(±)-Linalool

(±)-Linalool is a monoterpene alcohol that has been found in C. sativa, C. indica, and hemp with diverse biological activities.^1,2,3,4,5,6 It induces cell cycle arrest at the G₀/G₁ and G₂M phase in U937 and HeLa cells, respectively.² (±)-Linalool is cytotoxic to U937 and HeLa cells (IC₅₀s = 2.59 and 11.02 μM, respectively). It induces recruitment of a PGC-1α coactivator peptide to the PPARα ligand binding domain (EC₅₀ = 5.45 μM in a TR-FRET assay).³ In vivo, (±)-linalool reduces plasma triglyceride concentration in mice fed a Western diet and transgenic mice expressing human ApoE2, but not PPARα^-/- mice. It has molluscicidal and larvicidal effects in vitro (LC₅₀s = 0.25 and 0.07 mg/L for O. hupensis and S. japonicium, respectively), and it reduces the amount of schitosomulum recovered from mouse skin after S. japonicium challenge infection.⁴ (±)-Linalool (10-40 mg/kg) reduces the number of macrophages and neutrophils and the production of TNF-α, IL-6, IL-1β, IL-8, and MCP-1 in bronchoalveolar lavage fluid (BALF) in a mouse model of cigarette smoke-induced acute lung inflammation.⁵ It also decreases immobility time in the forced swim test in mice, indicating antidepressant-like activity.⁶

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1. Hazekamp, A., Tejkalová, K., and Papadimitriou, S. Cannabis: From cultivar to chemovar II—A metabolomics approach to Cannabis classification. Cannabis Cannabinoid Res. 1(1), 202-215 (2016).

2. Ständer, S., Ständer, H., Seeliger, S., et al. Topical pimecrolimus and tacrolimus transiently induce neuropeptide release and mast cell degranulation in murine skin. Br. J. Dermatol. 156(5), 1020-1026 (2007).

3. Jun, H.J., Lee, J.H., Kim, J., et al. Linalool is a PPARα ligand that reduces plasma TG levels and rewires the hepatic transcriptome and plasma metabolome. J. Lipid. Res. 55(6), 1098-1110 (2014).

4. Yang, F., Long, E., Wen, J., et al. Linalool, derived from Cinnamomum camphora (L.) Presl leaf extracts, possesses molluscicidal activity against Oncomelania hupensis and inhibits infection of Schistosoma japonicum. Parasit. Vectors 7, 407 (2014).

5. Jianqun, M., Hai, X., Wu, J., et al. Linalool inhibits cigarette smoke-induced lung inflammation by inhibiting NF-κB activation. Int. Immunopharmacol. 29(2), 708-713 (2015).

6. Guzmán-Gutiérrez, S.L., Bonilla-Jaime, H., Gómez-Cansino, R., et al. Linalool and β-pinene exert their antidepressant-like activity through the monoaminergic pathway. Life Sci. 128, 24-29 (2015).