A novel phenylpropanoid glycosides and a new derivation of phenolic glycoside from Paris Polyphylla var. yunnanensis

A novel phenylpropanoid glycosides 1, named parispolyside E and a novel derivation of phenolic glycoside 2, named parispolyside G, as well as two known flavonoid glycosides were isolated from the rhizome of Paris polyphylla var. yunnanensis. Their structures were elucidaed by spectroscopic methods.

Proteomics analysis on hypolipidemic mechanisms of total phenylpropanoid glycosides from Ligustrum robustum(Roxb.) Blume in hamsters fed a high fat diet

OBJECTIVE To explore the hypolipidemic mechanisms of the total phenylpropanoid glycosides fromLigustrum robustum(Roxb.) Blume(LRTPG) in hamsters using proteomics technique.METHODS The hamsters were fed with a high fat diet to induce hyperlipidemia.Then LRTPG of high(1.2 g·kg^(-1)),medium(0.6 g·kg^(-1)) and low(0.3 g·kg^(-1)) doses were administrated daily for 4 weeks.Then the concentrations of plasma and hepatic lipids were determined using enzymic methods.The total protein was extracted from livers of the model group and the group treated with the high dose of LRTPG for label-free quantitative proteomics.RESULTS LRTPG significantly reduced the concentrations of plasma and hepatic lipids in hamsters fed a high fat diet.The proteomics data showed that a total of 2231 proteins were identified,and 549 proteins were found to be differentially expressed between the model group and the group treated with LRTPG.Among the 549 proteins,93 proteins were up-regulated and 59 proteins were down-regulated,and 397 proteins were absent or not.And some of these proteins were much related to the lipid metabolism.Further,gene ontology(GO) analysis indicated metabolic process,transport,oxidation-reduction process,phosphorylation,signal transduction,lipid metabolic process were the main biological processes that those differentially expressed proteins participated.KEGG pathway analysis showed that those proteins were involved in several metabolic pathways including oxidative phosphorylation,non-alcoholic fatty liver disease(NAFLD),PI3K-Akt signaling pathway,cAMP signaling pathway,cGMP-PKG signaling pathway.CONCLUSION The proteomics study could provide valuable clues to help us to understand the hypolipidemic mechanisms of LRTPG much better.

Inhibitory Effect of Flavonoid Glycosides from Chlorophytum comosum on Nasopharyngeal Carcinoma 5-8F Cells and Its Mechanism

[Objectives]To study the inhibitory activity of two flavonoid glycosides isolated from Chlorophytum comosum Laxum R.Br on human nasopharyngeal carcinoma(NPC)cell line 5-8F in vitro and its mechanism.[Methods]The flavonoid glycosides were isolated and purified from the ethanol alcoholic extract of the roots of Liliaceae plant Chlorophytum comosum by silica gel column chromatography,macroporous resin column chromatography,Sephadex LH-20,and reverse column chromatography(ODS).The inhibitory activity of flavonoid glycosides on human nasopharyngeal carcinoma cells was analyzed by CCK-8 method,and the potential mechanism was preliminarily analyzed by molecular docking.[Results]Two flavonoid glycosides were identified as isovitexin 2″-0-rhamnoside and 7-2″-di-O-β-glucopyranosylisovitexin.Two flavonoid glycosides showed promising inhibitory effect on human nasopharyngeal carcinoma cell line 5-8F,with IC_(50) values of 24.8 and 27.5μmol/L,respectively.Molecular docking results showed that the potential targets of two flavonoid glycosides include CyclinD1,Bcl-2β-Catenin,ILK,TGF-β,in addition,two glycosides showed higher predicted binding affinity towards CyclinD1,which verifies the cytotoxicity of the two compounds on human nasopharyngeal carcinoma cell line 5-8F in vitro.[Conclusions]Two flavonoid glycosides are the active molecules in Chlorophytum comosum that can inhibit the proliferation of human nasopharyngeal carcinoma cells,and have the potential to be used in the research and development of anti nasopharyngeal carcinoma drugs.

