Leucoanthocyanidin
| |
| Names | |
|---|---|
| IUPAC name
2-phenyl-3,4-dihydro-2H-chromene-3,4-diol
| |
| Other names
Flavan-3,4-diol
| |
| Identifiers | |
3D model (JSmol)
|
|
PubChem CID
|
|
| |
| Properties | |
| C15H14O3 | |
| Molar mass | 242.26 g/mol |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
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 :
- Leucocyanidin
- Leucodelphinidin
- Leucomalvidin
- Leucopelargonidin
- Leucopeonidin
- leucorobinetinidin
- Melacacidin
- Teracacidin from Acacia obtusifolia and Acacia maidenii heartwoods[1]
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
- ^ 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
- ^ Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br. Werner Heller, Lothar Britsch, Gert Forkmann and Hans Grisebach, 1984
- ^ 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 )
- ^ leucoanthocyanidin dioxygenase on mondofacto.com
- ^ 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
- ^ Regulation of the leucoanthocyanidin dioxygenase gene expression in Vitis vinifera, Gollop R; Farhi S.; Perl A. 2001