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SMB00078

Sigma-Aldrich

Arctiin

≥95% (LC/MS-ELSD)

Synonym(s):

Arctigenin-4-glucoside, Arctigenin 4-glucoside

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About This Item

Empirical Formula (Hill Notation):
C27H34O11
CAS Number:
20362-31-6
Molecular Weight:
534.55
MDL number:
MFCD00870630
UNSPSC Code:
12352205
PubChem Substance ID:
329824756
NACRES:
NA.25
Pricing and availability is not currently available.

Assay

≥95% (LC/MS-ELSD)

form

solid

application(s)

metabolomics
vitamins, nutraceuticals, and natural products

storage temp.

−20°C

SMILES string

COc1ccc(C[C@H]2COC(=O)[C@@H]2Cc3ccc(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)c(OC)c3)cc1OC

InChI

1S/C27H34O11/c1-33-18-6-4-14(10-20(18)34-2)8-16-13-36-26(32)17(16)9-15-5-7-19(21(11-15)35-3)37-27-25(31)24(30)23(29)22(12-28)38-27/h4-7,10-11,16-17,22-25,27-31H,8-9,12-13H2,1-3H3/t16-,17+,22+,23+,24-,25+,27+/m0/s1

InChI key

XOJVHLIYNSOZOO-SWOBOCGESA-N

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General description

Natural product derived from plant source, such as Forsythiae Fructus and Arctium lappa L. Arctiin is a lignan.[1][2]

Biochem/physiol Actions

Arctiin has shown to be a suppressor of cyclin D1 protein expression in multiple types of human tumor cells, such as osteosarcoma, lung, colorectal, cervical, breast, melanoma, and prostate cancer. Arctiin has also shown antiviral activity against influenza A when used alone or in combination with oseltamivir. Arctiin plays an important role in the process of inflammation, by preventing the release of nitric oxide, prostaglandin E2, TNF-α (tumor necrosis factor − α), interleukin (IL)-1β and IL-6.[1] A study using rat model shows that arctiin possess anti-diabetic activity and might serve as an inhibitor of diabetic retinopathy.[2]
Arctiin has shown to be a suppressor of cyclin D1 protein expression in multiple types of human tumor cells, such as osteosarcoma, lung, colorectal, cervical, breast, melanoma, and prostate cancer. Arctiin has also shown antiviral activity against influenza A when used along or in combination with oseltamivir.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
122228118V
122228-118V

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Youichirou Matsuzaki et al.
Oncology reports, 19(3), 721-727 (2008-02-22)
Arctiin is a major lignan constituent of Arctium lappa and has anti-cancer properties in animal models. It was recently reported that arctiin induces growth inhibition in human prostate cancer PC-3 cells. However, the growth inhibitory mechanism of arctiin remains unknown.
Sung-Hee Cho et al.
BioFactors (Oxford, England), 22(1-4), 161-163 (2005-01-05)
A primary methanol extract (F-ME), secondary butanol-soluble fraction (F-BU), and lignans were prepared from forsythia fruit (Forsythia viridissima L.) and added to 0.5% (w/w) cholesterol diets for male Sprague-Dawley rats weighing 121 +/- 12 g. There were six experimental groups:
Jee-Hun Park et al.
Biological & pharmaceutical bulletin, 31(7), 1337-1342 (2008-07-02)
We tested the effects of SI000413, a new formula, consisting of Pyrolae herba and Trachelospermi caulis, on type II collagen-induced arthritis (CIA). CIA was induced in DBA/1J mice by immunization with bovine type II collagen (CII) on days 1 and
Yi-min Zheng et al.
Zhongguo Zhong yao za zhi = Zhongguo zhongyao zazhi = China journal of Chinese materia medica, 30(16), 1287-1289 (2005-10-26)
To study the metabolic chemistry and pharmaco-dynamics characters of ligan from seeds of Arctium lappa. HPLC method was used in the study. The analysis was carried out on C18 column. The mobile phase was CH3CN-0.05% H3PO4 (36:64) with flow-rate at
Yu Zeng et al.
Cancer letters, 222(2), 145-151 (2005-05-03)
Arctiin, a plant lignan that can be extracted from the Arctium lappa (burdock) seeds, is a possible environmental endocrine disruptor compounds and have been shown to influence sex hormone metabolism as well as protein synthesis, steroid biosynthesis. Modifying effects of
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