Browse
Submit Data
Databases
API
Help

Dataset Information

27 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization.

ABSTRACT: The application of oxidative dimerization for the biomimetic synthesis of balsaminone A and ellagic acid is described. Balsaminone A is synthesized via the oxidative dimerization of 1,2,4-trimethoxynaphthalene under anhydrous conditions using CAN, PIDA in BF₃ ·OEt₂ or PIFA in BF₃ ·OEt₂ in 7-8% yields over 3 steps. Ellagic acid is synthesized from its biosynthetic precursor gallic acid, in 83% yield over 2 steps.

SUBMITTER: Daley SK

PROVIDER: S-EPMC7445397 | biostudies-literature | 2020

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

The biomimetic synthesis of balsaminone A and ellagic acid via oxidative dimerization.

Daley Sharna-Kay SK Downer-Riley Nadale N

Beilstein journal of organic chemistry 20200818

The application of oxidative dimerization for the biomimetic synthesis of balsaminone A and ellagic acid is described. Balsaminone A is synthesized via the oxidative dimerization of 1,2,4-trimethoxynaphthalene under anhydrous conditions using CAN, PIDA in BF3 ·OEt2 or PIFA in BF3 ·OEt2 in 7-8% yields over 3 steps. Ellagic acid is synthesized from its biosynthetic precursor gallic acid, in 83% yield over 2 steps. ...[more]

PMID: 32874349

Similar Datasets

Studies on a biomimetic oxidative dimerization approach to the hibarimicins.

Project description:Nature utilizes dimerization as a method of producing structurally complex metabolites. The microbial metabolites known collectively as the hibarimicins are one example of complex natural products produced biosynthetically by dimerization of a phenolic aromatic polyketide. Described in this communication are model studies aimed at demonstrating regiocontrolled oxidative dimerization of phenolic ring systems related to the biosynthetic precursor of the hibarimicin family of natural products.

| S-EPMC4518470 | biostudies-literature

Synthesis and Antitumor Activity of Ellagic Acid Peracetate.

Project description:Ellagic acid (1) was synthesized for the first time from methyl gallate through 3-pentagalloylglucose (α-PGG), and ellagic acid peracetate (3,4,3',4'-tetra-O-acetylellagic acid, 2) was derived from 1 by acetylation. Oral administration of 2 suppressed melanoma growth significantly in C7BL/6 immunocompetent mice without having any effect on natural killer (NK) cell activity. Comparison of the immunoenhancing activities of 1 and 2 indicated that the latter compound increased white blood cell quantities in peripheral blood and immune cells enriched from the bone marrow and liver of mice. Therefore, both the antitumor efficacy and the immunity enhancement by 2 were greater than those by 1. In addition, on oral administration neither 1 nor 2 resulted in whole body, liver, or spleen weight changes of normal, tumor-free mice, indicating that these compounds are potentially non-toxic to mice. It was shown that ellagic acid peracetate (2) inhibits B16 melanoma cell growth in vitro, and induces B16 cell apoptosis, corresponding to BCL-2 down-regulation. Collectively, the present data imply that 2 can suppress tumor growth by enhancing mouse immunity and inducing tumor cell apoptosis without apparent side effects.

| S-EPMC3505040 | biostudies-literature

Ellagic Acid Suppresses the Oxidative Stress Induced by Dietary-Oxidized Tallow.

Project description:Dietary tallow was thermally oxidized at 180°C in an open fryer. The oxidized tallow (OT) and unoxidized tallow were characterized for oxidation parameters and fatty acid composition using GC-MS. Tallow samples were fed to rabbits along with 50, 100, and 150?mg/kg/day of ellagic acid (EA) for three weeks. Results revealed that the peroxide value (PV) and thiobarbituric acid reactive substances (TBARS) significantly increased, while radical scavenging activity (RSA) of the tallow decreased significantly with oxidation. GC-MS analysis showed eight fatty acids in the tallow samples, where palmitic acid (48.5-49.7?g/100?g), linoleic acid (18.7-23.7?g/100?g), stearic acid (13.5-15.6?g/100?g), and margaric acid (6.32-6.42?g/100?g) were the major fatty acids. Animal studies showed that oxidized tallow (OT) alone or in combination with EA significantly altered the body weight of the rabbits. Serum biochemical parameters and renal function tests were affected by OT and ameliorated by EA. The toxic effects of OT on haematological indices were minimized by EA. The supplementation of OT alone had significant effects on the liver structure and functions. The coadministration of EA reduced the toxic properties of OT on the liver, by increasing the antioxidant (GSH) system. The rabbit heart was also affected by the OT, which was ameliorated by EA supplementation. These results suggested that the supplementation of EA was beneficial against the OT-induced oxidative stress and may be considered for foods containing oxidized lipids.

