ent-11alpha-Hydroxy-15-oxokaur-16-en-19-oic acid | CAS:57719-81-0

ent-11alpha-Hydroxy-15-oxokaur-16-en-19-oic acid

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Description:

Ent-11alpha-Hydroxy-15-oxokaur-16-en-19-oic acid has anti-cancer activity, it induces apoptosis of human malignant cancer cells, it also inhibits hepatocellular carcinoma in vitro and in vivo via stabilizing IkBα.

Targets:

p65 | NF-kB | Bcl-2/Bax | ERK | p53 | p38MAPK | Caspase | JNK

In vitro:

Invest New Drugs. 2012 Dec;30(6):2210-8.

Ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid inhibits hepatocellular carcinoma in vitro and in vivo via stabilizing IkBα.[Pubmed: 22227815 ]

ent-11alpha-Hydroxy-15-oxokaur-16-en-19-oic acid(5F) isolated from Pteris Semipinnata L is known to inhibit certain tumor cells in vitro. The information on the in vivo effect of 5F is limited and its effect on hepatocellular carcinoma (HCC) is unknown.
METHODS AND RESULTS:
In this study, the anti-tumor effect of 5F was investigated in a diethylnitrosamine (DEN)-induced mouse HCC model. In addition to therapeutic effect, the potential side effect was monitored. A panel of cultured HCC cells was used to confirm the in vivo data and explore the responsible molecular pathway. The result showed that 5F significantly inhibited the DEN-induced HCC tumors by reducing the number of tumor foci and the volume of tumors. Furthermore, 5F induced the death of cultured HCC cells in dose- and time-dependent manners. The cell death was confirmed to be apoptotic by in vivo and in vitro TUNEL assays. 5F inhibited NF-kB by stabilizing its inhibitor IkBα, reducing the nuclear p65 and inhibiting NF-kB activity. Subsequently it affected the NF-kB downstream molecules with a decrease in anti-apoptotic Bcl-2 and increase in pro-apoptotic Bax and Bak. During the whole period of the experiment, mice receiving 5F appeared to be healthy, though they suffered from a mild degree of hair loss. 5F did not damage liver and renal functions.
CONCLUSIONS:
In conclusion, 5F is effective against HCC with minimal side effects. It induces apoptosis in HCC cells via inhibiting NF-kB, leading to the decrease of Bcl-2 but the increase of Bax and Bak.

ent-11alpha-Hydroxy-15-oxokaur-16-en-19-oic acid Description

Source:	The herbs of Pteris Semipinnata L.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Storage:	Providing storage is as stated on the product vial and the vial is kept tightly sealed, the product can be stored for up to 24 months(2-8C). Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20C. Generally, these will be useable for up to two weeks. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please email to: service@chemfaces.com
After receiving:	The packaging of the product may have turned upside down during transportation, resulting in the natural compounds adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.

Kinase Assay:

Curr Drug Targets. 2012 Dec;13(14):1730-7.

Ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic-acid induces apoptosis of human malignant cancer cells.[Pubmed: 23140284]

ent-11alpha-Hydroxy-15-oxokaur-16-en-19-oic acid(5F) is a chemical compound isolated from Pteris semipinnata L (PsL), a Chinese traditional herb.
METHODS AND RESULTS:
5F has been known to exert antitumor activity in several kinds of human malignant cancer cells by leading cancer cell to apoptosis. 5F translocated Bax into the mitochondria, down-regulated Bcl-2, activated caspase-9 and caspase-3, released cytochrome c into the cytosol and translocated AIF from the mitochondria to the nucleus. The presentation of a wild-type p53 in the cancer cells facilitated cancer cells sensitive to the 5F treatment. 5F induces apoptosis of cancer cells by inhibiting NF-κB activation/induction, which leading to the decrease of Bcl-2 but the increase of Bax and Bak. MAPK kinases and Akt are also involved in process of 5F inducing cancer cell apoptosis. In lung cancer, 5F activated ERK1/2 and the inhibition of ERK1/2 suppressed 5F-mediated changes in apoptotic molecules. 5F activated Akt and suggested that Akt activation was anti-apoptotic rather than pro-apoptotic. However, in anaplastic thyroid carcinoma, JNK activation was related to cell death induced by 5F. ERK and p38 were also activated but as survival signals in response to 5F treatment to counteract the induction of cell death.
CONCLUSIONS:
Collectively, 5F is effective against several malignant cancers both in vivo and in vitro with minimal side effects. It induces apoptosis through the mitochondrialmediated pathway, in which regulation of Bcl-2 family proteins expression, the activation of MAPK and inactivation of NF-κB are critical. The good ability of 5F to inhibit cancer cells makes it in line with the successful development of other anti-tumor agents.

