Identification of the absorptive constituents and their metabolites in vivo of Ziziphi Spinosae Semen by UPLC–ESI–Q‐TOF–MS/MS

Abstract

In this research, ultra‐performance liquid chromatography coupled with electrospray ionization quadrupole time‐of‐flight mass spectrometry (UPLC–ESI–Q‐TOF–MS/MS) was used for detection and identification of the absorptive constituents and their metabolites in rat plasma, urine and feces following oral administration of Ziziphi Spinosae Semen alcohol extract. After structure elucidation, a total of 12 compounds in rat plasma, comprising seven prototypes and five metabolites, 28 compounds in urine, comprising 17 prototypes and 11 metabolites, and 23 compounds in feces, comrpising 17 prototypes and six metabolites, have been tentatively identified by comparison with standard compounds and reference literature information. To the best of our knowledge, this is the first comprehensive and systematical metabolic study on the seed. Mostly importantly, we propose that gastric acid could convert jujubosides into an absorbable form of ebelin lactone oligosaccharides, which may be responsible for the low bioavailability and specific bioactivities of these compounds. Additionally, we deduced that the absorption site of ebelin lactone oligosaccharides is located in the stomach, and that the ebelin lactone form of jujubosides may be more suitable for absorption than its hydrolysis product. Our investigation will be helpful to narrow the scope for potentially active ingredients of the seed, and pave the way for determination of the pharmacological mechanism of the seed.

Mechanisms Underlying the Action of Ziziphi Spinosae Semen in the Treatment of Insomnia: A Study Involving Network Pharmacology and Experimental Validation

“…After degreasing, we added 8 volumes of 70% alcohol to the ZSS; the mixture was then fluxed three times (1.5 h each time) and the final filtrates were combined. The filtered extract was concentrated under a vacuum and then dried by a rotary evaporator (Shang et al, 2020). The total yield of alcohol extract from ZSS was 14.94% (w/w).…”

Comprehensive characterization of multiple components of Ziziphus jujuba Mill using UHPLC‐Q‐Exactive Orbitrap Mass Spectrometers

“…Compounds 226 and 230 had quasi‐molecular ions at m/z 296.1645 and 374.1598, yielded the fragment ions m/z 251.1069 and 329.1025, respectively, by the same loss of the C 2 H 7 N moieties (45 Da); they were deduced as nuciferine and chiloenamine, respectively (Yan et al, 2013 ). Likewise, compounds 93, 116, 120, 144, 158, 164, 167, 168, 169, 182, 186, 189, 191, 198, 207, and 239 were tentatively deduced based on previous reports (Shang et al, 2020 ; Tian et al, 2016 ; Xia et al, 2014 ).…”

“…Likewise, compounds 165, 206, and 225 were identified as juzirine, (r)-asimilobine isomer, and (r)-asimilobine isomer, respectively (Shang et al, 2020;Yan et al, 2013). 72, 3.86, 8.97, and 9.45 min, respectively; all these compounds yielded the fragment ions m/z 93.0331, which were consistent with 4-hydroxybenzoic acid (Huang et al, 2019).…”

“…Compounds 109 and 179, with the molecular formula C 19 H 24 NO 3 + , were found at 6.33 and 7.98 min, respectively; the molecular ions were obtained at m/z 314.1751 and the daughter ions were at m/z 269.1178 and 237.0913, respectively. These compounds were tentatively proposed as magnocurarine isomers (Shang et al, 2020 ). Compounds 107, 112, and 131 yielded a quasi‐molecular ion at m/z 356.1498, and were eluted at 6.26, 6.45, and 6.73 min, respectively.…”

Spinosin Attenuates Osteoclastogenesis Through Suppressing NF-κB by the Activation of Nrf2/HO-1 Signaling in Osteoporosis

“…Usually, SZS serves as a hypnoticsedative plant, and Asian medication practitioners generally utilize it to prescribe anxiety and insomnia (14). SZS includes more than fty active composites, such as C-glycoside avonoids, cyclopeptide alkaloids, and saponins (15). Among them, a C-glycoside avonoid called 2″-β-O-glucopyranosyl swertisin (Spinosin) is applied in Western countries as healthcare agents and exhibits biomedical activities, including hypnotic and anxiolytic impacts (16).…”