Procyanidin A1

Last updated
Procyanidin A1
Chemical structure of procyanidin A1 Proanthocyanidin A1.svg
Chemical structure of procyanidin A1
Names
IUPAC name
(2R,3S,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
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • InChI=1S/C30H24O13/c31-12-6-17(35)23-21(7-12)42-30(11-4-18(36)26(39)19(37)5-11)29(40)25(23)24-22(43-30)9-15(33)13-8-20(38)27(41-28(13)24)10-1-2-14(32)16(34)3-10/h1-7,9,20,25,27,29,31-40H,8H2/t20-,25-,27-,29-,30+/m1/s1
    Key: WODBGULXKVZGQF-QCPBNORNSA-N
  • 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
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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Procyanidin A1 is an A type proanthocyanidin dimer.

It is an epicatechin-(2β→7,4β→8)-catechin dimer found in Rhododendron spiciferum , [1] in peanut skins [2] and in Ecdysanthera utilis . [3]

Procyanidin B1 can be converted into procyanidin A1 by radical oxidation using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radicals under neutral conditions. [4]

References

  1. ↑ Liu, YZ; Cao, YG; Ye, JQ; Wang, WG; Song, KJ; Wang, XL; Wang, CH; Li, RT; Deng, XM (2009). "Immunomodulatory effects of proanthocyanidin A-1 derived in vitro from Rhododendron spiciferum". Fitoterapia. 81 (2): 108–14. doi:10.1016/j.fitote.2009.08.005. PMID   19686816.
  2. ↑ 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.
  3. ↑ 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.
  4. ↑ 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


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