Casuarinin

Last updated
Casuarinin
Casuarinin.png
Names
Other names
Stachyurin
Identifiers
3D model (JSmol)
PubChem CID
UNII
  • InChI=1S/C41H28O26/c42-11-1-7(2-12(43)23(11)47)37(58)64-16-6-63-38(59)8-3-13(44)24(48)27(51)17(8)18-9(4-14(45)25(49)28(18)52)39(60)65-34(16)36-35-32(56)22-21(41(62)66-35)20(30(54)33(57)31(22)55)19-10(40(61)67-36)5-15(46)26(50)29(19)53/h1-5,16,32,34-36,42-57H,6H2
    Key: MMQXBTULXAEKQE-UHFFFAOYSA-N
  • C1C(C(OC(=O)C2=CC(=C(C(=C2C3=C(C(=C(C=C3C(=O)O1)O)O)O)O)O)O)C4C5C(C6=C(C(=C(C(=C6C(=O)O5)C7=C(C(=C(C=C7C(=O)O4)O)O)O)O)O)O)O)OC(=O)C8=CC(=C(C(=C8)O)O)O
Properties
C41H28O26
Molar mass 936.64 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Casuarinin is an ellagitannin. It is found in the pericarp of pomegranates (Punica granatum). It is also found in Casuarina and Stachyurus species [1] and in Alnus sieboldiana . [2]

It is an isomer of casuarictin. It is a highly active carbonic anhydrase inhibitor. [3]

Biosynthesis

In some plants including oak and chestnut, the ellagitannins are formed from 1,2,3,4,6-pentagalloyl-glucose and further elaborated via oxidative dehydrogenation (tellimagrandin II and casuarictin formations). After conversion of casuarictin to pedunculagin, the pyranose ring of the glucose opens and the family of compounds including casuariin, casuarinin, castalagin, and castlin, vescalagin and vescalin forms. [4] [ self-published source? ]

Related Research Articles

Punicalagin Chemical compound

Punicalagin is an ellagitannin, a type of phenolic compound. It is found in forms alpha and beta in pomegranates, in Terminalia catappa and 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.

Carbonic anhydrase inhibitor Class of pharmaceuticals

Carbonic anhydrase inhibitors are a class of pharmaceuticals that suppress the activity of carbonic anhydrase. Their clinical use has been established as anti-glaucoma agents, diuretics, antiepileptics, in the management of mountain sickness, gastric and duodenal ulcers, idiopathic intracranial hypertension, neurological disorders, or osteoporosis.

Corilagin 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).

Casuarictin Chemical compound

Casuarictin is an ellagitannin, a type of hydrolysable tannin. It can be found in Casuarina and Stachyurus species.

<i>Stachyurus</i> Genus of flowering plants in the family Stachyuraceae

Stachyurus is the only genus in the flowering plant family Stachyuraceae, native to the Himalayas and eastern Asia. They are deciduous shrubs or small trees with pendent racemes of 4-petalled flowers which appear on the bare branches before the leaves. The plants have leaves with serrate margins.

Tellimagrandin II Chemical compound

Tellimagrandin II is the first of the ellagitannins formed from 1,2,3,4,6-pentagalloyl-glucose. It can be found in Geum japonicum and Syzygium aromaticum (clove).

Punigluconin Chemical compound

Punigluconin is an ellagitannin, a polyphenol compound. 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.

Punicacortein A Chemical compound

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

Punicalin 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.

Punicacortein C 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.

Punicacortein D 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.

Punicacortein B Chemical compound

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

Granatin A Chemical compound

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

Granatin B Chemical compound

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

Pomegranate ellagitannin 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 pomegranates.

Pedunculagin Chemical compound

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

Luteic acid Chemical compound

Luteic acid is a natural phenol found in numerous fruits. It is a monolactonized tergalloyl group. Maximilian Nierenstein showed in 1945 that luteic acid was a molecule present in the myrobalanitannin, a tannin found in the fruit of Terminalia chebula and is an intermediary compound in the synthesis of ellagic acid. It can form from hexahydroxydiphenic acid. It is also present in the structure of the tannins alnusiin and bicornin.

Alnusiin Chemical compound

Alnusiin is an ellagitannin found in Alnus sieboldiana.

<i>Alnus sieboldiana</i> Species of tree

Alnus sieboldiana is an alder species found on the islands of Honshū, Shikoku, and Suwanose-jima in Japan.

Bicornin Chemical compound

Bicornin is an ellagitannin found in the Myrtales Trapa bicornis and Syzygium aromaticum (clove).

References

  1. Okuda, T.; T. Yoshida; M. Ashida; K. Yazaki (1983). "Tannins of Casuarina and Stachyurus species. I: Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, and stachyurin". Journal of the Chemical Society (8): 1765–1772.
  2. 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)
  3. 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.
  4. Tannins chemistry by Hagerman A. E. Archived 2013-08-26 at the Wayback Machine