| S-EPMC6276410 | biostudies-literature

Ellagic acid ameliorates aging-induced renal oxidative damage through upregulating SIRT1 and NRF2.

Project description:BackgroundAging is associated with impaired renal function and structural alterations. Oxidative stress plays a vital role in renal senescence and damage. Sirtuin 1 (SIRT1) is thought to protect cells from oxidative stress through nuclear factor erythroid 2-related factor 2 (NRF2). Ellagic acid (EA), a natural antioxidant, has been demonstrated to have renoprotective roles in vitro and in vivo. This study investigated if SIRT1 and NRF2 mediate the protective effects of EA in aged kidneys.MethodsMale Wistar rats were divided into three groups including young (4 months), old, and old + EA (25 months). Young and old groups received EA solvent, while the old + EA group was treated with EA (30 mg/kg) by gavage for 30 days. Then, the level of renal oxidative stress, SIRT1 and NRF2 expression, kidney function parameters, and histopathological indices were measured.ResultsTreatment with EA significantly increased the level of antioxidant enzymes and reduced malondialdehyde concentration (P < 0.01). Moreover, EA administration remarkably upregulated mRNA and protein levels of SIRT1 and NRF2 as well as deacetylated NRF2 protein (P < 0.05). Additionally, EA treated rats improved kidney function and histopathological scores (P < 0.05).ConclusionsThese findings suggest that ellagic acid exerts protective effects on aged kidneys by activating SIRT1 and NRF2 signaling.

| S-EPMC9999491 | biostudies-literature

Potassium Hexacyanoferrate (III)-Catalyzed Dimerization of Hydroxystilbene: Biomimetic Synthesis of Indane Stilbene Dimers.

Project description:Using potassium hexacyanoferrate (III)-sodium acetate as oxidant, the oxidative coupling reaction of isorhapontigenin and resveratrol in aqueous acetone resulted in the isolation of three new indane dimers 4, 6, and 7, together with six known stilbene dimers. Indane dimer 5 was obtained for the first time by direct transformation from isorhapontigenin. The structures and relative configurations of the dimers were elucidated using spectral analysis, and their possible formation mechanisms were discussed. The results indicate that this reaction could be used as a convenient method for the semi-synthesis of indane dimers because of the mild conditions and simple reaction products.

| S-EPMC6332065 | biostudies-literature

Ellagic Acid Attenuates BLM-Induced Pulmonary Fibrosis via Inhibiting Wnt Signaling Pathway.

Project description:Idiopathic pulmonary fibrosis is a progressive lung disease with high mortality and limited therapy that is characterized by epithelial cell damage and fibroblast activation. Ellagic acid is a natural polyphenol compound widely found in fruits and nuts that has multiple pharmacological activities. In this study, we explored the potential effects and mechanisms of Ellagic acid on pulmonary fibrosis in vivo and in vitro. In vivo studies showed that Ellagic acid significantly alleviated bleomycin (BLM)-induced pulmonary fibrosis in mice. In vitro experiments indicated that Ellagic acid could suppress Wnt signaling and attenuate Wnt3a-induced myofibroblast activation and the phosphorylation of Erk2 and Akt. Further studies showed that Ellagic acid could induce autophagy formation in myofibroblasts mainly by suppressing mTOR signaling and promoting apoptosis of myofibroblasts. In vivo experiments revealed that Ellagic acid significantly inhibited myofibroblast activation and promoted autophagy formation. Taken together, our results show that Ellagic acid effectively attenuates BLM-induced pulmonary fibrosis in mice by suppressing myofibroblast activation and promoting autophagy and apoptosis of myofibroblasts by inhibiting the Wnt signaling pathway.

