:Leucoanthocyanidin
{{chembox
| Watchedfields = changed
| verifiedrevid = 438705534
| Name = Leucoanthocyanidin
| ImageFile = Flavan-3,4-diol.svg
| ImageFile2 = Leucoanthocyanidin 3D BS.png
| IUPACName = Flavan-3,4-diol
| SystematicName = 2-Phenyl-3,4-dihydro-2H-1-benzopyran-3,4-diol
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|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| CASNo = 5023-02-9
| ChemSpiderID = 4477408
| PubChem = 5318979
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = EH726HE44D
| StdInChI=1S/C15H14O3/c16-13-11-8-4-5-9-12(11)18-15(14(13)17)10-6-2-1-3-7-10/h1-9,13-17H
| StdInChIKey = XIMADJWJJOMVID-UHFFFAOYSA-N
| SMILES = C1=CC=C(C=C1)C2C(C(C3=CC=CC=C3O2)O)O
}}
|Section2={{Chembox Properties
| C=15 | H=14 | O=3
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|Section3={{Chembox Hazards
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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|date=December 2019|reason=removed citation to predatory publisher content}}
Such compounds include:
- Leucocyanidin
- Leucodelphinidin
- Leucofisetinidin
- Leucomalvidin
- Leucopelargonidin
- Leucopeonidin
- Leucorobinetinidin
- Melacacidin
- Teracacidin from Acacia obtusifolia and Acacia maidenii heartwoods{{cite journal | last1 = Clark-Lewis | first1 = JW | last2 = Dainis | first2 = I | year = 1967| title = 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 | journal = Australian Journal of Chemistry | volume = 20 | issue = 10| pages = 2191–2198 | doi = 10.1071/CH9672191 }}
Leucoanthocyanidins have been demonstrated to be intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana.{{cite journal | url=https://doi.org/10.1007%2FBF00393505 | doi=10.1007/BF00393505 | title=Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br. | year=1985 | last1=Heller | first1=Werner | last2=Britsch | first2=Lothar | last3=Forkmann | first3=Gert | last4=Grisebach | first4=Hans | journal=Planta | volume=163 | issue=2 | pages=191–196 | pmid=24249337 | bibcode=1985Plant.163..191H | s2cid=20854538 | url-access=subscription }}
Bate-smith recommended in 1954 the use of the Forestal solvent for the isolation of leuco-anthocyanins.{{cite journal | pmc = 1269852 | pmid=13198862 | volume=58 | issue=1 | title=Leuco-anthocyanins. 1. Detection and identification of anthocyanidins formed leuco-anthocyanins in plant tissues | date=September 1954 | journal=Biochem. J. | pages=122–5 | last1 = Bate-SMITH | first1 = EC | doi=10.1042/bj0580122}}
Metabolism
Leucoanthocyanidin dioxygenase uses flavan-3,4-diols to produce 3-hydroxyanthocyanidins.{{Cite web |url=http://www.mondofacto.com/facts/dictionary?leucoanthocyanidin+dioxygenase |title=leucoanthocyanidin dioxygenase on mondofacto.com |access-date=2009-09-03 |archive-url=https://web.archive.org/web/20120304214423/http://www.mondofacto.com/facts/dictionary?leucoanthocyanidin+dioxygenase |archive-date=2012-03-04 |url-status=dead }} The gene encoding the enzyme (PpLDOX) has been identified in peach{{cite journal | url=https://doi.org/10.1007%2Fs11295-007-0130-0 | doi=10.1007/s11295-007-0130-0 | title=Leucoanthocyanidin dioxygenase gene (PpLDOX): A potential functional marker for cold storage browning in peach | year=2008 | last1=Ogundiwin | first1=E. A. | last2=Peace | first2=C. P. | last3=Nicolet | first3=C. M. | last4=Rashbrook | first4=V. K. | last5=Gradziel | first5=T. M. | last6=Bliss | first6=F. A. | last7=Parfitt | first7=D. | last8=Crisosto | first8=C. H. | journal=Tree Genetics & Genomes | volume=4 | issue=3 | pages=543–554 | s2cid=22579882 | url-access=subscription }} and expression has been studied in Vitis vinifera.[http://www.ingentaconnect.com/content/els/01689452/2001/00000161/00000003/art00445 Regulation of the leucoanthocyanidin dioxygenase gene expression in Vitis vinifera, Gollop R; Farhi S.; Perl A. 2001]