Kaurenoic acid

CAS# 6730-83-2

Kaurenoic acid

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Quality Control of Kaurenoic acid

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Chemical structure

Kaurenoic acid

3D structure

Chemical Properties of Kaurenoic acid

Cas No. 6730-83-2 SDF Download SDF
PubChem ID 73062 Appearance White powder
Formula C20H30O2 M.Wt 302.46
Type of Compound Diterpenoids Storage Desiccate at -20°C
Synonyms Cunabic acid
Solubility Soluble in DMSO and methan
SMILES CC12CCCC(C1CCC34C2CCC(C3)C(=C)C4)(C)C(=O)O
Standard InChIKey NIKHGUQULKYIGE-OTCXFQBHSA-N
Standard InChI InChI=1S/C20H30O2/c1-13-11-20-10-7-15-18(2,16(20)6-5-14(13)12-20)8-4-9-19(15,3)17(21)22/h14-16H,1,4-12H2,2-3H3,(H,21,22)/t14-,15+,16+,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.
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 Kaurenoic acid

1 Aralia sp. 2 Mikania sp. 3 Montanao sp. 4 Stevia sp. 5 Wedelia sp.

Biological Activity of Kaurenoic acid

DescriptionKaurenoic acid has anti-inflammatory, analgesic, antimicrobial, cytotoxic and embryotoxic effects; it exerts a uterine relaxant effect acting principally through calcium blockade and in part, by the opening of ATP-sensitive potassium channels. Kaurenoic acid involves the inhibition of cytokine production and activation of the NO-cyclic GMP-protein kinase G-ATP-sensitive potassium channel signaling pathway.
TargetsNO | PGE | COX | NOS | NF-kB | ATP | GMP
In vitro

Kaurenoic Acid from Aralia continentalis Inhibits Biofilm Formation of Streptococcus mutans.[Pubmed: 23662113]

Evid Based Complement Alternat Med. 2013;2013:160592.

We isolated a single chemical compound from A. continentalis and identified it to be Kaurenoic acid (KA) and investigated the influence of anticariogenic properties.
METHODS AND RESULTS:
Inhibitory effects of KA on cariogenic properties such as growth, acid production, biofilm formation, and the adherence of S. mutans were evaluated. Furthermore, real-time PCR analysis was performed to evaluate the influence of KA on the genetic expression of virulence factors. KA significantly inhibited the growth and acid production of S. mutans at 2-4  μ g/mL and 4  μ g/mL of KA, respectively. Furthermore, the adherence onto S-HAs was inhibited at 3-4  μ g/mL of KA and biofilm formation was significantly inhibited when treated with 3  μ g/mL KA and completely inhibited at 4  μ g/mL. Also, the inhibitory effect of KA on biofilm formation was confirmed by SEM. In confocal laser scanning microscopy, bacterial viability gradually decreased by KA in a dose dependent manner. Real-time PCR analysis showed that the expressions of gtfB, gtfC, gbpB, spaP, brpA, relA, and vicR were significantly decreased in S. mutans when it was treated with KA.
CONCLUSIONS:
These results suggest that KA from A. continentalis may be a useful agent for inhibiting the cariogenic properties of S. mutans.

In vivo

Anticonvulsant effect of kaurenoic acid isolated from the root bark of Annona senegalensis.[Pubmed: 23664900]

Pharmacol Biochem Behav. 2013 Aug;109:38-43.

