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Arctiin (Arctii; NSC 315527; Arctigenin-4-glucoside)

Alias: Arctiin; Arctii; NSC 315527; NSC315527; NSC-315527; Arctigenin-4-glucoside
Cat No.:V5100 Purity: ≥98%
Arctiin (formerly known as NSC 315527), a plant lignan that is isolated 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.
Arctiin (Arctii; NSC 315527; Arctigenin-4-glucoside)
Arctiin (Arctii; NSC 315527; Arctigenin-4-glucoside) Chemical Structure CAS No.: 20362-31-6
Product category: AdipoR
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description
Arctiin (formerly known as NSC 315527), a plant lignan that is isolated 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. Arctiin can be found in many plants of the Asteraceae family, particularly the greater burdock (Arctium lappa) and Centaurea imperialis, and in Trachelospermum asiaticum, Saussurea heteromalla., and Forsythia viridissima. It is the glucoside of arctigenin. Arctiin and arctigenin have shown anticancer effects.


Arctiin is a plant lignan that can be extracted from the Arctium lappa (burdock) seeds, and is a possible environmental endocrine disruptor compound. It has been shown to influence sex hormone metabolism as well as protein synthesis and steroid biosynthesis [1]. Arctiin is a glycoside of arctigenin and abundant in the seeds of Arctium lappa, Carthamus tinctorius and Caulis tracherospermi, used as herbal medicines in China [1]. Plant lignans are taken up in the diet mainly from high-fiber foods and are converted by human intestinal bacteria to estrogenic and antiestrogenic substances [1]. Arctiin also induces drug metabolism enzymes such as CYP1A2 in rat liver [1].
Biological Activity I Assay Protocols (From Reference)
ln Vivo
Male probasin/SV40 T antigen transgenic rats were fed diets containing 0.1%, 0.02%, or 0.004% Arctiin for 18 weeks. Histopathological evaluation showed that all rats developed adenocarcinoma in the dorsolateral prostate except two rats in the 0.1% group and one rat in the 0.02% group without carcinoma [1]. However, there were no definite treatment-related changes with statistical significance in any parameters for prostate carcinomas measured, including incidences of PIN and adenocarcinoma, and quantitative analysis of histological components in dorsolateral and anterior lobes [1]. Arctiin did not exert significant modifying effect (either promoting or chemopreventive) on prostate carcinogenesis in this model [1].
Small cell carcinomas were found in the dorsolateral prostate of four rats, with no group difference in distribution [1]. Two rats with extremely large prostates (each in the 0.02% arctiin and control groups) developed small cell carcinoma [1]. The average percentage of PIN, well-differentiated adenocarcinoma, and moderately differentiated adenocarcinoma in dorsolateral and anterior lobes showed no significant differences among groups [1].
Animal Protocol
Heterozygous male SV40 T antigen transgenic rats (6 weeks old) were used [1]. Arctiin (purity >97%) was mixed into powdered soybean-free basal diet at concentrations of 0.1%, 0.02%, or 0.004% [1]. The control group received soybean-free basal diet alone [1]. Animals were housed 2 per cage on wood-chip bedding in an air-conditioned room at 23±2°C and 60±10% humidity, with diet and tap water available ad libitum [1]. The treatment duration was 18 weeks [1]. Body weight and food consumption were recorded biweekly [1]. At the end of week 18, all surviving rats were killed under ether anesthesia [1]. At autopsy, prostates were removed and fixed in 10% neutral buffered formalin; livers and kidneys were excised, weighed, and fixed [1]. After 48 hours of fixation, the dorsolateral and anterior lobes were carefully dissected, weighed, and 2-3 mm thick slices were made from each lobe, then embedded in paraffin for histopathological examination of hematoxylin and eosin stained sections [1]. Neoplastic lesions of the prostate were classified as prostatic intraepithelial neoplasia (PIN), well-differentiated adenocarcinoma, moderately differentiated adenocarcinoma, or poorly differentiated adenocarcinoma [1]. Each prostatic lobe was scored and the percentage area corresponding to each pathological stage was quantified using an image processor for analytical pathology [1].
References
Cancer Lett. 2005 May 26;222(2):145-51.
Additional Infomation
Arctiin is a glycoside and lignan. Arctiin has been reported in Saussurea involucrata, Saussurea salsa, and other organisms for which data are available. See also: Lignans (subclasses of lignans); Burdock fruit (part); Burdock root (part).
Arctiin is a plant lignan belonging to the class of phytoestrogens, which are nonsteroidal substances with weak estrogenic activity [1]. Phytoestrogens are 1000-fold less potent than estradiol but have similar relative affinity for estrogen receptor, acting as ER partial antagonists [1]. Arctiin has been found to influence sex hormone metabolism, protein synthesis, and steroid biosynthesis [1]. It is converted by human intestinal bacteria to estrogenic and antiestrogenic substances [1]. Arctiin induces drug metabolism enzymes such as CYP1A2 in rat liver [1]. In the present study, Arctiin showed no definite effects on prostate carcinogenesis in SV40 T antigen transgenic rats, although a weak inhibitory tendency was observed in high dose groups [1].
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C27H34O11
Molecular Weight
534.5523
Exact Mass
534.21
CAS #
20362-31-6
PubChem CID
100528
Appearance
White to off-white solid powder
Density
1.4±0.1 g/cm3
Boiling Point
756.4±60.0 °C at 760 mmHg
Melting Point
109 °C
Flash Point
250.1±26.4 °C
Vapour Pressure
0.0±2.7 mmHg at 25°C
Index of Refraction
1.601
LogP
0.23
Hydrogen Bond Donor Count
4
Hydrogen Bond Acceptor Count
11
Rotatable Bond Count
10
Heavy Atom Count
38
Complexity
753
Defined Atom Stereocenter Count
7
SMILES
COC1=C(C=C(C=C1)C[C@H]2COC(=O)[C@@H]2CC3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)OC
InChi Key
XOJVHLIYNSOZOO-SWOBOCGESA-N
InChi Code
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
Chemical Name
(3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-{[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl}oxolan-2-one
Synonyms
Arctiin; Arctii; NSC 315527; NSC315527; NSC-315527; Arctigenin-4-glucoside
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~467.68 mM)
H2O : ~10 mg/mL (~18.71 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (3.89 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (3.89 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (3.89 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 10 mg/mL (18.71 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.8707 mL 9.3537 mL 18.7073 mL
5 mM 0.3741 mL 1.8707 mL 3.7415 mL
10 mM 0.1871 mL 0.9354 mL 1.8707 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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