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SMB00075

Sigma-Aldrich

(−)-Arctigenin

≥95% (LC/MS-ELSD)

Synonyma:

2(3H)-Furanone, (3R,4R)-4-[(3,4-Dimethoxyphenyl)methyl]dihydro-3-[(4-hydroxy-3-methoxyphenyl)methyl]-2(3H)-furanone

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About This Item

Empirický vzorec (Hillův zápis):
C21H24O6
Číslo CAS:
7770-78-7
Molekulová hmotnost:
372.41
MDL number:
MFCD00870597
UNSPSC Code:
12352205
PubChem Substance ID:
329824754
NACRES:
NA.25

assay

≥95% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

COc1cc(C[C@@H]2[C@H](COC2=O)Cc3ccc(OC)c(OC)c3)ccc1O

InChI

1S/C21H24O6/c1-24-18-7-5-13(11-20(18)26-3)8-15-12-27-21(23)16(15)9-14-4-6-17(22)19(10-14)25-2/h4-7,10-11,15-16,22H,8-9,12H2,1-3H3/t15-,16+/m0/s1

InChI key

NQWVSMVXKMHKTF-JKSUJKDBSA-N

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General description

Arctigenin is a lignan found in the root of Arctium lappa L. It has been used in pharmacologic, as well as cosmetic, research and has demonstrated several antiviral and anticancer effects.

Biochem/physiol Actions

Dibenzylbutyrolactone ligand, natural product, viral integrase and topoisomerase II inhibitor, antioxidant, antiviral, anti-inflammatory, immunomodulator.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (COA)

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Secoisolariciresinol diglucoside ≥97% (HPLC)

Sigma-Aldrich

S0202

Secoisolariciresinol diglucoside

Adenine ≥99%

Sigma-Aldrich

A8626

Adenine

Ursolic acid ≥90%

Sigma-Aldrich

U6753

Ursolic acid

Chlorogenic acid ≥95% (titration)

Sigma-Aldrich

C3878

Chlorogenic acid

Shengrong Sun et al.
Planta medica, 77(2), 141-145 (2010-08-19)
The involvement of unfolded protein response (UPR) activation in tumor survival and resistance to chemotherapies suggests a new anticancer strategy targeting UPR pathway. Arctigenin, a natural product, has been recently identified for its antitumor activity with selective toxicity against cancer
Suresh Awale et al.
Cancer research, 66(3), 1751-1757 (2006-02-03)
Tumor cells generally proliferate rapidly and the demand for essential nutrients as well as oxygen always exceeds the supply due to the unregulated growth and the insufficient and inappropriate vascular supply. However, cancer cells show an inherent ability to tolerate
Ji Yun Lee et al.
Archives of pharmacal research, 33(6), 947-957 (2010-07-08)
We previously reported that arctigenin, a phenylpropanoid dibenzylbutyrolactone lignan isolated from Forsythia koreana, exhibits anti-inflammatory, antioxidant, and analgesic effects in animal models. In addition, arctigenin inhibited eosinophil peroxidase and activated myeloperoxidase in inflamed tissues. In this study, we tested the
Vivek Swarup et al.
The Journal of antimicrobial chemotherapy, 61(3), 679-688 (2008-01-31)
OBJECTIVES; To evaluate therapeutic efficacy of arctigenin in an experimental model of Japanese encephalitis (JE). Four- to 5-week-old BALB/c mice of either sex were infected intravenously with lethal dose of 3 x 10(5) pfu of Japanese encephalitis virus (JEV). By
Min Kyung Cho et al.
International immunopharmacology, 4(10-11), 1419-1429 (2004-08-18)
Arctigenin, naturally occurring in Bardanae fructus, Saussurea medusa, Arctium lappa L., Torreya nucifera and Ipomea cairica, is a phenylpropanoid dibenzylbutyrolactone lignan with antioxidant and anti-inflammatory activities. Previously, we showed that arctigenin potently inhibited the induction of nitric oxide synthase (iNOS)
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