Casuarictin
Casuarictin
Names
Systematic IUPAC name
(10aR ,11S ,12aR ,25aR ,25bS )-2,3,4,5,6,7,17,18,19,20,21,22-Dodecahydroxy-9,15,24,27-tetraoxo-9,10a,11,12a,13,15,24,25a,25b,27-decahydrodibenzo[g ,i ]dibenzo[6′,7′:8′,9′][1,4]dioxecino[2′,3′:4,5]pyrano[3,2-b ][1,5]dioxacycloundecin-11-yl 3,4,5-trihydroxybenzoate
Other names
Sanguiin H 11 Sanguiin H-11 1(β)-O -Galloylpedunculagin
Identifiers
ChEMBL
ChemSpider
InChI=1S/C41H28O26/c42-13-1-8(2-14(43)24(13)48)36(57)67-41-35-34(65-39(60)11-5-17(46)27(51)31(55)22(11)23-12(40(61)66-35)6-18(47)28(52)32(23)56)33-19(63-41)7-62-37(58)9-3-15(44)25(49)29(53)20(9)21-10(38(59)64-33)4-16(45)26(50)30(21)54/h1-6,19,33-35,41-56H,7H2/t19-,33-,34+,35-,41+/m1/s1
N Key: SWRFKGRMQVLMKA-JIZJWZDPSA-N
N InChI=1/C41H28O26/c42-13-1-8(2-14(43)24(13)48)36(57)67-41-35-34(65-39(60)11-5-17(46)27(51)31(55)22(11)23-12(40(61)66-35)6-18(47)28(52)32(23)56)33-19(63-41)7-62-37(58)9-3-15(44)25(49)29(53)20(9)21-10(38(59)64-33)4-16(45)26(50)30(21)54/h1-6,19,33-35,41-56H,7H2/t19-,33-,34+,35-,41+/m1/s1
Key: SWRFKGRMQVLMKA-JIZJWZDPBX
c1c(cc(c(c1O)O)O)C(=O)O[C@H]2[C@H]3[C@H]([C@H]4[C@H](O2)COC(=O)c5cc(c(c(c5-c6c(cc(c(c6O)O)O)C(=O)O4)O)O)O)OC(=O)c7cc(c(c(c7-c8c(cc(c(c8O)O)O)C(=O)O3)O)O)O
Properties
C41 H28 O26
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).
Chemical compound
Casuarictin is an ellagitannin , a type of hydrolysable tannin. It can be found in Casuarina and Stachyurus species.[ 1]
It is formed from two hexahydroxydiphenic acid units and one gallic acid unit linked to a glucose molecule.
The molecule is formed from tellimagrandin II , itself formed from pentagalloyl glucose via oxidation. Casuarictin is transformed into pedunculagin via loss of a gallate group, and further into castalagin via glucose pyranose ring opening.
Oligomers
Sanguiin H-6 is a dimer, Lambertianin C is trimer and lambertianin D is a tetramer of casuarictin.
References
^ Tannins of Casuarina and Stachyurus species. I: Structures of pendunculagin, casuarictin, strictinin, casuarinin, casuariin, and stachyurin. Okuda T., Yoshida T., Ashida M. and Yazaki K., Journal of the Chemical Society, 1983, number 8, pages 1765-1772, INIST 9467908
Moieties Lactones Monomers
Acetonyl geraniin
Alnusiin
Bicornin
Carlesiin
Casuarictin
Emblicanin A and B
Euscaphinin
Galloyl pedunculagin
Grandinin
Helioscopinin B
Jolkinin
Lagerstannin A , B and C
Macranganin
Myrobalanitannin
Nupharin A , B , C , D , E and F
Pedunculagin
Punicalagin
Punigluconin
Phyllanemblinin A , B , C , D , E and F
Punicalin
Roburin E
Rugosin E
Sanguiin H-5
Stenophyllanin A , B and C
Strictinin
Tellimagrandin I and II
Teracatain
Terchebulin
Terflavin A and B
Tergallic acid
Tergallic acid dilactone
Oligomers Other