Kaurenoic acid

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Kaurenoic acid
Kaurenoic acid Kaurenoic acid.svg
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
3D model (JSmol)
10784819
ChEBI
ChEMBL
ChemSpider
KEGG
PubChem CID
UNII
  • 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
  • C=C1C[C@@]23CC[C@]4([H])[C@@](C(O)=O)(C)CCC[C@@]4(C)[C@]2([H])CC[C@@H]1C3
Properties
C20H30O2
Molar mass 302.458 g·mol−1
Pharmacology
M09AX05 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

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

  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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