Gut microbiome-based thiamine metabolism contributes to the protective effect of one acidic polysaccharide from Selaginella uncinata(Desv.)Spring against inflammatory bowel disease

Inflammatory bowel disease(IBD)is a serious disorder,and exploration of active compounds to treat it is necessary.An acidic polysaccharide named SUSP-4 was purified from Selaginella uncinata(Desv.)Spring,which contained galacturonic acid,galactose,xylose,arabinose,and rhamnose with the main chain structure of→4)-α-d-GalAp-(1→and→6)-β-d-Galp-(1→and the branched structure of→5)-α-l-Araf-(1→.Animal experiments showed that compared with Model group,SUSP-4 significantly improved body weight status,disease activity index(DAI),colonic shortening,and histopathological damage,and elevated occludin and zonula occludens protein 1(ZO-1)expression in mice induced by dextran sulfate sodium salt(DSS).16S ribosomal RNA(rRNA)sequencing indicated that SUSP-4 markedly downregulated the level of Akkermansia and Alistipes.Metabolomics results confirmed that SUSP-4 obviously elevated thiamine levels compared with Model mice by adjusting thiamine metabolism,which was further confirmed by a targeted metabolism study.Fecal transplantation experiments showed that SUSP-4 exerted an anti-IBD effect by altering the intestinal flora in mice.A mechanistic study showed that SUSP-4 markedly inhibited macrophage activation by decreasing the levels of phospho-nuclear factor kappa-B(p-NF-κB)and cyclooxygenase-2(COX-2)and elevating NF-E2-related factor 2(Nrf2)levels compared with Model group.In conclusion,SUSP-4 affected thiamine metabolism by regulating Akkermania and inhibited macrophage activation to adjust NF-κB/Nrf2/COX-2-mediated inflammation and oxidative stress against IBD.This is the first time that plant polysaccharides have been shown to affect thiamine metabolism against IBD,showing great potential for in-depth research and development applications.

Isolation and Identification of Chemical Constituents of Selaginella tamariscina

[Objective] This study aimed to isolate and identify the chemical constituents of Selaginella tamariscina. [Method] The chemical compounds isolated from the whole plant of traditional Chinese herb S. tamariscina were purified through column chromatography and preparative thin-layer chromatography, and then chemical structures of the compounds were determined by NMR and mass spectrometry. Finally, the anticancer activity of the compounds 5, 6 and 7 was measured by MTT assay. [Result] Seven compounds, containing carnaubic acid (1), glucose (2), β-sitosterol (3), amentoflavone (4), selaginellin (5), selaginellin M (6) and selaginellin A (7), were isolated from methanol extracts of S. tamariscina. Among the three tested compounds, compound 7 exhibited the most effective activity to inhibit the HeLa cell growth. [Conclusion] This study will provide a basis for better development and utilization of Selaginella plant resources.

Neolignans from Selaginella moellendorffii

Two new neolignans selaginellol(1)and selaginellol 4'-O-β-D-glucopyranoside(2),together with seven known compounds(3–9),were isolated from the whole plant of Selaginella moellendorffii.The structures of the new isolates were determined through spectroscopic data analysis.Compounds 1–9,as well as compounds 10–18 previously isolated from the species,were measured for the activity against platelet aggregation induced by ADP or collagen.Three neoligans(8,11,and 12),one flavanone(14),and one alkaloid(16)showed inhibitory activity against ADP-or collagen-induced platelet aggregation as compared with tirofiban.The dihydrobenzofuran neolignans(8,11,and 12)are more potent than the benzofuran neolignan(13)and other types of neolignans(1–7).Glucosidation of the dihydrobenzofuran neolignans(11 and 12)is helpful for the activity.Graphical Abstract Two new neolignans selaginellol(1)and selaginellol 40-O-b-D-glucopyranoside(2)were isolated from the whole plant of Selaginella moellendorffii.Several compounds from this plant showed the activity against platelet aggregation induced by ADP or collagen.

A new dihydrobenzofuran lignanoside from Selaginella moellendorffii Hieron

A new lignanoside, （7R,8S）-7,8-dihydro-7-（4-hydroxy-3,5-dimethoxyphenyl）-1＇-formyl-3＇-y-methoxyl-8-hydroxymethylbenzo- furan-4-O-β-D-glucopyranoside （moellenoside A）, was isolated from Selaginella moellendorffii Hieron. Its structure was determined by spectroscopic evidences. 2007 Wei Sheng Feng. Published by Elsevier B.V. on behalf of Chinese Chemical Society. All rights reserved.

