Pedunculagin

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Pedunculagin
Chemical structure of pedunculagin
Identifiers
ChemSpider 391045
Jmol 3D model Interactive image
PubChem 442688
  • InChI=1S/C34H24O22/c35-10-1-6-15(23(43)19(10)39)16-7(2-11(36)20(40)24(16)44)31(48)54-27-14(5-52-30(6)47)53-34(51)29-28(27)55-32(49)8-3-12(37)21(41)25(45)17(8)18-9(33(50)56-29)4-13(38)22(42)26(18)46/h1-4,14,27-29,34-46,51H,5H2/t14-,27-,28+,29-,34?/m1/s1
    Key: IYMHVUYNBVWXKH-ZITZVVOASA-N
  • InChI=1/C34H24O22/c35-10-1-6-15(23(43)19(10)39)16-7(2-11(36)20(40)24(16)44)31(48)54-27-14(5-52-30(6)47)53-34(51)29-28(27)55-32(49)8-3-12(37)21(41)25(45)17(8)18-9(33(50)56-29)4-13(38)22(42)26(18)46/h1-4,14,27-29,34-46,51H,5H2/t14-,27-,28+,29-,34?/m1/s1
    Key: IYMHVUYNBVWXKH-ZITZVVOABK
  • c1c2c(c(c(c1O)O)O)-c3c(cc(c(c3O)O)O)C(=O)O[C@@H]4[C@@H](COC2=O)OC([C@H]5[C@H]4OC(=O)c6cc(c(c(c6-c7c(cc(c(c7O)O)O)C(=O)O5)O)O)O)O
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

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

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

Chemistry

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

References

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  1. ↑ 1.0 1.1 Lua error in package.lua at line 80: module 'strict' not found.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  7. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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