steviol has been researched along with isosteviol* in 13 studies
1 review(s) available for steviol and isosteviol
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Diterpenoid lead stevioside and its hydrolysis products steviol and isosteviol: Biological activity and structural modification.
The diterpenoids present highly varied oxidation patterns subjected to fascinating skeletal rearrangements, and possess antitumor, antibacterial, antihyperglycemic, anti-inflammatory activities and so on. While total synthesis is a possible solution to obtain required diterpenoid derivatives, the need for multisteps to build complex "privileged structures" is always prohibitive by semi-synthesis from naturally abundant related molecules. From this perspective, stevioside and its hydrolysis products steviol and isosteviol are good leads in the field of medicinal chemistry for diterpenoid drug discovery. Stevioside has a complex diterpenoid glycoside molecule comprised of an aglycone, steviol with the ent-kaurane skeleton and three molecules of glucose. Hydrolyzed under alkaline or acidic condition, stevioside generates ent-kaurane diterpenoid steviol or ent-beyerane diterpenoid isosteviol, respectively. Except for direct applications, they are widely used to provide ent-kaurane or ent-beyerane core structures for further medicinal chemistry study. Besides, these molecules also serve as model molecules, starting materials or catalysts in the field of synthetic chemistry. In this review, their biological activities and medicinal chemistry work are comprehensively summarized which are very helpful for diterpenoid drug exploration. Topics: Animals; Anti-Inflammatory Agents; Antineoplastic Agents; Chemistry Techniques, Synthetic; Diterpenes, Kaurane; Drug Discovery; Glucosides; Humans; Hydrolysis; Hypoglycemic Agents | 2018 |
12 other study(ies) available for steviol and isosteviol
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Antimicrobial and cytotoxic effects of ammonium derivatives of diterpenoids steviol and isosteviol.
Antimicrobial and cytotoxic activities of several ammonium derivatives of diterpenoids steviol and isosteviol have been investigated in vitro. The results have showed that these compounds possess high antibacterial activity against MRSA strains and cytotoxic effect against cancer cell lines MCF-7, M-HeLa, A-549, PC3, HepG2, T98G. Lead compounds 4 and 5 were detected, which, in the case of the MCF-7 cell line (human breast adenocarcinoma), showed IC Topics: Ammonium Compounds; Anti-Bacterial Agents; Antineoplastic Agents; Apoptosis; Cell Survival; Diterpenes, Kaurane; Dose-Response Relationship, Drug; Drug Screening Assays, Antitumor; Humans; Methicillin-Resistant Staphylococcus aureus; Microbial Sensitivity Tests; Molecular Structure; Structure-Activity Relationship; Tumor Cells, Cultured | 2021 |
Diversity-Oriented Library Synthesis from Steviol and Isosteviol-Derived Scaffolds.
The readily available natural product stevioside provides a unique diterpene core structure that can be explored for small molecule library development by diversity-oriented synthesis and functional group transformations. Validation arrays were prepared from steviol, isosteviol, and related analogues, derived from stevioside, to produce over 90 compounds. These compounds were submitted to the NIH Molecular Libraries Small Molecule Repository for screening in the Molecular Libraries Screening Center Network. Micromolar hits were identified in multiple high-throughput assays for several library members. A cheminformatics analysis of the compounds was performed that verified the expected diversity and complexity of this set of compounds. The screening results indicate that scaffolds-derived natural products can provide screening hits against multiple target proteins. Topics: Combinatorial Chemistry Techniques; Diterpenes, Kaurane; Molecular Conformation; Small Molecule Libraries; Stereoisomerism | 2020 |
HI-HPTLC-UV/Vis/FLD-HESI-HRMS and bioprofiling of steviol glycosides, steviol, and isosteviol in Stevia leaves and foods.
Food products and botanicals on the global market need to be investigated in a more comprehensive way to detect effects, falsifications or adulterations. This is especially true for such ones containing Stevia leaves, Stevia extracts, or steviol glycosides. A multi-imaging profiling was developed exploiting hydrophilic interaction liquid chromatography (HILIC). A minimalistic sample preparation, different mixtures of acetonitrile and water/buffer on the silica gel phase as well as derivatization reagents and optional hyphenation with high-resolution mass spectrometry were exploited. The hydrophilic interaction high-performance thin-layer chromatography (HI-HPTLC) development took 10 min for 48 analyses. It was used to screen Stevia leaf extracts and 20 different food products. For the first time, the biological and biochemical profiling of Stevia leaf products by HI-HPTLC-UV/Vis/FLD-assay pointed to 19 different bioactive compound bands found in the more natural multicomponent Stevia leaf extracts, whereas most of these activities were not existent for the steviol glycosides. The chemically isolated, purified, and EU-regulated steviol glycosides ease risk assessment and food product development. However, multipotent botanicals may have subtle impact on homeostasis via several metabolic pathways, providing benefits for the consumer's health. Analyzed side by side by means of the effect-directed profiling, their individual activity profiles were visualized as image and individual substances of importance were pointed out. Multi-imaging (comprehensive detection) plus non-targeted bioprofiling (focus on known and unknown bioactivity) allows for a fast detection of questionable product changes that occur along the global food chain and are particularly related to food safety. Graphical abstract. Topics: Chromatography, Thin Layer; Diterpenes, Kaurane; Food Analysis; Glucosides; Plant Leaves; Stevia | 2020 |
Stevioside Has the Maximum Biological Activity among Natural Stevia Diterpenes.
