Procyanidin A2

Procyanidin 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
CAS Number	41743-41-3
ChEBI	CHEBI:28472
ChemSpider	110541
Jmol 3D model	Interactive image
PubChem	124025
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/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
SMILES O[C@@H]1[C@@H](C2=C(O[C@H](C3=CC(O)=C(O)C=C3[C@H](O)C4)C4=C(O)C=C2O5)C6=C(C=C(O)C=C6O)O[C@]15C7=CC(O)=C(O)C=C7
Properties
Chemical formula	C30H24O12
Molar mass	576.51 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

Procyanidin A2 is a A type proanthocyanidin.

It is found in avocado,^[1] chestnut,^[2][3] cranberry juice concentrate,^[4] lychee fruit pericarb,^[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. 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.
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. doi:10.1080/13880200902933336.
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. Conversion of procyanidin B-type (catechin dimer) to A-type: evidence for abstraction of C-2 hydrogen in catechin during radical oxidation. Kazunari Kondo, Masaaki Kurihara, Kiyoshi Fukuhara, Takashi Tanaka, Takashi Suzuki, Naoki Miyata and Masatake Toyoda, Tetrahedron Letters, 22 January 2000, Volume 41, Issue 4, Pages 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. Identification of flavonoids in litchi (Litchi chinensis Sonn.) leaf and evaluation of anticancer activities. Journal of Functional Foods, 2014, 6, 555-563.