The herbal preparations of Annona senegalensis Pers. (Annonaceae) root bark are used in Nigerian ethnomedicine for the treatment of epilepsy and febrile seizures. The scientific evidence for this effect has been reported. The aim of this study was to identify and characterize the active constituent responsible for the anticonvulsant effect.
METHODS AND RESULTS:
Bioactive-guided fractionation of the methanol-methylene chloride root bark extract (MME) of A. senegalensis using pentylenetetrazole (PTZ)-induced seizures in mice, afforded a potent anticonvulsant ethyl-acetate fraction (EF). Further fractionation of the EF yielded eight sub-fractions (F₁-F₈) which were tested for anticonvulsant activity. The sub-fraction F₂ yielded white crystals that were purified to obtain A. senegalensis crystals, AS2. The AS2, which exhibited potent anticonvulsant effects, was characterized by 1D and 2D NMR spectroscopy, mass spectroscopy and X-ray crystallography. The AS2 was characterized as kaur-16-en-19-oic acid (KA), a diterpenoid. The AS2 indicated an oral LD₅₀ of 3800 mg/kg. The results showed that the MME, EF and AS2 significantly (P<0.05) and dose-dependently delayed the onset of myoclonic spasms and tonic-clonic phases of seizures induced by PTZ and maximal electroshock seizures (MES).
CONCLUSIONS:
Kaurenoic acid was identified as the anticonvulsant principle in the root bark extract of A. senegalensis. The anticonvulsant effect of the MME, EF and AS2 is most likely being mediated through central inhibitory mechanisms.

Inhibitory effects of kaurenoic acid from Aralia continentalis on LPS-induced inflammatory response in RAW264.7 macrophages.[Pubmed: 21211951]

Phytomedicine. 2011 Jun 15;18(8-9):677-82.

This study investigates the anti-inflammatory effects of a diterpenoid, Kaurenoic acid, isolated from the root of Aralia continentalis (Araliaceae).
METHODS AND RESULTS:
To determine its anti-inflammatory effects, LPS-induced RAW264.7 macrophages were treated with different concentrations of Kaurenoic acid and carrageenan-induced paw edema mice model was used in vivo. Kaurenoic acid (ent-kaur-16-en-19-oic acid) dose-dependently inhibited nitric oxide (NO) production, prostaglandin E(2) (PGE(2)) release, cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) expression at micromolar concentrations in LPS-induced RAW264.7 macrophages with IC(50) (the half maximal inhibitory concentration) values of 51.73 (±2.42) μM and 106.09 (±0.27) μM in NO production and PGE(2) release, respectively. Kaurenoic acid also dose-dependently inhibited LPS-induced activation of NF-κB as assayed by electrophorectic mobility shift assay (EMSA) and it almost abolished NF-κB DNA binding affinity at 100μM. Furthermore, the in vivo anti-inflammatory effect of Kaurenoic acid was examined in a carrageenan-induced paw edema model. Eight ICR mice in each group were injected with carrageenan and observed hourly, compared with the control group. Kaurenoic acid dose-dependently reduced paw swelling up to 34.4% at 5h after induction, demonstrating inhibition in an acute inflammation model.
CONCLUSIONS:
Taken together, our data suggest that Kaurenoic acid, a major diterpenoid from the root of A. continentalis shows anti-inflammatory activity and the inhibition of iNOS and COX-2 expression might be one of the mechanisms responsible for its anti-inflammatory properties.

Protocol of Kaurenoic acid

Cell Research

The epimer of kaurenoic acid from Croton antisyphiliticus is cytotoxic toward B-16 and HeLa tumor cells through apoptosis induction.[Pubmed: 23613246]

Genet Mol Res. 2013 Apr 2;12(2):1005-11.

Cancer has become the leading cause of death in developing countries due to increased life expectancy of the population and changes in lifestyle. Studies on active principles of plant have motivated researchers to develop new antitumor agents that are specific and effective for treatment of neoplasms. Kaurane diterpenes are considered important compounds in the development of new and highly effective anticancer chemotherapeutic agents due to their cytotoxic properties in the induction of apoptosis.
METHODS AND RESULTS:
We evaluated the cytotoxic and apoptotic activity of the epimer of Kaurenoic acid (EKA) isolated from the medicinal plant Croton antisyphiliticus (Euphorbiaceae) toward tumor cell lines HeLa and B-16 and normal fibroblasts 3T3. Based on analyses with the MTT test, EKA showed cytotoxic activity, with half maximal inhibitory concentration values of 59.41, 68.18 and 60.30 μg/mL for the B-16, HeLa and 3T3 cell lines, respectively. The assay for necrotic or apoptotic cells by differential staining showed induction of apoptosis in all three cell lines.
CONCLUSIONS:
We conclude that EKA is not selective between tumor and normal cell lines; the mechanism of action of EKA is induction of apoptosis, which is part of the innate mechanism of cell defense against neoplasia.