Single-cell transcriptome analysis uncovers underlying mechanisms of acute liver injury induced by tripterygium glycosides tablet in mice

Tripterygium glycosides tablet(TGT),the classical commercial drug of Tripterygium wilfordii Hook.F.has been effectively used in the treatment of rheumatoid arthritis,nephrotic syndrome,leprosy,Behcet's syndrome,leprosy reaction and autoimmune hepatitis.However,due to its narrow and limited treatment window,TGT-induced organ toxicity(among which liver injury accounts for about 40%of clinical reports)has gained increasing attention.The present study aimed to clarify the cellular and molecular events underlying TGT-induced acute liver injury using single-cell RNA sequencing(scRNA-seq)technology.The TGT-induced acute liver injury mouse model was constructed through short-term TGT exposure and further verified by hematoxylin-eosin staining and liver function-related serum indicators,including alanine aminotransferase,aspartate aminotransferase,alkaline phosphatase and total bilirubin.Using the mouse model,we identified 15 specific subtypes of cells in the liver tissue,including endothelial cells,hepatocytes,cholangiocytes,and hepatic stellate cells.Further analysis indicated that TGT caused a significant inflammatory response in liver endothelial cells at different spatial locations;led to marked inflammatory response,apoptosis and fatty acid metabolism dysfunction in hepatocytes;activated hepatic stellate cells;brought about the activation,inflammation,and phagocytosis of liver capsular macrophages cells;resulted in immune dysfunction of liver lymphocytes;disturbed the intercellular crosstalk in liver microenvironment by regulating various signaling pathways.Thus,these findings elaborate the mechanism underlying TGT-induced acute liver injury,provide new insights into the safe and rational applications in the clinic,and complement the identification of new biomarkers and therapeutic targets for liver protection.

Phenylethanoid glycosides from traditional Mongolian medicine Cymbaria daurica alleviate alloxan-induced INS-1 cells oxidative stress and apoptosis

Cymbaria daurica L. is a well-known traditional Mongolian medicine, which has been used to treat diabetesrelated conditions characterized by persistent thirst and hunger, copious urination, and weight loss. We aimed to investigate the protective effects of C. daurica extracts and phenylethanoid glycosides including verbascoside and isoacteoside on INS-1 cells. We discovered phenylethanoid glycosides from n-butanol extract with large content through extraction and separation. We continue to study the protective effects of phenylethanoid glycosides including verbascoside and isoacteoside on INS-1 cells. INS-1 cells were treated with C. daurica, cell viability assay, RNA-seq technology, superoxide dismutase activity and malonaldehyde content, quantitative real time-PCR and Western blot analysis were used to study the protective effects of C. daurica. Cell viability assay resulted that n-butanol extract and verbascoside, isoacteoside showed protective effects of C. daurica. According to the RNA-seq technology to identify the differentially expressed genes in INS-1 cells, the pathway of gene enrich the protective effect of C. daurica on oxidative stress. SOD activity and the content of MDA indicated that C. daurica could enhance the antioxidant capacity of INS-1 cells. Further investigation indicated C. daurica alleviate oxidative stress by inhibiting INS-1 cell apoptosis. C. daurica may play an anti-diabetic role by inhibiting islet cell apoptosis.

The effect and mechanism of stilbene glycosides on improving neuronal injury in Alzheimer's disease rats by regulating ASK/MKK7/JNK pathway

Objective:To investigate the mechanism of action of tetrahydroxy stilbene glycosides(TSG)in ameliorating neuronal damage in Alzheimer's disease rats by regulating MKK7 and JNK kinases.Methods:A total of 24-month-old 42 SD rats were randomly selected for the experiment in 7 groups:normal group,sham-operated group,model group,positive drug group,low,medium and high dose TSG group at 0.033 g/kg,0.1 g/kg,0.3 g/kg.The Model Group and the TSG groups were established by stereotaxic Aβ25-35 solution.After 28 days,the model rats were selected by passive avoidance test.After screening,each dosage group of TSG and positive drug group was given intragastrically according to the corresponding dosage,and the experiment was carried out after 28 days.The pathological changes of hippocampal CA1 region were observed by tissue staining,and the amount of MKK7 and JNK proteins and the expression content of MKK7 and JNK mRNA by histochemical method of protein,and qRTPCR assay.Results:(1)He staining observation:Compared with the normal group and the sham-operated group,the number of nerve cells in the model group decreased and arranged irregularly,the cell membrane shrank,and the nucleus deformed and dissolved.The number of neurons in the positive drug group and TSG Group also increased significantly,the order is also relatively well.(2)From the results of the Tunel staining experiments:the positive apoptotic cells in the model group were higher than control group and sham-operated group,positive drug group and TSG drugs group was significantly smaller than that in the model group(P<0.05).(3)Compared with the control group and the Virtual Operation Group,the MKK7 and JNK protein concentrations in the brain of the model group were increased(P<0.05)by data analysis of immunohistochemistry:Compared with the model group,the protein expression of positive drug and TSG each dose group were reduced(P<0.05).(4)The results of QRTPCR data showed that the levels of MKK7 and JNK mRNA in the brain tissue of the model group were increased compared with the normal group and sham-operated groups(P<0.05).Conclusion:Stilbene glycoside has a certain effect on neuronal injury and repair which may be related to the changes of mRNA transcription and protein expression of MKK7 and JNK kinases.

