KahweolCAS# 6894-43-5 |
2D Structure
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Number of papers citing our products
Cas No. | 6894-43-5 | SDF | Download SDF |
PubChem ID | 114778 | Appearance | White-light brown powder |
Formula | C20H26O3 | M.Wt | 314.4 |
Type of Compound | Diterpenoids | Storage | Desiccate at -20°C |
Solubility | Soluble in chloroform | ||
SMILES | CC12C=CC3=C(C1CCC45C2CCC(C4)C(C5)(CO)O)C=CO3 | ||
Standard InChIKey | JEKMKNDURXDJAD-HWUKTEKMSA-N | ||
Standard InChI | InChI=1S/C20H26O3/c1-18-7-5-16-14(6-9-23-16)15(18)4-8-19-10-13(2-3-17(18)19)20(22,11-19)12-21/h5-7,9,13,15,17,21-22H,2-4,8,10-12H2,1H3/t13-,15-,17+,18-,19+,20+/m1/s1 | ||
General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. |
Description | 1. Kahweol has anticarcinogenic activity. 2. Kahweol has anti-angiogenic activity. 3. Kahweol has anti-inflammatory activity, it can block the LPS-induced activation of NF-kappaB by preventing IkappaB degradation and inhibiting IkappaB kinase activity. 4. Kahweol has hepatoprotective and antioxidant effects on carbon tetrachloride-induced liver damage in mice. |
Targets | HO-1 | P450 (e.g. CYP17) | Nrf2 | COX | PGE | IkB | NF-kB | COX | MMP(e.g.TIMP) | IKK |
Kahweol Dilution Calculator
Kahweol Molarity Calculator
1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
1 mM | 3.1807 mL | 15.9033 mL | 31.8066 mL | 63.6132 mL | 79.5165 mL |
5 mM | 0.6361 mL | 3.1807 mL | 6.3613 mL | 12.7226 mL | 15.9033 mL |
10 mM | 0.3181 mL | 1.5903 mL | 3.1807 mL | 6.3613 mL | 7.9517 mL |
50 mM | 0.0636 mL | 0.3181 mL | 0.6361 mL | 1.2723 mL | 1.5903 mL |
100 mM | 0.0318 mL | 0.159 mL | 0.3181 mL | 0.6361 mL | 0.7952 mL |
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. |
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Suppression of PMA-induced human fibrosarcoma HT-1080 invasion and metastasis by kahweol via inhibiting Akt/JNK1/2/p38 MAPK signal pathway and NF-kappaB dependent transcriptional activities.[Pubmed:30590137]
Food Chem Toxicol. 2019 Mar;125:1-9.
Coffee is one of the widely sales beverage worldwide and contains numerous phytochemicals that are beneficial to health. Kahweol acetate (KA), a coffee-specific diterpene, exhibits anti-tumoric properties in human tumoric cells. However, the effect of KA on the metastasis and invasion of cancer cells and the underlying mechanisms remain unclear. The objectives of this study were to estimate the anti-tumor activity of KA and reveal the possible molecular mechanisms. KA markedly inhibited the cell proliferation enhanced by phorbol 12-myristate 13-acetate (PMA) in human fibrosarcoma cells. As well as, KA attenuated PMA-induced cell migration and invasion in a concentration-dependent manner. KA suppressed PMA-enhanced activation of matrix metalloproteinase-9 (MMP-9) through suppression of nuclear factor kappa B (NF-kappaB) activation. KA repressed the PMA-induced phosphorylation of Akt, c-Jun N-terminal kinase (JNK) 1/2, and p38 MAPK, which are signaling molecules upstream of MMP-9 expression. In summary, we demonstrated that the anti-tumor effects of KA might occur through the inhibition of Akt/JNK1/2/p38 MAPK phosphorylation and downregulation of NF-kappaB activation, leading to a decrease in MMP-9 expression. Thus, KA is a useful chemotherapeutic agent that may contribute to prevent to the metastatic tumor.
Coffee diterpenes kahweol acetate and cafestol synergistically inhibit the proliferation and migration of prostate cancer cells.[Pubmed:30569541]
Prostate. 2019 Apr;79(5):468-479.
BACKGROUND: Coffee inhibits the progression of prostate cancer; however, the direct mechanism through which coffee acts on prostate cancer cells remains unclear. This study aimed to identify the key compounds of coffee that possess anti-cancer effects and to investigate their mechanisms of action. METHODS: The anti-proliferation and anti-migration effects of six potentially active types of coffee compounds, including Kahweol acetate, cafestol, caffeine, caffeic acid, chlorogenic acid, and trigonelline hydrochloride, were evaluated using LNCaP, LNCaP-SF, PC-3, and DU145 human prostate cancer cells. The synergistic effects of these compounds were also investigated. Apoptosis-related and epithelial-mesenchymal transition-related proteins, androgen receptor in whole cell and in nucleus, and chemokines were assessed. A xenograft study of SCID mice was performed to examine the in vivo effect of coffee compounds. RESULTS: Among the evaluated compounds, only Kahweol acetate and cafestol inhibited the proliferation and migration of prostate cancer cells in a dose-dependent manner. The combination treatment involving Kahweol acetate and cafestol synergistically inhibited proliferation and migration (combination index <1) with the induction of apoptosis, the inhibition of epithelial-mesenchymal transition, and decrease in androgen receptor, resulting in the reduction of nuclear androgen receptor in androgen receptor-positive cells. Moreover, Kahweol acetate and cafestol downregulated CCR2 and CCR5 without an increase in their ligands, CCL2 and CCL5. The xenograft study showed that oral administration of Kahweol acetate and cafestol significantly inhibited tumor growth. CONCLUSION: Kahweol acetate and cafestol synergistically inhibit the progression of prostate cancer. These coffee compounds may be novel therapeutic candidates for prostate cancer.
