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P0023

Sigma-Aldrich

Punicalagin

≥98% (HPLC), from pomegranate

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About This Item

Empirical Formula (Hill Notation):
C48H28O30
CAS Number:
65995-63-3
Molecular Weight:
1084.72
MDL number:
MFCD09838017
UNSPSC Code:
12352205
PubChem Substance ID:
329819978
NACRES:
NA.25
Pricing and availability is not currently available.

biological source

pomegranate

Quality Level

100

Assay

≥98% (HPLC)

form

powder

color

faintly yellow to dark yellow

solubility

methanol: 5 mg/mL, clear

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

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.[1][2] 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.[3][4]

Application

Punicalagin has been used in the inhibition assay to check its anti-fungal effects on two C. albicans strains.[5] It has also been used as a polyphenolic compound to probe pyroptosis in macrophages[6] and monocytes.[7]

Biochem/physiol Actions

Potent immune suppressant isolated from pomegranate.
Punicalagin exhibits an antioxidant effect.[1][2] 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.[8] 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,[9] neuroinflammation, oxidative stress and memory impairment.[10] It has antimicrobial and antibiofilm activities against S. aureus.[11]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Choose from one of the most recent versions:

Certificates of Analysis (COA)

Lot/Batch Number
WXBF1309V
WXBD7254V
WXBD3150V
WXBD1235V
WXBC9041V

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NAMI-A ≥98% ruthenium (Ru) basis (elemental analysis)

Sigma-Aldrich

SML2090

NAMI-A

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
Young Eun Kim et al.
Neuropharmacology, 117, 21-32 (2017-01-31)
Neuroinflammation is significant in the pathogenesis and development of Alzheimer's disease (AD). Previously, we showed lipopolysaccharide (LPS)-induced neuroinflammation caused memory impairment. We investigated the possible preventive effects of punicalagin (PUN), a component of pomegranate, on memory deficiency caused by LPS
EFFECTIVE COMPOUNDS OF POMEGRANATE AND THEIR EFFECT ON ANIMAL CELLS
Packova D, et al.,
Journal of Microbiology, Biotechnology and Food Sciences, 2019, 142-144 (2019)
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
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
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Questions

1–3 of 3 Questions  

  1. How is shipping temperature determined? And how is it related to the product storage temperature?

    1 answer

    1. Products may be shipped at a different temperature than the recommended long-term storage temperature. If the product quality is sensitive to short-term exposure to conditions other than the recommended long-term storage, it will be shipped on wet or dry-ice. If the product quality is NOT affected by short-term exposure to conditions other than the recommended long-term storage, it will be shipped at ambient temperature. As shipping routes are configured for minimum transit times, shipping at ambient temperature helps control shipping costs for our customers. For more information, please refer to the Storage and Transport Conditions document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/316/622/storage-transport-conditions-mk.pdf

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  2. How can I determine the shelf life / expiration / retest date of this product?

    1 answer

    1. If this product has an expiration or retest date, it will be shown on the Certificate of Analysis (COA, CofA). If there is no retest or expiration date listed on the product's COA, we do not have suitable stability data to determine a shelf life. For these products, the only date on the COA will be the release date; a retest, expiration, or use-by-date will not be displayed.
      For all products, we recommend handling per defined conditions as printed in our product literature and website product descriptions. We recommend that products should be routinely inspected by customers to ensure they perform as expected.
      For products without retest or expiration dates, our standard warranty of 1 year from the date of shipment is applicable.
      For more information, please refer to the Product Dating Information document: https://www.sigmaaldrich.com/deepweb/assets/sigmaaldrich/marketing/global/documents/449/386/product-dating-information-mk.pdf

      Helpful?

  3. Is it good to penetrate the cell membrane in cell culture of HepG2 cells or which type of Punicalagin should i use ?

    1 answer

    1. No specific cell membrane permeability studies have been performed using Punicalagin. A review of the scientific literature does indicate an application involving punicalagin treatment of HepG2 cells using this product for a study involving lipid droplet and lipotoxicity. Please see the citation for this article below.

      I. Korovila, T. Jung, S. Deubel, T. Grune, C. Ott, Punicalagin Attenuates Palmitate-Induced Lipid Droplet Content by Simultaneously Improving Autophagy in Hepatocytes. Mol. Nutr. Food Res. 2020, 64, 2000816. https://doi.org/10.1002/mnfr.202000816

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