kaurenoic acid
kaurenoic acid Basic information
- Product Name:
- kaurenoic acid
- Synonyms:
-
- kaurenoic acid
- (-)-Kaur-16-en-18-oic acid
- Cunabic acid
- Kaurane-16-ene-18-oic acid
- ent-Kaur-16(17)-en-19-oic acid
- ent-Kaur-16-en-19-oic acid
- NSC 339145
- Kaur-16-en-18-oic acid,(4a)-
- CAS:
- 6730-83-2
- MF:
- C20H30O2
- MW:
- 302.45
- Mol File:
- 6730-83-2.mol
kaurenoic acid Chemical Properties
- Melting point:
- 171-172 °C
- Boiling point:
- 426.6±34.0 °C(Predicted)
- Density
- 1.10±0.1 g/cm3(Predicted)
- storage temp.
- Sealed in dry,Store in freezer, under -20°C
- solubility
- DMF: 10 mg/ml; DMSO: 25 mg/ml; DMSO:PBS (pH 7.2) (1:2): 0.3 mg/ml; Ethanol: 10 mg/ml
- form
- A solid
- pka
- 4.70±0.40(Predicted)
- color
- White to off-white
kaurenoic acid Usage And Synthesis
Description
Kaurenoic acid is a diterpene that has been found in C. langsdorffii and has diverse biological activities, including anticancer, antibacterial, antioxidant, and anti-inflammatory properties. It is cytotoxic to 22Rv1 and LNCaP prostate, HT-29, HCT116, SW480, and SW620 colon, and MCF-7 breast cancer cells with IC50 values ranging from 15.03 to 48.87 μg/ml. Kaurenoic acid is active against S. epidermidis, S. capitis, E. faecalis, and S. haemolyticus in vitro (MICs = 6.25-12.5 μg/ml). Kaurenoic acid (50 and 100 mg/kg) reduces colonic myeloperoxidase (MPO) activity and malondialdehyde (MDA) levels in a rat model of acetic acid-induced colitis, as well as colonic tissue damage, leukocytic infiltration, and submucosal edema when administered at a dose of 100 mg/kg.
Chemical Properties
White crystalline powder, soluble in organic solvents such as methanol, ethanol, and DMSO, derived from plants such as Acanthopanax Cortex (1% content) and Bletilla striata leaves.
Uses
ent-Kaurenoic Acid can be used in biological study. Kinetic profile of guaco syrup metabolites like coumarin, 7-hydroxycoumarin, o-coumaric acid, kaurenoic acid can be performed for identification of alternative route of coumarin metabolism in human plasma.
Definition
ChEBI: An ent-kaurane diterpenoid that is ent-kauran-19-oic acid in which a double bond is present at position 16(17); exhibits anticancer and anti-HIV 1 activity.
in vivo
Kaurenoic acid (1-10 mg/kg, i.g., single dose) reduces peritonitis and pain induced by lipopolysaccharides (HY-D1056) in mice[2].
Kaurenoic acid (as a diterpene compound) is the main active ingredient in the root bark extract of A. senegalensis that exhibits anticonvulsant effects in mice[3].
| Animal Model: | Mice induced by LPS[2] |
| Dosage: | 1, 3, 10 mg/kg; single dose |
| Administration: | i.g. |
| Result: | Inhibited LPS-induced mechanical and thermal hyperalgesia, suppressed MPO activity, regulated the redox state of mouse paws, inhibited the production of pro-inflammatory/pain cytokines (such as TNF-α, IL-1β, and IL-33), and enhanced the production of anti-inflammatory/analgesic cytokine IL-10. |
References
[1] L.A.F. PAIVA . Anti-inflammatory effect of kaurenoic acid, a diterpene from Copaifera langsdorffii on acetic acid-induced colitis in rats[J]. Vascular pharmacology, 2002, 39 6: Pages 303-307. DOI: 10.1016/s1537-1891(03)00028-4
[2] GENEIVE E. HENRY . Kaurene diterpenes from Laetia thamnia inhibit the growth of human cancer cells in vitro[J]. Cancer letters, 2006, 244 2: Pages 190-194. DOI: 10.1016/j.canlet.2005.12.022
[3] A. C. F. SOARES. Variability of the antibacterial potential among analogue diterpenes against Gram-positive bacteria: considerations on the structure–activity relationship[J]. Canadian Journal of Chemistry, 2019, 62 1. DOI: 10.1139/cjc-2018-0369
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kaurenoic acid(6730-83-2)Related Product Information
- ISOEGOMAKETONE
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- DARUTOSIDE
- 10-Deacetylbaccatin III
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- STEVIOL METHYL ESTER