Sulfated Sterols Isolated from Starfish Asterias amurensis Lutken

Aim To study the chemical constituents of starfish Asterias amurensis. Methods The constituents were separated and purified by different chromatographic methods, and their structures were elucidated by MS and NMR. Results Six compounds were isolated from Asterias amurensis Lutken. Their structures were identified as 3β-O-sulfated-cholest-5-en sodium salt （1）, 3β-O-sulfated-6α-ol- pregn-9（ 11 ） -en-20-one sodium salt （ 2 ）, 3β-O-sulfated-6α-ol-cholest-9 （ 11 ） -en-23-one sodium salt （3）, 3β-O-sulfated-6α, 20β-diol-cholest-9 （ 11 ）-en-23-one sodium salt （ 4 ）, 3β-O-sulfated-6α-ol- cholesta-9 （ 11 ）, 20 （ 22 ） -dien-23-one sodium salt （ 5 ）, and 3β-O-sulfated-6ct-ol-ergost-9 （ 11 ） -en-23- one sodium salt （6）. Conclusion Compounds 1 - 6 were obtained from this species for the first time.

Occurrence of Different Forms and Implications of Compound Specific Sterols in Continental Sediments of the Northeast South China Sea

The South China Sea(SCS) is one of the most productive and accumulative marginal shelves of organic carbon in the world. To expound the transformation and preservation of organic carbon in the Northeast SCS, where abundant oil and gas resources have been reported, compound specific sterols in free(FR), base hydrolytic(BH), and acid hydrolytic(AH) forms were analyzed in surface and columnar sediments in May, 2016. The results showed that the total contents of sterols detected ranged from 0.15 to 3.74 ppm dry weight in the surface sediments, and gradually decreased from 3.41 to0.17 ppm dry weight from surface to deep sediments, in which cholesterol(27^(△5)) was the most abundant component. Sterols mainly existed in the BH form(54.51%-74.20%), followed by the FR form(25.50%-45.49%) and then the AH form(0-3.77%) in turn, in the surface sediments. BH and FR sterols accounted for 0-49.08% and 50.92%-100% in the columnar sediments, while AH sterols were undetectable. The contents of specific sterols indicated that, the primary source of marine organic carbon was about 5 times as much as that from terrestrial input. More and more FR sterols transformed into BH sterols with increasing sedimentary depth, and BH sterols absolutely dominated in sediment depths under 25 cm. The forms of Sterols C27 were maintained at a relative consistence state, but Sterols C28 to C30 degraded gradually during the sedimentation process. It was suggested that the stability of sterols, based on the chemical structures, might be the primary factor controlling their degradation and preservation in deeper sediments. These results would help to understand the organic carbon(OC) transformation in a hydrate formation area in a marginal sea.

Two New Sterols from Adenophora Stenanthina Subsp.Xifengensi

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SIMULATED THERMAL ALTERATION OF STEROLS AND KETO-ALCOHOLS IN MARINE SEDIMENTS OF THE OKINAWA TROUGH

Compositional data on the sterol and alcohol fractions isolated from deep-sea marine sediments from the Okinawa Trough were obtained to determine the relative contribution from. marine and terrestrial inputs. Following extraction, the sterol plus alcohol fraction was isolated by layer chromatography, derivatized with BSTFA and then analysed by capillary GC and GC-MS. A suite of C26-C29 stenols and stanols and C30-C32 keto - alcohols were identified in the sediments. The thermal stability of the compounds in these sediments was studied by heating portions of the surface sediment in glass tubes fpr 16 hours at temperatures from 50℃ to 200℃.The C27 stanol/stenol ratio increased when temperatures went up to 175℃ , but the distribution of C30-C32 Keto - alcohols remained unaffected. At 200℃ most of the sterols and Keto - alcohols were destroyed.

