Punicacortein A

Punicacortein A
Names

IUPAC name (1R,2R)-1-[(14S,15S,19S)-2,3,4,7,8,9,19-Heptahydroxy-12,17-dioxo-13,16-dioxatetracyclo[13.3.1.0^5,18.0^6,11]nonadeca-1(18),2,4,6,8,10-hexaen-14-yl]-1,3-dihydroxy-2-propanyl 3,4,5-trihydroxybenzoate
Identifiers
CAS Number	unspec: 103488-35-3^N
3D model (JSmol)	Interactive image
ChemSpider	16738325
PubChem CID	14035447
CompTox Dashboard (EPA)	DTXSID601030153
InChI InChI=1S/C27H22O18/c28-4-10(43-25(40)5-1-7(29)15(32)8(30)2-5)17(34)23-24-21(38)14-13(27(42)45-24)12(19(36)22(39)20(14)37)11-6(26(41)44-23)3-9(31)16(33)18(11)35/h1-3,10,17,21,23-24,28-39H,4H2/t10-,17-,21+,23+,24+/m1/s1 Key: TXPZOUVETLGUPE-MEZSAOBOSA-N
SMILES Oc1cc(cc(O)c1O)C(=O)O[C@H](CO)[C@@H](O)[C@@H]5OC(=O)c2cc(O)c(O)c(O)c2c3c(O)c(O)c(O)c4[C@H](O)[C@@H]5OC(=O)c34
Properties
Chemical formula	C₂₇H₂₂O₁₈
Molar mass	634.43 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Chemical compound

Punicacortein A is an ellagitannin, a polyphenol compound. It is found in the bark of Punica granatum (pomegranate)^[1] and in Osbeckia chinensis.^[2]

References

^ Tannins and Related Compounds. XLI. : Isolation and Characterization of Novel Ellagitannins, Punicacorteins A, B, C, and D, and Punigluconin from the Bark of Punica granatum L. Tanaka Takashi, Nonaka Gen-Ichiro and Nishioka Itsuo, Chemical & Pharmaceutical Bulletin, 1986-02-25, 34(2), pages 656-663 (abstract)
^ Tannin antioxidants from Osbeckia chinensis. Jeng-De Su, Toshihiko Osawa, Shunro Kawakishi and Mitsuo Namiki, Phytochemistry, Volume 27, Issue 5, 1988, Pages 1315–1319, doi:10.1016/0031-9422(88)80184-5

Types of ellagitannins

Moieties

Diphenolic acid : Hexahydroxydiphenic acid (HHDP)
Triphenolic acids : Nonahydroxytriphenic acid
Sanguisorbic acid
Valoneic acid
Tetraphenolic acids : Isoterchebulic acid
Terchebulinic acid

Lactones

Ellagic acid
Gallagic acid
Gallagic acid dilactone
Luteic acid
Sanguisorbic acid dilactone
Valoneic acid dilactone

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

C-glycosidic ellagitannins

Castalagin (Vescalagin)
Castalin
Casuariin
Casuarinin
Punicacortein A, B, C and D

Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)

Alnicortin
Euphorbin A
Euphorscopin
Excoecarianin
Geraniin
Granatin A and B
Helioscopinin A
Mallotusinic acid
Supinanin
Terchebin

Transformed ellagitannins

molecules with chebulic acid	Chebulagic acid Chebulinic acid
molecules with Elaeocarpusinic acid	Elaeocarpusin Helioscopin B Mallojaponin (1-O-Galloyl-2,4-elaeocarpusinoyl-3,6-(R)-valoneayl-beta-D-glucose)

Oligomers

Dimers: Agrimoniin; Cornusiin E (dimer of tellimagrandin II); Lambertianin A and B; Nobotanin B; Roburin A, B, C and D; Sanguiin H-6

Trimers: Lambertianin C; Raspberry ellagitannin

Tetramers: Lambertianin D; Nobotanin S

Pentamer: Melastoflorin A

Other

v t e Types of pomegranate ellagitannins
Aglycones	Ellagic acid Gallagic acid Gallic acid Hexahydroxydiphenic acid
Sugars	Glucose Gluconic acid
Examples	Casuarinin Gallagyldilactone Granatin A and B Pedunculagin Punicacortein A, B, C and D 5-O-galloylpunicacortein D Punicafolin Punigluconin Punicalagin 1-alpha-O-Galloylpunicalagin Punicalin 2-O-galloyl-punicalin Strictinin