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Journal of Food Science and Technology Jul 2020Plants consist of triterpenoids such as phytosterols (PT) (CHO) with steroidal nuclei, including sitosterol, stigmasterol, brassicasterol and campesterol. They are... (Review)
Review
Plants consist of triterpenoids such as phytosterols (PT) (CHO) with steroidal nuclei, including sitosterol, stigmasterol, brassicasterol and campesterol. They are hydrophobic but soluble in alcohol and other organic solvents and are isolated from industrial waste deodorizer distillates of various edible oil industries. They exist as free PT or their ester derivatives in soybean, rice, wheat, oat, cottonseed and corn fiber, and other cereals and grains. Conventional isolation techniques such as solvent extraction, distillation, evaporative fractionation, saponification and chemical esterification are employed for isolation and purification of PT. The present article reviews the various advanced separation techniques like solvent crystallization, supercritical fluid extraction, high speed counter-current chromatography and enzymatic process as strategic methods to isolate and purify sterols.
PubMed: 32549589
DOI: 10.1007/s13197-019-04209-3 -
Infectious Agents and Cancer Apr 2023Hepatitis B virus (HBV)-associated hepatocellular carcinoma (HCC) does not respond well to current treatment options like sorafenib, and there is an urgent need for...
BACKGROUND
Hepatitis B virus (HBV)-associated hepatocellular carcinoma (HCC) does not respond well to current treatment options like sorafenib, and there is an urgent need for developing therapeutical strategies for HBV + HCC. Brassicasterol has previously shown anti-cancer and anti-viral activities, however, its value against HBV + HCC remains to be explored.
METHODS
The inhibitory effect of brassicasterol and sorafenib was evaluated on HBV + HCC cell lines and xenograft mouse model. The cytotoxicity of brassicasterol on normal liver cells were measured by LDH assay. AKT agonist was used to identify the targeted signaling pathway by brassicasterol.
RESULTS
Brassicasterol induced HBV + HCC cell death in a both dose-dependent and time-dependent manner, and such inhibition was more potent than sorafenib. Brassicasterol did not show apparent cytotoxicity to normal liver cells. Xenograft mouse model further confirmed the inhibitory effect of brassicasterol on the growth of HBV + HCC. Furthermore, signaling pathway analysis showed that brassicasterol-treated HBV + HCC cells had decreased level of phosphor-AKT expression while the addition of AKT agonist could counteract the inhibitory effect of brassicasterol on HCC, indicating that brassicasterol suppressed AKT pathway to exhibit anti-cancer activity in HBV + HCC cells. In addition, brassicasterol showed similar levels of inhibition on HBV- and HBV + HCC cells.
CONCLUSION
Brassicasterol possesses anti-cancer activity against HCC through the downregulation of AKT pathway and such activity is independent of HBV infection.
PubMed: 37081537
DOI: 10.1186/s13027-023-00502-1 -
Animals : An Open Access Journal From... May 2022The study of milk fat composition is a priority topic at the international level; however, there are few studies on the composition of triacylglycerides (TAG) and...
The study of milk fat composition is a priority topic at the international level; however, there are few studies on the composition of triacylglycerides (TAG) and sterols in cow’s milk produced in organic production systems. The objective of this study was to determine the profile of TAG, cholesterol, and other sterols in the fat of raw cow’s milk produced under organic conditions in the municipality of Tecpatán, Chiapas. Every month for one year, milk samples were obtained from three production units (PU 1, 2 and 3) and from the collecting tank (CT) of the municipality (12 months × 4 = 48 samples), in accordance with Mexican regulations. Milk fat was extracted by detergent solution and TAG and sterol analyses were performed by gas chromatography with a flame ionization detector and capillary columns. Chromatographic analyses identified and quantified 15 TAG in all milk fats, from C26 to C54, with a bimodal behavior; the maximum value (% w/w) for the first mode was located at C38 (14.48) and, for the second mode, C50 and C52 were considered with values of 11.55 and 11.60, respectively. Analysis of variance (ANOVA) followed by Tukey’s test only yielded significance (p < 0.05) for C26; most TAG values over time showed homogeneous variability. Cholesterol, brassicasterol, and campesterol were also determined; ANOVA did not show statistical significance (p ≥ 0.05) between them in the production units and collecting tank. Cholesterol had the highest percentage of the sterols with a mean value of 96.41%. The TAG and cholesterol profiles found in this study were similar to those reported in other countries.
