Triterpenoids from Rubus buergeri

A new triterpenoid, methyl buergericate (12a), which was elucidated as 2 alpha, 3 alpha, 19 alpha, 24-tetrahydroxyl olean-12-en-28-oic acid methyl ester by spectroscopic methods, together with eleven known triterpenoids was isolated from Rubus buergeri Miq. The isolation of the above chemical constituents from this plant was reported for the first time.

Neuroprotective effects of total saponins from Rubus parvifolius L. on cerebral ischemia/reperfusion injury in rats

This study examines the neuroprotective effects and mechanisms of action of total saponins from Rubus parvifolius L. （TSRP） on focal cerebral ischemia and reperfusion injury in rats. Focal cerebral ischemia and reperfusion injury was performed in rats using the suture method. The results indicate that intragastric injection of TSRP, at 5, 10 and 20 mg/kg, could decrease neurological impairment, reduce cerebral infarct volume, diminish pathological changes, and significantly inhibit the apoptosis of neurons surrounding the ischemic area. In addition, TSRP upregulated the expression of the anti-apoptotic factor Bcl-2, at the protein and mRNA levels, and it downregulated the expression of the pro-apoptotic factor Bax, at the protein and mRNA levels. These findings indicate that TSRP protects against cerebral ischemia/reperfusion injury, and that it may do so by regulating the expression of Bcl-2 and Bax.

A Novel Ursane Triterpene from Rubus swinhoei

A novel ursane triterpene, named swinhoeic acid, was isolated from the roots of Rubus swinhoei. Its structure was elucidated as 18, 19-seco, 2 alpha, 3 beta -dihydroxy-19-oxo-urs-11, 13(18)-dien-28-oic acid by means of MS, 1 DNMR and 2DNMR.

Chemical Composition of Rubus pirifolius Smith

[Objectives]This paper aimed to study the chemical composition of Rubus pirifolius Smith[Methods]A preliminary experiment was carried out using the qualitative reactions of various chemical constituents,in order to roughly detect the types of chemical constituents that may be contained in R.pirifolius Smith The ethanol extract of R.pirifolius Smith were separated and purified using silica gel column chromatography,silica gel thin-layer chromatography and recrystallization,and the chemicals obtained were identified using mass spectrometry,nuclear magnetic resonance and literature reference.[Results]The main constituents of R.pirifolius Smith are saponins,tannins,flavonoids,phytosterols,triterpenes and anthraquinones.A total of five compounds were isolated from the ethanol extract of R.pirifolius Smith,and they were identified asβ-sitosterol(1),arjunolic acid(2),stigmasterol-3-O-β-D-glucopyranoside(3),euscaphic acid(4)and 3,3′,4-trimethyle llegic acid(5).[Conclusions]Compounds 1,2,3,4 and 5 were isolated from R.pirifolius Smith for the first time.

Two New Glycosides from Rubus amabilis

A pregnane glycoside and a lignan glycoside were isolated from the aerial parts of Rubus amabilis. Their structures were elucidated as 3-O-beta-D-glucopyranosyl-3 beta.15 alpha-dihydroxypregn-5-en-20-one and (-)-secoisolariciresinol-O-alpha-L-rhamnopyranoside using spectroscopic and chemical methods.

Two Triterpenoid Dimers from Rubus pungens Camb var. oldhamii

Two new triterpenoid saponin dimers, named rubupungenoside A (1) and B (2), have been isolated from the aerial parts of Rubus pungens Camb. var. oldhamii. Their structures have been established on the basis of spectroscopic methods and chemical transformation's.

Total Flavonoid Content, the Antioxidant Capacity, Fingerprinting and Quantitative Analysis of Fupenzi (<i>Rubus chingii</i>Hu.)