卷柏属(Selaginella)管状分子的研究

[目的]研究卷柏管状分子的类型和特点。[方法]用扫描电子显微镜对经离析法处理的4种卷柏属植物的茎进行观察。[结果]中华卷柏和蔓出卷柏中具有管胞,其中蔓出卷柏中还可见梯状穿孔的管状分子,推测可能为导管;圆枝卷柏、垫状卷柏仅观察到导管,有梯状穿孔以及网状-梯状混合型穿孔2种类型。这4种卷柏中,圆枝卷柏和垫状卷柏的管状分子最为进化,蔓出卷柏次之,中华卷柏最原始。垫状卷柏、蔓出卷柏和中华卷柏的管状分子类型为首次报道。卷柏管状分子类型的不同可能与其生境有关。[结论]该研究为验证同形叶和异形叶类型卷柏管状分子的差别以及探讨卷柏管状分子的演化问题奠定了基础。

A new sesquilignan from Selaginella sinensis (Desv.) Spring

A new sesquilignan, namely sinensiol A, was isolated from the plant of Selaginella sinensis （Desv.） Spring. Its structure was identified on the basis of various spectroscopic data analysis.

Preliminary phytochemical and antimicrobial studies on a spike-moss Selaginella inaequalifolia(hook.& grev.) Spring

Objective:To screen the anti-cancer spike-mosses for the presence of various bioactivities and to identify the important bioactive chemicals present in Selaginella inaequalifolia(S. inaequalifolia)(Hook.& Grev.) Spring.Methods:Preliminary phytochemical screening was done by following the method of Brindha et al.Antimicrobial study was carried out by disc diffusion method.Results:Results of preliminary phytochemical screening on five different extracts(petroleum ether,benzene,chloroform,ethanol and distilled water) of the spike-moss S.inaequalifolia show the presence steroids,triterpenes,phenolic group,tannin,sugars and catechin.Alkaloids,amino acids,anthraquinone and reducing sugar did not show any positive result.Among the five different extracts,ethanol and chloroform extracts show the presence of maximum number(4 each) of compounds.The results on antimicrobial studies show that all the three microbes[Staphylococcus aureus(S.aureus),Escherichia coli(E.coli) and Candida albicans (C.albicans)]tested are resistant to the ethanol extract and susceptible to petroleum ether extract.The petroleum ether extract shows maximum inhibition with 45 mm of inhibition zone in C.albicans.The inhibition zone in S.aureus and E.coli are 26 mm and 22 mm respectively. Conclusions:The present study shows S.inaequalifolia having potent antibacterial and anticandidal activities.

A new flavonoid with a benzoic acid substituent from Selaginella uncinata

6-（5-Carboxyl-2-methoxyphenyl）-apigenin （1）, a new flavonoid, was isolated from the 60% ethanol extract of Selaginella uncinata （Desv.） Spring. Its structure was established by spectroscopic methods. Compound 1 represents the first example of the flavonoids possessing a benzoic acid substituent at C-6.

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.

A new flavonoid from Selaginella tamariscina

6-（2-Hydroxy-5-acetylphenyl）-apigenin （1）, a new flavonoid with a phenyl substituent, was first isolated from Selaginella tamariscina. Its structure was elucidated on the basis of 1D and 2D NMR as well as ESI-HR-MS spectroscopic analysis.

湖南卷柏属Selaginella Spring资料

报道湖南产的卷柏属植物22种,编了这些种的检索表。其中圆枝卷柏、耳基卷柏、布朗卷柏、毛枝卷柏、硬毛卷柏、疏叶卷柏、地卷柏、缘毛卷柏、峨眉卷柏等9种属湖南新分布。

Isolation,Structural Assignment of Isoselagintamarlin A from Selaginella tamariscina and Its Biomimetic Synthesis

Isoselagintamarlin A(1),a selaginellin analogue featured a rare benzofuran unit,was isolated from Selaginella tamariscina.Its complete structural assignment was established through a combination of high-feld NMR technique and biomimetic synthesis.Notably,isoselagintamarlin A(1)was successfully synthesized via sequential oxidations and intramolecular cyclization.

