Pedunculagin
| |
| Identifiers | |
|---|---|
3D model (JSmol)
|
|
| ChEBI | |
| ChEMBL | |
| ChemSpider | |
| KEGG | |
PubChem CID
|
|
| UNII | |
CompTox Dashboard (EPA)
|
|
| |
| |
| Properties | |
| C34H24O22 | |
| Molar mass | 784.544 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
| |
Pedunculagin is an ellagitannin. It is formed from casuarictin via the loss of a gallate group.
Natural occurrence[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]
Research[edit]
Pedunculagin is a highly active carbonic anhydrase inhibitor in vitro.[1]
Chemistry[edit]
A total synthesis of pedunculagin has been reported.[8]
Pedunculagin is an isomer of terflavin B.
References[edit]
- ^ 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.
- ^ 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.
- ^ 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)
- ^ 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. S2CID 25752299.
- ^ 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.
- ^ 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.
- ^ 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. hdl:10069/8378. PMID 12419947.
- ^ 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.