Antileishmanial activity of prenylated coumarins isolated from Ferulago angulata and Prangos asperula

Abstract

Leishmaniasis has a wide spectrum of signs and symptoms due to infection to numbers of Leishmania species and makes enormous mortality and morbidity. There are clues of antileishmanial effects of prenylated coumarins. Apiaceae family is one of the most important sources of coumarins. Air-dried aerial parts of Ferulago angulata and fruits of Prangos asperula were extracted with n-hexane, using a soxhlet apparatus. The solvents were evaporated under reduced pressure. Column chromatography and crystallization process resulted to isolation of three prenylated coumarins. 1H-nuclear magnetic resonance, electron ionization Mass and Infrared spectra were used for elucidation of isolated compounds. Leishmanicidal activity of isolated coumarins was assessed on Leishmania major strain (MRHO/IR/75/ER) for the first time. Suberosin epoxide and suberosin were isolated from aerial parts of F. angulata and osthol was extracted from grounded fruits of P. asperula. Osthol showed a significant antileishmanial effect on promastigotes in early hours of exposure with IC50 of 14.40 µg/mL but suberosin epoxide showed only a weak antileishmanial activity. IC50 of osthol and suberosin epoxide after 48 h were 10.79 and 54.0 µg/mL, respectively. Suberosin showed no remarkable effect in these concentrations. This is the first report on the pharmacological activity of suberosin epoxide. Substantial difference between efficacies of two isomers, osthol and suberosin remarks the importance of prenyl substituent location on C-8.

Essential Oil Analysis and Isolation of Coumarins and Flavonol Glycosides of Ferulago angulata (Schltdl.) Boiss. Fruits

“…Monitoring of the column chromatography was carried out by thin layer chromatography (Pre-coated silica gel GF 254 plates, Merck) and fractions giving similar spots under UV (254 and 366 nm) were combined. The structures of the compounds were elucidated by 1 H-NMR and 13 C-NMR (Bruker Avance 400 DRX, 400 MHz for 1 H and 100 MHz for 13 C) spectral analysis, as well as by comparing with the data published in the literature.…”

“…[6][7][8][9][10][11][12] In 2006, Sajjadi et al reported the isolation of two prenylated coumarins, suberosin and suberosin epoxide, from aerial parts of this plant. 13 In their further studies, suberosin epoxide has been demonstrated to possess considerable antiprotozoal activity against Leishmania major and Plasmodium berghei. 13,14 Xanthotoxin, isoimperatorin, oxypeucedanin, oxypeucedanin hydrate, prantschimgin, quercetin, rutin, along with stigmasterol, β-sitosterol and β-sitosterol linoleate are the other compounds reported from the aerial parts of F. angulata during previous phytochemical studies.…”

“…13 In their further studies, suberosin epoxide has been demonstrated to possess considerable antiprotozoal activity against Leishmania major and Plasmodium berghei. 13,14 Xanthotoxin, isoimperatorin, oxypeucedanin, oxypeucedanin hydrate, prantschimgin, quercetin, rutin, along with stigmasterol, β-sitosterol and β-sitosterol linoleate are the other compounds reported from the aerial parts of F. angulata during previous phytochemical studies. [15][16][17] There are also some reports in the literature on essential oil constituents of F. angulata.…”

Synthesis and antileishmanial effect of a few cyclic and non-cyclic n-aryl enamino amide derivatives

“…Leishmaniasis is caused by protozoan parasites of the genus Leishmania and transferred into the host by the bite of infected female phlebotomine sandflies. Based on WHO reports, the pathogen is endemic over 90 countries ( 1 ) and Iran is one of the endemic areas of this pathogen ( 2 3 ). Leishmaniasis is estimated to involve about 2 million new cases per year ( 4 ) and despite such prevalence, leishmaniasis is categorized as a neglected tropical disease due to its strong relationship with poverty and also considering the limited resources invested in its diagnosis, treatment, and control ( 5 ).…”

Potential Anticancer Properties of Osthol: A Comprehensive Mechanistic Review

“…Coumarins have various biological properties related to their chemical structure [ 25 , 26 , 27 ]. Some coumarins have vasorelaxant activity in coronary vessels and some other showed hypotensive [ 22 ], antiviral [ 28 ], antileishmanial [ 29 ] anti-inflammatory [ 30 ] and antispasmodic [ 31 ] effects. Furanocoumarins are also widely used in the treatment of leucoderma and psoriasis due to their photosensitivity properties [ 32 , 33 ].…”