Objective: In this study, one of the objectives was to investigate the total flavonoid contents of Fupenzi (R. chingii Hu.) obtained from different regions of China and to evaluate their anatioxidant activities. And the second objective of this study was to develop a validated HPLC method for chromatographic fingerprints of the samples extracts of Fupenzi. Method: The total flavonoid contents were determined by a colorimetric method and the antioxidant activity was determined spectrophotometrically by DPPH and ABTS radical scavenging assays. The chromatographic fingerprint was developed by high-performance liquid chromatography coupled with diode array detection for the control of Fupenzi. Results: A significant correlation between antioxidant activity and the total flavonoid content was observed for the DPPH assay (r2 = 0.758, ρ = 0.004) and the ABTS assay (r2 = 0.788, ρ = 0.002). Under the optimized chromatographic conditions, the validated method was successfully applied to assessment of chemical fingerprinting of 12 batches of FPZ collected from different regions of China. Comparisons of the chromatograms showed that 15 characteristic peaks could be selected as markers for identification and evaluation of Fupenzi. In addition, the proposed method was also successfully applied to simultaneous determination of five compounds (including puerarin, rutin, hyperin, quercetin and kaempferol) in these samples. Conclusions: The qualitative and quantitative analysis described in this paper could be used for identification and evaluation of Fupenzi.

Isolation and Crystal Structure of Ent-kaurane Diterpenes from Rubus corchorifolius L. f.

In this study, ent-Kaurane-3β,16β,17-trioi （1） and ent-kaurane-2a,16β,17-triol （2）, were isolated from the leaves ofRubus corchorifolius L. f. Their structures were elucidated based on extensive spectroscopic analysis. NMR experiments identified the two compounds and X-ray crystallographic analysis confirmed their crystal structures. The crystal of 1 belongs to monoclinic with space group P21 and a = 10.7641（3）, b = 7.2789（3）, c = 11.7862（4） A, β = 95.275（3）°, V = 919.55（6） A3, Z = 2, C20H34O4, Mr = 322.49 g/mol, Dc = 1.230 g/m3, F（000） = 376, 2 = 1.54178 A,μ = 0.661 mm-1, R = 0.0319, and wR = 0.0811 for 10889 observed reflections （I〉 2σ（I））. The crystal of 2 is classified as orthorhombic with space group P212121 and a = 10.7641（3）, b = 12.72224（19）, c = 21.3929（3） A, V= 1748.94（4） A3, Z= 4, C20H3404, Mr = 322.47, De = 1.225 Mg/m3 F（000） = 712, λ = 1.54184 A,μ = 0.625 mm-1, R = 0.0303 and wR = 0.0759 for 10470 observed reflections （1〉 2σ（I））. Meanwhile, the compound revealed low inhibitory activities toward HepG2, MCF-7, and SCG-7901 cells.

A New Polyphenolic Compound from Rubus aleaefolius and Its Inhibitory Activity on Mammalian Cell Cycle at G_0/G_1 Phase

Rubuphenol (1), a new polyphenolic compound, was isolated together with the known ellagic acid (2) as new cell cycle inhibitors from Rubus aleaefolius Poir. through a bioassay-guided separation procedure and the structure of 1 was elucidated by spectroscopic method. Compounds 1 and 2 inhibited the cell cycle of tsFT210 cells at the G0/G1 phase respectively with the MIC values of 14.6 mM and 10.3 mM.

Total saponins in Rubus parvifolius L.induce lymphoma cells apoptosis through upregulated Bax/Fas and downregulated Bcl-2 in vivo and in vitro

Purpose:To investigate the effect of total saponins of Rubus parvifolius L.(TSRP)on lymphoma Raji cells and further discuss its mechanism.Methods:The model of nude mice bearing Raji cells was established,the volume,weight and inhibition rate of the transplanted tumor were analyzed and compared after different concentrations of TSRP treatment.Cell apoptosis and expression of Bcl-2,Bax,Fas proteins were detected by TUNEL and immunohistochemiscal method respectively.Effects of TSRP on cell proliferation were tested with MTT assay in vitro.Cell apoptosis and expression of Caspase-9,Caspase-3,Bcl-2,Bax and Fas proteins were tested with DAPI staining and Western blot.Results:TSRP significantly reduced the volume and tumor weight of Raji subcutaneous transplanted tumor and induced the apoptosis of Raji cells in vivo.The tumor inhibition rate of high-dose(100 mg/kg)TSRP is 90.84%.The TUNEL test results show that the fluorescence intensity of the tumor issue treated with TSRP is significantly improved.Compared with the control group,the fluorescence intensity of high-concentration TSRP is 82.43 ± 7.81,which is significantly different(P<0.001).The results of immunohistochemistry test showed that the Bcl-2 expression of Raji cell treated with TSRP is obviously reduced,and Bax expression is obviously increased.Meanwhile,compared with that of control group,Fas expression is obviously reduced.MTT assay showed that TSRP can significantly inhibit proliferation of Raji cells with dose dependence.The inhibition rate of 400 μg/mL TSRP is 53.46 ± 4.90%(P<0.001).DAPI staining results showed that TSRP can significantly induce cell apoptosis.According to Western blot results,it is found that TSRP can significantly inhibit activity of Bcl-2 and increase Bax expression,and TSRP can also inhibit Fas expression.Meanwhile,expression of Caspase-9 and Caspase-3 is also increased.Conclusion:TSRP could inhibit the proliferation of lymphoma via induction of apoptosis in a time and dose-dependent manner.Apoptotic signaling induced by TSRP was characterized by up-regulating Bax,Fas and Caspase-8 protein expression,and down-regulating of Bcl-2 protein expression.

