Procyanidin A2

Procyanidin A2 is an A type proanthocyanidin.

Procyanidin 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-methanobenzo[7,8][1,3]dioxocino[4,5-h]chromene-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
3D model (JSmol)
ChEBI
ChemSpider
UNII
  • 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/s1
    Key: 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/s1
    Key: NSEWTSAADLNHNH-LSBOWGMIBO
  • C1[C@H]([C@H](OC2=C3[C@@H]4[C@H]([C@@](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
C30H24O12
Molar mass 576.510 g·mol−1
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

It is found in avocado,[1] chestnut,[2][3] cranberry juice concentrate,[4] lychee fruit pericarp,[5] peanut[4] skins,[6] Cinchona cortex, cinnamon cortex, Urvillea ulmaceae,[7] and Ecdysanthera utilis.[8]

Synthesis

Procyanidin B2 can be converted into procyanidin A2 by radical oxidation using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals under neutral conditions.[9]

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.


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