STUDIES ON GLYCOSIDES ⅤⅢ.TOTAL SYNTHESIS OF NEW ALKALOID GLYCOSIDES FROM SELAGINELLA DOEDERIENII

Two new alkaloids,hordenine-O- -L-rhamnopyranoside(Ⅰ)and hordenine -0-(6′-trans-cinnamoyl)-4′-O-β-D-glucopyranosyl- -L-rhamnopyranoside(Ⅲ) isolated from Selaginella doederleinii have been synthesized the first time. A new method,in which trifluoroacetoxyl group was used both as a good leaving group and a protecting group for synthesis of O-glycosides with high stereo- selectivity was reported.

Reaction of hydroxyl radical with phenylpropanoid glycosides from Pedicularis species: a pulse radiolysis study

Using pulse radiolysis technique, the reaction between hydroxyl radical and 7 phenylpropanoidglycosides: echinacoside, verbascoside, leucosceptoside A, martynoside, pediculariosides A, M and N which were isolated from Pedicularis were examined. The rate constants of these reactions were determined by transient absorption spectra. All 7 phenylpropanoid glycosides react with hydroxyl radical at high rate constants within (0.97-1.91)×1010L · mol-1 · s-1. suggesting that they are effective hydroxyl radical scavengers. The results demonstrate that the numbers of phenolic hydroxyl groups of phenylpropanoid glycosides are directly related to their scavenging activities. The scavenging activities are likely related to o-dihydroxy group of phenylpropanoid glycosides as well.

Two new phenylpropanoid glycosides from the aerial parts of Lespedeza cuneata

Two new phenylpropanoid glycosides named cuneataside E(1) and cuneataside F(2), were isolated from the aerial parts of Lespedeza cuneata(Dum. Cours.) G. Don, whose structures were E and Z isomer, respectively. Their structures were elucidated on the basis of comprehensive spectroscopic analysis(UV, IR, HR-ESI-MS, 1D and 2D NMR). In in vitro bioassays at 10 μmol/L, compound 1showed moderate hepatoprotective activity against N-acetyl-p-aminophenol(APAP)-induced toxicity in He G2 cells.

Minor antifungal aromatic glycosides from the roots of Gentiana rigescens(Gentianaceae)

Two new phenolic glycosides, 2,3-dihydroxybenzoic acid methyl ester 3-O-β-o-glucopyranosyl-（1-6）-β-D-glucopyranoside （1） and 2,5-dihydroxylbenzofuran 5-O-β-D-xylopyranosyl-（1-6）-O-β-D-glucopyranoside （2）, were isolated as the minor chemical constituents from the roots of Gentiana rigescens, along with 15 known compounds. Their structures were elucidated by detailed spectroscopic analysis, including 1D, 2D NMR and chemical method. All of these compounds were isolated for the first time from the title plant. Moreover, compounds 1 and 2 were tested for the antifungal activities on three plant pathogens Peronophythora litchi, Glomerella cingulata, and Glorosprium musarum.

Isolation and purification of phenylethanoid glycosides from plant extract of Plantago asiatica by high performance centrifugal partition chromatography

Two phenylethanoid glycosides （PhGs） were isolated and purified from the aerial parts of Plantago asiatica for the first time by high performance centrifugal partition chromatography （HPCPC） using ethyl acetate-n-butanol-ethanol-water （0.5：0.5：0.1：1, v/v/v/v）. A total of 45.6 mg of compound 1 and 293.8 mg of compound 2 were purified from 1341 mg of the n-butanol extract of P. asiatica. The structures of the two PhGs were tentatively identified as plantamajoside and aeteoside or isoacteoside by eleetrospray ionization multi stage tandem mass spectrometry （ESI-MS^n） in the negative ion mode.

Two new phenylpropanoid glycosides from Sanguisorba officinalis

Two new phenylpropanoid glycosides, 9-O-[6-O-acetyl-β-D-glucopyranosyl]-4-hydroxycinnamic acid （1） and 8-O-β-D-glucopyranosyl-（R）-（＋）-3,4,8-trihydroxy methyl phenylpropionate （2） were isolated from the 80% EtOH extract of the roots of Sanguisorba officinalis. Their slructures were characterized by spectroscopic analysis and chemical method, including 1D NMR, 2D NMR, and HR-ESI-MS. Compounds 1 and 2 exhibited the moderate antimicrobial activities against all Gram-positive and Gram-negative bacteria tested.

