orthologous Myb Transcription Regulators of 3 Deoxyflavonoid Biosynthesis Plant Molecular Biology 60 2 185 199 doi 10 1007 s11103 005 3568 1 PMID 16429259 S2CID 23841582 Dihydroquercetin dimers by oxidative coupling reactions Gonzalez Laredo Ruben F Malan Johannes C S Chen Jie Todd Jim Karchesy Joseph J 2nd International Electronic Conference on Synthetic Organic Chemistry ECSOC 2 September 1 30 1998 Dingler s Polytech Journ C Etti 1878 p 354 Warden C J H Pharm Jour 3 xviii 985 Sealy Fisher V J Pizzi A 1992 Increased pine tannins extraction and wood adhesives development by phlobaphenes minimization Holz Als Roh und Werkstoff 50 5 212 doi 10 1007 BF02663290 S2CID 6585979 Georg Grasser March 2007 Synthetic Tannins ISBN 978 1 4067 7301 9 External links editPhlobaphene on www liberherbarum com Retrieved from https en wikipedia org w index php title Phlobaphene amp oldid 1104836774, wikipedia, wiki, book, books, library,

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