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. The dehydrated tergallic acid C-glucoside and tergallic acid O-glucoside can be characterised in the acorns of Quercus macrocarpa. Dehydrated tergallic-C-glucoside (m/z 613) can be found in the cork from Quercus suber.

Tergallic acid glucosides can also be found in Terminalia chebula.

Tergallic acid dilactone can be found in Rhynchosia volubilis seeds.

The chemical formula is not the same as given by Kinjo et al. (molecule with an ether link between the ellagic and gallic acid residues) or by Cantos, Chapman and Fernandes et al. (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. called the molecule with a carbon-carbon link flavogallonic acid dilactone.

References

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.
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.
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.
↑ Terminalia chebula on www.mmh-mms.com
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. hdl:10069/8375. PMID 11767121. INIST 13400364.
↑ 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. S2CID 19496595.

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[Cantos-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.

[Chapman-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.

[Fernandes-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

[Kinjo-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. hdl:10069/8375. 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. S2CID 19496595.