| Identification | Back Directory | [Name]
kaurenoic acid | [CAS]
6730-83-2 | [Synonyms]
NSC 339145
Cunabic acid
kaurenoic acid
Kauren-19-oic acid
ent-kaur-16-en-19-oicaci
ent-Kaur-16-en-19-oic acid
(-)-Kaur-16-en-18-oic acid
Kaurane-16-ene-18-oic acid
Kaur-16-en-18-oic acid,(4a)-
ent-Kaur-16(17)-en-19-oic acid
(4R,4aS,6aS,9R,11aR,11bS)-4,11b-dimethyl-8-methylenetetradecahydro-6a,9-methanocyclohepta[a]naphthalene-4-carboxylic acid | [Molecular Formula]
C20H30O2 | [MDL Number]
MFCD28978039 | [MOL File]
6730-83-2.mol | [Molecular Weight]
302.45 |
| Chemical Properties | Back Directory | [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 | [Major Application]
metabolomics
vitamins, nutraceuticals, and natural products | [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 | [InChIKey]
NIKHGUQULKYIGE-OTCXFQBHSA-N | [SMILES]
C=C1C[C@@]23CC[C@]4([H])[C@@](C(O)=O)(C)CCC[C@@]4(C)[C@]2([H])CC[C@@H]1C3 |
| Hazard Information | Back Directory | [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.1,2,3 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.2 Kaurenoic acid is active against S. epidermidis, S. capitis, E. faecalis, and S. haemolyticus in vitro (MICs = 6.25-12.5 μg/ml).3 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.1 | [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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