Kahweol inhibits proliferation and induces apoptosis by suppressing fatty acid synthase in HER2-overexpressing cancer cells.[Pubmed:30205135]
Food Chem Toxicol. 2018 Nov;121:326-335.
Kahweol is a coffee-specific diterpene found in the beans of Coffea arabica and has been reported to demonstrate various biological activities, including anti-inflammatory, antioxidant, and apoptotic properties. In the present study, we examined the molecular mechanism of Kahweol in human epidermal growth factor receptor-2 (HER2)-overexpressing breast cancer cells. Kahweol preferentially inhibited cell proliferation and induced cell death through the induction of a caspase 3-dependent pathway in HER2-overexpression breast cancer cell lines. Kahweol treatment substantially reduced the levels of HER2 protein, mRNA, and transcriptional activity in SKBR3 cells. Kahweol exerts its potent anticancer efficacy by the upregulation of polyomavirus enhancer activator 3 (PEA3) and downregulation of activator protein 2 (AP-2) to inhibit aberrantly activated HER2 signaling. Fatty acid synthase (FASN) expression and sterol regulatory element-binding protein-1c (SREBP-1c) activity were downregulated by Kahweol. In addition, Kahweol lowered the levels of phosphorylated Akt and its downstream targets mammalian target of rapamycin (mTOR) and cyclin D1. Furthermore, we found that blocking Akt signaling through Kahweol treatment significantly reduced FASN expression and subsequently suppressed cell proliferation in HER2-overexpressing cancer cells. Overall, this study suggests that Kahweol could be a useful adjuvant therapeutic agent in the treatment of HER2-overexpressing breast cancer.
Kahweol Ameliorates the Liver Inflammation through the Inhibition of NF-kappaB and STAT3 Activation in Primary Kupffer Cells and Primary Hepatocytes.[Pubmed:29973533]
Nutrients. 2018 Jul 4;10(7). pii: nu10070863.
Gut derived bacterial endotoxins, such as lipopolysaccharide (LPS), are involved in one of the important mechanisms that lead to inflammation associated with various liver diseases, including nonalcoholic fatty liver disease and alcoholic liver disease. Kahweol is a coffee-specific diterpene present in coffee bean and exhibits anti-angiogenic and anti-inflammatory activities. However, to date, the effect of Kahweol on liver inflammation remains unknown. In this study, we examined whether Kahweol exhibits a protective effect by inhibiting liver inflammation in primary Kupffer cells and primary hepatocytes cultures as well as their co-cultures. Kahweol decreased the LPS-induced production of interleukin 1 alpha, interleukin 1 beta, interleukin 6, and tumor necrosis factor alpha. The inhibitory effect of Kahweol on the liver inflammation was associated with the down regulation of LPS-stimulated phospho-nuclear factor kappa B and -signal transducer and activator of transcription 3 expression. These results suggest that Kahweol might be a novel potent agent to treat liver inflammation induced by LPS.
Kahweol decreases hepatic fibrosis by inhibiting the expression of connective tissue growth factor via the transforming growth factor-beta signaling pathway.[Pubmed:29152065]
Oncotarget. 2017 Aug 1;8(50):87086-87094.
Kahweol is a diterpene molecule found in Coffea Arabica beans. Previous studies have shown that coffee reduces liver fibrosis, but it is not clear which component of coffee has the protective effect. In this study, we examined whether Kahweol has a protective effect on hepatic fibrosis in vivo and in vitro. Kahweol decreased hepatic fibrosis by inhibiting connective tissue growth factor (CTGF) expression in thioacetamide (TAA)-treated mice. The expression of phospho-Smad3, signal transducer and activator of transcription 3 (STAT3), extracellular signal-regulated kinases (ERK), and c-Jun N-terminal protein kinase (JNK) increased in the livers of TAA-treated mice and decreased in the Kahweol-treated group. Kahweol significantly decreased the expression of transforming growth factor beta (TGF-beta)-stimulated type I collagen and CTGF expression in vitro. In addition, Kahweol significantly decreased the expression of Smad3, STAT3, ERK and JNK, which are involved in the induction of CTGF expression by TGF-beta in hepatocytes, but not in HSCs. These results suggest that Kahweol may be a new candidate for treatment of liver fibrosis.