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11,15-Dihydroxy-16-kauren-19-oic acid

CAS# 57719-76-3

11,15-Dihydroxy-16-kauren-19-oic acid

Catalog No. BCN1413----Order now to get a substantial discount!

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11,15-Dihydroxy-16-kauren-19-oic acid: 5mg $828 In Stock
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Quality Control of 11,15-Dihydroxy-16-kauren-19-oic acid

Number of papers citing our products

Chemical structure

11,15-Dihydroxy-16-kauren-19-oic acid

3D structure

Chemical Properties of 11,15-Dihydroxy-16-kauren-19-oic acid

Cas No. 57719-76-3 SDF Download SDF
PubChem ID 133612145 Appearance Powder
Formula C20H30O4 M.Wt 334.5
Type of Compound Diterpenoids Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
SMILES CC12CCCC(C1CCC34C2C(CC(C3)C(=C)C4O)O)(C)C(=O)O
Standard InChIKey VRVOLALMVUEAHP-MRHRFJSUSA-N
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.
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.
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.

Source of 11,15-Dihydroxy-16-kauren-19-oic acid

The herbs of Cerbera manghas

Biological Activity of 11,15-Dihydroxy-16-kauren-19-oic acid

In vitro

Kaurane-type diterpenes from Adenostemma lavenia O. Kuntze.[Reference: WebLink]

CHEMICAL & PHARMACEUTICAL BULLETIN, 1990, 38(5):1308-1312.


METHODS AND RESULTS:
Ten 11-oxygenated kauran-19-oic acids, ent-11α, 15α-dihydroxykaur-16-en-19-oic acid(11,15-Dihydroxy-16-kauren-19-oic acid), ent-11α-hydroxy-15α-acetoxykaur-16-en-19-oic acid, ent-11α-hydroxy-15-oxo-kaur-16-en-19-oic acid and adenostemmoic acids A-G and their nine glycosides, paniculosides II and III and adenostemmosides A-G were characterized from Adenostemma lavenia O. KUNTZE. ent-11α-Hydroxy-15-oxo-kaur-16-en-19-oic acid and adenostemmoic acid B showed cytotoxic activity against L-5178Y cultured cell and prolonged the survival of mice.

Protocol of 11,15-Dihydroxy-16-kauren-19-oic acid

Structure Identification
Journal of Natural Products, 1979, 42(2):183-186.

Isolation of 11-Hydroxyated Kauranic Acids From Adenostemma lavenia.[Reference: WebLink]


METHODS AND RESULTS:
Four 11-hydroxylated kauranic acids were characterized from Adenostemma lavenia (L.) O. Kuntze, namely: ent-11α-hydroxy-15α-acetoxykaur-16-en-19-oic acid (1), ent-11α, 15α-dihydroxykaur-16-en-19-oic acid (11,15-Dihydroxy-16-kauren-19-oic acid ,2), (16R)-ent-11α-hydroxy-15-oxokauran-19-oic acid (3), and ent-11α-hydroxy-15-oxokaur-16-en-19-oic acid (4).

11,15-Dihydroxy-16-kauren-19-oic acid Dilution Calculator

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11,15-Dihydroxy-16-kauren-19-oic acid Molarity Calculator

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Preparing Stock Solutions of 11,15-Dihydroxy-16-kauren-19-oic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.9895 mL 14.9477 mL 29.8954 mL 59.7907 mL 74.7384 mL
5 mM 0.5979 mL 2.9895 mL 5.9791 mL 11.9581 mL 14.9477 mL
10 mM 0.299 mL 1.4948 mL 2.9895 mL 5.9791 mL 7.4738 mL
50 mM 0.0598 mL 0.299 mL 0.5979 mL 1.1958 mL 1.4948 mL
100 mM 0.0299 mL 0.1495 mL 0.299 mL 0.5979 mL 0.7474 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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References on 11,15-Dihydroxy-16-kauren-19-oic acid

11,12-Epoxyeicosatrienoic acid induces vasodilator response in the rat perfused mesenteric vasculature.[Pubmed:28332266]

Auton Autacoid Pharmacol. 2017 Jan;37(1):3-12.

Epoxyeicosatrienoic acids (EETs) are endogenous ligands that undergo hydrolysis by soluble epoxide hydrolase (sEH). The responses of 11, 12-EET in comparison with other vasodilator agonists including carbachol and sodium nitroprusside (SNP) were investigated. The effect of 1-cyclohexyl-3-dodecyl urea (CDU), a sEH, was tested on the vasodilator effect induced by 11, 12-EET in the perfused mesenteric beds isolated from normo-glycaemic and type-1 STZ-diabetic rats. In the perfused mesenteric beds of control and diabetic animals, 11, 12-EET produced vasodilation in a dose-dependent manner. The vasodilator response induced by 11, 12-EET was significantly decreased in tissues obtained from diabetic animals, but this was significantly corrected through inhibition of sEH. The effects of nitric oxide synthase inhibitor, cyclo-oxygenase inhibitor, specific potassium channel inhibitors, soluble guanylyl cyclase inhibitor and transient receptor potential channel V4 inhibitor, on vasodilator response to 11, 12-EET were investigated. In tissues isolated from control animals, vasodilator responses to 11, 12-EET were not inhibited by acute incubation with l-NAME, l-NAME with indomethacin, glibenclamide, iberiotoxin, charybdotoxin, apamin or ODQ. Incubation with the transient receptor potential channel V4 inhibitor ruthenium red caused significantly reduced vasodilator responses induced by 11, 12-EET. In conclusion, results from this study indicate that 11, 12-EET has a vasodilator effect in the perfused mesenteric bed, partly through activation of vanilloid receptor. A strategy to elevate the levels of EETs may have a significant impact in correcting microvascular abnormality associated with diabetes.

