Xanthotoxol - a secondary product originated from imperatorin – University of Copenhagen

NaToxAq > Toxin of the week > Xanthotoxol

04 March 2019

Xanthotoxol - a secondary product originated from imperatorin

Fig. 1. Chemical structure of Xanthotoxol. Click image for interactive 3D model

Xanthotocxol or 8-hydroxypsoralen is a furanocoumarin generally isolated from Aegle marmelos (bael fruit) Angelica archangelica (angelica) Glehnia littoralis and the seeds of Pastinaca sativa (parsnip).

This toxin has different pharmacological activities. It has been showed that this toxin can be rapidly metabolized to a mono-glucuronide in both human intestine microsomes (HIM) and human liver microsomes.

Fig. 2. Angelica archangelica

Xanthotoxol is a secondary product originated by the imperatorin, another toxin which is originated by the umbelliferone, a plant metabolite. Evaluation of the pharmacokinetic properties of impera-torin is quite necessary due to the high importance in determining whether imperatorin can be pur-sued as a chemical entity. To date, some studies on imperatorin pharmacokinetics in rat plasma and rat liver after oral administration of imperatorin have been reported. Xanthotoxol is being rec-ognised to have stronger toxic activity. It is also clear that this compound can also be used as a marker for the indirect analysis of imperatorin. Toxicological activity includes cardio-inhibitory ac-tivity on frog and guinea pig isolated perfused heart and on isolated paired guinea pig atria anti-cholinesterase activity (low doses) and anticholinergic activity (high doses). In addition, xanthotoxol has been shown to possess antiadrenergic and possible tranquilizer activity1 antiserotonergic activi-ty (Sethi and Naik, 1979) tinicotinic and antiadrenergic activity2 and antihistaminic and anticholinergic activity3

SMILES: C1=CC(=O)OC2=C(C3=C(C=CO3)C=C21)O

References:
[1] Sethi, O.P., Desai, D.G., Bhatia, 0.S and Derasari, H.R. (1977a) An investigation on the effects of xantho-toxol (XT), a crystalline substance of plant origin. Indian Journal of Physiology and Pharmacology 2 1, 247.
[2] Sethi, O.P., Zala, B.J., Bhatia, OS. and Derasari, H.R. (1977b) Antiadrenergic and CNS depressant activity of xanthotoxol (XT), a crystalline substance of plant origin. Indian Journal of Physiology and Pharmacology 2 1, 249.
[3] Shah, A. (1980) Antinicotinic and Antiadrenergic Activity of Xanfhotoxol (XT). M. Pharm. thesis, Gujarat University, Ahmedabad, India. Shah, S. (1980) Antihistaminic and Anticholinergic Activity of Xanrhotoxol (XT). M. Pharm. thesis, Gujarat University, Ahmedabad, India.

Photo credits:
1)  Chemical structure comes from https://es.m.wikipedia.org/wiki/Archivo:Xanthotoxol.png
2) Plant picture (Angelica archangelica) comes from: https://www.google.com/search?q=angelica&source=lnms&tbm=isch&sa=X&ved=0ahUKEwjUmIPV7uDgAhXwThUIHeLYC00Q
_AUIDigB&biw=1920&bih=969#imgrc=bh7C7Jj7pdeQ3M