Procyanidin A1
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| Procyanidin A1 | ||
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| 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 | ||
| CAS number | 103883-03-0  | |
| PubChem | 637122 | |
| Jmol-3D images | {{#if: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|Image 1 | |
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| Properties | ||
| Molecular formula | C30H24O12 | |
| Molar mass | 576.50 g mol−1 | |
(verify) (what is:  /?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa) | ||
| Infobox references | ||
Procyanidin A1 is a A type proanthocyanidin dimer.
It is an epicatechin-(2β→7,4β→8)-epicatechin 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
- ↑ Liu, YZ; Cao, YG; Ye, JQ; Wang, WG; Song, KJ; Wang, XL; Wang, CH; Li, RT et al. (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.
- ↑ 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.
- ↑ Lin, Lie-Chwen; Kuo, Yuh-Chi; Chou, Cheng-Jen (2002). "Immunomodulatory Proanthocyanidins fromEcdysantherautilis". Journal of Natural Products 65 (4): 505–8. doi:10.1021/np010414l. PMID 11975489.
- ↑ 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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