Two new secoiridoid glycosides from the roots of Picrorhiza scrophulariiflora

From the roots ofPicrorhiza scrophulariiflora, two new secoifidoid glycosides, named picrosecosides Ⅰ and Ⅱ （1, 2） have been isolated. Their structures were elucidated on the basis of chemical and spectropic evidences.

The Synthesis of Gracillin and Dioscin: Two Typical Representatives of Spirostanol Glycosides

Two spirostanol saponins (gracillin and dioscin) which have the typical sugar moieties were synthesized facilely by a general approach.

A new macrolide and glycosides from the stem of Sargentodoxa cuneata

A new macrolide glycoside, cuneataside F was isolated from the n-butanol extract of the stem of Sargentodoxa cuneata. The structure was elucidated on the basis of extensive 1D and 2D NMR as well as HRESI-MS spectroscopic analysis.

Two New Xanthone Glycosides from Polygala tenuifolia

Two new xanthone glycosides, polygalaxanthone IV and V were isolated from the roots of Polygala tenuifolia Willd. Their structures were established as 6-O-[a-L-rhamnopyranosyl- (12)-b-D-glucopyranosyl]-1-hydroxy-3, 7-dimethoxyxanthone (polygalaxanthone IV), and 6-O- [a-L-rhamnopyranosyl-(12)-b-D-glucopyranosyl]-1, 3-dihydroxy-7-methoxyxanthone (polyga- laxanthone V), respectively, on the basis of chemical and spectral evidence.

Two New Chromone Glycosides from Selaginella uncinata

Two new chromone glycosides, 5-hydroxy-2,6,8-trimethylchromon-7-O-b-D-gluco- pyranoside, named uncinoside A; 5-acetoxy-2,6,8-trimethylchromone-7-O-b-D-glucopyranoside, named uncinoside B, and a known chromone compound named 8-methyl eugenitol were isolated from Selaginella uncinata. Their structures were elucidated by spectra analysis of FAB-MS, 1D NMR and 2D NMR including 1H NMR, 13C NMR, HMQC, HMBC and single-crystal X-ray diffraction techniques.

Two New Dammarane Glycosides from the Acid Hydrolysis Product of Panax Notoginseng

Two new dammarane glycosides named notoginsenoside T-1 and T-2 were isolated from the mild acid hydrolysis products of the root saponins of Panax notoginseng. On the basis of spectroscopic evidences, their structures were elucidated to be 6-O-beta -D-glucopyranosyl-24(25)-epoxy-3 beta ,6 alpha ,12 beta ,23 xi -tetrahydroxydammar-20(22)(E)-ene 1 and 6-O-beta -D-glucopyranosyl-24(25)-epoxy-23 xi -methoxyl-3 beta ,6 alpha ,12 beta -trihydroxydamm-ar-20(22)(E)-ene 2, respectively.

Two New Steroidal Glycosides from Ophiopogon japonicus

Two new C-27 steroidal: glycosides, named ophiopojaponin A(1)and B(2), were isolated from the tubers of famous traditional Chinese herb-Ophiopogon japonicus. The spectroscopic and chemical evidences revealed their structures to be Pennogenin 3-O-[2'-O-acetyl-alpha-L-rhamnopyranosyl (1-->2)]-beta-D-xylopyranosyl (1-->3)-beta-D-glucopyranoside (1) and 26-O-beta-D-glucopyranosyl-(22 xi, 25R)-3 beta, 14 alpha, 22 xi, 26-tetrahydroxyfurost-5-ene 3-O-alpha-L-rhamnopyranosyl (1-->2)-beta-D-glucopyranoside (2), respectively.

Chemical Components of Helicia nilagirica Beed.I.Structure of Three New Flavonol Glycosides

Three new flavonol glycosides were isolated from the leaves of Helicia nilagirica Beed.. The structures were elucidated as kaempferol-3-O-b-D-xylopyranosyl-(16)-b-D-glyco- pyranosyl-(12)-a-L-rhamnopyranoside, quercetin-3-O-b-D-xylopyranosyl-(16)-b-D-glycopy- ranosyl-(12)-[-b-D-xylopyranosyl-(14)]-a-L-rhamnopyranoside, and quercetin-3-O-b-D- xylopyranosyl-(16)-b-D-glycopyranosyl-(12)-a-L-rhamnopyranoside, named as Helicianeoside A、B and C, respectively.