Phenol Compounds of Blackberry （Rubus caucasicus Focke and Rubus anatolicus L.） Fruit and Leaf

It is investigated of the effect of plant blackberry （Rubus caucasicus Focke and Rubus anatolicus L.） flower, fruit and leaf content of phenol compounds qualitative and quantitative HPLC （high-pressure liquid chromatography） and spectral methods. HPLC analysis revealed that the fetus was a major of both species, cyanidin-3-glucoside, and it reached full maturity period 1,493.54 ± 44.81 and 1,636.58 ±49.10 mg/kg （cyanidin-3-O-glucoside chloride equivalents） calculated on the dry weight. In mature fetus flavonols is （884.8±26.54）-（979.0 ± 29.37） mg/kg （rutin equivalents） calculated on the dry weight, catechins （21.2± 0.64）-（25.01 ± 0.7537） mg/kg （（＋） catechin equivalents） calculated on the dry weight, leucoantocyanins （48.8 ±1.46）-（52.1± 1.56） mg/kg （cyanidin equivalents） calculated on the dry weight. In this regard, there was a slight difference between the species. Most of the leaf flavonols were presented 3.7 ± 0.111 g/kg. Phenol carbonic acids--the leaves of 13.4 ± 0.402 mg/kg calculated on the dry weight, the flowers of 8.8± 0.264 mg/kg, calculated on the dry weight. Full maturity period, the number of phenol carbonic acids cent is （3,707.8 ± 111.23）-（4,287.5 ± 128.63） mg/kg, （caffeic acid equivalents） is calculated on the dry weight of the unit. Also been determined HPLC following the method of compounds is： cyanidin-3-glucoside, quercetin-3-rutinoside, quercetin-3-glucoside, ellagic acid, gallic acid and chlorogenic acid.

Study on the Cutting Propagation Technique of Rubus spp. Raspberry

[Objective] The research aimed to study the effects of different matrices and hormones on the rooting rate of Rubus spp. Raspberry. [Method] Different ma- trices and different hormones with different concentrations were adopted to design completely randomized block test, thus to conduct cutting experiment of Rubus spp. Raspberry, in order to discuss the effects of different matrices and hormones on the rooting rate of Rubus spp. Raspberry. [Result] The rooting rate was significantly af- fected by different hormones and matrices, whereas the effect of hormone concen- tration was not significant. The suitable combination was 200 mg/kg ABT ＋ river sand. The effect of growth hormone on hard wood cutting of Rubus spp. Raspberry in river sand was not significant. [Conclusion] This test can provide a reference for the industrialized seedling production of Rubus spp. Raspberry.

Chemical composition,pharmacological activity and development strategies of Rubus chingii:A review

Raspberries are used for both food and medicine,but it has not yet attracted widespread attention.In this paper,the chemical constituen of the original plant raspberry.R.chingii is one of the new“Zhe Bawei”medicinal materials selected in 2017.“Zhe Bawei”refers to eight kinds of genuine medicinal materials in Zhejiang Province.The chemical constituents,pharmacological effects,processing,and application of Rubus chingii Hu were reviewed to provide a reference for its further development.Relevant literature in recent years was collected in databases such as China Knowledge Network,Web of Science,Elsevier,PubMed,and X-Mol,using“raspberry”,“Rubus chingii”,“traditional use”,“chemical composition”,“pharmacology”,etc.as keywords individually or in combination.The summary of pharmacological activities shows that the relationship between the pharmacological activities of raspberry is still not deep enough.More in-depth research should be carried out in this direction to explore the mechanism of action of its active ingredients and provide effective reference for the further development of the raspberry industry.In the future,with the participation of more researchers,it is expected to develop innovative drugs based on raspberry for the treatment of diseases.

