Rapid Evaluation of Chemical Consistency of Artificially Induced and Natural Resina Draconis Using Ultra-Performance Liquid Chromatography Quadrupole-Time-of-Flight Mass Spectrometry-Based Chemical Profiling

Abstract

Resina Draconis is a highly valued traditional medicine widely used in Arabia since ancient times, and it has been commonly used as an antidiarrheic, antimicrobial, antiulcer, blood circulation promoter as well as an anti-inflammatory agent. The tree source from which this medicine orignates grows extremely slowly, producing a very low yield of Resina Draconis. To meet the increasing market demand, artificial methods for stimulating Resina Draconis formation have been developed and applied. However, the chemical differences between artificially induced Resina Draconis (AIRD) and natural Resina Draconis (NRD) have been rarely studied. The aim of this research was to explore and identify the chemical constituents of AIRD and NRD using ultra-performance liquid chromatography-quadrupole-time-of-flight mass spectrometry (UHPLC-QTOF-MS/MS) based chemical profiling. A total of 56 chromatographic peaks were detected in AIRD, of these, 44 peaks have had their structures tentatively characterized based on high-resolution mass spectra (HRMS) data, fragmentation ions information, reference standards data and literature review. In total, 40 peaks were found both in AIRD and NRD. The potential chemical transformation mechanisms active in Resina Draconis during formation were explored. To the best of our knowledge, this is the first evaluation of the chemical profiles of both AIRD and NRD. Furthermore, these findings are expected to provide a rational basis for the quality assessment of AIRD and the use of AIRD as a substitute for NRD.

Phytochemical analysis of Vietnamese propolis produced by the stingless bee Lisotrigona cacciae

“…Further, selected isolated compounds were used as standards and subjected to GC/MS analysis in order to obtain information for their mass spectral characteristics as TMS derivatives, and then to recognize them in the TIC chromatogram. The data obtained (Table 2) revealed that the fragmentation pathways of the flavonoids 1 – 4 are in accordance with those proposed by Su et al [39] and Chen et al [40], who studied Chinese dragon's blood and its constituents by means of IT-TOF HRMS n and UHPLC-QTOF-MS/MS, respectively. In the mass spectra of the homoisoflavans 2 and 3 , the molecular ion was the most prominent peak (base peak), followed by B-ring and AC-rings fragments due to C 3 –C 9 and C 9 –C 1’ bond cleavages, which have been regarded as diagnostic for this type of flavonoids [40,41].…”

“…The data obtained (Table 2) revealed that the fragmentation pathways of the flavonoids 1 – 4 are in accordance with those proposed by Su et al [39] and Chen et al [40], who studied Chinese dragon's blood and its constituents by means of IT-TOF HRMS n and UHPLC-QTOF-MS/MS, respectively. In the mass spectra of the homoisoflavans 2 and 3 , the molecular ion was the most prominent peak (base peak), followed by B-ring and AC-rings fragments due to C 3 –C 9 and C 9 –C 1’ bond cleavages, which have been regarded as diagnostic for this type of flavonoids [40,41]. Compounds 4 and 1 gave fragmentation patterns identical to those of the homoisoflavanes and flavan-3-ols [42], respectively.…”

Active Antioxidant Phenolics from Brazilian Red Propolis: An Optimization Study for Their Recovery and Identification by LC-ESI-QTOF-MS/MS

“…Retro–Diels–Alder (RDA) is the pathway fragmentation commonly used by flavanones. Fragment ions resulting from RDA fragments are more abundant than the loss of other radical ions, such as CH 3 , CO, OH, or H 2 O [ 37 ]. Liquiritigenin (compound 7 ) was detected with [M–H] − at m / z 255.0667.…”

“…The compound 5,6-Dihydroxy-3′,4′-dimethoxyflavanon (compound 10 with [M–H] − at m / z 315.0882), which was found for the first time in BRP, was tentatively identified based on a product ion at m / z 315.0881. Lastly, 6-Hydroxyflavanone displayed a product ion at m / z 239.0732 in the MS 2 spectra [ 37 ].…”

“…. The compound 5,6-Dihydroxy-3′,4′dimethoxyflavanon (compound 10 with [M − H] − at m/z 315.0882), which was found for the first time in BRP, was tentatively identified based on a product ion at m/z 315.0881.Lastly, 6-Hydroxyflavanone displayed a product ion at m/z 239.0732 in the MS 2 spectra[37].3.4.4. ChalconesIsoliquiritigenin (compound 12 with [M ₋ H]¯ at m/z 255.0676) was previously described in the literature and tentatively identified herein based on product ions at m/z 119.0496 and 135.0082[41].…”