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.

Genome Analysis of the Ancient Tracheophyte Selaginella tama#scina Reveals Evolutionary Features Relevant to the Acquisition of Desiccation Tolerance

Resurrection plants, which are the ＂gifts＂ of natural evolution, are ideal models for studying the genetic basis of plant desiccation tolerance. Here, we report a high-quality genome assembly of 301 Mb for the diploid spike moss Selaginella tamariscina, a primitive vascular resurrection plant. We predicated 27 761 protein-coding genes from the assembled S. tarnariscina genome, 11.38% （2363） of which showed signifi- cant expression changes in response to desiccation. Approximately 60.58% of the S. tamariscina genome was annotated as repetitive DNA, which is an almost 2-fold increase of that in the genome of desiccation- sensitive Selaginella moellendorffii. Genomic and transcriptomic analyses highlight the unique evolution and complex regulations of the desiccation response in S. tamariscina, including species-specific expan- sion of the oleosin and pentatricopeptide repeat gene families, unique genes and pathways for reactive oxygen species generation and scavenging, and enhanced abscisic acid （ABA） biosynthesis and potentially distinct regulation of ABA signaling and response. Comparative analysis of chloroplast genomes of several Selaginella species revealed a unique structural rearrangement and the complete loss of chloroplast NAD（P） H dehydrogenase （NDH） genes in S. tamariscina, suggesting a link between the absence of the NDH com- plex and desiccation tolerance. Taken together, our comparative genomic and transcriptomic analyses reveal common and species-specific desiccation tolerance strategies in S. tamariscina, providing signifi- cant insights into the desiccation tolerance mechanism and the evolution of resurrection plants.

Metabolomic Profiling in Selaginella lepidophylla at Various Hydration States Provides New Insights into the Mechanistic Basis of Desiccation Tolerance

Selaginella lepidophylla is one of only a few species of spike mosses （Selaginellaceae） that have evolved des-iccation tolerance （DT） or the ability to ＇resurrect＇ from an air-dried state. In order to understand the metabolic basis of DT, S, lepidophylla was subjected to a five-stage, rehydration/dehydration cycle, then analyzed using non-biased, global metabolomics profiling technology based on GC/MS and UHLC/MS/MS2 platforms. A total of 251 metabolites including 167 named （66.5%） and 84 （33.4%） unnamed compounds were characterized. Only 42 （16.7%） and 74 （29.5%） of compounds showed significantly increased or decreased abundance, respectively, indicating that most compounds were produced con-stitutively, including highly abundant trehalose, sucrose, and glucose. Several glycolysis/gluconeogenesis and tricarboxylic acid （TCA） cycle intermediates showed increased abundance at 100% relative water content （RWC） and 50% RWC. Vanillate, a potent antioxidant, was also more abundant in the hydrated state. Many different sugar alcohols and sugar acids were more abundant in the hydrated state. These polyols likely decelerate the rate of water loss during the drying process as well as slow water absorption during rehydration, stabilize proteins, and scavenge reactive oxygen species （ROS）. In contrast, nitrogen-rich and y-glutamyl amino acids, citrulline, and nucleotide catabolism products （e.g. allantoin） were more abundant in the dry states, suggesting that these compounds might play important roles in nitrogen remobilization during rehydration or in ROS scavenging. UV-protective compounds such as 3-（3-hydroxyphenyl）propionate, apigenin, and naringenin, were more abundant in the dry states. Most lipids were produced constitutively, with the exception of choline phosphate, which was more abundant in dry states and likely plays a role in membrane hydration and stabilization. In contrast, several poly- unsaturated fatty acids were more abundant in the hydrated states, suggesting that these compounds likely help maintain membrane fluidity during dehydration. Lastly, S, lepidophylla contained seven unnamed compounds that displayed twofold or greater abundance in dry or rehydrating states, suggesting that these compounds might play adaptive roles in DT.

