Mass spectral analysis of secondary metabolites from Zingiber montanum rhizome extract using UHPLC‐HR‐ESI‐QTOF‐MS/MS

Abstract

Introduction: Zingiber montanum (J.Koenig) Link ex A.Dietr. is a popular medicinal plant in Thailand. Its rhizomes have been used as an ingredient in various Thai traditional medicine formulas. While many reports have focused on the chemical constituents and biological activities of this plant, a comprehensive study on secondary metabolite profiling using tandem mass spectrometry has, to this point, never been documented. Objective:To analyze the chemical constituents in Z. montanum rhizomes using ultra-high performance liquid chromatography coupled with ultra-high-resolution electrospray ionization quadrupole time-of-flight tandem mass spectrometry (UHPLC-HR-ESI-QTOF-MS/MS) analyses and to utilize the characteristic fragmentation patterns of these compounds to facilitate their identification.Methodology: UHPLC-HR-ESI-QTOF-MS/MS in positive ion mode was used for chemical identification of secondary metabolites from the ethanolic extract of the plant material. MS/MS data of some known reference compounds, together with detailed fragmentation pattern information of several compounds obtained from the crude extract, were used to elucidate their chemical structures. Results:In this work, one benzaldehyde, ten phenylbutenoid monomers, six curcuminoids, and nine phenylbutenoid dimers were assigned based on their characteristic fragment ions. Among these compounds, 2-(3,4-dimethoxystyryl)oxirane was tentatively suggested as a potential new compound. Several characteristic fragment ions from these compounds were assigned and the relative ion abundance of these was also used to differentiate the chemical structures of compounds having the same molecular mass. Conclusions:The results will benefit future high-throughput screening of bioactive compounds and method development for the quality control of raw materials and herbal drugs derived from Z. montanum rhizome extracts.

Rapid profiling of potential antitumor polymethoxylated flavonoids in natural products by integrating cell biospecific extraction with neutral loss/diagnostic ion filtering‐based high‐performance liquid chromatography–quadrupole time‐of‐flight tandem mass spectrometry

“…QTOF‐MS/MS is a high‐resolution MS technique which allows for efficient characterization of compounds in complex natural products 17–19 . After neutral loss/diagnostic ion filtering (extraction width at ± 5 mDa), 12 polymethoxylated flavones and four polymethoxylated flavanones were fished out from the ethanol extract of lysed MCF‐7 cells.…”

“…After living cell biospecific extraction, HPLC–quadrupole time‐of‐flight–MS/MS (HPLC‐QTOF‐MS/MS) plays an increasingly critical role in the analysis and identification of bioactive compounds 17–19 . However, overwhelming amounts of MS datasets are generated, which makes manual data analysis challenging, especially for achieving MS information of low‐abundance compounds being overwhelmed by major compounds or background noise 20 .…”

“…After living cell biospecific extraction, HPLC-quadrupole time-offlight-MS/MS (HPLC-QTOF-MS/MS) plays an increasingly critical role in the analysis and identification of bioactive compounds. [17][18][19] However, overwhelming amounts of MS datasets are generated, which makes manual data analysis challenging, especially for achieving MS information of low-abundance compounds being overwhelmed by major compounds or background noise. 20 To facilitate and simplify post-acquisition MS data processing, various data mining technologies have been developed with excellent resolution, high sensitivity, outstanding selectivity, and excellent accuracy, such as neutral loss filtering, diagnostic ion filtering, de novo identification, mass defect filtering, isotope pattern filtering, predicted compound screening, and database-assisted peak annotation.…”

Ultra‐high‐performance liquid chromatography quadrupole time‐of‐flight tandem mass spectrometry coupled with three‐step data post‐processing techniques for comprehensive profiling of the multiple components in Fufang Xianzhuli Ye

“…Eleven compounds (4,6,10,13,14,15,16,20,21,25 T A B L E 1 The chromatographic and mass spectrometric data of compounds identified from Fufang Xianzhuli (FXZL) using ultra-high-performance liquid chromatography quadrupole time-offlight tandem mass spectrometry (UHPLC-QTOF-MS/MS). Vanillin has antioxidant and anti-inflammatory effects, and it aids in cough relief and phlegm reduction.…”

“…Recently, ultra‐high‐performance liquid chromatography quadrupole time‐of‐flight mass spectrometry (UHPLC‐QTOF‐MS) has been proven to be highly effective at thoroughly analysing the chemical components of herbal medicines. The high separation efficiency of UHPLC coupled with QTOF‐MS, which has excellent structural characterisation capabilities, makes UHPLC‐QTOF‐MS suitable for the analysis of trace or minor amounts, enabling the integral analysis of TCM extracts within minutes 16–19 . However, manual identification of compound structures from the total ion chromatogram based on their mass spectral fragmentation patterns is ineffective and labour‐intensive.…”