Tergallic acid

Tergallic acids are trimers of gallic acid, often found naturally in the form of glycosides. Tergallic acid O- or C-glucosides that can be found in acorns of several Quercus (oak) species.[1] The dehydrated tergallic acid C-glucoside and tergallic acid O-glucoside can be characterised in the acorns of Quercus macrocarpa.[2] Dehydrated tergallic-C-glucoside (m/z 613) can be found in the cork from Quercus suber.[3]

Tergallic acid glucosides can also be found in Terminalia chebula.[4]

Tergallic acid dilactone can be found in Rhynchosia volubilis seeds.[5]

The chemical formula is not the same as given by Kinjo et al.[5] (molecule with an ether link between the ellagic and gallic acid residues) or by Cantos,[1] Chapman[2] and Fernandes et al.[3] (molecule with a carbon-carbon link). Cantos, Fernandes and Chapman called the molecule with an ether link valoneic acid dilactone while Kinjo and Shuaibu et al.[6] called the molecule with a carbon-carbon link flavogallonic acid dilactone.

References

  1. 1 2 Cantos, E.; Espín, J. C.; López-Bote, C.; de la Hoz, L.; Ordóñez, J. A.; Tomás-Barberán, F. A. (2003). "Phenolic Compounds and Fatty Acids from Acorns (Quercus spp.), the Main Dietary Constituent of Free-Ranged Iberian Pigs". Journal of Agricultural and Food Chemistry. 51 (21): 6248–6255. doi:10.1021/jf030216v. PMID 14518951.
  2. 1 2 Chapman, J. M.; Nast, J. R.; Scholes, C.; Niemann, S. (2006). "Application of LC/ESI/MS and LC/EI/MS to the Characterization of Tannins and Flavonoids from the Acorns of Quercus macrocarpa" (pdf). Rockhurst University.
  3. 1 2 Fernandes, A.; Sousa, A.; Mateus, N.; Cabral, M.; de Freitas, V. (2011). "Analysis of Phenolic Compounds in Cork from Quercus suber L. by HPLC–DAD/ESI–MS". Food Chemistry. 125 (4): 1398–1405. doi:10.1016/j.foodchem.2010.10.016.
  4. ↑ Terminalia chebula on www.mmh-mms.com
  5. 1 2 Kinjo, J.; Nagao, T.; Tanaka, T.; Nonaka, G.; Okabe, H. (2001). "Antiproliferative Constituents in the Plant 8. Seeds of Rhynchosia volubilis" (pdf). Biological & Pharmaceutical Bulletin. 24 (12): 1443–1445. doi:10.1248/bpb.24.1443. PMID 11767121. INIST:13400364.
  6. ↑ Shuaibu, M. N.; Wuyep, P. A.; Yanagi, T.; Hirayama, K.; Tanaka, T.; Kouno, I. (2008). "The use of microfluorometric method for activity-guided isolation of antiplasmodial compound from plant extracts". Parasitology Research. 102 (6): 1119–1127. doi:10.1007/s00436-008-0879-6. PMID 18214539.


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