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Merck
CN

SMB01357

Sigma-Aldrich

Curcumin glucuronide

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别名:
4-[(1E,6E)-7-(4-Hydroxy-3-methoxyphenyl)-3,5-dioxo-1,6-heptadien-1-yl]-2-methoxyphenyl β-D-glucopyranosiduronic acid, Curcumin-beta-D-glucuronide
经验公式(希尔记法):
C27H28O12
分子量:
544.50
UNSPSC代码:
12352205
NACRES:
NA.22

形式

powder

质量水平

储存温度

2-8°C

SMILES字符串

O[C@@H]1[C@@H](O)[C@H](OC2=CC=C(/C=C/C(CC(/C=C/C3=CC=C(O)C(OC)=C3)=O)=O)C=C2OC)O[C@H](C(O)=O)[C@H]1O

InChI

1S/C27H28O12/c1-36-20-11-14(5-9-18(20)30)3-7-16(28)13-17(29)8-4-15-6-10-19(21(12-15)37-2)38-27-24(33)22(31)23(32)25(39-27)26(34)35/h3-12,22-25,27,30-33H,13H2,1-2H3,(H,34,35)/b7-3+,8-4+/t22-,23-,24+,25-,27+/m0/s1

InChI key

BNSAVBGHRVFVNN-XSCLDSQRSA-N

一般描述

Curcumin glucuronide, a diarylheptanoid, is a major conjugated metabolite of Curcumin, present in hepatic tissue, human blood plasma, and urine following oral intake. Curcumin, a potent antioxidant and anti-inflammatory agent, faces bioavailability challenges due to poor solubility and rapid metabolism. Curcumin glucuronide, featuring a glucuronic acid moiety attached to curcumin′s phenolic hydroxyl groups, offers improved solubility and stability, making it a promising candidate for drug discovery research in the fields of biochemical and biomedical sciences. Additionally, it regulates enzymes involved in fatty acid and cholesterol metabolism, impacts transcription factors, and interacts with immune system regulators. Its potential in combating inflammation, oxidative stress, and cell death is of interest for researching cardiovascular disease, cancer, diabetes, Alzheimer′s disease, and cognitive function. Intriguingly, while in vitro studies suggest conjugated curcumin′s reduced efficacy against tumor cells, in vivo, these metabolites significantly enhance curcumin′s therapeutic activity, due to enzymes like β-glucuronidase/sulfatases swiftly activating the curcumin compound.

应用

Curcumin glucuronide finds application in metabolomics, oncology, phytochemical and drug discovery research.

生化/生理作用

Studies have demonstrated that Curcumin β-D-glucuronide exhibits anticancer properties in mouse tumor models and human metastatic colorectal cancer cell lines by promoting apoptosis. Additionally, it has shown potential as a colon cancer prevention agent through metabolism by rat liver microsomes. This compound also possesses anti-inflammatory attributes attributed to its ability to inhibit prostaglandin E2 (PGE2) levels in humans.

特点和优势

  • High quality compound suitable for multiple research applications
  • Compatible with a wide variety of chromatographic and spectrometry techniques

其他说明

For additional information on our range of Biochemicals, please complete this form.
This product is intended for research purposes only, and it is not meant for human consumption.

WGK

WGK 3

闪点(°F)

Not applicable

闪点(°C)

Not applicable

法规信息

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Hitomi Ozawa-Umeta et al.
Cancer science, 111(5), 1785-1793 (2020-03-13)
The NF-kappa B (NF-κB) pathway plays a pivotal role in tumor progression and chemoresistance, and its inhibition has been shown to suppress tumor growth in a variety of preclinical models. Recently, we succeeded in synthesizing a water-soluble injectable type of
Paula B Luis et al.
Molecular nutrition & food research, 64(6), e1901037-e1901037 (2020-01-22)
The diphenol curcumin from turmeric is rapidly metabolized into phase II conjugates following oral administration, resulting in negligible plasma concentration of the free compound, which is considered the bioactive form. Total plasma concentration of curcumin is often quantified after treatment
Lynne M Howells et al.
The Journal of nutrition, 149(7), 1133-1139 (2019-05-28)
Curcumin is the main active ingredient of the spice turmeric, investigated extensively for putative anticancer properties. This phase IIa open-labelled randomized controlled trial aimed to assess safety, efficacy, quality of life, neurotoxicity, curcuminoids, and C-X-C-motif chemokine ligand 1 (CXCL1) in

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