The concentrations of steviol and its derivatives stimulating the growth of wheat plants were measured: 10 Topics: Diterpenes; Diterpenes, Kaurane; Glucosides; Plant Leaves; Stevia; Triticum | 2020 |
Quantification of steviol glycosides in food products, Stevia leaves and formulations by planar chromatography, including proof of absence for steviol and isosteviol.
Steviol glycosides may degrade in food products under certain processing and storage conditions. Hence, a method was developed that separated in the same chromatographic run seven important steviol glycosides, and additionally as a sum parameter, their reported breakdown products steviol and isosteviol. Through derivatizations with the 2-naphthol and the primuline reagent, the detection was selective and inexpensive. In case needed, the baseline separation of steviol and isosteviol was also demonstrated after a plate cut and subsequent short development (two-step method). The HPTLC method was robust with regard to varying sample matrix loads, as the stationary phase was used only once. A high sample throughput was achieved, i.e. 23 separations were performed in parallel on one plate. The total analysis time took 1h (30min application, 15min separation and 15min derivatization/densitometry) leading to a calculated analysis time of 2.6min per sample. The solvent consumption was 8mL in total (0.4mL per analysis). HPTLC-ESI-MS was employed for confirmation of the results obtained. Mass spectra were recorded only from the zones of interest, and not from matrix or background, leading to decisive advantages, such as less need for MS cleaning. The optimized HPTLC method was shown to effectively support quality control, as marketed samples may be falsified with cheaper synthetic sweeteners, which was also demonstrated in this study. The accuracy of the densitometric quantification in HPTLC was considered as high, as standards and samples were separated on fresh adsorbent and detected simultaneously under identical conditions, which minimized the influence of errors. Finally, the Aliivibrio fischeri bioassay was employed to obtain information on bioactive compounds in Stevia leaf extracts. Topics: Chromatography, High Pressure Liquid; Diterpenes, Kaurane; Food Analysis; Glycosides; Mass Spectrometry; Plant Extracts; Plant Leaves; Stevia; Sweetening Agents | 2017 |
Validation of an HPLC method for direct measurement of steviol equivalents in foods.
Steviol glycosides are intense natural sweeteners used in foods and beverages. Their acceptable daily intake, expressed as steviol equivalents, is set at 0-4 mg/kg body weight. We report the development and validation of a RP-HPLC method with fluorometric detection of derivatized isosteviol, formed by acid hydrolysis of steviol glycosides. Dihydroisosteviol was used as an internal standard. Using this method, the amount of steviol equivalents in commercial steviol glycoside mixtures and different foods can be directly quantified. The method was successfully tested on strawberry jam, low-fat milk, soft drink, yogurt and a commercial mixture of steviol glycosides. Calibration curves were linear between 0.01 and 1.61 mM steviol equivalents, with a quantification limit of 0.2 nmol. The % RSD of intra-day precision varied between 0.4% and 4%, whereas inter-day precision varied between 0.4% and 5%, for high and medium concentrations, and between 3% and 8% for low concentrations. Accuracy of the analysis varied between 99% and 115%. Topics: Beverages; Chromatography, High Pressure Liquid; Diterpenes, Kaurane; Glycosides; Models, Molecular; Sweetening Agents | 2016 |
Digital NMR profiles as building blocks: assembling ¹H fingerprints of steviol glycosides.
This report describes a fragment-based approach to the examination of congeneric organic compounds by NMR spectroscopy. The method combines the classic interpretation of 1D- and 2D-NMR data sets with contemporary computer-assisted NMR analysis. Characteristic NMR profiles of key structural motifs were generated by (1)H iterative full spin analysis and then joined together as building blocks to recreate the (1)H NMR spectra of increasingly complex molecules. To illustrate the methodology described, a comprehensive analysis of steviol (1), seven steviol glycosides (2-8) and two structurally related isosteviol compounds (9, 10) was carried out. The study also assessed the potential impact of this method on relevant aspects of natural product research including structural verification, chemical dereplication, and mixture analysis. Topics: Diterpenes, Kaurane; Glucosides; Glycosides; Molecular Structure; Nuclear Magnetic Resonance, Biomolecular; Stevia | 2015 |
Cytotoxic and apoptosis-inducing activities of steviol and isosteviol derivatives against human cancer cell lines.
