Metabolite Profiling by Hyphenated Liquid Chromatographic Mass Spectrometric Technique (HPLC‐DAD‐ESI‐Q‐TOF‐MS/MS) and Neurobiological Potential of Haplophyllum sahinii and H. vulcanicum Extracts

Abstract

In the current study, the ethanol extracts of flower, stem, and root parts of two endemic Turkish species, e. g., Haplophyllum sahinii O. Tugay & D. Ulukuş and H. vulcanicum Boiss. & Heldr., were screened against acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) associated with Alzheimer's disease as well as tyrosinase (TYR) linked to Parkinson's disease using ELISA microplate assay at 200 μg/mL. Among the extracts, the highest inhibition was caused by the stem extract of H. sahinii against BChE (IC50=64.93±1.38 μg/mL). Consistently, all of the extracts were found to exert a selective inhibition towards BChE to some extent. It was only the root extract of H. vulcanicum that could inhibit AChE at low level (IC50=203.18±5.33 μg/mL). None of the extracts displayed an inhibition over 50 % against TYR. Metabolite profiling of the extracts was achieved by a highly hyphenated liquid chromatographic mass spectrometric technique (HPLC‐DAD‐ESI‐Q‐TOF‐MS/MS), which revealed the presence of furoquinoline (β‐fagarine, γ‐fagarine) and amide (tubasenicine, tubacetine) alkaloids; furano‐ (rutamarin), pyrano‐ (xanthyletine), and geranyloxy coumarins; phenylpropanoid (secoisolariciresinol), arylnaphthalene (mono‐O‐acetyldiphyllin apioside), and dibenzylbutyrolactone (kusunokinin, haplomyrfolin) lignans. Several important differences were observed between the extracts analyzed. β‐Fagarine was the major alkaloid in H. vulcanicum, whereas γ‐fagarine was present only in the roots of both Haplophyllum species; moreover, secoisolariciresinol and secoisolariciresinol dimethyl ether were the main lignans in the stems and flowers. This is the first study identifying ChE and TYR inhibitory effect and metabolic profiles of H. vulcanicum and H. sahinii.

Untargeted‐based metabolomics analysis and in vitro/in silico antiviral activity of extracts from Phyllanthus brasiliensis (Aubl.) Poir

“…Once justicidin B and its isomers have the same MS/MS spectrum (Table 1), literature data (MS/MS spectrum and RT) were used to improve the level of confidence 35 . One justicidin B derived (+16 Da) was annotated as diphyllin ([M + H] + of m/z 381.0983) 33,35,36 . The main fragmentation pathways include neutral loss of water ([M + H − 18] + , m/z 363), loss of methanal ([M + H – 18 – 30] + , m/z 333), loss of two groups of CO 2 to produce the fragments of m/z 305 and 277, respectively.…”

“…35 One justicidin B derived (+16 Da) was annotated as diphyllin ([M + H] + of m/z 381.0983). 33,35,36 The main fragmentation pathways include neutral loss of water ([M + H À 18] + , m/z 363), loss of methanal ([M + H -18 -30] + , m/z 333), loss of two groups of CO 2 to produce the fragments of m/z 305 and 277, respectively. A diphyllin isomer was annotated as justicidin H (also called 6 0hydroxyjusticidin B).…”

IL-6 Inhibitory Compounds from the Aerial Parts of Piper attenuatum and Their Anticancer Activities on Ovarian Cancer Cell Lines

“…However, compounds 1-3 represent structures with a maleimide moiety, a benzene ring bearing a methylenedioxy group, and fully methylated hydroxy groups. Interestingly, (-)-kusunokinin (5), a naturally occurring compound, shares structural similarities with compounds 1-3, including the presence of a methylenedioxy group and fully methylated hydroxy groups [19,20]. While this suggests the potential natural origin of compounds 1-3, the presence of methyl ether groups raises concerns about the possibility of artificial methylation during the extraction and isolation process.…”

Acetylated Rhamnose Triterpenoid Saponins from Glechoma longituba Analyzed by LC‐Q‐TOFMS

“…However, due to the similar structure and polarity of these compounds, they are difficult to separate with ordinary technology unless some special combined detection and separation technologies, such as HPLC‐ESIMS n , HPLC‐DAD‐MS, and HPLC‐PDA‐(HRMS)‐SPE‐NMR, which are wildly used to rapidly direct the isolation and identification of target compounds from crude extracts of medicinal plants [3–5] . Among them, by analyzing retention time ( t R ), UV spectrum data, fluorescence characteristics, extracted ion current (EIC) results, molecular weight and mass fragment behavior information based on HPLC/MS technology, it is easy to infer the corresponding components in a complex mixture [6–8] . Especially through the extraction of EIC, the analysis results were improved by ultrahigh‐performance liquid chromatography‐high‐resolution mass spectrometry [9,10] …”