LC-MS N-alkylamide Profiling of an Ethanolic Anacyclus pyrethrum Root Extract

Abstract

The roots of Anacyclus pyrethrum DC (AP) (Asteraceae) are frequently used in traditional medicine as Vajikarana Rasayana. An ethanolic extract of root of Anacyclus pyrethrum demonstrated its potential to enhance the sexual behaviour of male rats, with a dose dependent effect on sperm count and androgens concentration. Phytochemical analysis of ethanolic extract of Anacyclus pyrethrum revealed that it is rich in N-alkylamide. This study therefore sought to assess characterization of ethanolic extract of Anacyclus pyrethrum root. Root extract was performed using a gradient reversed phase high performance liquid chromatography/UV/electrospray ionization ion trap mass spectrometry (HPLC/ESI-MS) method on an embedded polar column. MS 1 and MS 2 fragmentation data were used for identification purposes, while UV was used for quantification. Thirteen N-alkylamides (five N-isobutylamides, three N-methyl isobutylamides, four tyramides and one 2-phenylethylamide) were detected. Five of them identified as undeca-2E,4E-diene-8,10-diynoic acid N-methyl isobutylamide, tetradeca-2E,4E-diene-8,10-diynoic acid tyramide, deca-2E,4E-dienoic acid N-methyl isobutylamide, tetradeca-2E,4E,XE/Z-trienoic acid tyramide and tetradeca-2E,4E,8Z,10Z-tetraenoic isobutylamide are novel compounds, which have never been identified in Anacyclus pyrethrum.

Androgenic and Spermatogenic Activity of Alkylamide‐Rich Ethanol Solution Extract of Anacyclus pyrethrum DC

“…An N ‐alkylamide profiling (Boonen et al ., ; Boonen et al ., , ) from the ethanol solution of the root extract of A. pyrethrum was performed using a gradient reversed‐phase HPLC/UV/electrospray ionization–ion trap mass spectrometry (MS) method on an embedded polar column. MS 1 and MS 2 fragmentation data were used for identification purposes, whereas UV was used for quantification.…”

Quantitative transdermal behavior of pellitorine from Anacyclus pyrethrum extract

“…The Anacyclus pyrethrum root extract was prepared as previously described (Boonen et al, 2012a). For the analytical characterisation of the extract, the extract was dissolved in ethanol, vortexed, sonificated for 2 h and centrifuged for 15 min at 3220 × g at room temperature.…”

“…The HPLC-MS analysis was done on a HPLC system which consisted of a Spectra System SN4000 interface, a Spectra System SCM1000 degasser, a Spectra System P1000XR pump, a Spectra System AS3000 autosampler, and a Finnigan LCQ Classic ion trap mass spectrometer in positive ion mode (all Thermo, San José, CA, USA) equipped with a SPD-10A UV-vis detector (Shimadzu, Kyoto, Japan) and Xcalibur 2.0 software (Thermo) for data acquisition. The extract, dissolved in 50:50 ACN:H 2 O (V/V), was injected into the LC-MS apparatus and the MS method according to Boonen et al (2012a) was used.…”

“…Thirteen NAAs were identified in an ethanolic AP root extract with HPLC-UV/ESI-MS: N-isobutylamides, N-methylisobutylamides, 4-hydroxyphenylethylamides and 2-phenylethylamides. The most abundant NAA in this AP extract is pellitorine (deca-2E,4E-dienoic acid isobutylamide) (Boonen et al, 2012a). The structure of pellitorine is given in Fig.…”

Micropropagation of Anacyclus pyrethrum and chemical profiling of the regenerated plants for pellitorine, the active principle

“…Spilanthes acmella var. calva) as both reduce the mutagenic potential of tobacco by inhibiting nitrosation (Boonen et al 2012). Pellitorine, an isobutylamide, is the main active principle of A. pyrethrum (Gulland and Hopton 1930;Annalakshmi et al 2012).…”