Isovaleryl Sucrose Esters from Atractylodes japonica and Their Cytotoxic Activity
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PROVIDER: S-EPMC11243297 | biostudies-literature | 2024 Jun
REPOSITORIES: biostudies-literature
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Project description:PremiseAtractylodes japonica (Asteraceae) is endemic to East Asia, where its rhizomes are used in traditional medicine. To investigate the genetic diversity of this species, we developed polymorphic microsatellite markers.Methods and resultsWe obtained a total of 175,825 simple sequence repeat (SSR) loci using the Illumina HiSeq 2500 system. Eighteen polymorphic SSR primer pairs were selected to determine heterozygosity levels and allele numbers in 80 individuals from four A. japonica populations. The levels of observed and expected heterozygosity ranged from 0.000 to 1.000 and from 0.133 to 0.892, respectively. Cross-amplification in the related species A. macrocephala and A. lancea was successful in 15 and 14 of the 18 markers, respectively.ConclusionsThese microsatellite markers will be useful for future studies involving A. japonica population genetics and breeding.
| S-EPMC7249270 | biostudies-literature
Project description:Glioblastoma multiforme (GBM) is an aggressive brain tumor that correlates with short patient survival and for which therapeutic options are limited. Polyphenolic compounds, including caffeic acid phenethyl ester (CAPE, 1a), have been investigated for their anticancer properties in several types of cancer. To further explore these properties in brain cancer cells, a series of caffeic and ferulic acid esters bearing additional oxygens moieties (OH or OCH?) were designed and synthesized. (CAPE, 1a), but not ferulic acid phenethyl ester (FAPE, 1b), displayed substantial cytotoxicity against two glioma cell lines. Some but not all selected compounds derived from both (CAPE, 1a) and (FAPE, 1b) also displayed cytotoxicity. All CAPE-derived compounds were able to significantly inhibit 5-lipoxygenase (5-LO), however FAPE-derived compounds were largely ineffective 5-LO inhibitors. Molecular docking revealed new hydrogen bonds and ?-? interactions between the enzyme and some of the investigated compounds. Overall, this work highlights the relevance of exploring polyphenolic compounds in cancer models and provides additional leads in the development of novel therapeutic strategies in gliomas.
| S-EPMC6152019 | biostudies-literature
Project description:In this study, we report on an orthogonal strategy for the precise synthesis of 3,3'-, 3,4'-, and 3,6'-phenylpropanoid sucrose esters (PSEs). The strategy relies on carefully selected protecting groups and deprotecting agents, taking into consideration the reactivity of the four free hydroxyl groups of the key starting material: di-isopropylidene sucrose 2. The synthetic strategy is general, and potentially applies to the preparation of many natural and unnatural PSEs, especially those substituted at 3-, 3'-, 4'- and 6'-positions of PSEs.
| S-EPMC8780461 | biostudies-literature
Project description:Atractylodes japonica Koidz. ex Kitam. is a perennial herbal plant, and its dried rhizomes have been widely used as traditional medicine in China and Japan. In this study, we assembled and annotated the complete chloroplast (cp) genome sequence of A. japonica using the high-throughput sequencing approach. The cp genome of A. japonica is 153,208 bp in length with the overall GC content of 37.7%, including two inverted repeat (IR) regions of 25,147 bp, which was separated by a large single-copy (LSC) region of 84,255 bp and a small single-copy (SSC) region of 18,659 bp. 113 unique genes were annotated in the genome, including 80 protein-coding genes, 29 represented tRNA genes, and four denoted rRNA genes. A maximum-likelihood phylogenetic analysis with 38 complete cp sequences showed that Atractylodes formed a monophyletic clade, and A. japonica and A. koreana formed a subclade in Atractylodes. This study provides the chloroplast genome structure features and phylogenetic relationship of A. japonica.
| S-EPMC8344787 | biostudies-literature
Project description:Chemical investigation of the whole plants of Phyllanthus cochinchinensis (Euphorbiaceae) led to the isolation of five new sucrose benzoyl esters, 3,6?-di-O-benzoylsucrose (1), 3,6?-di-O-benzoyl-2?-O-acetylsucrose (2), 3,6?-di-O-benzoyl-4?-Oacetylsucrose (3), 3,6?-di-O-benzoyl-3?-O-acetylsucrose (4) and 3-O-benzoyl-6?-O-(E)-cinnamoylsucrose (5), together with two known secoiridoid glycosides, jasminoside (6) and jaslanceoside B (7). Their structures were established on the basis of detailed spectroscopic analysis and chemical method. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-013-0026-7 and is accessible for authorized users.
