Punigluconin - Misplaced Pages

Punigluconin
Names

Systematic IUPAC name (2R,3S)-3-dioxacycloundecin-7-yl]-2,3-bispropanoic acid
Other names 2,5-di-O-galloyl-4,6-O-(S)-hexahydroxy-diphenoyl-D-gluconic acid
Identifiers
CAS Number	103488-38-6
3D model (JSmol)	Interactive image
ChemSpider	10272889
PubChem CID	44631480
UNII	9D6FCK37Q3
CompTox Dashboard (EPA)	DTXSID50616539
InChI InChI=1S/C34H26O23/c35-12-1-8(2-13(36)21(12)42)31(50)56-28(29(30(48)49)57-32(51)9-3-14(37)22(43)15(38)4-9)27-18(41)7-54-33(52)10-5-16(39)23(44)25(46)19(10)20-11(34(53)55-27)6-17(40)24(45)26(20)47/h1-6,18,27-29,35-47H,7H2,(H,48,49)/t18-,27-,28+,29-/m1/s1Key: KZEYIYXACMUTRM-WIMKJKQSSA-N
SMILES Oc1cc(cc(O)c1O)C(=O)O(C(O)=O)(OC(=O)c2cc(O)c(O)c(O)c2)4OC(=O)c5cc(O)c(O)c(O)c5c3c(O)c(O)c(O)cc3C(=O)OC4O
Properties
Chemical formula	C₃₄H₂₆O₂₃
Molar mass	802.53 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

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.

References

^ Tanaka Takashi; Tong Hui-Hong; Xu Ya-Ming; Ishimaru Kanji; Nonaka Gen-ichiro; Nishioka Itsuo (1992-11-25). "Tannins and Related Compounds. CXVII. Isolation and Characterization of Three New Ellagitannins, Lagerstannins A, B and C, Having a Gluconic Acid Core, from Lagerstroemia speciosa (L.) PERS". Chemical & Pharmaceutical Bulletin. 40 (11): 2975–2980. doi:10.1248/cpb.40.2975.
Tanaka Takashi, Nonaka Gen-Ichiro & Nishioka Itsuo (1986-02-25). "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". Chemical & Pharmaceutical Bulletin. 34 (2): 656–663. doi:10.1248/cpb.34.656.
Bhattacharya, A; Chatterjee, A; Ghosal, S; Bhattacharya, SK (1999). "Antioxidant activity of active tannoid principles of Emblica officinalis (amla)". Indian Journal of Experimental Biology. 37 (7): 676–80. PMID 10522157.

Moieties

Lactones

Monomers

C-glycosidic ellagitannins

Dehydroellagitannins (molecules with
dehydrohexahydroxydiphenic acid (DHHDP)

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

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

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