Pedunculagin

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Pedunculagin
Chemical structure of pedunculagin
Identifiers
Jmol-3D images Image
PubChem 442688
Properties
C34H24O22
Molar mass 784.54 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.

Natural occurrences[edit]

Pedunculagin is found in plants in orders in the clade Rosidae. It can be found the pericarp of pomegranates (Punica granatum), in the family Lythraceae, in the order Myrtales.[1] It is also found in plants in the order Fagales such as walnuts (Juglans regia) in the family Juglandaceae,[2] in Alnus sieboldiana[3] and in the Manchurian alder (Alnus hirsuta var. microphylla), both species in the family Betulaceae[4] and it is one of the main oak wood ellagitannins along with castalagin, vescalagin, grandinin and roburins A-E (genus Quercus, in the family Fagaceae).[5] It is also found in the Indian gooseberry (Phyllanthus emblica), a plant in the family Phyllanthaceae, in the order Malpighiales.[6]

Galloyl pedunculagin can be found in Platycarya strobilacea.[7]

Health effect[edit]

It is a highly active carbonic anhydrase inhibitors.[1]

Chemistry[edit]

It is an isomer of terflavin B. It can be synthetized.[8]

References[edit]

  1. ^ a b Satomi, H.; Umemura, K.; Ueno, A.; Hatano, T.; Okuda, T.; Noro, T. (1993). "Carbonic anhydrase inhibitors from the pericarps of Punica granatum L". Biological & Pharmaceutical Bulletin 16 (8): 787–790. doi:10.1248/bpb.16.787. PMID 8220326. 
  2. ^ Cerdá, B. A.; Tomás-Barberán, F. A.; Espín, J. C. (2005). "Metabolism of Antioxidant and Chemopreventive Ellagitannins from Strawberries, Raspberries, Walnuts, and Oak-Aged Wine in Humans: Identification of Biomarkers and Individual Variability". Journal of Agricultural and Food Chemistry 53 (2): 227–235. doi:10.1021/jf049144d. PMID 15656654. 
  3. ^ Structures of alnusiin and bicornin, new hydrolyzable tannins having a monolactonized tergalloyl group. Yoshida T, Yazaki K, Memon M.U, Maruyama I, Kurokawa K, Shingu T and Okuda T, Chemical and pharmaceutical bulletin, 1989, volume 37, number 10, pages 2655-2660, INIST:19467830 (abstract)
  4. ^ Lee, O.; Choi, M.; Ha, S.; Lee, G.; Kim, J.; Park, G.; Lee, M.; Choi, Y.; Kim, M.; Oh, C. H. (2010). "Effect of pedunculagin investigated by non-invasive evaluation on atopic-like dermatitis in NC/Nga mice". Skin Research and Technology 16 (3): 371–377. doi:10.1111/j.1600-0846.2010.00443.x. PMID 20637007. 
  5. ^ Azorín-Ortuño, M. A.; Urbán, C.; Cerón, J. J.; Tecles, F.; Gil-Izquierdo, A.; Pallarés, F. J.; Tomás-Barberán, F. A.; Espín, J. C. (2008). "Safety Evaluation of an Oak-Flavored Milk Powder Containing Ellagitannins upon Oral Administration in the Rat". Journal of Agricultural and Food Chemistry 56 (8): 2857–2865. doi:10.1021/jf8000857. PMID 18370397. 
  6. ^ Bhattacharya, A.; Chatterjee, A.; Ghosal, S.; Bhattacharya, S. K. (1999). "Antioxidant activity of active tannoid principles of Emblica officinalis (amla)". Indian journal of experimental biology 37 (7): 676–680. PMID 10522157. 
  7. ^ Ueno, T.; Miyanaga, T.; Kawakami, F.; Okano, M.; Tanaka, T.; Ohtsuki, K. (2002). "Further characterization of galloyl pedunculagin as an effective autophosphorylation inhibitor of C-kinase in vitro". Biological & pharmaceutical bulletin 25 (11): 1401–1404. doi:10.1248/bpb.25.1401. PMID 12419947. 
  8. ^ Feldman, K. S.; Smith, R. S. (1996). "Ellagitannin Chemistry. First Total Synthesis of the 2,3- and 4,6-Coupled Ellagitannin Pedunculagin". The Journal of Organic Chemistry 61 (8): 2606–2612. doi:10.1021/jo952130+. PMID 11667089.