Combined Effects of Plant Sterols with Low Ratio of n-6/n-3 Polyunsaturated Fatty Acids against Atherosclerosis in ApoE–/–Mice

The effects of low ratio of n-6/n-3 polyunsaturated fatty acids(PUFA)have been clarified against atherosclerosis.Increasing evidence indicated that plant sterols(PS)have a significant cholesterol-lowering effect.This study explored the effects of PS combined with n-6/n-3(2:1)PUFA on atherosclerosis and investigated the possible mechanism.In ApoE−/−mice,the milk fat in high fat diets was replaced with n-6/n-3(2:1)PUFA alone or supplemented with 6%PS for 16 weeks.Results demonstrated that PS combined with PUFA exerted commentary and synergistic effects on ameliorating atherosclerosis,improving lipid metabolism and lipid deposition in liver,and alleviating inflammatory response.These changes were accompanied with decreased serum TC,TG,LDL-C and increased fecal cholesterol efflux,as well as the lower inflammatory cytokine CRP,IL-6,TNF-α.It is suggested that the underlying mechanism of PS combined with n-6/n-3(2:1)PUFA promoting the fecal cholesterol efflux may be mediated by liver X receptorα/ATP-binding cassette transporter A1 pathway.

Triterpenoids and Sterols from the Leaves and Twigs of Melia azedarach

Two new triterpenoids(1 and 2)and a new sterol(3),together with six known constituents(4–9),were isolated from the leaves and twigs of Melia azedarach.Their chemical structures were elucidated on the basis of spectroscopic analysis.

The substance composition of sterols in the sediments from the Chukchi Sea,the Bering Sea and global climatic significance

The compounds of sterols such as C27 ,C2s ,C29 and C30 are recorded from C-8 core of the Chukchi Sea. The double bond position is located at 5-, 5,22 as well as 22-,24-. The compound of sterols such as C27 ,C28 ,C29 are recorded from B2-9 core of the Bering Sea. The double bond position is located at 5-, 5, 22 as well as 22. The composition characteristics of sterols indicate that the substance is mainly contributed by the terrigenous origin and marine silicate organisms. The results are also suggest that the record of abnormal sterols from the surface sediments （2 -0 era）in the Chukchi Sea and the Bering Sea represent the period from 1980s to the late 1990s. The strong signal of the Arctic warming is preserved in the sediments, which indicates the eco - environmental change responding to climatic effect of circumjacent.

The Identification of Two New Sterols from Marine Organism

Two new sterol have been isolated from the South China Sea marine organism. Compound 1 was isolated from the sponge Polymastia sobustia and compound 2 was obtained from the soft coral Sinularia inexplicata. Their structures were established as 3 beta-hydroxy-stigmast-5en-7-one and 24-methylene cholestan -3 beta, 6 beta, 9 alpha, 19-tetrol by variety of spectral analysis such as IR, EIMS, 1DNMR, H-1-H-1 COSY, HMQC, HMBC, NOESY.

Crystallographic and NMR studies on sterols from green alga Chaetomorpha basiretorsa Setchell

Chemical investigation of the ethanol extract of the marine green alga Chaetomorpha basiretorsa Setchell led to the isolation of a new sterol stigmast-4,28-dien-3α,6β-diol 1 in addition to the five known sterols of β-lawsaritol 2, saringosterol 3, 24-hydroperoxy-24-vinyl - cholesterol 4, β-stigmasterol 5, 29-hydroxystigmasta-5, 24 （28） -dien-3β-ol 6. Compounds were isolated by normal phase silica gel and Sephadex LH - 20 gel colum chromatography, reverse phase HPLC and recrystalization. Their structures were elucidated by spectroscopic methods including MS, IR 1D/2D NMR and X-ray analysis. Cytotoxicity of compounds was screened by using the standard MTF method. All these compounds were isolated from the green alga Chaetomorpha basiretorsa Setchell for the first time and they were inactive （50% inhibitory concentration was greater than 10 μg/cm^3） against KB, Bel -7402, PC - 3M, Ketr 3 and MCF-7 cell lines.

