9(S),12(S),13(S)-TriHODE

9(S),12(S),13(S)-TriHODE is an α-linolenic acid-derived oxylipin that has been found in C. olitorius.^1,2,3 It is formed from α-linolenic acid via a 9(S)-HpOTrE intermediate.^[1] Tumor levels of 9(S),12(S),13(S)-TriHODE are decreased compared with adjacent healthy tissue in dogs with mammary cancer.^[4]

References:
[1].Hamberg, M., Sanz, A., Rodriguez, M.J., et al.Activation of the fatty acid α-dioxygenase pathway during bacterial infection of tobacco leaves. Formation of oxylipins protecting against cell deathJ. Biol. Chem.278(51)51796-51805(2003).
[2].Yoshikawa, M., Murakami, T., Shimada, H., et al.Medicinal foodstuffs. XIV. On the bioactive constituents of moroheiya. (2): New fatty acids, corchorifatty acids A, B, C, D, E, and F, from the leaves of Corchorus olitorius L. (Tiliaceae): Structures and inhibitory effect on NO production in mouse peritoneal macrophagesChem. Pharm. Bull. (Tokyo)46(6)1008-1014(1998).
[3].Prost, I., Dhondt, S., Rothe, G., et al.Evaluation of the antimicrobial activities of plant oxylipins supports their involvement in defense against pathogensPlant Physiol.139(4)1902-1913(2005).
[4].Yu, C., Zheng, H.-H., Zhang, Y.-Z., et al.Identification of canine mammary tumor-associated metabolites using untargeted metabolomicsTheriogenology21184-96(2023).