Leucoanthocyanidin

Leucoanthocyanidin
IUPAC name

2-phenyl-3,4-dihydro-2H-chromene-3,4-diol
Other names

Flavan-3,4-diol
Identifiers
PubChem 5318979
Jmol-3D images Image 1
Properties
Molecular formula C15H14O3
Molar mass 242.26 g/mol
Exact mass 242.094294 u
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Leucoanthocyanidin (flavan-3,4-diols) are colorless chemical compounds related to anthocyanidins and anthocyanins. Leucoanthocyanins can be found in Anadenanthera peregrina and in several species of Nepenthes including Nepenthes rajah, Nepenthes burbidgeae, Nepenthes tentaculata, Nepenthes × alisaputrana and Nepenthes muluensis.

Such compounds are :

Leucoanthocyanidins have been demonstrated to be intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana[2].

Bate-smith recommended in 1954 the use of the Forestal solvent for the isolation of leuco-anthocyanins.[3]

Metabolism

Leucoanthocyanidin dioxygenase uses flavan-3,4-diols to produce 3-hydroxyanthocyanidins[4]. The gene encoding the enzyme (PpLDOX) has been identified in peach[5] and expression has been studied in Vitis vinifera[6].

References

  1. ^ Flavan derivatives. XIX. Teracacidin and isoteracacidin from Acacia obtusifolia and Acacia maidenii heartwoods; Phenolic hydroxylation patterns of heartwood flavonoids characteristic of sections and subsections of the genus Acacia. JW Clark-Lewis and I Dainis, Australian Journal of Chemistry, 20(10), pp. 2191-2198, doi:10.1071/CH9672191
  2. ^ Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br. Werner Heller, Lothar Britsch, Gert Forkmann and Hans Grisebach, 1984
  3. ^ Bate-Smith, E. C., Leuco-Anthocyanins, Biochem J. 1954 Sept; 58(1), pp. 122–125. (retrieved 27 sept 2010 http://www.ncbi.nlm.nih.gov/pmc/articles/PMC1269852/pdf/biochemj01081-0129.pdf )
  4. ^ leucoanthocyanidin dioxygenase on mondofacto.com
  5. ^ Leucoanthocyanidin dioxygenase gene (PpLDOX): a potential functional marker for cold storage browning in peach, E. A. Ogundiwin, C. P. Peace, C. M. Nicolet, V. K. Rashbrook, T. M. Gradziel, F. A. Bliss, D. Parfitt and C. H. Crisosto, 2008
  6. ^ Regulation of the leucoanthocyanidin dioxygenase gene expression in Vitis vinifera, Gollop R; Farhi S.; Perl A. 2001
Types of Flavonoids
Flavonoids
Isoflavonoids
Neoflavonoids
Aurones
Other categories
Types of leucoanthocyanidins
leucoanthocyanidins:
Leucocyanidin | Leucodelphinidin | Leucomalvidin | Leucopelargonidin | Leucopeonidin | leucorobinetinidin | Melacacidin | Teracacidin