Coenzyme A thioester formation of 11- and 15-oxo-eicosatetraenoic acid.[Pubmed:28238887]

Prostaglandins Other Lipid Mediat. 2017 May;130:1-7.

Release of arachidonic acid (AA) by cytoplasmic phospholipase A2 (cPLA2), followed by metabolism through cyclooxygenase-2 (COX-2) and 15-hydroxyprostaglandin dehydrogenase (15-PGDH), results in the formation of the eicosanoids 11-oxo- and 15-oxo-eicosatetraenoic acid (oxo-ETE). Both 11-oxo- and 15-oxo-ETE have been identified in human biospecimens but their function and further metabolism is poorly described. The oxo-ETEs contain an alpha,beta-unsaturated ketone and a free carboxyclic acid, and thus may form Michael adducts with a nucleophile or a thioester with the free thiol of Coenzyme A (CoA). To examine the potential for eicosanoid-CoA formation, which has not previously been a metabolic route examined for this class of lipids, we applied a semi-targeted neutral loss scanning approach following arachidonic acid treatment in cell culture and detected inducible long-chain acyl-CoAs including a predominant AA-CoA peak. Interestingly, a series of AA-inducible acyl-CoAs at lower abundance but higher mass, likely corresponding to eicosanoid metabolites, was detected. Using a targeted LC-MS/MS approach we detected the formation of CoA thioesters of both 11-oxo- and 15-oxo-ETE and monitored the kinetics of their formation. Subsequently, we demonstrated that these acyl-CoA species undergo up to four double bond reductions. We confirmed the generation of 15-oxo-ETE-CoA in human platelets via LC-high resolution MS. Acyl-CoA thioesters of eicosanoids may provide a route to generate reducing equivalents, substrates for fatty acid oxidation, and substrates for acyl-transferases through cPLA2-dependent eicosanoid metabolism outside of the signaling contexts traditionally ascribed to eicosanoid metabolites.

Understanding the role of 3-O-Acetyl-11-keto-beta-boswellic acid in conditions of oxidative-stress mediated hepatic dysfunction during benzo(a)pyrene induced toxicity.[Pubmed:28363852]

Food Chem Toxicol. 2017 Nov;109(Pt 2):871-878.

The present study was planned to see whether 3-O-Acetyl-11- keto-beta-boswellic acid has any protective effects against benzo(a)pyrene (BaP) induced toxicity or not. In vitro studies show concentration dependent linear association of radical scavenging activity of AK which is comparable to ascorbic acid taken as reference compound. For in vivo studies, the animals were divided randomly into five groups which included a) normal control, b) vehicle treated (olive oil), c) BaP treated, d) AK treated and e) AK + BaP (combined treated). BaP was administered at a dose of 50mg/kg in olive oil twice a week orally for 4 weeks and AK (50mg/kg) was given in olive oil thrice a week for 4 weeks before and after BaP exposure. BaP treated animals showed a significant increase (p < 0.001) in lipid peroxidation (LPO) and protein carbonyl contents (PCC) in hepatic tissue. Further, a significant increase (p < 0.001) in the liver marker enzymes as well as citrulline and nitric oxide levels in the hepatic tissue was also observed. Interestingly, AK when supplemented to BaP treated animals ameliorated the above said biochemical indices appreciately. The histopathological observations also showed appreciable improvement when BaP treated animals were supplemented with AK, thus emphasing the protective potential of AK.

An open sandwich immunoassay for detection of 13(R,S)-hydroxy-9(E),11(E)-octadecadienoic acid.[Pubmed:28144646]

Analyst. 2017 Feb 27;142(5):787-793.

Lipid peroxidation is involved in many disorders and diseases such as cardiovascular disease, cancers, neurodegenerative diseases, and even aging. Lipid peroxidation products existing in blood or bodily fluids are very important biomarkers for the diagnosis of such diseases. In particular, 13(R,S)-hydroxy-9(E),11(E)-octadecadienoic acid (13-(E,E)-HODE) is an oxidiation product of linoleic acid, which is an important biomarker for many diseases such as diabetes and Alzheimer's disease. In this study, we successfully displayed the antigen-binding fragment of an antibody produced by hybridoma 1213-1 on the M13 phage and performed analysis of the antibody variable region genes. The blast results suggested that it is a novel antibody. We also developed a phage-antibody-based competitive ELISA and a novel Open Sandwich ELISA (OS ELISA) for the detection of 13-(E,E)-HODE. The OS ELISA showed a limit of detection (LOD) of 15.6 nM of 13-(E,E)-HODE and low cross-reactivity with other HODE such as 9-(E,E)-HODE. Another format of the open sandwich ELISA with purified maltose binding protein-fused VL and VH-phage showed a lower LOD of 2.2 nM of 13-(E,E)-HODE, which may be sensitive enough to detect the concentration of 13-(E,E)-HODE in patients' blood samples. This is the first OS ELISA for the detection of lipids, and we believe it also represents the first molecular cloning of anti-HODE antibody genes.

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