Chrysophanic Acid (Chrysophanol)

Alias: Chrysophanic acid; Chrysophanol
Cat No.:V0207 Purity: ≥98%
Chrysophanic acid (also called Chrysophanol), a naturally occuring anthraquinone isolated from Dianella longifolia, is a selective and potent inhibitor of EGFR/mTOR (epidermal growth factor (EGF) receptor/mammalian target of rapamycin) with potential anti-obesity and antitumor activity.
Chrysophanic Acid (Chrysophanol) Chemical Structure CAS No.: 481-74-3
Product category: EGFR
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

Chrysophanic acid (also called Chrysophanol), a naturally occuring anthraquinone isolated from Dianella longifolia, is a selective and potent inhibitor of EGFR/mTOR (epidermal growth factor (EGF) receptor/mammalian target of rapamycin) with potential anti-obesity and antitumor activity. In C57BL/6 mice, a high-fat diet (HFD)-induced obesity is ameliorated by chyrsophanol (CA). Additionally, in EGFR-overexpressing SNU-C5 human colon cancer cells, it demonstrated strong antiproliferative and anticancer activity. It did not affect other cell lines with low levels of EGFR expression, but it specifically inhibited the proliferation of SNU-C5 cells.

Biological Activity I Assay Protocols (From Reference)
Targets
EGFR; mTOR
ln Vitro

Chrysophanic acid (Chrysophanol) is a EGFR/mTOR pathway inhibitor. In EGFR-overexpressing SNU-C5 human colon cancer cells, chyrsophanic acid, also known as chyrsophanol, a naturally occurring anthraquinone, presents anticancer properties. Some cell lines (HT7, HT29, KM12C, SW480, HCT116, and SNU-C4) with low levels of EGFR expression are not selectively blocked from proliferating by chyrsophanic acid (chrysophanol). After treating SNU-C5 cells with chyrophanic acid (also known as chyrophanol), EGFR's phosphorylation by EGF is inhibited, and the activation of downstream signaling molecules, including AKT, ERK, and p70S6K (ribosomal protein S6 kinase/mTOR) is suppressed. [1] Chrysophanic acid also prevents the poliovirus-induced cytopathic effects in the kidney cells of BGM (Buffalo Green Monkeys) and the replication of poliovirus types 2 and 3 (Picornaviridae).[2]

ln Vivo
Chrysophanol (CA) ameliorates the obesity brought on by HFD in C57BL/6 Mice. Chrysophanol is tested in vivo in male C57BL/6J mice in order to assess the effectiveness of using this dietary supplement. The HFD-fed mice put on a notably greater weight gain than the mice on the regular diet. But compared to the untreated HFD, the Chrysophanol group's weight gain is noticeably lower. Over a 16-week period, mice in the HFD group gained 23.92 ± 1.74 g of weight, while those in the Chrysophanol group gained 16.72 ±2 g.
Cell Assay
In 96-well microplates, the cells are seeded at 5×103 cells/mL and given 24 hours to attach. The medium is supplemented with chrysophanol (20, 50, 80, and 120 μM) at varying concentrations up to 120 μM and for varying amounts of time. A Cell Counting Kit-8 is used to measure the cytotoxicity and/or proliferation of treated cells (CCK-8). In a nutshell, formazan, an orange-colored water-soluble product, is produced by the highly water-soluble tetrazolium salt WST-8. The number of living cells is exactly proportional to the amount of formazan dye produced by cell dehydrogenases. A microplate reader is used to measure the absorbance at 450 nm to determine the cytotoxicity and proliferation of cells after adding 10 μL of CCK-8 to each well and letting it sit at 37°C for three hours. For every experimental condition, three replicated wells are used[1].
Animal Protocol
5 mg/kg
Mice: One week is spent in maintenance before experiments begin with 4-week-old male C57BL/6J mice. In a pathogen-free animal facility, mice are kept on a 12-hour light/dark cycle and given unlimited access to water and a laboratory diet. The mice receive a high-fat, high-calorie diet (HFD) to induce obesity. Commercial standard chow is fed to the control group (C). Mice in the HFD group (HFD) are given only HFD. HFD + CA group (CA): Four weeks of HFD are given to the mice prior to the administration of 5 mg/kg/day of chyrsophanol. For sixteen weeks, the mice are split into three groups (n = 5) and fed three different diets: chow diet, HFD, and HFD plus Chrysophanol. Three times a week, food intake and body weight are measured.
References

[1]. Phytother Res . 2011 Jun;25(6):833-7.

[2]. Antiviral Res . 2001 Mar;49(3):169-78.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C15H10O4
Molecular Weight
254.24
Exact Mass
254.06
Elemental Analysis
C, 70.86; H, 3.96; O, 25.17
CAS #
481-74-3
Appearance
Solid powder
SMILES
CC1=CC2=C(C(=C1)O)C(=O)C3=C(C2=O)C=CC=C3O
InChi Key
LQGUBLBATBMXHT-UHFFFAOYSA-N
InChi Code
InChI=1S/C15H10O4/c1-7-5-9-13(11(17)6-7)15(19)12-8(14(9)18)3-2-4-10(12)16/h2-6,16-17H,1H3
Chemical Name
1,8-dihydroxy-3-methylanthracene-9,10-dione
Synonyms
Chrysophanic acid; Chrysophanol
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: ~5 mg/mL (~19.7 mM)
Water: <1 mg/mL
Ethanol: <1 mg/mL
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 3.9333 mL 19.6665 mL 39.3329 mL
5 mM 0.7867 mL 3.9333 mL 7.8666 mL
10 mM 0.3933 mL 1.9666 mL 3.9333 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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