Absorbable Phenylpropenoyl Sucroses from Polygala tenuifolia

She, Gaimei; Ba, Yinying; Yang, Liu; Lv, Hang; Wang, Wei; Shi, Renbing

doi:10.3390/molecules16075507

Cited by 13 publications

(11 citation statements)

References 12 publications

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“…After removing its lipophilic constituents using differential extraction in water (H 2 O) and dichloromethane (DCM), successive chromatographic techniques were applied for the fractionation and isolation of the secondary metabolites, as detailed in Section 4 . In total, nine compounds were isolated, including six sucrose esters, namely 6,3′-disinapoyl-sucrose ( 1 ) [ 74 ], 6- O -sinapoyl,3′- O -trimethoxy-cinnamoyl-sucrose (tenuifoliside C) ( 2 ) [ 51 , 75 ], 3′- O -( O -methyl-feruloyl)-sucrose ( 3 ) [ 76 ], 3′- O -sinapoyl-sucrose ( 4 ) [ 77 ], 3′- O -trimethoxy-cinnamoyl-sucrose (glomeratose) ( 5 ) [ 78 ], and 3′- O -feruloyl-sucrose (sibiricose A5) ( 6 ) [ 79 ]. Additionally, a monomeric phenylpropane glycoside, sinapyl alcohol 4- O -glucoside (syringin or eleutheroside B) ( 7 ) [ 80 , 81 ], a tetrahydrofurofuran-type lignan diglycoside, liriodendrin ( 8 ) [ 82 , 83 , 84 ], and a flavonol glycoside, and 7,4-di- O -methylquercetin-3- O -β-rutinoside (ombuin 3- O -rutinoside or ombuoside) ( 9 ) [ 47 , 85 ] were isolated ( Figure 1 ).…”

Section: Resultsmentioning

confidence: 99%

Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of Polygala inexpectata Peşmen & Erik

et al. 2022

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Polygala species are frequently used worldwide in the treatment of various diseases, such as inflammatory and autoimmune disorders as well as metabolic and neurodegenerative diseases, due to the large number of secondary metabolites they contain. The present study was performed on Polygala inexpectata, which is a narrow endemic species for the flora of Turkey, and resulted in the isolation of nine known compounds, 6,3′-disinapoyl-sucrose (1), 6-O-sinapoyl,3′-O-trimethoxy-cinnamoyl-sucrose (tenuifoliside C) (2), 3′-O-(O-methyl-feruloyl)-sucrose (3), 3′-O-(sinapoyl)-sucrose (4), 3′-O-trimethoxy-cinnamoyl-sucrose (glomeratose) (5), 3′-O-feruloyl-sucrose (sibiricose A5) (6), sinapyl alcohol 4-O-glucoside (syringin or eleutheroside B) (7), liriodendrin (8), and 7,4′-di-O-methylquercetin-3-O-β-rutinoside (ombuin 3-O-rutinoside or ombuoside) (9). The structures of the compounds were determined by the spectroscopic methods including 1D-NMR (1H NMR, 13C NMR, DEPT-135), 2D-NMR (COSY, NOESY, HSQC, HMBC), and HRMS. The isolated compounds were shown in an in silico setting to be accommodated well within the inhibitor-binding pockets of myeloperoxidase and inducible nitric oxide synthase and anchored mainly through hydrogen-bonding interactions and π-effects. It is therefore plausible to suggest that the previously established anti-inflammatory properties of some Polygala-derived phytochemicals may be due, in part, to the modulation of pro-inflammatory enzyme activities.

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Section: Resultsmentioning

confidence: 99%

Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of Polygala inexpectata Peşmen & Erik

et al. 2022

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“…These may result in the faster absorption of POL and GRe in AD rats than normal rats. A6, the representative oligosaccharide ester, which is considered to be an anti‐AD active constituent and may possess radical scavenging activity. Further molecular mechanisms need to be investigated.…”