Therapeutic Effects of Selaginella tamariscina on the Model of Acute Gout with Hyperuricemia in Rats Based on Metabolomics Analysis

Gout is a disease of purine metabolic disorders which results from long-term hyperuricemia and the sodium urate deposition in and around the joints. Selaginella tamariscina （ST） is an important traditional Chinese herbal medicine and is used for the treatment of gout and hyperuricemia. In this study, the rat model of acute gout with hyperuricemia was established by intraperitoneal injection of xanthine and oxonic acid potassium salt and articular injection monosodium urate （MSU）. The effect of ST in the treatment of gout was investigated by measuring joint swelling, the expression of IL-1 !3 in serum and histological changes of joint by haematoxylin eosin （H＆E） staining. Subsequently, urine metabolomics analysis for biomarkers discovery in acute gout with hyperuricemia rats was performed by the ultra-performance liquid chromatography-electrospray ionization quadruple time-of-flight mass spectrometry （UPLC-ESI-QTOF/MS） combined with chemometric approach. Principal component analysis （PCA） and orthogonal partial least squares-discriminant analysis （OPLS-DA） were used to detect potential biomarkers. A total of 18 potential biomarkers were identified mainly including tryptophan metabolism; tyrosine metabolism; ly- sine methylation; pyrimidine metabolism; purine metabolism; TCA cycle and fatty acid metabolisms. This study in- dicates that ST could efficiently ameliorate the disease of acute gout with hyperuricemia in rats. The related meta- bolic biomarkers could provide useful information and the metabolic mechanism could be used for further study about the model of acute gout with hyperuricemia in rats.

Sinensioside A, a new sesquilignan glycoside from Selaginella sinensis

AIM: To investigate the chemical constituents of Selaginella sinensis(Desv.) Spring. METHODS: Chromatographic separations on Diaion HP-20, silica gel, and Sephadex LH-20 were used. The structures of the isolates were elucidated on the basis of spectroscopic analysis, as well as chemical methods. RESULTS: Eight compounds were obtained and their structures were identified as sinensioside A(1), syringaresinol-4-O-β-D-glucopyranoside(2),(+)-medioresinol-4-O-β-D-glucopyranoside(3), pinoresinol-4, 4′-di-O-β-D-glucopyranoside(4), quercetin(5), eucomic acid(6), shikimic acid(7), and 2, 3-dihydroamentoflavone(8). CONCLUSION: Compound 1 is a new dihydrobenzofuran sesquilignan glycoside from Selaginella sinensis.

A new norlignan lignanoside from Selaginella moellendorffii Hieron

This study reports an investigation into the chemical constituents of the whole plant of Selaginella moellendorffii Hieron.Ten compounds,isolated and purified by column chromatography,were identified on the basis of spectral analysis and their physicochemical properties to be:(8R)-3,5-dimethoxy-4-hydroxyphenylpropylalcohol-8-(1-acetyl-3-methoxy-4-hydroxyphenyl)-9-O-b-D-glucopyranoside(moellenoside B)(1),amentoflavone(2),hinokiflavone(3),apigenin-7-O-bneohesperidoside(4),apigenin-8-C-b-D-glucopyranoside(5),adenosine(6),uridine(7),2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylic acid(8),vanillic acid(9),and lariciresinol(10).Compound 1 is a new norlignan lignanoside and compounds 4–10 were isolated from this plant for the first time.

Bioactive compounds from Selaginella involven Spring that protect PC-12 cells

Two new compounds named as 3b 12 16-trihydroxy-6 8 11 13-abietatrien（1） （8R 80S）-4 40 8-trihydroxyl-3 30-dimethoxyl-90-lignanolide（2） and a new natural product 4 40-dihydroxyl-3 30 5 50-dimethoxyldiphenyl diketone（3） were isolated from the whole herbs of Selaginella involven Spring.The structures were elucidated by spectroscopic analyses including UV,IR,1D,2D NMR and MS methods.Additionally,these three compounds exhibited potent protective effect against the injury of PC-12 cells induced by hypoxia/reoxygenation.

Uncinatic acids A-C,three new carboxylated flavonoids from Selaginella uncinata

Three new carboxylated flavonoids, uncinatic acids A-C（1–3）, were isolated from the whole herb of Selaginella uncinata. Their structures were established on the basis of extensive NMR analysis including1 D, 2D NMR experiments and HR-ESIMS techniques. All of them share the carboxylation structural characteristic. Compounds 1 and 2 belong to novel naturally occuring furanoflavonoids which is firstly reported in genus Selaginella. Such furanoflavonoids with dicarboxylic acid structrure have never been discovered before. In addition, the isolates were tested for their cytotoxicity against A549 and BGC-823 cell lines in vitro.