| S-EPMC8072668 | biostudies-literature

Mitochondrial fatty acid synthesis coordinates mitochondrial oxidative metabolism

Project description:Cells harbor two systems for the synthesis of fatty acids, one in the cytoplasm (FASN or fatty acid synthase) and one in the mitochondria (mtFAS). In contrast to FASN, mtFAS is poorly characterized, with the major product(s), metabolic roles, and cellular function(s) essentially unknown. Here we show that hypomorphic mtFAS mutants display a profound loss of electron transport chain (ETC) complexes and exhibit compensatory reductive carboxylation. This effect on ETC complexes is independent of the synthesis of lipoic acid, the best characterized function of mtFAS, as mutants lacking lipoic acid synthesis have an intact ETC. Finally, mtFAS impairment blocks the differentiation of skeletal myoblasts in vitro. These data suggest that ETC activity in mammals is profoundly controlled by mtFAS function, thereby connecting anabolic fatty acid synthesis with the oxidation of carbon fuels.

2020-08-17 | GSE148617 | GEO

Total synthesis of (±)-decursivine via BINOL-phosphoric acid catalyzed tandem oxidative cyclization.

Project description:The synthesis of tetracyclic indole alkaloid (±)-decursivine was accomplished using BINOL-phosphoric acid catalyzed tandem oxidative cyclization as a key step with (bis(trifluoroacetoxy)iodo)benzene (PIFA) as an oxidizing agent. This represents one of the shortest and highest yielding routes for the synthesis of (±)-decursivine from readily available starting materials.

| S-EPMC8497573 | biostudies-literature

Oxidative coupling as a biomimetic approach to the synthesis of scytonemin.

Project description:The first total synthesis of the dimeric alkaloid pigment scytonemin is described. The key transformations in its synthesis from 3-indole acetic acid are a Heck carbocyclization and a Suzuki-Miyaura cross-coupling, orchestrated in a stereospecific tandem fashion, followed by a biosynthetically inspired oxidative dimerization. The tandem sequence generates a tetracyclic (E)-3-(arylidene)-3,4-dihydrocyclopenta[b]indol-2(1H)-one that is subsequently dimerized into the unique homodimeric core structure of scytonemin.

| S-EPMC3164230 | biostudies-literature

Anti-Inflammatory Effects of Ellagic Acid on Keratinocytes via MAPK and STAT Pathways.

Project description:Atopic dermatitis (AD) is a chronic inflammatory skin disease that is characterized by an impaired skin barrier and intense itchiness, which decreases the individual's quality of life. No fully effective therapeutic agents have prevailed for AD due to an insufficient grasp of the complex etiology. Ellagic acid (EA), a natural compound, has anti-inflammatory properties in chronic diseases. The effects of EA on AD have not yet been explored. The present study investigated the effects of EA on TNF-α/IFN-γ-stimulated HaCaT keratinocytes and house dust mite-induced AD-like skin lesions in NC/Nga mice. Treatment with EA suppressed inflammatory responses in keratinocytes by regulating critical inflammatory signaling pathways, such as mitogen-activated protein kinases and signal transducers and activators of transcription. In vivo studies using a DfE-induced AD mouse model showed the effects of EA administration through ameliorated skin lesions via decremented histological inflammatory reactions. These results suggest that EA could be a potential therapeutic alternative for the treatment of AD by inhibiting inflammatory signaling pathways.

| S-EPMC7865693 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

Tweets

OmicsDI Databases

PRIDE
PeptideAtlas
MassIVE
JPOST Repository
Physiome Model Repository

EGA
EVA
ENA
LINCS
PAXDB
Cell Collective

MetaboLights
Metabolomics Workbench
MetabolomeExpress
GNPS
BioModels
FAIRDOMHub

ArrayExpress
dbGaP
ExpressionAtlas
GEO
NODE

Information

Databases
Help
API
Contact us
Code on GitHub
Terms of use
Submit Data