Tergallic acid

Tergallic acid
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Tergallic acid a trimer of the gallic acid being connected with glucose. 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. ^ a b Phenolic compounds and fatty acids from acorns (Quercus spp.), the main dietary constituent of free-ranged Iberian pigs. Cantos E, Espín JC, López-Bote C, de la Hoz L, Ordóñez JA and Tomás-Barberán FA, J Agric Food Chem. 2003 Oct 8, 51(21), pp. 6248-6255, PubMed, doi:10.1021/jf030216v
  2. ^ a b Application of LC/ESI/MS and LC/EI/MS to the Characterization of Tannins and Flavonoids from the Acorns of Quercus macrocapra. James M. Chapman, Joshua R. Nast, Chad Scholes and Scott Niemann
  3. ^ a b Analysis of phenolic compounds in cork from Quercus suber L. by HPLC–DAD/ESI–MS. Ana Fernandes, André Sousa, Nuno Mateus, Miguel Cabral and Victor de Freitas, Food Chemistry,Volume 125, Issue 4, 15 April 2011, pp. 1398-1405, doi:10.1016/j.foodchem.2010.10.016
  4. ^ Terminalia chebula on www.mmh-mms.com
  5. ^ a b Antiproliferative constituents in the plant 8. Seeds of Rhynchosia volubilis. Kinjo Junei, Nagao Tsuneatsu, Tanaka Takashi, Nonaka Gen-Ichiro and Okabe Hikaru, Biological & pharmaceutical bulletin, 2001, vol. 24, no12, pp. 1443-1445, INIST:13400364 , doi:10.1248/bpb.24.1443
  6. ^ The use of microfluorometric method for activity-guided isolation of antiplasmodial compound from plant extracts. M. N. Shuaibu, P. A. Wuyep, T. Yanagi, K. Hirayama, T. Tanaka and I. Kouno, Parasitol Res (2008) 102, pp. 1119–1127, doi:10.1007/s00436-008-0879-6
Types of ellagitannins
Aglycones
Ellagic acid | Gallagic acid | Hexahydroxydiphenic acid | Terchebulinic acid | Tergallic acid
Examples
Acetonyl geraniin | Castalagin (Vescalagin) | Castalin | Casuarictin | Casuariin | Casuarinin | Cornusiin E | Elaeocarpusin | Euphorscopin | Geraniin | Grandinin | Helioscopin B, Helioscopinin A | Helioscopinin B | Jolkinin | Lambertianin C | Macranganin | Pedunculagin | Punicacortein C | Punigluconin | Punicalagin | 1-alpha-O-galloylpunicalagin | Punicalin | 2-O-galloyl-punicalin | Raspberry ellagitannin | Roburin A | Roburin B | Roburin C | Roburin D | Roburin E | Rugosin E | Sanguiin H-6 | Stachyurin | Strictinin | Supinanin | Tellimagrandin II | Teracatain | Terchebulin | Terflavin A | Terflavin B
Other