From Wikipedia, the free encyclopedia
Leucoanthocyanidin
Names
IUPAC name
Flavan-3,4-diol
Systematic IUPAC name
2-Phenyl-3,4-dihydro-2H -1-benzopyran-3,4-diol
Identifiers
UNII
C1=CC=C(C=C1)C2C(C(C3=CC=CC=C3O2)O)O
Properties
C 15 H 14 O 3
Molar mass
242.274 g·mol−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
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
N. burbidgeae ,
N. muluensis ,
N. rajah ,
N. tentaculata , and
N. × alisaputrana .[
citation needed ]
Such compounds include:
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
^ Clark-Lewis, JW; Dainis, I (1967). "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 ". Australian Journal of Chemistry . 20 (10): 2191–2198.
doi :
10.1071/CH9672191 .
^ Heller, Werner; Britsch, Lothar; Forkmann, Gert; Grisebach, Hans (1985).
"Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br" . Planta . 163 (2): 191–196.
doi :
10.1007/BF00393505 .
PMID
24249337 .
S2CID
20854538 .
^ Bate-SMITH, EC (September 1954).
"Leuco-anthocyanins. 1. Detection and identification of anthocyanidins formed leuco-anthocyanins in plant tissues" . Biochem. J . 58 (1): 122–5.
doi :
10.1042/bj0580122 .
PMC
1269852 .
PMID
13198862 .
^
"leucoanthocyanidin dioxygenase on mondofacto.com" . Archived from
the original on 2012-03-04. Retrieved 2009-09-03 .
^ Ogundiwin, E. A.; Peace, C. P.; Nicolet, C. M.; Rashbrook, V. K.; Gradziel, T. M.; Bliss, F. A.; Parfitt, D.; Crisosto, C. H. (2008).
"Leucoanthocyanidin dioxygenase gene (PpLDOX): A potential functional marker for cold storage browning in peach" . Tree Genetics & Genomes . 4 (3): 543–554.
doi :
10.1007/s11295-007-0130-0 .
S2CID
22579882 .
^
Regulation of the leucoanthocyanidin dioxygenase gene expression in Vitis vinifera , Gollop R; Farhi S.; Perl A. 2001