Analysis of Flavonoids in Dalbergia odorifera by Ultra-Performance Liquid Chromatography with Tandem Mass Spectrometry

Abstract

Dalbergia odorifera, a traditional Chinese medicine, has been used to treat cardio- and cerebrovascular diseases in China for thousands of years. Flavonoids are major active compounds in D. odorifera. In this paper, a rapid and sensitive ultra-high performance liquid chromatography-triple quadrupole mass spectrometry method was developed and validated for simultaneous determination of 17 flavonoids in D. odorifera. Quantification was performed by multiple reaction monitoring using electrospray ionization in negative ion mode. Under the optimum conditions, calibration curves for the 17 analytes displayed good linearity (r2 > 0.9980). The intra- and inter-day precisions (relative standard deviations) were lower than 5.0%. The limit of quantitation ranged from 0.256 to 18.840 ng/mL. The mean recovery range at three spiked concentrations was 94.18–101.97%. The validated approach was successfully applied to 18 samples of D. odorifera. Large variation was observed for the contents of the 17 analytes. Sativanone and 3′-O-methylviolanone were the dominant compounds. The fragmentation behaviors of six flavonoids were investigated using UPLC with quadrupole time-of-flight tandem mass spectrometry. In negative ion electrospray ionization mass spectrometry, all the flavonoids yielded prominent [M − H]− ions. Fragments for losses of CH3, CO, and CO2 were observed in the mass spectra. Formononetin, liquiritigenin, isoliquiritigenin, sativanone, and alpinetin underwent retro-Diels–Alder fragmentations. The proposed method will be helpful for quality control of D. odorifera.

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

“…Liquiritigenin (compound 7 ) was detected with [M–H] − at m / z 255.0667. Its identity was confirmed by comparing with data from a previous study, in which Dalbergia odorifera was characterized by LC-MS/MS and based on the spectrum of product ions at m / z 119.0495 ([M–H–C 8 H 8 O 2 ] − ) and m / z 135.0083, corresponding to breaks of [1,3A–H] − and [1,3B–H] − fragmen [ 38 ]. Four flavanones and derivates (compounds 8 , 9 , 10 and 11 ) were tentatively identified in the optimized BRP extract as naringenin, pinocembrin, 5,6-Dihydroxy-3′,4′-dimethoxyflavanon and 6-Hydroxyflavanone, according to the precursor ions [M–H] − at m / z 271.0619, 255.0668, 315.0882 and 239.0722, respectively.…”

“…Fragment ions resulting from RDA fragments are more abundant than the loss of other radical ions, such as CH3, CO, OH, or H2O [37]. Liquiritigenin [38]. Four flavanones and derivates (compounds 8, 9, 10 and 11) were tentatively identified in the optimized BRP extract as naringenin, pinocembrin, 5,6-Dihydroxy-3′,4′-dimethoxyflavanon and 6-Hydroxyflavanone, according to the precursor ions [M−H] − at m/z 271.0619, 255.0668, 315.0882 and 239.0722, respectively.…”

LC-ESI-QTOF-MS/MS Characterization of Seaweed Phenolics and Their Antioxidant Potential

“…Three [50]. To the best of our knowledge, this is the first time that isoflavonoids derivatives were identified and characterized in seaweeds.…”

Chemical Composition of Essential Oil from Dalbergia odorifera Flowers and HPLC Analysis of Tectorigenin in Its Leaves and Branches

“…Flavonoids are considered the important active principle components in many herbs because of the extensive pharmacological activities (Zhao et al 2020a). As previously reported, flavonoids are the main secondary metabolites and about 99 flavonoids have been identified from D. odorifera (Zhao et al 2020b).…”

“…Dalbergia odorifera T. Chen (Family: Fabaceae) is a valuable tree indigenous to Hainan Province and has been gradually cultivated in South China (Sun et al 2015;Zhao et al 2020a). In view of its distinctive color, aromatic trunk, and high density, this valuable rosewood tree is particularly popular for manufacturing luxurious furniture, artifacts, and musical instruments (Tao and Wang 2010;Wariss et al 2018).…”