| S-EPMC4131661 | biostudies-literature
Project description:Cinnamoyl sucrose esters (CSEs) were evaluated as AGIs and their enzyme inhibition activity and potency were compared with gold standard acarbose. The inhibition activity of the CSEs against α-glucosidase and α-amylase depended on their structure including the number of the cinnamoyl moieties, their position, and the presence or absence of the acetyl moieties. The inhibitory values of the CSEs 2-9 generally increases in the order of mono-cinnamoyl moieties < di-cinnamoyl ≤ tri-cinnamoyl < tetra-cinnamoyl. This trend was supported from both in vitro and in silico results. Both tetra-cinnamoyl CSEs 5 and 9 showed the highest α-glucosidase inhibitory activities of 77 ± 5%, 74 ± 9%, respectively, against acarbose at 27 ± 4%, and highest α-amylase inhibitory activities of 98 ± 2%, 99 ± 1%, respectively, against acarbose at 93 ± 2%. CSEs 3, 4, 6, 7, 8 showed desired higher inhibition of α-glucosidase than α-amylase suggesting potential for further development as AGIs with reduced side effects. Molecular docking studies on CSEs 5 and 9 attributed the high inhibition of these compounds to multiple π-π interactions and favorable projection of the cinnamoyl moieties (especially O-3 cinnamoyl) in the enzyme pockets. This work proposes CSEs as new AGIs with potentially reduced side effects.
| S-EPMC7830900 | biostudies-literature
Project description: Not available
| S-EPMC11677600 | biostudies-literature
Project description:ObjectiveTo study the chemical constituents of the EtOAc extract of Armillaria gallica 012m.MethodsThe chemical constituents of the EtOAc extract of A. gallica 012m were isolated and purified by various column chromatography and their structures were elucidated on the basis of the 1D and 2D NMR spectroscopic and HRESIMS data. Cytotoxicity of all isolates against A549, HCT-116, M231 and W256 human tumor cells was determined by the MTT method.ResultsA new sesquiterpene aryl ester, armimelleolide C (1), and eight known ones including armillarivin (2), melleolide F (3), 6'-chloromelleolide F (4), melleolide (5), melleolide K (6), melledonol (7), 13-hydroxydihydromelleolide (8), and armillane (9), were isolated from the EtOAc extract of A. gallica 012m. All isolates showed potential cytotoxic activities against at least one of the human cancer cell lines with IC50 values ranging from (3.17 ± 0.54) to (17.57 ± 0.47) μmol/L. Compound 1 showed significant inhibitory activity against M231 with an IC50 value of (7.54 ± 0.24) μmol/L compared with paclitaxel as the positive control. Compounds 2, 3, and 7, 9 showed obvious inhibitory activity against HCT-116 and were better than that of the positive control.ConclusionThe chemical constituents including a new sesquiterpene aryl ester armimelleolide C (1) from the EtOAc extract of A. gallica 012m have a variety of structures and potential antitumor activities.
| S-EPMC10230622 | biostudies-literature
Project description:Sucrose esters (SE) have been investigated as structuring agents in oleogels. Due to the low structuration power of SE as single agent, this component has recently been explored in combination with other oleogelators to form multicomponent systems. This study aimed to evaluate binary blends of SEs with different hydrophilic-lipophilic balances (HLBs) with lecithin (LE), monoglycerides (MGs) and hard-fat (HF), according to their physical properties. The following SEs, SP10-HLB2, SP30-HLB6, SP50-HLB11, and SP70-HLB15, were structured using three different routes: "traditional", "ethanol" and "foam-template". All binary blends were made using a 10% oleogelator in 1:1 proportion for binary mixtures; they were then evaluated for their microstructure, melting behavior, mechanical properties, polymorphism and oil-binding capacity. SP10 and SP30 did not form well-structure and self-standing oleogels in any combination. Although SP50 showed some potential blends with HF and MG, their combination with SP70 led to even more well-structured oleogels, with a higher hardness (~0.8 N) and viscoelasticity (160 kPa), and 100% oil-binding capacity. This positive result might be attributed to the reinforcement of the H-bond between the foam and the oil by MG and HF.
| S-EPMC10217855 | biostudies-literature
Project description:Essential oils are volatile liquids which evaporate and lose their pharmacological effect when exposed to the environment. The aim of this study is to protect nutmeg essential oil from environmental factors by encapsulation (shell material, sodium alginate) and determine the influence of crosslinker concentration (2%, 5% calcium chloride), different emulsifiers (polysorbate 80, sucrose esters), and magnesium aluminometasilicate on microcapsule physical parameters, encapsulation efficiency (EE), swelling index (SI), and other parameters. Nutmeg essential oil (NEO)-loaded calcium alginate microcapsules were prepared by extrusion. The swelling test was performed with and without enzymes in simulated gastric, intestinal, and gastrointestinal media. This study shows that the crosslinker concentration has a significant influence on EE, with 2% calcium chloride solution being more effective than 5%, and capsules being softer with 2% crosslinker solution. Using sucrose esters, EE is higher when polysorbate 80 is used. The swelling index is nearly three times higher in an intestinal medium without enzymes than in the medium with pancreatin. Microcapsule physical parameters depend on the excipients: the hardest capsules were obtained with the biggest amount of sodium alginate; the largest with magnesium aluminometasilicate. Sucrose esters and magnesium aluminometasilicate are new materials used in extrusion.
| S-EPMC7408566 | biostudies-literature