PubMed: 35625137
DOI: 10.3390/ani12101292 -
Scientific Reports Jul 2022Dysbiosis and perturbations of fecal metabolic profiles have been reported in dogs with inflammatory bowel disease. Currently the incidence of dysbiosis and the fecal... (Observational Study)
Observational Study
Dysbiosis and perturbations of fecal metabolic profiles have been reported in dogs with inflammatory bowel disease. Currently the incidence of dysbiosis and the fecal metabolomic profile in Yorkshire Terriers with chronic enteropathy (YTE) and the effects of treatment are unknown. This prospective observational study analyzed the dysbiosis index (DI) and fecal bile acid, sterol and fatty acid profiles in 14 Yorkshire Terriers with active YTE, 11 dogs in clinical remission, and 26 healthy Yorkshire Terriers. YTE was associated with dysbiosis and a significant increase in fatty acids (docosanoate, p = 0.002; gondoate, p = 0.026; erucate, p < 0.001; nervonate, p < 0.001; linolenate, p < 0.001), and plant sterols (campesterol, p < 0.001; brassicasterol, p = 0.024). The abundances of Fusobacterium (p < 0.001) and Cl. hiranonis (p = 0.018) and the concentrations of the secondary bile acid ursodeoxycholic acid (p = 0.033) and the plant sterol sitostanol (p = 0.003) were significantly decreased compared to healthy dogs. Dysbiosis, abundances of Fusobacterium, Cl. hiranonis and fecal concentrations of bile acids and sterols did not recover after treatment, while fecal fatty acid concentrations decreased in treated dogs. YTE is associated with dysbiosis and changes in bile acid, fatty acid, and sterol metabolism. These changes only recovered partially despite clinical remission. They might be breed-specific and involved in the pathogenesis of YTE.
Topics: Animals; Bile Acids and Salts; Dog Diseases; Dogs; Dysbiosis; Fatty Acids; Feces; Inflammatory Bowel Diseases; Sterols
PubMed: 35902689
DOI: 10.1038/s41598-022-17244-6 -
Biochimica Et Biophysica Acta Jul 2014We present a comparative differential scanning calorimetric study of the effects of the animal sterol cholesterol (Chol) and the plant sterols campesterol (Camp) and...
A comparative calorimetric study of the effects of cholesterol and the plant sterols campesterol and brassicasterol on the thermotropic phase behavior of dipalmitoylphosphatidylcholine bilayer membranes.
We present a comparative differential scanning calorimetric study of the effects of the animal sterol cholesterol (Chol) and the plant sterols campesterol (Camp) and brassicasterol (Bras) on the thermotropic phase behavior of dipalmitoylphosphatidylcholine (DPPC) bilayers. Camp and Bras differ from Chol in having a C24 methyl group and, additionally for Bras, a C22 trans-double bond. Camp and especially Bras decrease the temperature, cooperativity and enthalpy of the DPPC pretransition more than Chol, although these effects are attenuated at higher sterol levels. This indicates that they destabilize gel-state DPPC bilayers to a greater extent, but are less soluble, than Chol. Not surprisingly, all three sterols have similar effects on the sterol-poor sharp component of the DPPC main phase transition. However, Camp and especially Bras less effectively increase the temperature and decrease the cooperativity and enthalpy of the broad component of the main transition than Chol. This indicates that at higher sterol concentrations, Camp and Bras are less miscible and less effective than Chol at ordering the hydrocarbon chains of the sterol-enriched fluid DPPC bilayers. Overall, these alkyl side chain modifications generally reduce the ability of Chol to produce its characteristic effects on DPPC bilayer physical properties. These differences are likely due to the less extended and more bent conformations of the alkyl side chains of Camp and Bras, producing sterols with a greater effective cross-sectional area and reduced length than Chol. Hence, the structure of Chol is likely optimized for maximum solubility in, as opposed to maximum ordering of, phospholipid bilayers.
