Falcarinol

Falcarinol is a C17-polyacetylene produced by the Apiaceae family that has antimicrobial properties due to its inhibition of fatty acid biosynthesis. [1] [2] Falcarinol binds to the human recombinant cannabinoid (CB) receptors, CB1 and CB2, (Kis = 594 and 2,100 nM, respectively) in an [3H]anandamide displacement assay in HEK293 cells.[3]  It differentially modulates synaptic and extrasynaptic GABAA receptors in a recombinant HEK293 system. [4] In vitro assays of ATPase activity demonstrate that falcarinol inhibits breast cancer resistance protein ATP-binding cassette sub-family G member 2 (ABCG2; IC50 = 79.3 μM), a drug efflux transporter and mediator of drug resistance. [5] Falcarinol (6.88 μg/g feed) also inhibits aberrant crypt foci by 26.6% in azoxymethane-induced rats. [6] 

Reference:
[1]. Dawid, C., Dunemann, F., Schwab, W., et al. Bioactive C₁₇-polyacetylenes in carrots (Daucus carota L.): Current knowledge and future perspectives. J. Agric. Food Chem. 63(42), 9211-9222 (2015).
[2]. Li, H., Cowie, A., Johnson, J.A., et al. Determining the mode of action of antimycobacterial C17 diyne natural products using expression profiling: Evidence for fatty acid biosynthesis inhibition. BMC Genomics 17(1), 621 (2016).
[3]. Leonti, M., Casu, L., Raduner, S., et al. Falcarinol is a covalent cannabinoid CB1 receptor antagonist and induces pro-allergic effects in skin. Biochem. Pharmacol. 79(12), 1815-1826 (2010).
[4]. Czyzewska, M.M., Chrobok, L., Kania, A., et al. Dietary acetylenic oxylipin falcarinol differentially modulates GABAA receptors. J. Nat. Prod. 77(12), 2671-2677 (2014).
[5]. Tan, K.W., Killeen, D.P., Li, Y., et al. Dietary polyacetylenes of the falcarinol type are inhibitors of breast cancer resistance protein (BCRP/ABCG2). Eur. J. Pharmacol. 723, 346-352 (2014).
[6]. Kobaek-Larsen, M., El-Houri, R.B., Christensen, L.P., et al. Dietary polyacetylenes, falcarinol and falcarindiol, isolated from carrots prevents the formation of neoplastic lesions in the colon of azoxymethane-induced rats. Food Funct. 8(3), 964-974 (2017).