Kaurenoic acid: Difference between revisions

Kaurenoic acid.svg
Names
	IUPAC name (5beta,8alpha,9beta,10alpha,13alpha)-kaur-16-en-18-oic acid
	Other names Cunabic acid; Kaurenic acid;
Identifiers
CAS Number	6730-83-2;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:15417;
ChemSpider	21258059;
PubChem CID	73062;
	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 Key: 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;
Properties
Chemical formula	C20H30O2
Molar mass	302.45
Pharmacology
ATC code	M09AX05 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Next edit →

Content deleted Content added

VisualWikitext

Inline

Revision as of 00:07, 4 February 2021

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.^[1] 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.^[2]

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.^[3]

Kaurenoic acid decreases leukocyte migration. It seems to inhibit histamine and serotonin pathways, in addition to antiprotozoal activities against Trypanosoma. cruzi and Leishmania amazonensis.^[4]

References

^ 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. Retrieved 2021-01-24.
^ "Showing Compound Kaurenoic acid (FDB021671) - FooDB". Retrieved 2021-01-24.
^ 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 (2019-06-01). "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. Retrieved 2021-01-24.
^ al, D. Kian et. "Trypanocidal activity of copaiba oil and kaurenoic acid does not depend on macrophage killing machinery | EndNote Click". Retrieved 2021-01-24. {{cite journal}}: Cite journal requires |journal= (help)

[novel-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. Retrieved 2021-01-24.

[2] "Showing Compound Kaurenoic acid (FDB021671) - FooDB". Retrieved 2021-01-24.

[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 (2019-06-01). "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. Retrieved 2021-01-24.

[trep-4] , D. Kian et. "Trypanocidal activity of copaiba oil and kaurenoic acid does not depend on macrophage killing machinery | EndNote Click". Retrieved 2021-01-24. {{cite journal}}: Cite journal requires |journal= (help)

[1]

[2]

[3]

[4]