Two New Sterols from Bolbostemma paniculatum

Two new sterols were isolated from bulbs of Bolbostemma paniculatum (Maxim.) Franquet. Their structures were elucidated as stigmasta-7, 22, 25-triene-3-O-nonadecanoic acid ester (1) and stigmasta-7, 22, 25-triene-3-O-B-D- (6'-palmitoyl) glucopyranoside (2) by chemical and spectroscopic methods.

Determination of sterols in tobacco leaves by gas chromatography-tandem mass spectrometry

The purpose of the study was to establish an analytical method to simultaneously determine multiple sterols in tobacco leaves rapidly and accurately.In this gas chromatography-triple quadruple tandem mass spectrometry(GC-MS/MS)based method,various conditions for sterols extraction were assessed and the instrumental operation parameters were optimized with 5α-cholane as an internal standard.Using this method,eight plant sterols,namely lanosterol,campesterol,chenodeoxycholic acid,cholesterol,β-sitosterol,stigmasterol,dihydrotachysterol and ergosterol,were separated in less than 30 min.The linear correlation coefficients were over 0.998 9,the low detection limits were in the range of 0.010 3-0.141 4 μg/g.The recoveries were from 87.30% to 115.60%,with low standard deviations.In conclusion,this method demonstrates good repeatability,accuracy,and high sensitivity,and is best suited for rapid analysis of multiple sterols in tobacco leaves.

Two New C_(29) Sterols from Clerodendrum colebrookianum

From the aerial parts of Clerodendrum colebrookianum Walp., two new C_29 sterols colebrin A and colebrin B, were isolated, along with a known compound, clerosterol. The structures of the new compounds were elucidated on the basis of spectral evidence.

Extracts of Zanthoxylum bungeanum regulate cholesterol accumulation induced by sterols and LPS in vitro and in vivo

In this investigation,the effects of PE,EtOAc,and BuOH fractions from Zanthoxylum bungeanum on cholesterol accumulation induced by sterols and LPS were determined in vitro and in vivo.HepG2 cells induced by 25-hydroxychoelsterol and cholesterol were employed as cell model.After treatment with PE,EtOAC,or BuOH fractions,cellular total cholesterol and apolipoprotein B secretion were significantly reduced.In addition,compared with control group,expressions of SREBP2,HMGCR,and ACAT decreased,while CYP27A1,ABCA1,and LDLR levels increased.Cholesterol accumulation was also induced in C57BL/6 mice by LPS and the mice were used as the animal model.Determination of serum TNF-α level and hepatic mRNA expression of TNF-α,IL-6,iNOS,COX-2 revealed that EtOAc and BuOH fractions had anti-inflammatory effects.Furthermore,hepatic total cholesterol was reduced,accompanied by the elevation of LXR-α and ABCA1 gene expression in BuOH fraction treated mice.Since EtOAc and BuOH fractions were found active,bioassay-guided isolation was performed and β-sitosterol,eudesmin,sesamin and syringaresinol-β-D-glucoside were isolated from the fractions.

Faecal sterols as sewage markers in the Langat River,Malaysia:Integration of biomarker and multivariate statistical approaches

The Langat River in Malaysia has been experiencing anthropogenic input from urban, rural and industrial activities for many years. Sewage contamination, possibly originating from the greater than three million inhabitants of the Langat River Basin, were examined. Sediment samples from 22 stations （SL01-SL22） along the Langat River were collected, extracted and analysed by GC-MS. Six different sterols were identified and quantified. The highest sterol concentration was found at station SL02 （618.29 ng/g dry weight）, which situated in the Balak River whereas the other sediment samples ranged between 11.60 and 446.52 ng/g dry weight. Sterol ratios were used to identify sources, occurrence and partitioning of faecal matter in sediments and majority of the ratios clearly demonstrated that sewage contamination was occurring at most stations in the Langat River. A multivariate statistical analysis was used in conjunction with a combination of biomarkers to better understand the data that clearly separated the compounds. Most sediments of the Langat River were found to contain low to mid-range sewage contamination with some containing ＇significant＇ levels of contamination. This is the first report on sewage pollution in the Langat River based on a combination of biomarker and multivariate statistical approaches that will establish a new standard for sewage detection using faecal sterols.