基于简化基因组测序的树莓(Rubus corchorifolius)遗传分析

为了比较不同树莓种间的亲缘关系远近,分析群体的遗传进化关系,开发特异性SNP标记。本试验选用23份栽培种树莓利用简化基因组测序技术SLAF-seq测序,以黑树莓(Rubus occidentalis)基因组为参考基因组进行酶切预测,对照选择粳稻(Oryza sativa spp.japonica)品种日本晴的测序数据进行比对分析。本研究共获得59.93 Mb的读长数据,读长范围在1960847~5046748之间,对照数据的双端比对效率为95.60%,酶切效率为93.52%,测序质量值Q30平均为95.07%,所有样品GC含量均值为39.16%,共获得425402个SLAF标签,其中多态性的SLAF标签共有121610个。获得749811个有效单核苷酸多态性(single nucleotide polymorphisms,SNP),利用这些SNP对23份树莓材料完成系统进化树,群体的PCA分析,从群体结构分析结果发现这23份树莓都来源于同一祖先,只是在生长发育过程中发生了遗传分化。

Isolation and Chemotaxonomic Significance of Chemical Constituents from Rubus parvifolius

Objective To study the chemical constituents from the roots of Rubus parvifolius. Methods The chemical constituents were extracted and purified by silica gel column chromatography. NMR spectra were used for structural identification. Results Phytochemical study on the roots of R. parvifolius led to the isolation of one ceramide （1）, two anthraquinones （2 and 3）, four triterpenoids （4-7）, two flavonoids （8 and 9）, one fatty acid ester （10）, and two sterols （1 1 and 12）. Conclusion Compound 1 is isolated from the plants of family Rosaceae for the first time, and compounds 2-5 are isolated from genus Rubus for the first time. Though R. parvifolius shares the same major chemical types （triterpenoid, flavonoid, and anthraquinone） with those of R. alceaefolius, a substituent of R. parvifolius, their individual constituents are different. In addition, R. parvifolius contains ceramide （1） with high concentration, while caffeoylquinic acid reported in R. alceaefolius has not been found in R. parvifolius. Furthermore, the results from our phytochemical study are consistent with the DNA phylogenic relationship between R. parvifolius and R. alceaefolius （two separated subgenera）, suggesting that the substitution of the former species with the latter one in folk medicine might not be suitable.

Triterpenoids from the roots of Rubus parvifolius

Two new oleanane-type triterpenoids, parvifolactone A(1) and rubuside P(2), together with 11 known triterpenoids, fupenzic acid(3), 18,19-seco,2α,3α-dihydroxyl-19-oxo-urs-11,13(18)-dien-28-oic acid(4), euscaphic acid(5), maslinic acid(6), 1β-hydroxyeuscaphic acid(7), 2α,3α,19α,23-tetrahydroxyolean-12-en-28-oic acid(8), 2α,3β,19α,23-tetrahydroxyurs-12-en-28-oic acid(9), glucosyl pinfaensate(10), rubuside J(11), 2α,3α,19α,23-tetrahydroxyurs-12-en-24,28-dioic acid(12), and 2α,3β,19α- trihydroxyurs-12-en-23,28-dioic acid(13), were isolated from the roots of Rubus parvifolius.

Involvement of pro-inflammatory and anti-inflammatory cytokines in the anti-inflammatory activity of Rubus idaeus L.on LPS-treated RAW 264.7 cells

Anti-inflammatory activity ofRubus idaeus L. and possible mechanisms involved were explored in lipopolysaccharide （LPS）-treated RAW 264.7 cells. The effects of ethanol extract of R. idaeus on the levels of pro-inflammatory cytokines, including tumor necrosis factor-alfa （TNF-α）, interleukin-6 （IL-6） and interleukin-1 beta （IL-1β）, as well as pro-inflammatory mediators, such as nitric oxide （NO）, inducible nitric oxide synthase （iNOS） and cyclooxygenase-2 （COX-2） were studied by Sandwich ELISA, real-time PCR, and Western blot analysis. Moreover, the effects of ethanol extract of R. idaeus on anti-inflammatory cytokine interleukin-10 （IL-10） and anti-inflammatory mediator heme oxygenase-1 （HO-1） were also investigated using the same methods. Furthermore, nuclear factor-gB （NF-κB） level was assayed by immunocytochemistry. The results showed that the production of IL-1β, IL-6, NO, TNF-α and COX-2 in LPS-treated cells could be significantly inhibited （P〈0.01 or P〈0.05） by ethanol extract ofR. idaeus compared with that in the cells treated with LPS only. Meanwhile, the production of NF-r,B was also inhibited by the extract. Based on these results, the anti-inflammatory activity ofR. idaeus was attributed to the down-regulation of IL-6, IL-1β and TNF-α levels as well as gene expression of iNOS and COX-2 through the suppression of NF-κB activation, and induction of anti-inflammatory cytokine IL- 10 and anti-inflammatory mediator HO- 1.