Topics: 1,2-Dipalmitoylphosphatidylcholine; Calorimetry, Differential Scanning; Cholestadienols; Cholesterol; Lipid Bilayers; Membranes; Models, Molecular; Phase Transition; Phytosterols; Temperature
PubMed: 24704414
DOI: 10.1016/j.bbamem.2014.03.019 -
Biomedicines May 2020While few studies have revealed the biological properties of brassicasterol, a phytosterol, against some biological and molecular targets, it is believed that there are...
While few studies have revealed the biological properties of brassicasterol, a phytosterol, against some biological and molecular targets, it is believed that there are still many activities yet to be studied. In this work, brassicasterol exerts a therapeutic utility in an in vitro setting against herpes simplex virus type 1 (HSV-1) and (Mtb) as well as a considerable inhibitory property against human angiotensin-converting enzyme (ACE) that plays a dynamic role in regulating blood pressure. The antireplicative effect of brassicasterol against HSV-1 is remarkably detected (50% inhibitory concentration (IC): 1.2 µM; selectivity index (SI): 41.7), while the potency of its effect is ameliorated through the combination with standard acyclovir with proper SI (IC: 0.7 µM; SI: 71.4). Moreover, the capacity of this compound to induce an adequate level of antituberculosis activity against all Mtb strains examined (minimum inhibitory concentration values ranging from 1.9 to 2.4 µM) is revealed. The anti-ACE effect (12.3 µg/mL; 91.2% inhibition) is also ascertained. Molecular docking analyses propose that the mechanisms by which brassicasterol induces anti-HSV-1 and anti-Mtb might be related to inhibiting vital enzymes involved in HSV-1 replication and Mtb cell wall biosynthesis. In summary, the obtained results suggest that brassicasterol might be promising for future anti-HSV-1, antituberculosis, and anti-ACE drug design.
PubMed: 32456343
DOI: 10.3390/biomedicines8050132 -
Biomedicines Sep 2020In the Compendium of Materia Medica, seahorse () is considered effective for the reinforcement of kidney and men's health. However, the role of seahorse on human health...
In the Compendium of Materia Medica, seahorse () is considered effective for the reinforcement of kidney and men's health. However, the role of seahorse on human health lacks scientific evidence. Therefore, we evaluated the effect of seahorse on human prostate cancer using various in vitro methods and identified bioactive compound. Seahorse lipid extract (SHL) decreased androgen receptor (AR) and prostate-specific antigen (PSA) expression in dihydrotestosterone (DHT)-induced LNCaP cells of prostate cancer. Gas Chromatography (GC)-mass spectrometry data showed that brassicasterol was present in . Brassicasterol downregulated the expression of AR and PSA in DHT-induced LNCaP cells. Brassicasterol induced apoptosis accompanied by sub-G1 phase arrest and inhibited migration in LNCaP cells. We confirmed that AKT and AR mediated the anti-cancer effect of brassicasterol using siRNA transfection. Brassicasterol exerts an anti-cancer effect in AR-independent cancer as well as in AR-dependent cells by AKT inhibiting. Our findings suggest that SHL has the anticancer potential via inhibition of AR and demonstrated that brassicasterol from exerted an anti-cancer effect by dual-targeting AKT and AR signaling in prostate cancer.
PubMed: 32972001
DOI: 10.3390/biomedicines8090370 -
Frontiers in Plant Science 2021Sterols are integral components of membrane lipid bilayers in eukaryotic organisms and serve as precursors to steroid hormones in vertebrates and brassinosteroids (BR)...
Sterols are integral components of membrane lipid bilayers in eukaryotic organisms and serve as precursors to steroid hormones in vertebrates and brassinosteroids (BR) in plants. In vertebrates, cholesterol is the terminal sterol serving both indirect and direct roles in cell signaling. Plants synthesize a mixture of sterols including cholesterol, sitosterol, campesterol, and stigmasterol but the signaling role for the free forms of individual plant sterols is unclear. Since stigmasterol is the terminal sterol in the sitosterol branch and produced from a single enzymatic step, modifying stigmasterol concentration may shed light on its role in plant metabolism. Although has been the model of choice to study sterol function, the functional redundancy of genes and the presence of brassicasterol may hinder our ability to test the biological function of stigmasterol. We report here the identification and characterization of , the sole maize C-22 sterol desaturase involved in stigmasterol biosynthesis and the identification of a stigmasterol-free mutant. mRNA expression pattern correlated with transcripts for several sterol biosynthesis genes and loss of stigmasterol impacted sterol composition. Exogenous stigmasterol also had a stimulatory effect on mRNA for and . This demonstrates the potential of in understanding the role of stigmasterol in modulating sterol biosynthesis and global cellular metabolism. Several amino acids accumulate in the mutant, offering opportunity for genetic enhancement of nutritional quality of maize. Other cellular metabolites in roots and shoots of maize and were also impacted by genetic modification of stigmasterol content. Yet lack of obvious developmental defects in suggest that stigmasterol might not be essential for plant growth under normal conditions. Nonetheless, the mutant reported here is of great utility to advance our understanding of the additional roles of stigmasterol in plant metabolism. A number of biological and agronomic questions can be interrogated using this tool such as gene expression studies, spatio-temporal localization of sterols, cellular metabolism, pathway regulation, physiological studies, and crop improvement.