Product Name	ent-11alpha-Hydroxy-15-oxokaur-16-en-19-oic acid
Price:
CAS No.:	57719-81-0
Catalog No.:	CFN89078
Molecular Formula:	C₂₀H₂₈O₄
Molecular Weight:	332.44 g/mol
Purity:	>=98%
Type of Compound:	Diterpenoids
Physical Desc.:	Powder
Source:	The herbs of Pteris Semipinnata L.
Solvent:	Chloroform, Dichloromethane, Ethyl Acetate, DMSO, Acetone, etc.
Download:	COA MSDS
Similar structural:	Comparison (Web) (SDF)
Guestbook:

Size /Price /Stock	10 mM * 100 uL in DMSO / Inquiry / In-stock 10 mM * 1 mL in DMSO / Inquiry / In-stock
Related Libraries	Anticancer Compound Library Pro-apoptotic Compound Library Diterpenoids Compound Library p65 Inhibitor Library p53 Inhibitor Library p38MAPK Inhibitor Library NF-kB Inhibitor Library JNK Inhibitor Library ERK Inhibitor Library Caspase Inhibitor Library Bcl-2/Bax Inhibitor Library

	1 mg	5 mg	10 mg	20 mg	25 mg
1 mM	3.0081 mL	15.0403 mL	30.0806 mL	60.1612 mL	75.2015 mL
5 mM	0.6016 mL	3.0081 mL	6.0161 mL	12.0322 mL	15.0403 mL
10 mM	0.3008 mL	1.504 mL	3.0081 mL	6.0161 mL	7.5202 mL
50 mM	0.0602 mL	0.3008 mL	0.6016 mL	1.2032 mL	1.504 mL
100 mM	0.0301 mL	0.1504 mL	0.3008 mL	0.6016 mL	0.752 mL

CFN97261	ent-9-Hydroxy-15-oxo-16-kauren-19-oic acid	77658-39-0	332.4	C₂₀H₂₈O₄
CFN97294	ent-6,9-Dihydroxy-15-oxo-16-kauren-19-oic acid	81264-00-8	348.4	C₂₀H₂₈O₅
CFN89107	ent-7alpha,9-Dihydroxy-15-oxokaur-16-en-19,6bet-olide	59885-89-1	346.42	C₂₀H₂₆O₅
CFN97975	Pterisolic acid A	1401419-85-9	346.4	C₂₀H₂₆O₅
CFN97976	Pterisolic acid B	1401419-86-0	330.4	C₂₀H₂₆O₄
CFN89078	ent-11alpha-Hydroxy-15-oxokaur-16-en-19-oic acid	57719-81-0	332.44	C₂₀H₂₈O₄
CFN89216	Paniculoside III	60129-65-9	494.58	C₂₆H₃₈O₉
CFN96331	ent-16-Kaurene-3beta,15beta,18-triol	921211-29-2	320.5	C₂₀H₃₂O₃
CFN97780	Grandifloric acid	22338-69-8	318.46	C₂₀H₃₀O₃
CFN97131	Deacetylxylopic acid	6619-95-0	318.5	C₂₀H₃₀O₃