Seventeen steviol derivatives, i.e., 2-18, and 19 isosteviol derivatives, i.e., 19-37, were prepared from a diterpenoid glycoside, stevioside (1). Upon evaluation of the cytotoxic activities of these compounds against leukemia (HL60), lung (A549), stomach (AZ521), and breast (SK-BR-3) cancer cell lines, nine steviol derivatives, i.e., 5-9 and 11-14, and five isosteviol derivatives, i.e., 28-32, exhibited activities with single-digit micromolar IC(50) values against one or more cell lines. All of these active compounds possess C(19)-O-acyl group, and among which, ent-kaur-16-ene-13,19-diol 19-O-4',4',4'-trifluorocrotonate (14) exhibited potent cytotoxicities against four cell lines with IC(50) values in the range of 1.2-4.1 μM. Compound 14 induced typical apoptotic cell death in HL60 cells upon evaluation of the apoptosis-inducing activity by flow-cytometric analysis. These results suggested that acylation of the 19-OH group of kaurane- and beyerane-type diterpenoids might be useful for enhancement of their cytotoxicities with apoptosis-inducing activity. Topics: Antineoplastic Agents, Phytogenic; Apoptosis; Cell Line, Tumor; Cell Survival; Diterpenes, Kaurane; Humans; Neoplasms; Stevia | 2013 |
Synthesis of skeletally diverse and stereochemically complex library templates derived from isosteviol and steviol.
We have applied a diversity-oriented approach for the synthesis of skeletally diverse and stereochemically complex templates for small-molecule library production by performing Beckmann rearrangement and Beckmann fragmentation reactions on the bicyclo[3.2.1]octane rings of steviol and isosteviol, aglycones derived from the diterpene natural product stevioside. The optimization of these two reaction pathways is presented along with the successful application of a photo-Beckmann rearrangement. This work also led to the discovery of cyano-Prins-type and Thorpe-Ziegler-type cyclization reactions. Topics: Biological Products; Combinatorial Chemistry Techniques; Cyclization; Diterpenes, Kaurane; Glucosides; Nuclear Magnetic Resonance, Biomolecular; Octanes | 2013 |
Synthesis and biological evaluation of novel exo-methylene cyclopentanone tetracyclic diterpenoids as antitumor agents.
The structure of exo-methylene cyclopentanone, which exists in nature tetracyclic diterpenoids products, has been proved to be an innate group for the treatment of cancer and inflammation. In this letter, four different scaffolds of tetracyclic diterpenoids including the structure exo-methylene cyclopentanone were synthesized from steviol and isosteviol and evaluated in vitro for their antitumor activity against three human cancer lines. Compounds 1a, 1b, 2b and 3b showed significant cytotoxicity, particularly, tetracyclic diterpenoids 2b, 3b were identified as the most potent and selective anticancer agents superior to adriamycin with IC(50) values of 0.9 μM and 1.5 μM, against Hep-G2 and MDA-MB-231 cell lines, respectively. Topics: Antineoplastic Agents; Cell Line, Tumor; Cyclopentanes; Diterpenes; Diterpenes, Kaurane; Drug Screening Assays, Antitumor; Humans; Neoplasms | 2011 |
Synthesis of ent-kaurane diterpene monoglycosides.
Synthesis of two ent-kaurane diterpene glycosides, steviol 19-O-β-D-glucopyranosiduronic acid (steviol glucuronide, 5), and 13-hydroxy ent-kaur-16-en-19-oic acid-β-D-glucopyranosyl ester (7) has been achieved from a common starting material, steviol, using phase transfer catalyst. Also, synthesis of an additional 17-nor-ent-kaurane glycoside, namely 13-methyl-16-oxo-17-nor-ent-kauran-19-oic acid-β-D-glucopyranosyl ester (10) was performed using the starting material isosteviol and similar synthetic methodology. Synthesis of all three steviol glycosides was performed using straightforward chemistry and their structures were characterized on the basis of 1D and 2D NMR as well as mass spectral (MS) data. Topics: Catalysis; Diterpenes, Kaurane; Food; Magnetic Resonance Spectroscopy; Stevia; Sweetening Agents | 2011 |
Cancer preventive agents. Part 8: Chemopreventive effects of stevioside and related compounds.
In a search for potential cancer chemopreventive agents from natural resources, stevioside (1), a sweetener, and six related compounds, including two aglycones steviol (6) and isosteviol (7), were screened in an in vitro assay for inhibitory effects on Epstein-Barr virus early antigen activation. Compounds 1, 6 and 7 showed significant activity in this assay and also exhibited strong inhibitory effects in a two-stage carcinogenesis test using mouse skin induced by 7,12-dimethylbenz[a]anthracene (DMBA) and 12-O-tetradecanoylphorbol-13-acetate (TPA). The inhibitory effects of these three compounds were greater than that of glycyrrhizin. Furthermore, these three compounds significantly inhibited mouse skin carcinogenesis initiated by peroxynitrite and promoted by TPA. Their activities were comparable to that of curcumin. These results suggested that 1, as well as 6 and 7, could be valuable as chemopreventive agents for chemical carcinogenesis. Topics: Animals; Antineoplastic Agents; Carcinogenicity Tests; Chemoprevention; Curcumin; Diterpenes, Kaurane; Glucosides; Glycyrrhizic Acid; Herpesvirus 4, Human; Mice; Skin Neoplasms | 2009 |