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Kaurenoic acid

$166

  • Brand : BIOFRON

  • Catalogue Number : BD-P0641

  • Specification : 98.0%(HPLC)

  • CAS number : 6730-83-2

  • Formula : C20H30O2

  • Molecular Weight : 302.46

  • PUBCHEM ID : 73062

  • Volume : 25mg

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Catalogue Number

BD-P0641

Analysis Method

Specification

98.0%(HPLC)

Storage

-20℃

Molecular Weight

302.46

Appearance

Cryst.

Botanical Source

This product is isolated and purified from the herbs of Croton antisyphiliticus

Structure Type

Category

SMILES

CC12CCCC(C1CCC34C2CCC(C3)C(=C)C4)(C)C(=O)O

Synonyms

Kaurenoic acid/Cunabic acid/(5β,8α,9β,10α,13α)-Kaur-16-en-18-oic acid/(5β,8α,9β,10α)-Kaur-16-en-18-oic acid/KAUREN-19-OIC ACID/Kaurane-16-ene-18-oic acid/ent-kaur-16-en-19-oic acid

IUPAC Name

Applications

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.

Density

1.1±0.1 g/cm3

Solubility

Methanol; Dichloromethane

Flash Point

202.8±20.3 °C

Boiling Point

426.6±34.0 °C at 760 mmHg

Melting Point

InChl

InChl Key

NIKHGUQULKYIGE-OTCXFQBHSA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:6730-83-2) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

28732811

Abstract

BACKGROUND:
Kaurenoic acid (ent-kaur-16-en-19-oic acid: KA) is a key constituent found in the roots of Aralia continentalis Kitagawa (Araliaceae) that has been used for treating rheumatism in traditional Asian medicine.

HYPOTHESIS:
Although KA was reported to suppress inflammation by activating Nrf2, the anti-inflammatory function of KA is less characterized. Given the complex nature of the inflammatory response and the critical role of TGF-β in resolving inflammation, we hypothesized that KA suppresses inflammatory response by activating TGF-β signaling.

METHODS:
Murine macrophage RAW 264.7, human lung epithelial cell MRC-5, and a TGFβRII defective cell HCT116 were treated with various amounts of KA. KA was also administered to mouse lung via intratracheal (i.t.) route. Phosphorylated Smad2 and Smad3 were analyzed by western blot. TGFβ-dependent gene expression was determined by immunoblotting of α-SMA and luciferase assay.

RESULTS:
KA induced the phosphorylation of Smad2 and Smad3, key activator molecules in TGF-β signaling. EW7197, an inhibitor for activin receptor-like kinase 5/TGF-β receptor I (TGFβR1) suppressed KA-mediated phosphorylation of Smad2. Similarly, KA failed to phosphorylate Smad2 in HCT116, suggesting that KA acts through the prototypic TGFβR. KA treatment increased the transcriptional activity driven by a Smad-binding element in a luciferase reporter assay and induced the α-smooth muscle actin (α-SMA). Similarly, i.t. KA induced the phosphorylation of Smad2 and increased the expression ofα-SMA in mouse lungs.

CONCLUSION:
KA activated TGF-β signaling, suggesting that TGFβ signaling is associated with KA suppressing inflammation.

Copyright © 2017 Elsevier GmbH. All rights reserved.

KEYWORDS

Anti-inflammation; Gene expression; Kaurenoic acid; Smad2; TGF-β signaling

Title

Kaurenoic acid activates TGF-β signaling.

Author

Kim KH1, Han JW2, Jung SK2, Park BJ3, Han CW4, Joo M5.

Publish date

2017 Aug 15

PMID

30339948

Abstract

Kaurenoic acid (KA), a kaurane diterpene found in several medicinal plants, is an active ingredient with potential anti-inflammatory, anticonvulsant, antibacterial and antitumor activities. In this work, an ultra-performance liquid chromatography-tandem mass spectrometry method (UPLC-MS/MS) was firstly developed and validated to quantify kaurenoic acid in rat plasma. Rhein was chosen as the internal standard (IS) and the plasma was processed with one-step acetonitrile protein precipitation; the chromatographic separation was achieved on a HSS T3 (2.1 × 50 mm, 1.8 μm) column with the mobile phase consisting of acetonitrile and water containing 0.1% formic acid via gradient elution. An electrospray ionization source was applied and operated in the negative ion and multiple reaction monitoring (MRM) modes. Kaurenoic acid and IS were quantified using the transitions of m/z 301.2→301.2 (pseudo MRM) and m/z 283.2 → 238.9, respectively. The calibration curves were linear over the range of 5∼ 100 ng/mL (R2 = 0.990). The lower limit of quantification (LLOQ) was 5 ng/mL. The intra- and inter- day precision (RSD) ranged from 3.0% to 11.4%. The matrix effect and extraction recovery were within acceptable limits. The validated method was successfully applied to the pharmacokinetic study of kaurenoic acid in rats after oral administration at three dosages.

Copyright © 2018. Published by Elsevier B.V.

KEYWORDS

Bioavailability; Kaurenoic acid; Pharmacokinetic; UPLC-MS/MS

Title

Determination of kaurenoic acid in rat plasma using UPLC-MS/MS and its application to a pharmacokinetic study.

Author

Jiang X1, Shen Y1, Wang H2, Wang C1, Ye X3, Xiang Z4.

Publish date

2019 Feb 5

PMID

30822460

Title

Effect of the kaurenoic acid on genotoxicity and cell cycle progression in cervical cancer cells lines.

Author

Rocha SMMD1, Cardoso PCDS2, Bahia MO2, Pessoa CDo3, Soares PC4, Rocha SMD5, Burbano RMR6, Rocha CAMD7.

Publish date

2019 Jun