Granatin B

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Granatin B
Granatin B.PNG
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
PubChem CID
  • InChI=1S/C41H28O27/c42-13-1-8(2-14(43)24(13)48)34(54)67-39-33-32-30(64-37(57)11-5-17(46)27(51)31-22(11)23-12(38(58)66-33)6-19(47)40(59,60)41(23,61)68-31)18(63-39)7-62-35(55)9-3-15(44)25(49)28(52)20(9)21-10(36(56)65-32)4-16(45)26(50)29(21)53/h1-6,18,23,30,32-33,39,42-46,48-53,59-61H,7H2/t18-,23?,30-,32+,33-,39+,41?/m1/s1
    Key: FFNTWLBZRJZJEJ-PYGBXMOSSA-N
  • C1[C@@H]2[C@@H]3[C@@H]([C@H]([C@@H](O2)OC(=O)C4=CC(=C(C(=C4)O)O)O)OC(=O)C5=CC(=O)C(C6(C5C7=C(O6)C(=C(C=C7C(=O)O3)O)O)O)(O)O)OC(=O)C8=CC(=C(C(=C8C9=C(C(=C(C=C9C(=O)O1)O)O)O)O)O)O
Properties
C41H28O27
Molar mass 952.648 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Granatin B is an ellagitannin found in the fruit of Punica granatum (pomegranate). [2] [3] It is a molecule having an enantiomeric dehydrohexahydroxydiphenoyl group. [4]

It is a highly active carbonic anhydrase inhibitor. [2]

Related Research Articles

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Punicalagin (Pyuni-cala-jen) is an ellagitannin, a type of phenolic compound. It is found as alpha and beta isomers in pomegranates, Terminalia catappa, Terminalia myriocarpa, and in Combretum molle, the velvet bushwillow, a plant species found in South Africa. These three genera are all Myrtales and the last two are both Combretaceae.

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<span class="mw-page-title-main">Ellagitannin</span> Diverse class of hydrolyzable tannins, a type of polyphenol

The ellagitannins are a diverse class of hydrolyzable tannins, a type of polyphenol formed primarily from the oxidative linkage of galloyl groups in 1,2,3,4,6-pentagalloyl glucose. Ellagitannins differ from gallotannins, in that their galloyl groups are linked through C-C bonds, whereas the galloyl groups in gallotannins are linked by depside bonds.

<span class="mw-page-title-main">Corilagin</span> Chemical compound

Corilagin is an ellagitannin. Corilagin was first isolated in 1951 from Dividivi extract and from Caesalpinia coriaria, hence the name of the molecule. It can also be found in Alchornea glandulosa and in the leaves of Punica granatum (pomegranate).

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<span class="mw-page-title-main">Punigluconin</span> Chemical compound

Punigluconin is an ellagitannin, a polyphenol compound.(pu-ni-glue-co-nin) It is found in the bark of Punica granatum (pomegranate) and in Emblica officinalis. It is a molecule having a hexahydroxydiphenic acid group and two gallic acids attached to a gluconic acid core.

<span class="mw-page-title-main">Punicacortein A</span> Chemical compound

Punicacortein A is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate) and in Osbeckia chinensis.

<span class="mw-page-title-main">Punicalin</span> Chemical compound

Punicalin is an ellagitannin. It can be found in Punica granatum (pomegranate) or in the leaves of Terminalia catappa, a plant used to treat dermatitis and hepatitis. It is also reported in Combretum glutinosum, all three species being Myrtales, the two last being Combretaceae.

<span class="mw-page-title-main">Punicacortein C</span> Chemical compound

Punicacortein C is an ellagitannin, a phenolic compound. It is found in the bark of Punica granatum (pomegranate). The molecule contains a gallagic acid component.

<span class="mw-page-title-main">Punicacortein D</span> Chemical compound

Punicacortein D is an ellagitannin, a type of phenolic compound. It is found in the bark and heartwood of Punica granatum (pomegranate). The molecule contains a gallagic acid component.

<span class="mw-page-title-main">Punicacortein B</span> Chemical compound

Punicacortein B is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate).

<span class="mw-page-title-main">Punicafolin</span> Chemical compound

Punicafolin is an ellagitannin from the leaves of Punica granatum (pomegranate) and in Phyllanthus emblica.

<span class="mw-page-title-main">Granatin A</span> Chemical compound

Granatin A is an ellagitannin found in the pericarp of Punica granatum (pomegranate). It is a weak carbonic anhydrase inhibitor.

<span class="mw-page-title-main">Pomegranate ellagitannin</span> Ellagitannins found in the pomegranate fruit

The pomegranate ellagitannins, which include punicalagin isomers, are ellagitannins found in the sarcotestas, rind (peel), bark or heartwood of the pomegranate fruit.

<span class="mw-page-title-main">Casuarinin</span> Chemical compound

Casuarinin is an ellagitannin. It is found in the pericarp of pomegranates. It is also found in Casuarina and Stachyurus species and in Alnus sieboldiana.

<span class="mw-page-title-main">Pedunculagin</span> Chemical compound

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

<span class="mw-page-title-main">Carbonic anhydrase</span> Class of enzymes

The carbonic anhydrases form a family of enzymes that catalyze the interconversion between carbon dioxide and water and the dissociated ions of carbonic acid. The active site of most carbonic anhydrases contains a zinc ion. They are therefore classified as metalloenzymes. The enzyme maintains acid-base balance and helps transport carbon dioxide.

<span class="mw-page-title-main">Tellimagrandin I</span> Chemical compound

Tellimagrandin I is an ellagitannin found in plants, such as Cornus canadensis, Eucalyptus globulus, Melaleuca styphelioides, Rosa rugosa, and walnut. It is composed of two galloyl and one hexahydroxydiphenyl groups bound to a glucose residue. It differs from Tellimagrandin II only by a hydroxyl group instead of a third galloyl group. It is also structurally similar to punigluconin and pedunculagin, two more ellagitannin monomers.

References

  1. ↑ www.chemicalbook.com
  2. 1 2 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.
  3. ↑ Steinmetz, W. E. (2010). "NMR assignment and characterization of proton exchange of the ellagitannin granatin B". Magnetic Resonance in Chemistry. 48 (7): 565–570. doi:10.1002/mrc.2615. PMID   20535776. S2CID   19592324.
  4. ↑ Okuda, T.; Hatano, T.; Nitta, H.; Fujii, R. (1980). "Hydrolysable tannins having enantiomeric dehydrohexahydroxydiphenoyl group: Revised structure of terchebin and structure of granatin B". Tetrahedron Letters. 21 (45): 4361. doi:10.1016/S0040-4039(00)77858-0.


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