Profiling the metabolic differences of anthraquinone derivatives using liquid chromatography/tandem mass spectrometry with data‐dependent acquisition

Abstract

This work concentrates on the in vitro metabolism of anthraquinone derivatives from rhubarb. Different metabolic reactions for anthraquinone derivatives were dependent on the substituent group in the skeleton. Monohydroxylation in the exocyclic methyl group was the major metabolic modification for emodin. Aloe-emodin containing a hydroxymethyl group was mainly metabolized through a methylation reaction. For rhein, both hydrogenation and methyl substitution on the benzene ring were the major metabolic reactions. Hydroxyl substitution on the benzene ring was the predominant metabolic reaction for chrysophanol. For physcion, demethylation of the exocyclic methoxy group was the most important metabolic reaction.

In vivo metabolism study of rhubarb decoction in rat using high-performance liquid chromatography with UV photodiode-array and mass-spectrometric detection: A strategy for systematic analysis of metabolites from traditional Chinese medicines in biological samples

“…S-1. The UV spectra, chemical structures and ESI-MS/MS fragmentation behaviors of five free anthraquinones were reported in our previous publication [22]. As most of these metabolites remained the structural features of the parent compounds, the analysis of the fragmentation pathways greatly facilitated the identification of metabolites from rhubarb decoction.…”

“…4(b)). According to our previous studies on ESI-MS/MS fragmentation behaviors of aloe-emodin [22], the aglycone of M59 was assigned as aloeemodin. However, as shown in Fig.…”

“…5). According to our previous work concentrated on the in vitro metabolism of anthraquinone derivatives [22], the aglycone of M76 was assigned as 2-hydroxyaloe-emodin. Besides, by comparing the UV spectrum (Fig.…”

Analysis of the pharmacokinetics and metabolism of aloe‐emodin following intravenous and oral administrations in rats

“…Our previous study reported that oral emodin, an anthraquinone constituent in rhubarb, presented exclusively as emodin glucuronides in the bloodstream (Shia et al, 2010). In regard to the metabolic fate of aloe-emodin, a previous study using hepatic microsomes had identified several metabolites including 2-hydroxy aloe-emodin, 4-hydroxy aloeemodin and rhein (Song et al, 2009). However, until now there has been limited information regarding the pharmacokinetics and metabolism of aloe-emodin in animals.…”

Anthraquinones from the bark of Senna macranthera

“…Only the fraction 8-9 showed the presence of peaks the typical fragmentation pattern of anthraquinones: intense molecular ion, loss of CO (28 Da) and other fragmentations with weak intensity (Song et al 2009). Figure 2 and Table I show Thus, the GC-MS analyses permitted the identification of chrysophanol (3), chrysophanol-8-methyl ether (100) 253 (9) 251 (8) 240 (4) 238 (5) 225 (12) 211 ( (4) and physcion (5) in S. macranthera.…”