Yangonin (Y) #3
Kavalactone #3 in Chemotypes. Yangonin.
Kava, the plant we understand and love, is turning out to be a deeper mystery than we had first imagined. The actions of this plant are complex and will continue to be researched. Of the 6 kavalactones commonly found in kava in the most abundance, yangonin will be of interest today.
What is yangonin? Yangonin (4-Methoxy-6-[(E)-2-(4-methoxyphenyl)ethenyl]pyran-2-one) is one of the six major kavalactones found in the kava plant [1]. It took 18–19 min to travel through the high performance liquid chromatography (HPLC) column, making it the third fastest and as such received the designation chemotype number 3 [2]. Yangonin was found to have a number of functions among many likely unknown functions. First, yangonin exerts a protective effect against cholestasis or when the flow of bile from the liver is reduced or blocked. Yangonin has a regulative effect on hepatic genes that contribute to the increased transport and metabolism of toxic bile acids, as well as decreased bile acid synthesis [4]. Yangonin decreased dopamine levels in the brain [5]. Yangonin has a measurable affinity for the cannabinoid receptor CB1. It is the same receptor that is strongly activated by Δ9-THC, the main active substance in cannabis. Yangonin has approximately 170 times less affinity for the CB1 receptor than THC [3]. The effect, if present, will be slight, which could provide evidence to support the hypothesis that yangonin contributes to the anxiolytic effect of kava in this manner.
[1]Yangonin. (2020, December 02). Retrieved December 23, 2020, from https://en.wikipedia.org/wiki/Yangonin
[2] Lebot, V. and J. Levesque. “The origin and distribution of kava piper methysticum forst. f. piperaceae a phytochemical approach.” (1989).
[3]Ligresti A, Villano R, Allarà M, Ujváry I, Di Marzo V. Kavalactones and the endocannabinoid system: the plant-derived yangonin is a novel CB₁ receptor ligand. Pharmacol Res. 2012 Aug;66(2):163-9. doi: 10.1016/j.phrs.2012.04.003. Epub 2012 Apr 14. PMID: 22525682.
[4]Kong, Y., Gao, X., Wang, C., Ning, C., Liu, K., Liu, Z., . . . Meng, Q. (2018). Protective effects of yangonin from an edible botanical Kava against lithocholic acid-induced cholestasis and hepatotoxicity. European Journal of Pharmacology, 824, 64-71. doi:10.1016/j.ejphar.2018.02.002
[5]Baum SS, Hill R, Rommelspacher H. Effect of kava extract and individual kavapyrones on neurotransmitter levels in the nucleus accumbens of rats. Prog Neuropsychopharmacol Biol Psychiatry. 1998 Oct;22(7):1105-20. doi: 10.1016/s0278-5846(98)00062-1. PMID: 9829291.