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Procyanidin A2

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Procyanidin A2
Chemical structure of proanthocyanidin A2
Chemical structure of proanthocyanidin A2
Names
IUPAC name (2R,3R,8S,14R,15R)-2,8-bis(3,4-dihydroxyphenyl)-2,3,4,14-tetrahydro-8,14-methanobenzodioxocinochromene-3,5,11,13,15-pentaol
Other names Dimeric catechin
Procyanidin A2
Procyanidol A2
Proanthocyanidin A-2
Procyanidin dimer A2
(+)-Proanthocyanidin A2
Epicatechin-(2β→7,4β→8)-epicatechin
Identifiers
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1Key: NSEWTSAADLNHNH-LSBOWGMISA-N
  • InChI=1/C30H24O12/c31-13-7-20(37)24-22(8-13)41-30(12-2-4-16(33)19(36)6-12)29(39)26(24)25-23(42-30)10-17(34)14-9-21(38)27(40-28(14)25)11-1-3-15(32)18(35)5-11/h1-8,10,21,26-27,29,31-39H,9H2/t21-,26-,27-,29-,30+/m1/s1Key: NSEWTSAADLNHNH-LSBOWGMIBO
SMILES
  • C1((OC2=C34((OC5=CC(=CC(=C45)O)O)(OC3=CC(=C21)O)C6=CC(=C(C=C6)O)O)O)C7=CC(=C(C=C7)O)O)O
Properties
Chemical formula C30H24O12
Molar mass 576.510 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Procyanidin A2 is an A type proanthocyanidin.

It is found in avocado, chestnut, cranberry juice concentrate, lychee fruit pericarp, peanut skins, Cinchona cortex, cinnamon cortex, Urvillea ulmaceae, and Ecdysanthera utilis.

Synthesis

Procyanidin B2 can be converted into procyanidin A2 by radical oxidation using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals under neutral conditions.

References

  1. Proanthocyanidin-A-2 on liberherbarum.com
  2. Facino, R. Maffei; Carini, M.; Brambilla, A.; Bombardelli, E.; Morazzoni, P. (1996). "Proanthocyanidin-A2: a new polyphenol". Cosmetics & Toiletries.
  3. Kimura, H; Ogawa, S; Akihiro, T; Yokota, K (2011). "Structural analysis of A-type or B-type highly polymeric proanthocyanidins by thiolytic degradation and the implication in their inhibitory effects on pancreatic lipase". J Chromatogr A. 1218 (42): 7704–12. doi:10.1016/j.chroma.2011.07.024. PMID 21803362.
  4. ^ Koerner Jayma, Hsu Victor, Lee Jungmin, Kennedy, James (2009). "Determination of Proanthocyanidin A2 Content in Phenolic Polymer Isolates by Reversed-Phase High Performance Liquid Chromatography". Journal of Chromatography A. 1216 (9): 1403–1409. doi:10.1016/j.chroma.2008.12.086. PMID 19168185.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  5. Sarni-Manchado P, Le Roux E, Le Guerneve C, Lozano Y, Cheynier V. Phenolic composition of litchi fruit pericarp" J Agric Food Chem 2000;48(12):5995-6002.
  6. Hongxiang Lou; Yamazaku Y.; Sasaku T.; Uchida M.; Tanaka H.; Oka S. (1999). "A-type proanthocyanidins from peanut skins". Phytochemistry. 51 (2): 297–308. doi:10.1016/S0031-9422(98)00736-5.
  7. Dias, Suziane A.; Cardoso (Gazio), Flávia P.; Santin, Silvana M. O.; Da Costa, Willian F.; Vidotti, Gentil J.; De Souza, Maria Conceição; Sarragiotto, Maria Helena (2009). "Free radical scavenging activity and chemical constituents of Urvillea ulmaceae". Pharmaceutical Biology. 47 (8): 717–720. doi:10.1080/13880200902933336. S2CID 54906659.
  8. Lin, Lie-Chwen; Kuo, Yuh-Chi; Chou, Cheng-Jen (2002). "Immunomodulatory Proanthocyanidins from Ecdysantherautilis". Journal of Natural Products. 65 (4): 505–8. doi:10.1021/np010414l. PMID 11975489.
  9. Kondo, Kazunari; Kurihara, Masaaki; Fukuhara, Kiyoshi; Tanaka, Takashi; Suzuki, Takashi; Miyata, Naoki; Toyoda, Masatake (2000). "Conversion of procyanidin B-type (catechin dimer) to A-type: evidence for abstraction of C-2 hydrogen in catechin during radical oxidation". Tetrahedron Letters. 41 (4): 485–488. doi:10.1016/S0040-4039(99)02097-3.
  • Wen, LR; Wu, D; Jiang, YM; Prasad, KN; Lin, S; Jiang, GX; He, JR; Zhao, MM; Luo, W; Yang, B (2014). "Identification of flavonoids in litchi (Litchi chinensis Sonn.) leaf and evaluation of anticancer activities". Journal of Functional Foods. 6: 555–563. doi:10.1016/j.jff.2013.11.022.
Types of procyanidins
A-type proanthocyanidins
B type proanthocyanidins
Types


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