PubMed: 34804084
DOI: 10.3389/fpls.2021.732216 -
Metabolites Aug 2019Rapeseed is an important oilseed with proper fatty acid composition and abundant bioactive components. Canada and China are the two major rapeseed-producing countries...
Rapeseed is an important oilseed with proper fatty acid composition and abundant bioactive components. Canada and China are the two major rapeseed-producing countries all over the world. Meanwhile, Canada and Mongolia are major importers of rapeseed due to the great demand for rapeseed in China. To investigate the metabolites in rapeseeds from three countries, ultra-performance liquid chromatography-quadrupole time-of-flight mass spectrometry (UPLC-Q-TOF/MS)-based metabolomics was employed to analyze rapeseeds from China, Canada, and Mongolia. As results, 67, 53, and 68 metabolites showed significant differences between Chinese and Canadian, Chinese and Mongolian, and Canadian and Mongolian rapeseeds, respectively. Differential metabolites were mainly distributed in the metabolic pathways including phenylpropanoid biosynthesis, flavone and flavonol biosynthesis, and ubiquinone and other terpenoid-quinone biosynthesis. Among the differential metabolites, contents of sinapate and sinapine were higher in Chinese rapeseeds, while the contents of brassicasterol, stigmasterol, and campestanol were higher in Canadian rapeseeds. These findings might provide insight into the metabolic characteristics of rapeseeds from three countries to guide processing and consumption of the products of rapeseed.
PubMed: 31374906
DOI: 10.3390/metabo9080161 -
Molecules (Basel, Switzerland) Jan 2022Despite research on the molecular bases of Alzheimer's disease (AD), effective therapies against its progression are still needed. Recent studies have shown direct links...
BACKGROUND
Despite research on the molecular bases of Alzheimer's disease (AD), effective therapies against its progression are still needed. Recent studies have shown direct links between AD progression and neurovascular dysfunction, highlighting it as a potential target for new therapeutics development. In this work, we screened and evaluated the inhibitory effect of natural compounds from native Peruvian plants against tau protein, amyloid beta, and angiotensin II type 1 receptor (AT1R) pathologic AD markers.
METHODS
We applied in silico analysis, such as virtual screening, molecular docking, molecular dynamics simulation (MD), and MM/GBSA estimation, to identify metabolites from Peruvian plants with inhibitory properties, and compared them to nicotinamide, telmisartan, and grapeseed extract drugs in clinical trials.
RESULTS
Our results demonstrated the increased bioactivity of three plants' metabolites against tau protein, amyloid beta, and AT1R. The MD simulations indicated the stability of the AT1R:floribundic acid, amyloid beta:rutin, and tau:brassicasterol systems. A polypharmaceutical potential was observed for rutin due to its high affinity to AT1R, amyloid beta, and tau. The metabolite floribundic acid showed bioactivity against the AT1R and tau, and the metabolite brassicasterol showed bioactivity against the amyloid beta and tau.
CONCLUSIONS
This study has identified molecules from native Peruvian plants that have the potential to bind three pathologic markers of AD.
Topics: Alzheimer Disease; Amyloid beta-Peptides; Angiotensin II Type 1 Receptor Blockers; Drug Discovery; Humans; Molecular Docking Simulation; Peru; Phytochemicals; Plants; Receptor, Angiotensin, Type 1; tau Proteins
PubMed: 35164183
DOI: 10.3390/molecules27030918