Rubus chingii Hu: an overview of botany, traditional uses,phytochemistry, and pharmacology

Rubus chingii Hu, a member of the rosaceae family, is extensively distributed in China and Japan. Its unripe fruits(Fupenzi in Chinese) have a long history of use as an herbal tonic in traditional Chinese medicine for treating various diseases commonly associated with kidney deficiency, and they are still in use today. Phytochemical investigations on the fruits and leaves of R. chingii indicate the presence of terpenoids, flavonoids, steroids, alkaloids, phenylpropanoids, phenolics, and organic acids. Extracts or active substances from this plant are reported to have various pharmacological properties, including antioxidant, anti-inflammatory, antitumor, antifungal, antithrombotic, antiosteoporotic, hypoglycemic, and central nervous system-regulating effects. This review provides up-to-date information on the botanical characterizations, traditional usages, chemical constituents, pharmacological activities, toxicity,and quality control of R. chingii. Possible directions for future research are also briefly proposed. This review aims to supply fundamental data for the further study of R. chingii and contribute to the development of its clinical use.

Protein tyrosine phosphatase 1B inhibitory activities of ursane-type triterpenes from Chinese raspberry, fruits of Rubus chingii

Protein tyrosine phosphatase 1 B(PTP1 B) has led to an intense interest in developing its inhibitors as anti-diabetes, anti-obesity and anti-cancer agents. The fruits of Rubus chingii(Chinese raspberry) were used as a kind of dietary traditional Chinese medicine. The methanolic extract of R. chingii fruits exhibited significant PTP1 B inhibitory activity. Further bioactivity-guided fractionation resulted in the isolation of three PTP1 B inhibitory ursane-type triterpenes: ursolic acid(1), 2-oxopomolic acid(2), and 2α, 19α-dihydroxy-3-oxo-urs-12-en-28-oic acid(3). Kinetics analyses revealed that 1 was a non-competitive PTP1 B inhibitor, and 2 and 3 were mixed type PTP1 B inhibitors. Compounds 1-3 and structurally related triterpenes(4-8) were further analyzed the structure-activity relationship, and were evaluated the inhibitory selectivity against four homologous protein tyrosine phosphatases(TCPTP, VHR, SHP-1 and SHP-2). Molecular docking simulations were also carried out, and the result indicated that 1, 3-acetoxyurs-12-ene-28-oic acid(5), and pomolic acid-3β-acetate(6) bound at the allosteric site including α3, α6, and α7 helix of PTP1 B.

Evaluation of the hepatoprotective and antioxidant activities of Rubus parvifolius L.

The hepatoprotective and antioxidant activities of the n-butanol extract of Rubus parvifolius L. （RPL）, a widely used medicinal plant, were evaluated. Results demonstrated that RPL extract possessed pronounced hepatoprotective effects against carbon tetrachloride （CCI4）-induced hepatic injury in mice, which was at least partially attributed to its strong antioxidant capacity. Treatment with RPL extract markedly attenuated the increases in serum alanine ami- notransferase （ALT） and aspartate aminotransferase （AST） levels caused by CCI4 intoxication. It also significantly prevented the decrease in superoxide dismutase （SOD） activity and the increase in malondialdehyde （MDA） content of liver tissue. Meanwhile, histopathological changes of hepatic damage were also remarkably ameliorated. Phytochemical analysis based on high-performance liquid chromatography/tandem mass spectrometry （HPLC-MS/MS） revealed the presence of various phenolic compounds, including caffeic acid conjugates, ellagic acid glycosides, and flavonol glycosides, which might be responsible for the hepatoprotective and antioxidant activities of RPL.