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Kaurenoic acid

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Kaurenoic acid
Kaurenoic acid
Names
IUPAC name 5β,8α,9β,10α,13α-Kaur-16-en-18-oic acid
Systematic IUPAC name (4R,4aS,6aS,9R,11aR,11bS)-4,11b-Dimethyl-8-methylidenetetradecahydro-6a,9-methanocycloheptanaphthalene-4-carboxylic acid
Other names
  • Cunabic acid
  • Kaurenic acid
Identifiers
CAS Number
3D model (JSmol)
Beilstein Reference 10784819
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
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/s1Key: NIKHGUQULKYIGE-OTCXFQBHSA-N
SMILES
  • C=C1C23CC4()(C(O)=O)(C)CCC4(C)2()CC1C3
Properties
Chemical formula C20H30O2
Molar mass 302.458 g·mol
Pharmacology
ATC code M09AX05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references
Chemical compound

Kaurenoic acid (ent-kaur-16-en-19-oic acid or kauren-19-oic acid) is a diterpene with antibacterial activity against Gram-positive bacteria. However its low solubility and blood lytic activity on erythrocytes might make it a poor pharmaceutical candidate. Kaurenoic acid also has uterine relaxant activity via calcium blockade and opening ATP-sensitive potassium channels.

Kaurenoic acid is found in several plants such as Copaifera. It is a potential biomarker for the presence of sunflower in foods.

Medical use

Kaurenoic acid has been studied for its medicinal properties and seems to have anti-inflammatory, antiulcerogenic, antitumor, antinociceptive, antimelanoma, antitilipoperoxidation, antioxidant and antimicrobial properties.

Kaurenoic acid decreases leukocyte migration. It seems to inhibit histamine and serotonin pathways, in addition to antiprotozoal activities against Trypanosoma cruzi and Leishmania amazonensis.

References

  1. Vieira, Henriete S.; Takahashi, Jacqueline A.; Oliveira, Alaíde B. de; Chiari, Egler; Boaventura, Maria Amélia D. (2002). "Novel Derivatives of Kaurenoic Acid". Journal of the Brazilian Chemical Society. 13 (2): 151–157. doi:10.1590/S0103-50532002000200004. ISSN 0103-5053.
  2. "Showing Compound Kaurenoic acid (FDB021671) - FooDB". Retrieved 24 January 2021.
  3. Rocha, Silvia Maria Machado da; Cardoso, Plínio Cerqueira dos Santos; Bahia, Marcelo de Oliveira; Pessoa, Claudia do Ó; Soares, Paulo Cardoso; Rocha, Simone Machado da; Burbano, Rommel Mário Rodríguez; Rocha, Carlos Alberto Machado da (1 June 2019). "Effect of the kaurenoic acid on genotoxicity and cell cycle progression in cervical cancer cells lines". Toxicology in Vitro. 57: 126–131. doi:10.1016/j.tiv.2019.02.022. ISSN 0887-2333. PMID 30822460. S2CID 73485393. Retrieved 24 January 2021.
  4. Silva, Matheus L.; Costa‐Silva, Thais A.; Antar, Guilherme M.; Tempone, Andre G.; Lago, João Henrique G. (October 2021). "Front Cover: Chemical Constituents from Aerial Parts of Baccharis sphenophylla and Effects against Intracellular Forms of Trypanosoma cruzi (Chem. Biodiversity 10/2021)". Chemistry & Biodiversity. 18 (10). doi:10.1002/cbdv.202100695. ISSN 1612-1872. S2CID 244986153.
  5. da Costa-Silva, Thais A.; Silva, Matheus L.; Antar, Guilherme M.; Tempone, Andre G.; Lago, João Henrique G. (1 December 2021). "Ent-kaurane diterpenes isolated from n-hexane extract of Baccharis sphenophylla by bioactivity-guided fractionation target the acidocalcisomes in Trypanosoma cruzi". Phytomedicine. 93: 153748. doi:10.1016/j.phymed.2021.153748. ISSN 0944-7113. PMID 34628240. S2CID 238581510.
  6. al, D. Kian et (2018). "Trypanocidal activity of copaiba oil and kaurenoic acid does not depend on macrophage killing machinery |". Biomedicine & Pharmacotherapy. 103: 1294–1301. doi:10.1016/j.biopha.2018.04.164. PMID 29864911. S2CID 46930282. Retrieved 24 January 2021.
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