Kaurenoic acid Dilution Calculator

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Preparing Stock Solutions of Kaurenoic acid

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.3062 mL 16.5311 mL 33.0622 mL 66.1244 mL 82.6556 mL
5 mM 0.6612 mL 3.3062 mL 6.6124 mL 13.2249 mL 16.5311 mL
10 mM 0.3306 mL 1.6531 mL 3.3062 mL 6.6124 mL 8.2656 mL
50 mM 0.0661 mL 0.3306 mL 0.6612 mL 1.3225 mL 1.6531 mL
100 mM 0.0331 mL 0.1653 mL 0.3306 mL 0.6612 mL 0.8266 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 Kaurenoic acid

Kaurenoic Acid from Aralia continentalis Inhibits Biofilm Formation of Streptococcus mutans.[Pubmed:23662113]

Evid Based Complement Alternat Med. 2013;2013:160592.

We isolated a single chemical compound from A. continentalis and identified it to be Kaurenoic acid (KA) and investigated the influence of anticariogenic properties. Inhibitory effects of KA on cariogenic properties such as growth, acid production, biofilm formation, and the adherence of S. mutans were evaluated. Furthermore, real-time PCR analysis was performed to evaluate the influence of KA on the genetic expression of virulence factors. KA significantly inhibited the growth and acid production of S. mutans at 2-4 mu g/mL and 4 mu g/mL of KA, respectively. Furthermore, the adherence onto S-HAs was inhibited at 3-4 mu g/mL of KA and biofilm formation was significantly inhibited when treated with 3 mu g/mL KA and completely inhibited at 4 mu g/mL. Also, the inhibitory effect of KA on biofilm formation was confirmed by SEM. In confocal laser scanning microscopy, bacterial viability gradually decreased by KA in a dose dependent manner. Real-time PCR analysis showed that the expressions of gtfB, gtfC, gbpB, spaP, brpA, relA, and vicR were significantly decreased in S. mutans when it was treated with KA. These results suggest that KA from A. continentalis may be a useful agent for inhibiting the cariogenic properties of S. mutans.

Inhibitory effects of kaurenoic acid from Aralia continentalis on LPS-induced inflammatory response in RAW264.7 macrophages.[Pubmed:21211951]

Phytomedicine. 2011 Jun 15;18(8-9):677-82.

This study investigates the anti-inflammatory effects of a diterpenoid, Kaurenoic acid, isolated from the root of Aralia continentalis (Araliaceae). To determine its anti-inflammatory effects, LPS-induced RAW264.7 macrophages were treated with different concentrations of Kaurenoic acid and carrageenan-induced paw edema mice model was used in vivo. Kaurenoic acid (ent-kaur-16-en-19-oic acid) dose-dependently inhibited nitric oxide (NO) production, prostaglandin E(2) (PGE(2)) release, cyclooxygenase-2 (COX-2) and inducible nitric oxide synthase (iNOS) expression at micromolar concentrations in LPS-induced RAW264.7 macrophages with IC(50) (the half maximal inhibitory concentration) values of 51.73 (+/-2.42) muM and 106.09 (+/-0.27) muM in NO production and PGE(2) release, respectively. Kaurenoic acid also dose-dependently inhibited LPS-induced activation of NF-kappaB as assayed by electrophorectic mobility shift assay (EMSA) and it almost abolished NF-kappaB DNA binding affinity at 100muM. Furthermore, the in vivo anti-inflammatory effect of Kaurenoic acid was examined in a carrageenan-induced paw edema model. Eight ICR mice in each group were injected with carrageenan and observed hourly, compared with the control group. Kaurenoic acid dose-dependently reduced paw swelling up to 34.4% at 5h after induction, demonstrating inhibition in an acute inflammation model. Taken together, our data suggest that Kaurenoic acid, a major diterpenoid from the root of A. continentalis shows anti-inflammatory activity and the inhibition of iNOS and COX-2 expression might be one of the mechanisms responsible for its anti-inflammatory properties.

