Leucocyanidin

Leucocyanidin
Names
IUPAC name
(2R,3S,4S)-Flavan-3,3′,4,4′,5,7-hexol
Systematic IUPAC name
(2R,3S,4S)-2-(3,4-Dihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-3,4,5,7-tetrol
Other names
Leucocianidol
Leucocianidolum
Leucocyanidol
Leukocyanidine
Procyanidol
Resivit
Leucoanthocyanidol
Vitamin P faktor
3,4-Cyanidiol
(2R,3S,4S)-3,4,5,7,4-pentahydroxyflavan
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C15H14O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,13-21H/t13-,14-,15+/m0/s1 checkY
    Key: SBZWTSHAFILOTE-SOUVJXGZSA-N checkY
SMILES
  • C1=CC(=C(C=C1[C@@H]2[C@H]([C@H](C3=C(C=C(C=C3O2)O)O)O)O)O)O
Properties
Chemical formula
 C15H14O7
Molar mass 306.26 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Leucocyanidin is a colorless chemical compound that is a member of the class of natural products known as leucoanthocyanidins.

Chemistry

(+)-Leucocyanidin can be synthesized from (+)-dihydroquercetin by reduction with sodium borohydride.[1]

Molar equivalents of synthetic (2R,3S,4R or S)-leucocyanidin and (+)-catechin condense with exceptional rapidity at pH 5 under ambient conditions to give the all-trans-[4,8]- and [4,6]-bi-[(+)-catechins] (procyanidins B3, B6) the all-trans-[4,8:4,8]- and [4,8:4,6]-tri-[(+)-catechins] (procyanidin C2 and isomer).[2]

Metabolism

Leucocyanidin oxygenase uses leucocyanidin, 2-oxoglutarate, and O2 to produce cis-dihydroquercetin, trans-dihydroquercetin (taxifolin), succinate, CO2, and H2O.

Leucoanthocyanidin reductase (LAR or leucocyanidin reductase LCR) uses (2R,3S)-catechin, NADP+, and H2O to produce 2,3-trans-3,4-cis-leucocyanidin, NADPH, and H+. Its gene expression has been studied in developing grape berries and grapevine leaves.[3] Its activity has also been measured in leaves, flowers, and seeds of the legumes Medicago sativa, Lotus japonicus, Lotus uliginosus, Hedysarum sulfurescens, and Robinia pseudoacacia.[4]

The C-4 stereochemistry of leucocyanidin substrates affects anthocyanidin synthase (ANS) products. This enzyme is an iron(II) and 2-oxoglutarate (2OG) dependent oxygenase.[5]

Occurrence

Leucoyanidin can be found in these plants:[6]

  • Aesculus hippocastanum (Horse chestnut)
  • Anacardium occidentale (Cashew, acajou)
  • Arachis hypogaea (peanut)
  • Areca catechu (Areca nut)
  • Asimina triloba (American custardapple)
  • Cerasus vulgaris (Cherry)
  • Cinnamomum camphora (Camphor)
  • Erythroxylon coca (coca)
  • Gleditsia triacanthos (Honey locust)
  • Hamamelis virginiana (American Witch Hazel)
  • Hippophae rhamnoides (Hippophae berry Sanddorn)
  • Hordeum vulgare (Barley)
  • Humulus lupulus (bine)
  • Hypericum perforatum (perikon Amber)
  • Laurus nobilis
  • Magnolia denudata (Hsin-I Yulan-Magnolie)
  • Malva sylvestris (Blue mallow)
  • Musa acuminata × balbisiana (Banana)
  • Nelumbo nucifera (Baladi bean)
  • Pinus strobus (Eastern white pine)
  • Prunus serotina ssp. serotina (black cherry)
  • Psidium guajava (Common guava)
  • Quercus alba (White oak)
  • Quercus robur (Common oak)
  • Rumex hymenosepalus (Arizona dock)
  • Schinus terebinthifolius (Brazilian pepper tree)
  • Terminalia arjuna (arjun)
  • Terminalia catappa (Indian almond)
  • Theobroma cacao (Cacao)
  • Drimia maritima (Sea Squill)
  • Vicia faba (bell-bean)
  • Vitis vinifera (common grape vine)
  • Zea mays (corn, maize)
  • Ziziphus jujuba (jujube, Chinese date).

References

  1. ^ Heller, Werner; Britsch, Lothar; Forkmann, Gert; Grisebach, Hans (1985-02-01). "Leucoanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana R. Br". Planta. 163 (2): 191–196. doi:10.1007/BF00393505. ISSN 0032-0935. PMID 24249337.
  2. ^ Synthesis of condensed tannins. Part 9. The condensation sequence of leucocyanidin with (+)-catechin and with the resultant procyanidins. Jan. A. Delcour, Daneel Ferreira and David G. Roux, J. Chem. Soc., Perkin Trans. 1, 1983, pages 1711-1717, doi:10.1039/P19830001711
  3. ^ Bogs, Jochen; Downey, Mark O.; Harvey, John S.; Ashton, Anthony R.; Tanner, Gregory J.; Robinson, Simon P. (2005-10-01). "Proanthocyanidin Synthesis and Expression of Genes Encoding Leucoanthocyanidin Reductase and Anthocyanidin Reductase in Developing Grape Berries and Grapevine Leaves". Plant Physiology. 139 (2): 652–663. doi:10.1104/pp.105.064238. ISSN 0032-0889. PMC 1255985. PMID 16169968.
  4. ^ Skadhauge, B.; Gruber, M. Y.; Thomsen, K. K.; Wettstein, D. V. (1997-04-01). "Leucocyanidin reductase activity and accumulation of proanthocyanidins in developing legume tissues". American Journal of Botany. 84 (4): 494. doi:10.2307/2446026. ISSN 0002-9122. JSTOR 2446026. (subscription required)
  5. ^ "The C-4 stereochemistry of leucocyanidin substrates for anthocyanidin synthase affects product selectivity TURNBULL Jonathan J.; NAGLE Michael J.; SEIBEL Jürgen F.; WELFORD Richard W. D.; GRANT Guy H.; SCHOFIELD Christopher J. 2003". Archived from the original on 2012-06-16. Retrieved 2009-09-04.
  6. ^ "Liber Herbarum II: DK: Leucocyanidin/ UK: Leucocyanidin/ D: Leucocyanidin". www.liberherbarum.com. Retrieved 2017-12-03.
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