Procyanidin A2

From Wikipedia, the free encyclopedia
  (Redirected from Proanthocyanidin A2)
Jump to: navigation, search
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
41743-41-3 N
3D model (Jmol) Interactive image
ChEBI CHEBI:28472 YesY
ChemSpider 110541
PubChem 124025
Properties
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).
N verify (what is YesYN ?)
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[edit]

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

References[edit]

  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. ^ a b 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.