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Casuarinin

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]

Casuarinin
Names
Other names
Stachyurin
Identifiers
  • 79786-01-9 Y
  • 81739-27-7 Y
3D model (JSmol)
  • Interactive image
  • 157395
UNII
  • S45A8T6Q4C Y
  • DTXSID101000731
  • 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).

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

Biosynthesis edit

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?]

References edit

  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. 2013-08-26 at the Wayback Machine

casuarinin, ellagitannin, found, pericarp, pomegranates, punica, granatum, also, found, casuarina, stachyurus, species, alnus, sieboldiana, names, other, names, stachyurin, identifiers, number, 79786, y81739, model, jsmol, interactive, image, pubchem, 157395, . 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 Casuarinin Names Other names Stachyurin Identifiers CAS Number 79786 01 9 Y81739 27 7 Y 3D model JSmol Interactive image PubChem CID 157395 UNII S45A8T6Q4C Y CompTox Dashboard EPA DTXSID101000731 InChI 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 6H2Key MMQXBTULXAEKQE UHFFFAOYSA N SMILES 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 Chemical formula 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 Infobox references It is an isomer of casuarictin It is a highly active carbonic anhydrase inhibitor 3 Biosynthesis editIn 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 References edit 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 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 Satomi H Umemura K Ueno A Hatano T Okuda T Noro T 1993 Carbonic anhydrase inhibitors from the pericarps of Punica granatum L Biological amp Pharmaceutical Bulletin 16 8 787 790 doi 10 1248 bpb 16 787 PMID 8220326 Tannins chemistry by Hagerman A E Archived 2013 08 26 at the Wayback Machine Retrieved from https en wikipedia org w index php title Casuarinin amp oldid 1105343543, wikipedia, wiki, book, books, library,

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