Comprehensive prognostic and immune analysis of sterol Oacyltransferase 1 in patients with hepatocellular carcinoma

BACKGROUND Sterol O-acyltransferase 1(SOAT1)is an important target in the diagnosis and treatment of liver cancer.However,the prognostic value of SOAT1 in patients with hepatocellular carcinoma(HCC)is still not clear.AIM To investigate the correlation of SOAT1 expression with HCC,using RNA-seq and gene expression data of The Cancer Genome Atlas(TCGA)-liver hepatocellular carcinoma(LIHC)and pan-cancer.METHODS The correlation between SOAT1 expression and HCC was analyzed.Cox hazard regression models were conducted to investigate the prognostic value of SOAT1 in HCC.Overall survival and disease-specific survival were explored based on TCGA-LIHC data.Biological processes and functional pathways mediated by SOAT1 were characterized by gene ontology(GO)analysis and the Kyoto Encyclopedia of Genes and Genomes(KEGG)analysis of differentially expressed genes.In addition,the protein-protein interaction network and co-expression analyses of SOAT1 in HCC were performed to better understand the regulatory mechanisms of SOAT1 in this malignancy.RESULTS SOAT1 and SOAT2 were highly expressed in unpaired samples,while only SOAT1 was highly expressed in paired samples.The area under the receiver operating characteristic curve of SOAT1 expression in tumor samples from LIHC patients compared with para-carcinoma tissues was 0.748,while the area under the curve of SOAT1 expression in tumor samples from LIHC patients compared with GTEx was 0.676.Patients with higher SOAT1 expression had lower survival rates.Results from GO/KEGG and gene set enrichment analyses suggested that the PI3K/AKT signaling pathway,the IL-18 signaling pathway,the calcium signaling pathway,secreted factors,the Wnt signaling pathway,the Jak/STAT signaling pathway,the MAPK family signaling pathway,and cell–cell communication were involved in such association.SOAT1 expression was positively associated with the abundance of macrophages,Th2 cells,T helper cells,CD56bright natural killer cells,and Th1 cells,and negatively linked to the abundance of Th17 cells,dendritic cells,and cytotoxic cells.CONCLUSION Our findings demonstrate that SOAT1 may serve as a novel target for HCC treatment,which is helpful for the development of new strategies for immunotherapy and metabolic therapy.

Sterols from the Fungus Catathelasma imperiale

Eight ergostane type sterols and three their derivatives (one mono linoleate and two mono glucosides) were isolated from the ethyl acetate soluble fraction of the fungus Catathelasma imperiale . Two of them are novel compounds, namely 22 E ,24 R ergosta 7,22 diene 3 β ,5 α diol 6 β linoleate (1) and 22 E ,24 R ergosta 7,22 diene 3 β ,5 β ,6 α triol (5) with an uncommon cis fused A/B ring. Structures of these compounds were demonstrated on the basis of their chemical evidences and spectroscopic methods, especially 2D NMR techniques.

Effects of free sterols on the fluidity of polar lipids in rice dry embryo

Free sterols from rice dry embryo reduce the onset phase transition temperature and widen the transition range of total polar lipids and phosphatidylglycerol, which increases the membrane fluidity below their phase transition temperature and decreases the fluidity of membranes above their phase transition temperature. And 50% of free sterols result in a complete disappearance of phase transition. The fluidity of other main components of polar lipids is decreased by free sterols above 0℃. The results confirm that free sterols can modulate membrane lipid fluidity.

