Structure Database (LMSD)

Common Name
Jacaric acid
Systematic Name
8Z,10E,12Z-octadecatrienoic acid
Synonyms
  • cis-8, trans-10, cis-12-octadecatrienoic acid
  • C18:3n-6,8,10
  • Jacaranda acid
LM ID
LMFA01030143
Formula
C18H30O2
Exact Mass
Calculate m/z
278.22458
Sum Composition
FA 18:3
Status
Curated
Show lipids differing only in stereochemistry/bond geometry
View NP-MRD ID(NMR) spectrum

Classification

Category
Main Class
Sub Class
Fatty Acyls [FA]
Fatty Acids and Conjugates [FA01]
Unsaturated fatty acids [FA0103]
Octadecanoids [FA02]

Biological Context

Jacaric acid is a conjugated polyunsaturated fatty acid first isolated from seeds of Jacaranda plants.1 Structurally, it is an 18-carbon ω-6 triene isomer of γ-linolenic acid . Jacaric acid induces cell cycle arrest and apoptosis in a variety of cancer cell lines (GI50 = 1-5 µM).2,3,4 It increases the production of reactive oxygen species, and cytotoxicity is abolished by the antioxidant α-tocopherol, suggesting that apoptosis results from oxidative stress.3,4 Jacaric acid is metabolized in vivo to conjugated linoleic acid , which is also cytotoxic to cancer cells.5 Jacaric acid inhibits cyclooxygenase-1 in vitro (Ki = 1.7 µM) and, with long term feeding, decreases stearoyl-CoA desaturase expression and activity in mice.6,7

This information has been provided by Cayman Chemical

References

1. Shultz, T.D., Chew, B.P., Seaman, W.R., et al. Inhibitory effect of conjugated dienoic derivatives of linoleic acid and β-carotene on the in vitro growth of human cancer cells. Cancer Lett. 63(2), 125-133 (1992).
2. Yamasaki, M., Motonaga, C., Yokoyama, M., et al. Induction of apoptotic cell death in HL-60 cells by jacaranda seed oil derived fatty acids. J. Oleo Sci. 62(11), 925-932 (2013).
3. Gasmi, J., and Sanderson, J.T. Jacaric acid and its octadecatrienoic acid geoisomers induce apoptosis selectively in cancerous human prostate cells: A mechanistic and 3-D structure-activity study. Phytomedicine 20(8-9), 734-742 (2013).
4. Liu, W.N., and Leung, K.N. Jacaric acid inhibits the growth of murine macrophage-like leukemia PU5-1.8 cells by inducing cell cycle arrest and apoptosis. Cancer Cell Int. 15, (2015).
5. Miranda, J., Fernández-Quintela, A., Macarulla, M.T., et al. A comparison between CLNA and CLA effects on body fat, serum parameters and liver composition. J. Physiol. Biochem. 65(1), 25-32 (2009).
6. Shinohara, N., Ito, J., Tsuduki, T., et al. Jacaric acid, a linolenic acid isomer with a conjugated triene system, reduces stearoyl-CoA desaturase expression in liver of mice. J. Oleo Sci. 61(8), 433-441 (2012).
7. Mashhadi, Z., Boeglin, W.E., and Brash, A.R. Robust inhibitory effects of conjugated linolenic acids on a cyclooxygenase-related linoleate 10S-dioxygenase: Comparison with COX-1 and COX-2. Biochim. Biophys. Acta 1851(10), 1346-1352 (2015).

Reactions

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References

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Jacaranda mimosifolia (#185774)
Magnoliopsida (#3398)
Isolation and Structure of a New Conjugated Triene Fatty Acid,
J Org Chem, 1962

String Representations

InChiKey (Click to copy)
DQGMPXYVZZCNDQ-KDQYYBQISA-N
InChi (Click to copy)
InChI=1S/C18H30O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h6-11H,2-5,12-17H2,1H3,(H,19,20)/b7-6-,9-8+,11-10-
SMILES (Click to copy)
C(=C/C=C/C=C\CCCCC)/CCCCCCC(=O)O

Other Databases

CHEBI ID
180177
LIPIDBANK ID
DFA0182
PubChem CID
5282817
PlantFA ID
10103
Cayman ID
16036

Calculated Physicochemical Properties

Heavy Atoms 20
Rings 0
Aromatic Rings 0
Rotatable Bonds 13
Van der Waals Molecular Volume 326.98
Topological Polar Surface Area 37.30
Hydrogen Bond Donors 1
Hydrogen Bond Acceptors 2
logP 5.66
Molar Refractivity 86.90

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Created at
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Updated at
25th Apr 2022