Inhibitory Effects of Metabolites Isolated from Artemisia dracunculus L. Against the Human Carbonic Anhydrase I (hCA I) and II (hCA II)

Abstract

Tarragon or Dragon's-wort (Artemisia dracunculus L.) is widely used as spice and in traditional medicine in various regions of the world. Inhibitory effects of the n-hexane, dichloromethane, ethanol and methanol extracts of the leaves of tarragon on the human carbonic anhydrase (hCA) I and II enzymes were investigated. Dichloromethane extract exhibited the strongest activity with lowest IC50 value (0.020 and 0.031 μg/mL, respectively). The chromatographic studies on the dichloromethane extract of tarragon allowed the isolation of six known strong inhibitors of hCA isozymes as trans-anethole, stigmasterol, herniarin, (2E,4E)-N-isobutylundeca-2,4-dien-8,10diynamide, (2E,4E)-1-(piperidin-1-yl)undeca-2,4-diene-8,10-diyn-1-one and 1-(4'-methoxyphenyl)-1,2,3trihydroxypropane. The compound, 1-(4'-methoxyphenyl)-1,2,3-trihydroxypropane was isolated from tarragon for the first time in this study. Among the tested compounds, 1-(4'-methoxyphenyl)-1,2,3-trihydroxypropane showed the highest inhibitiory impact on both hCA isozymes. Also its IC50 values were found lower than positive control, acetazolamide.

Artemisia dracunculus (Tarragon): A Review of Its Traditional Uses, Phytochemistry and Pharmacology

“…The action of 1-(4′-methoxyphenyl)-1,2,3-trihydroxypropane was more potent than that of the control acetazolamide. On the basis of their research, the authors of the study concluded that A. dracunculus herb extracts, like anhydrase I and II inhibitors, can reduce the accumulation of fluid inside the eyeball and thus be used in the treatment of glaucoma ( Aydın et al, 2019 ).…”

The chemistry and pharmacology of alkaloids and allied nitrogen compounds from Artemisia species: A review

“…The inhibitory effects of Neopellitorine A ( 39 ) and Neopellitorine B ( 40 ) against the human carbonic anhydrases I (hCA I) and II (hCA II) were tested by Aydın, Yurtvermez, Şentürk, Kazaz, and Çakır (). Both compounds 39 and 40 showed significant inhibition of hCA1/hCA2 with IC 50 15.8 ± 0.142/11.2 ± 0.008 and IC 50 8.6 ± 0.129/8.9 ± 0.125, respectively, as compared with the standard Acetazolamide with IC 50 72.5 ± 1.0875/0.77 ± 0.011 μM, respectively.…”

In vitro and in silico Evaluation of Some Natural Molecules as Potent Glutathione Reductase Inhibitors

“…β-sitosterol, diosgenin and jervine compounds were purified from the acetone extract of Veratrum album according to the procedure in our 2014 study [9]. The stigmasterol was purified from the dichloromethane extract of Artemisia dracunculus L. according to the procedure in our previous study [16]. The spectroscopic findings of the compounds were showed as in the our previous study [9,16].…”

“…The stigmasterol was purified from the dichloromethane extract of Artemisia dracunculus L. according to the procedure in our previous study [16]. The spectroscopic findings of the compounds were showed as in the our previous study [9,16].…”

“…It has proapoptotic and anticancer properties [15]. In the previous study by our team, the stigmasterol was isolated from tarragon (Artemisia dracunculus L.) [16]. Stigmasterol is a common plant steroid and has anti-inflammatory and anti-angiogenic activities [17].…”