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P0023

Sigma-Aldrich

Punicalagin

≥98% (HPLC), from pomegranate

Empirical Formula (Hill Notation):
C48H28O30
CAS Number:
Molecular Weight:
1084.72
MDL number:
PubChem Substance ID:
NACRES:
NA.25

Quality Level

biological source

pomegranate

assay

≥98% (HPLC)

form

powder

color

faintly yellow to dark yellow

solubility

methanol: 5 mg/mL, clear

storage temp.

2-8°C

SMILES string

OC1O[C@@H]2COC(=O)c3cc(O)c(O)c(O)c3-c4c(O)c(O)c5OC(=O)c6c(c(O)c(O)c7OC(=O)c4c5-c67)-c8c(O)c(O)c(O)cc8C(=O)O[C@H]2[C@@H]9OC(=O)c%10cc(O)c(O)c(O)c%10-c%11c(O)c(O)c(O)cc%11C(=O)O[C@@H]19

InChI

1S/C48H28O30/c49-10-1-6-17(31(59)27(10)55)19-23-21-22-24(47(70)76-38(21)35(63)33(19)61)20(34(62)36(64)39(22)75-46(23)69)18-9(4-13(52)28(56)32(18)60)43(66)74-37-14(5-72-42(6)65)73-48(71)41-40(37)77-44(67)7-2-11(50)25(53)29(57)15(7)16-8(45(68)78-41)3-12(51)26(54)30(16)58/h1-4,14,37,40-41,48-64,71H,5H2/t14-,37-,40+,41-,48?/m1/s1

InChI key

ZJVUMAFASBFUBG-UYMKNUMKSA-N

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General description

Punicalagin is one of the main ellagitannins (ETs) or hydrolyzable tannins present in pomegranate. The chemical structure of punicalagin consists of gallagic acid and ellagic acid connected through a glucose molecule. It has two (α and β) isomeric forms that can be found in the pomegranate.

Application

Punicalagin has been used in the inhibition assay to check its anti-fungal effects on two C. albicans strains. It has also been used as a polyphenolic compound to probe pyroptosis in macrophages and monocytes.

Packaging

1, 10 mg in glass bottle

Biochem/physiol Actions

Punicalagin exhibits an antioxidant effect. Ellagitannins like punicalagin cannot be absorbed directly in humans. First, it converts to ellagic acid, which is further converted to bioavailable urolithin A derivative by human colonic microflora. It elicits an inhibitory effect on nuclear factor kappa-light-chain-enhancer of activated B cells (NF-κB) signaling pathway which in turn protects against cancer, neuroinflammation, oxidative stress and memory impairment. It has antimicrobial and antibiofilm activities against S. aureus.
Potent immune suppressant isolated from pomegranate.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

Gaihua Qin et al.
The Plant journal : for cell and molecular biology, 91(6), 1108-1128 (2017-06-28)
Pomegranate (Punica granatum L.) is a perennial fruit crop grown since ancient times that has been planted worldwide and is known for its functional metabolites, particularly punicalagins. We have sequenced and assembled the pomegranate genome with 328 Mb anchored into nine pseudo-chromosomes and annotated 29 229
Nathalia M de Vasconcelos et al.
Cell death and differentiation, 26(1), 146-161 (2018-04-19)
Pyroptosis is rapidly emerging as a mechanism of anti-microbial host defense, and of extracellular release of the inflammasome-dependent cytokines interleukin (IL)-1β and IL-18, which contributes to autoinflammatory pathology. Caspases 1, 4, 5 and 11 trigger this regulated form of necrosis
Rafaela Alves da Silva et al.
Oral diseases, 26(8), 1810-1819 (2020-06-26)
Oral candidiasis is the most common opportunistic fungal infection of oral mucosa and results from an overgrowth of Candida, especially Candida albicans. The potential anti-C. albicans and cytotoxicity of punicalagin (PCG), isolated from Punica granatum, alone or with nystatin (NYS) were evaluated. Activity of compounds alone
Antioxidant activity of pomegranate juice and punicalagin
Aloqbi A, et al.,
Nature and Science, 8(06), 235-235 (2016)
Yunfeng Xu et al.
Foodborne pathogens and disease, 14(5), 282-287 (2017-01-28)
Punicalagin, one of the main active compounds in pomegranate peel, has been reported to possess many properties, including antioxidant, antimicrobial, antiviral, and immunosuppressive activities. The aim of this study was to investigate the antibacterial effect of punicalagin against Staphylococcus aureus

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