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-methanocyclohepta[a]naphthalene-4-carboxylic acid
	Other names Cunabic acid; Kaurenic acid;
Identifiers
CAS Number	6730-83-2 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	10784819
ChEBI	CHEBI:15417;
ChEMBL	ChEMBL489140;
ChemSpider	21258059;
KEGG	C11874;
PubChem CID	73062;
UNII	D572D9R2TZ ;
	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

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[4][5] and Leishmania amazonensis.[6]

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.
"Showing Compound Kaurenoic acid (FDB021671) - FooDB". Retrieved 24 January 2021.
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.
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.
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.
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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[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.

[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] 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.

[trep-6] , 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.