Section: Resultsmentioning

confidence: 99%

Ultra-fast liquid chromatography with tandem mass spectrometry determination of eight bioactive components of Kai-Xin-San in rat plasma and its application to a comparative pharmacokinetic study in normal and Alzheimer's disease rats

et al. 2017

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A method of ultra-fast liquid chromatography with tandem mass spectrometry was developed and validated for the simultaneous quantitation of eight bioactive components, including polygalaxanthone III, sibiricaxanthone B, tenuifolin, sibiricose A5, sibiricose A6, tenuifoliside A, ginsenoside Re and ginsenoside Rb1 in rat plasma after oral administration of Kai-Xin-San. The plasma samples were extracted by liquid-liquid extraction using digoxin as an internal standard. Chromatographic separation was performed on a Venusil MP C column (100 mm × 2.1 mm, 3 μm) with methanol and 0.05% acetic acid in water as mobile phase. The tandem mass spectrometric detection was performed in the multiple reaction monitoring with turbo ion spray source in the negative ionization. Validation parameters were within acceptable ranges. The established method has been successfully applied to compare the pharmacokinetic profiles of the analytes between normal and Alzheimer's disease rats. The results indicated that there were significant differences in pharmacokinetic parameters of some components between two groups, which may be due to the mechanisms of Alzheimer's disease and pharmacological effects of the analytes. The pharmacokinetic research in the pathological state might provide more useful information to guide the clinical usage of herbal medicine.

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“…The roots were identified by Yuting Chen (Beijing University of Chinese Medicine). Sibiricose A5 and sibiricose A6 were isolated from Polygala tenuifolia in our laboratory [16]. Their structures were elucidated based on their spectral data (IR, MS, 1 H-NMR, and 13 C-NMR) and their purity was determined by HPLC (purity ≥ 96%).…”

Section: Methodsmentioning

confidence: 99%

“…They also cause improvements in the function of the central cholinergic system [12–15]. Sibiricose A5 (SA5), sibiricose A6 (SA6), and 3,6′-disinapoyl sucrose (DISS) are the main components of oligosaccharide esters [16]. These three oligosaccharide esters have been shown to have protective effects in neurotoxicity.…”

Section: Introductionmentioning

confidence: 99%

Intestinal Absorption Profile of Three Polygala Oligosaccharide Esters in Polygalae Radix and the Effects of Other Components in Polygalae Radix on Their Absorption

Wang

Zhang

et al. 2019

Evidence-Based Complementary and Alternative Medicine

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Oligosaccharide esters, which are among the main active components of Polygalae Radix (PR), demonstrate significant pharmacological activities in the human nervous system. In our previous research, some other constituents in PR were able to improve the bioavailability of oligosaccharide esters such as sibiricose A5 (SA5), sibiricose A6 (SA6), and 3,6′-disinapoyl sucrose (DISS), but the related components and their underlying mechanisms remain unknown. The present study aimed to investigate the intestinal absorptive profile of SA5, SA6, and DISS and the absorptive behavior influenced by the coadministration of polygalaxanthone III and total saponins of PR (TS) using an in vitro everted rat gut sac model, along with the possible mechanisms that may influence absorption. The results showed that TS could significantly enhance the absorption of SA5, SA6, and DISS monomers. Verapamil, a P-glycoprotein inhibitor, was able to elevate the absorption of SA5 and SA6, and an absorption experiment using Rho123 led us to conclude that TS influenced the absorption of SA5 and SA6 in a manner similar to that of a P-glycoprotein inhibitor. Sodium caprate, a paracellular absorption enhancer, was found to increase the absorption of SA5, SA6, and DISS. Results showed that the absorption mechanisms of SA5 and SA6 may combine active transport with paracellular passive penetration, while DISS’s absorption was dominated by paracellular passive penetration. However, the relationship between polygala saponins and the absorption of SA5, SA6, and DISS by paracellular passive penetration remain to be examined. This is the direction of our future research.

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Absorbable Phenylpropenoyl Sucroses from Polygala tenuifolia

Cited by 13 publications

References 12 publications

Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of Polygala inexpectata Peşmen & Erik

Isolation, Characterization and In Silico Studies of Secondary Metabolites from the Whole Plant of Polygala inexpectata Peşmen & Erik

Ultra-fast liquid chromatography with tandem mass spectrometry determination of eight bioactive components of Kai-Xin-San in rat plasma and its application to a comparative pharmacokinetic study in normal and Alzheimer's disease rats

Intestinal Absorption Profile of Three Polygala Oligosaccharide Esters in Polygalae Radix and the Effects of Other Components in Polygalae Radix on Their Absorption

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