Anticonvulsant effect of kaurenoic acid isolated from the root bark of Annona senegalensis.[Pubmed:23664900]

Pharmacol Biochem Behav. 2013 Aug;109:38-43.

CONTEXT: The herbal preparations of Annona senegalensis Pers. (Annonaceae) root bark are used in Nigerian ethnomedicine for the treatment of epilepsy and febrile seizures. The scientific evidence for this effect has been reported. OBJECTIVE: The aim of this study was to identify and characterize the active constituent responsible for the anticonvulsant effect. MATERIALS AND METHODS: Bioactive-guided fractionation of the methanol-methylene chloride root bark extract (MME) of A. senegalensis using pentylenetetrazole (PTZ)-induced seizures in mice, afforded a potent anticonvulsant ethyl-acetate fraction (EF). Further fractionation of the EF yielded eight sub-fractions (F(1)-F(8)) which were tested for anticonvulsant activity. The sub-fraction F(2) yielded white crystals that were purified to obtain A. senegalensis crystals, AS2. The AS2, which exhibited potent anticonvulsant effects, was characterized by 1D and 2D NMR spectroscopy, mass spectroscopy and X-ray crystallography. RESULTS: The AS2 was characterized as kaur-16-en-19-oic acid (KA), a diterpenoid. The AS2 indicated an oral LD(5)(0) of 3800 mg/kg. The results showed that the MME, EF and AS2 significantly (P<0.05) and dose-dependently delayed the onset of myoclonic spasms and tonic-clonic phases of seizures induced by PTZ and maximal electroshock seizures (MES). DISCUSSION AND CONCLUSION: Kaurenoic acid was identified as the anticonvulsant principle in the root bark extract of A. senegalensis. The anticonvulsant effect of the MME, EF and AS2 is most likely being mediated through central inhibitory mechanisms.

The epimer of kaurenoic acid from Croton antisyphiliticus is cytotoxic toward B-16 and HeLa tumor cells through apoptosis induction.[Pubmed:23613246]

Genet Mol Res. 2013 Apr 2;12(2):1005-11.

Cancer has become the leading cause of death in developing countries due to increased life expectancy of the population and changes in lifestyle. Studies on active principles of plant have motivated researchers to develop new antitumor agents that are specific and effective for treatment of neoplasms. Kaurane diterpenes are considered important compounds in the development of new and highly effective anticancer chemotherapeutic agents due to their cytotoxic properties in the induction of apoptosis. We evaluated the cytotoxic and apoptotic activity of the epimer of Kaurenoic acid (EKA) isolated from the medicinal plant Croton antisyphiliticus (Euphorbiaceae) toward tumor cell lines HeLa and B-16 and normal fibroblasts 3T3. Based on analyses with the MTT test, EKA showed cytotoxic activity, with half maximal inhibitory concentration values of 59.41, 68.18 and 60.30 microg/mL for the B-16, HeLa and 3T3 cell lines, respectively. The assay for necrotic or apoptotic cells by differential staining showed induction of apoptosis in all three cell lines. We conclude that EKA is not selective between tumor and normal cell lines; the mechanism of action of EKA is induction of apoptosis, which is part of the innate mechanism of cell defense against neoplasia.

Description

Kaurenoic acid is a diterpene from Sphagneticola trilobata, inhibits Inflammatory Pain by the inhibition of cytokine production and activation of the NO–cyclic GMP–PKG–ATP-sensitive potassium channel signaling pathway.

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