RESUMEN
ABSTRACT The root of Anacyclus pyrethrum (L.) Lag., Asteraceae, is very widely used for treating various diseases in Traditional Uygur Medicine, particularly in the treatment of vitiligo. However, there have been few studies on the quality standards of A. pyrethrum in China. A. pyrethrum contains abundant N-alkylamides, which are considered to be the principal components. Therefore, based on the previous research in our group, six N-alkylamides were obtained by using column chromatography. We used ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry to determine the mass spectrometry cleavage mechanism of these six monomer components and established the mass spectrometry cleavage law of N-alkylamides. Then, we used the ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry method to rapidly identify and analyze the N-alkylamide components of the A. pyrethrum methanol extract. Finally, twenty N-alkylamides were identified, including eleven N-isobutylamides, two N-methyl isobutylamides, six 4-hydroxyphenylethyl-amide and one 2-phenylethylamide. Five of these compounds were identified as new compounds that have not been reported to date. Two of these compounds were identified for the first time in this herb. Therefore, this work provides an approach for the quality analysis of N-alkylamides in the root of A. pyrethrum. A search of the literature showed that the content determination in the A. pyrethrum quality standard is still a remaining problem. N-alkylamides are the main components of A. pyrethrum. Even though ultra-performance liquid chromatography quadrupole time-of-flight mass spectrometry has the advantages of lower time and higher efficiency compared to high-performance liquid chromatography, considering the ease of repeatability and universality of the quality control method, we chose to use high-performance liquid chromatography for content determination. In this experiment, high-performance liquid chromatography was used for the first time to establish a simple, rapid and accurate method for evaluating the N-alkylamide content in A. pyrethrum with five N-alkylamides used as the standards. Finally, this work provides a qualitative and quantitative method for the analysis of N-alkylamides in A. pyrethrum, improving the quality control standards for A. pyrethrum.
RESUMEN
Achillea millefolium and Achillea ptarmica are both plants belonging to the Asteracea family and are traditionally used for their medicinal properties. It has already been shown that some N-alkylamides (NAAs) are responsible for these pharmacological actions. Therefore, in the present study, the NAA content of the two plants was analytically characterised. Different extracts were prepared from the roots, the leaves, the stems and the flowers. The structures of NAAs have been assigned in ethanolic extracts of Achillea millefolium and Achillea ptarmica using high performance liquid chromatography – electrospray ionisation – mass spectro-metry (HPLC–ESI–MS) and gas chromatography–electron impact–mass spectrometry (GC–EI–MS). Using both analytical techniques, the structures of 14 and 15 NAAs have been assigned in Achillea ptarmica and Achillea millefolium, respectively. Structures of two new NAAs, previously never observed in Achillea ptarmica, were assigned: deca-2E,6Z,8E-trienoic acid 2-methylbutylamide (homospilanthol) or a related isomeric compound and deca-2E,4E-dienoic acid N-methyl isobutylamide. The structure of homospilanthol or a related isomeric compound was also assigned in Achillea millefolium for the first time.
RESUMEN
Components that systematic separated from the root of Anaycclus pyrethrum were identified, in order to lay a foundation for future study of the root of A. pyrethrum. The CCK-8 assay showed that dichloromethane fraction exhibited the highest degree of cytotoxicity than others. Ten monomeric components were obtained from dichloromethane fraction and ethyl acetate fraction extracted from the root of A. pyrethrum, including 7 N-alkylamides, one coumarin and two flavonoid glycosides. They were identified as tetradeca-2E,4E,8E-trienoic acid 4-hydroxyphenylethylamide(1), deca-2E,4E-dienoicacid isobutylamide(2), undeca-2E,4E-diene-8,10-diynoic acid phenylethylamide(3), tetradeca-2E,4E-dienoic acid 4-hydroxyphenylethylamide(4), tetradeca-2E,4E-diene-8,10-diynoic acid isobutylamide(5), deca-2E,4E- dienoic acid 4-hydroxyphenylethylamide(6), dodeca-2E,4E-dienoic acid 4-hydroxy -phenyl-ethylamide(7), isoscopoletin(8), quercetin-7-O-β-D-glucopyranoside(9), isorhamnetin-7-O-β-D-glucopyranoside(10). Among them, compound 1 was identified as a new compound, Compounds 2-4, 8-10 were isolated from this herb for the first time.
RESUMEN
Zanthoxylum chiloperone var. angustifolium Engl., Rutaceae, is used in traditional medicine to treat fungal and protozoal infections in the central area of South America. Considering the increasing resistance of Plasmodium falciparum in malarial ridden areas, we explored the anti-plasmodial effects of three compounds isolated from Z. chiloperone. The pyranocoumarin transavicennol and the canthinone alkaloids, canthin-6-one and 5-methoxycanthin-6-one, were found to have IC50 on chloroquine/mefloquine resistant and sensitive strains of P. falciparum of 0.5-2.7, 2.0-5.3 and 5.1-10.4 Êg/mL, respectively. Moreover, the formation of heme adducts by these compounds is described by a novel alternative method based on MS-CID methods. The alkylamide sanshool was also identified, for first time in this plant, in the dichloromethanic and ethanolic extracts and the extracts were found to be notably non-toxic and displayed good anti-plasmodial effects.