A streamlined high throughput screening method for the Mycobacterium neoaurum mutants with expected yield of biotransformation derivatives from sterols

Steroidal drugs have wide indications such as anti-inflammation, anti-tumor, endocrine regulation,fertility management. Phytosterol is the main starting materials for the industrial synthesis of steroid drugs. Microbial transformation of phytosterol is a simple and environmentally friendly process. Efficient microbial strains for industrial phytosterol transformation are critical for the commercial success. To this end, a 96-well plate based method was developed to discriminate the mixture of 4-androstene-3,17-dione, androsta-1,4-diene-3,17-dione, and bisnoraldehyde, with different ratio of the 3 components in the mixture, which mimics the sterol bioconversion products by using the Mycobacterium neoaurum. The M. neoaurum bioconversed broth test using phytosterol as substrate also found that the spectrum methodology can evaluate the relative content of different compounds. The method is practical, high throughput and can replace the conventional HPLC-based assay for rapid selection of desired microbial strains.

Kuroshio Intrusion Combined with Coastal Currents Affects Phytoplankton in the Northern South China Sea Revealed by Lipid Biomarkers

The northern South China Sea(NSCS)is significantly influenced by the Kuroshio intrusion and the coastal currents.Our knowledge on the roles of both currents on phytoplankton spatial variations is still inadequate.Here,we investigated the concentrations of phytoplankton biomarkers and their proportions in surface suspended particles from 47 sites of the NSCS during summer of 2017 and 2019.Brassicasterol/epi-brassicasterol,dinosterol,and C37 alkenones were used as proxies of biomass for diatoms,dinoflagellates,and haptophytes,respectively,and their sum indicating total phytoplankton biomass.A three end-member mixing model was applied to quantitatively assess the influence extent of the Kuroshio intrusion and the coastal currents.Our results showed that the Kuroshio intrusion and the coastal currents contributed equally to the overall surface water masses in the study area;however,the two currents had distinct effects on the spatial distribution of phytoplankton.For phytoplankton biomass,the eutrophic coastal currents were likely to be the main controlling factors,while the impact of the Kuroshio intrusion was weak and stimulated significant increases in phytoplankton biomass only at certain boundary sites.For phytoplankton community structures,the Kuroshio and its intrusion were the main factors,resulting in an increase in the proportions of dinoflagellates and haptophytes.The proportion of diatoms slightly increased due to the influence of the coastal currents.Our study quantifies the effects of the Kuroshio and the coastal currents on phytoplankton in the NSCS in terms of hydrological parameters,providing an important basis for the understanding of ecological functions and biogeochemical cycles in marginal sea-open ocean boundary regions.

Anti-Biofilm, Anti-Quorum Sensing, and Anti-Proliferative Activities of Methanolic and Aqueous Roots Extracts of Carica papaya L. and Cocos nucifera L.

Objective: This study focused on the antibacterial and anti-proliferative activity of extracts from Carica papaya and Cocos nucifera roots. Methodology: The minimum inhibitory concentration and the minimum bactericidal concentration of the extracts on Escherichia coli, Pseudomonas aeruginosa, Streptococcus mutans, and Staphylococcus aureus were deduced by the microdilution method. The anti-biofilm activity was determined on all four strains and anti-quorum sensing activity by inhibition of violacein production in Chromobacterium violaceum. Anti-proliferative activity on prostate cultured cancer cells was evaluated by MTT assay. Sterols and triterpenes were also assayed in this study. Results: The methanolic extract of Carica papaya showed the best anti-biofilm effect with a percentage inhibition of 66.10 ± 1.79. The methanolic extract of Cocos nucifera had the strongest inhibition on the production of quorum sensing (61.42 ± 0.28). In addition, the methanolic extract of Cocos nucifera roots showed the best cytotoxic effect on prostate cancer LNCaP cell lines (IC50 = 26.98 ± 2.6 μg/mL) and Carica papaya on the PC-3 lines (IC50 = 127.20 ± 5.99 μg/mL). The extracts were also rich in triterpenes and sterols. Conclusion: This study provides support for the ethnomedical use of Carica papaya and Cocos nucifera roots as an antimicrobial and anticancer.