Sphagnorubine

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The sphagnorubins are a group of red dyes that were discovered in the cell walls of peat moss .

Representative

So far, sphagnorubins A, B and C are known.

Sphagnorubine
Surname Sphagnorubin A. Sphagnoruby B. Sphagnorubin C
Structural formula Sphagnorubin A.svg Sphagnorubin B.svg Sphagnorubin C.svg
other names 2- (3,4-Dihydroxyphenyl) -8,11-dihydroxy-9 H -phenanthro [2,1- b ] pyran-9-one 2- (3,4-Dihydroxyphenyl) -8-hydroxy-11-methoxy-9 H -phenanthro [2,1- b ] pyran-9-one 2- (4-Hydroxy-3-methoxyphenyl) -8-hydroxy-11-methoxy-9 H -phenanthro [2,1- b ] pyran-9-one
CAS number 55483-18-6 84018-30-4 84018-31-5
PubChem ? ? ?
Molecular formula C 23 H 14 O 6 C 24 H 16 O 6 C 25 H 18 O 6
Molar mass 386.36 g mol −1 400.39 g mol −1 414.41 g mol −1
Physical state firmly
Melting point > 350 ° C
description garnet-red rhombuses ruby red needles ruby red needles
solubility almost insoluble in non-polar and weakly polar solvents, 0.1% in DMSO
GHS
labeling
no classification available
H and P phrases see above
see above

Occurrence

The secondary plant substances are found on the cell wall of peat mosses such as Sphagnum rubellum or Sphagnum magellanicum . Phenylpropanoids as Sphagnorubin are essential structural components of an important carbon sink serving Moore .

description

The one with the anthocyanins related substances have a phenyl - phenanthro - pyran skeleton.

The solubility of the sphagnorubins is low in polar solvents, but this is sufficient for a deeply colored solution, while it is practically insoluble in non-polar solvents.

function

At low temperatures, which are typical for raised bogs, for example, the metabolism of the peat moss is slowed down. If high light intensity occurs under these conditions, i.e. if the sun is at a suitable position without shade, the moss can be damaged by photooxidation . Since the moss produces more sphagnorubins during the day at cool temperatures than at warm temperatures, the plant material is assigned a protective function. A second biological function could be the direct absorption of residual heat from the environment, as is concluded from an analogous situation in copepods .

biosynthesis

The biosynthesis is related to that of lignin in that it starts from phenylalanine . Intermediate is the hydroxy derivative at a coenzyme A bonded Zimtsäurerestes . The complex process has not yet been fully clarified, although the technical synthesis was described as early as 1975.

Web links

literature

  • Rudolph H., Vowinkel E .: Sphagnorubin, a crystalline membranochrome from Sphagnum magellanicum. In: Journal of Nature Research B . 24, 1969, pp. 1211-1212 ( online ).
  • Rolf Mentlein, Erich Vowinkel: The red wall pigments of the peat moss Sphagnum rubellum. In: Liebig's annals of chemistry. 1984, 1984, pp. 1024-1035, doi: 10.1002 / jlac.198419840520 .

Individual evidence

  1. ↑ Rolf Mentlein, Erich Vowinkel: The red wall pigments of the peat moss Sphagnum rubellum. In: Liebig's annals of chemistry. 1984, 1984, pp. 1024-1035, doi: 10.1002 / jlac.198419840520 .
  2. ↑ a b c d e Entry on Sphagnorubine. In: Römpp Online . Georg Thieme Verlag, accessed on March 2, 2012.
  3. ↑ Geoffrey D. Abbott, Aminu Muhammad, Lisa Belyea, Chris Laing, Greg L. Cowie: The Biogeochemistry of Sphagnum mosses - the effects of substrate source on their phenolic composition. (PDF; 163 kB).
  4. ^ RN Chopra: Biology of Bryophytes. New Age International, 2005, ISBN 978-81-224-1343-4 , p. 221 ( limited preview in Google book search).
  5. ↑ Janice M. Glime: Bryophyte Ecology, Volume 1, Physiological Ecology, 2007 (PDF; 709 kB).
  6. ↑ Zea mays mays Pathway: trans-cinnamoyl-CoA biosynthesis. Article at Gramene.org, March 10, 2010.
  7. ↑ Susanne Rasmussen, Hansjörg Rudolph: Isolation, purification and characterization of UDP-glucose: Cis-p-coumaric acid-β-d-glucosyltransferase from sphagnum fallax. In: Phytochemistry. 46, 1997, pp. 449-453, doi: 10.1016 / S0031-9422 (97) 00337-3 .
  8. ↑ Maike Petersen, Joachim Hans, Ulrich Matern: Biosynthesis of Phenylpropanoids and Related Compounds . In: Michael Wink (Ed.): Annual Plant Reviews . 2nd Edition. tape 40 : Biochemistry of Plant Secondary Metabolism . Wiley-Blackwell, Oxford 2010, ISBN 978-1-4443-2050-3 , pp. 214 , doi : 10.1002 / 9781444320503.ch4 / summary .
  9. ↑ Eckart Voss: Total synthesis of Sphagnorubin. Kiel, 1975 ( limited preview in Google Book search).