Browse
Submit Data
Databases
API
Help

Dataset Information

21 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate.

ABSTRACT: Rhodomyrtusials?A-C, the first examples of triketone-sesquiterpene meroterpenoids featuring a unique 6/5/5/9/4 fused pentacyclic ring system were isolated from Rhodomyrtus tomentosa, along with several biogenetically-related dihydropyran isomers. Two bis-furans and one dihydropyran isomer showed acetylcholinesterase (AChE) inhibitory activity. Structures of the isolates were unambiguously established by a combination of spectroscopic data, ECD analysis, and total synthesis. Bioinspired total syntheses of six isolates were achieved in six steps utilizing a reactive enetrione intermediate generated in situ from a readily available hydroxy-endoperoxide precursor.

SUBMITTER: Qin XJ

PROVIDER: S-EPMC6583783 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Isolation and Synthesis of Novel Meroterpenoids from Rhodomyrtus tomentosa: Investigation of a Reactive Enetrione Intermediate.

Qin Xu-Jie XJ Rauwolf Tyler J TJ Li Pan-Pan PP Liu Hui H McNeely James J Hua Yan Y Liu Hai-Yang HY Porco John A JA

Angewandte Chemie (International ed. in English) 20190220 13

Rhodomyrtusials A-C, the first examples of triketone-sesquiterpene meroterpenoids featuring a unique 6/5/5/9/4 fused pentacyclic ring system were isolated from Rhodomyrtus tomentosa, along with several biogenetically-related dihydropyran isomers. Two bis-furans and one dihydropyran isomer showed acetylcholinesterase (AChE) inhibitory activity. Structures of the isolates were unambiguously established by a combination of spectroscopic data, ECD analysis, and total synthesis. Bioinspired total syn ...[more]

PMID: 30681258

Similar Datasets

Comprehensive Analysis of <i>Rhodomyrtus tomentosa</i> Chloroplast Genome.

Project description:In the last decade, several studies have relied on a small number of plastid genomes to deduce deep phylogenetic relationships in the species-rich Myrtaceae. Nevertheless, the plastome of Rhodomyrtus tomentosa, an important representative plant of the Rhodomyrtus (DC.) genera, has not yet been reported yet. Here, we sequenced and analyzed the complete chloroplast (CP) genome of R. tomentosa, which is a 156,129-bp-long circular molecule with 37.1% GC content. This CP genome displays a typical quadripartite structure with two inverted repeats (IRa and IRb), of 25,824 bp each, that are separated by a small single copy region (SSC, 18,183 bp) and one large single copy region (LSC, 86,298 bp). The CP genome encodes 129 genes, including 84 protein-coding genes, 37 tRNA genes, eight rRNA genes and three pseudogenes (ycf1, rps19, ndhF). A considerable number of protein-coding genes have a universal ATG start codon, except for psbL and ndhD. Premature termination codons (PTCs) were found in one protein-coding gene, namely atpE, which is rarely reported in the CP genome of plants. Phylogenetic analysis revealed that R. tomentosa has a sister relationship with Eugenia uniflora and Psidium guajava. In conclusion, this study identified unique characteristics of the R. tomentosa CP genome providing valuable information for further investigations on species identification and the phylogenetic evolution between R. tomentosa and related species.

| S-EPMC6524380 | biostudies-literature

Rhodomyrtus tomentosa

Project description:Rhodomyrtus tomentosa Raw sequence reads

| PRJNA380314 | ENA

Rhodomyrtus tomentosa

Project description:Rhodomyrtus tomentosa overview

| PRJNA433262 | ENA

Rhodomyrtus tomentosa

Project description:Rhodomyrtus tomentosa Transcriptome or Gene expression

| PRJNA433249 | ENA

Optimization of Bioactive Compound Extraction from Rose Myrtle Fruit (Rhodomyrtus tomentosa, (W.Ait), Myrtaceae) as the Antioxidant Source.

Project description:Rose myrtle fruit (Rhodomyrtus tomentosa, (W.Ait), Myrtaceae) is one of fruits widely found in Kalimantan. This fruit contains a bioactive compound that has a potential to be used as medicine. The aim of this study was to obtain optimal temperature and time of extraction in maintaining and protecting the bioactive compound in rose myrtle fruit extract by using water as solvent. This research applied the response surface method with central composite design for two factors, namely, X1 (temperature/°C) consisting of three levels: 70, 80, and 90°C and X2 (time/minute) which consisted of three levels of 60, 90, and 120 minutes. Research parameters included total phenol and antioxidant activity. Moreover, GC-MS was used for the characterization of the chemical compound component contained in rose myrtle fruit extract. Optimization of extraction condition resulted in an optimum temperature for extraction of 80.43°C and optimum time for extraction of 85 minutes with an optimum yield of total phenol of 73.77?mg/100?g fresh fruit and antioxidant activity of 1.0385?µg/ml with desirability of 0.892 or 89.2%.

| S-EPMC7201856 | biostudies-literature

<i>Rhodomyrtus tomentosa</i> Fruits in Two Ripening Stages: Chemical Compositions, Antioxidant Capacity and Digestive Enzymes Inhibitory Activity.

Project description:Rhodomyrtus tomentosa fruit (RTF) has been known as a food source with multiple health-care components. In this work, nutrition characteristics, free and bound phenolic profiles, antioxidant properties in vitro and digestive enzymes inhibitory activities of un-fully mature RTF (UM-RTF) and fully mature RTF (FM-RTF) were evaluated for the first time. Results verified that high levels of energy, ascorbic acid, organic acids and total phenolics were observed in FM-RTF. Moreover, FM-RTF had significant higher total phenolic content (TPC), but significantly lower total flavonoid content (TFC) than UM-RTF. In addition, twenty phenolic compounds in RTF were identified by high performance liquid chromatography-electrospray ionization-quadrupole time-of-flight tandem mass spectrometry (HPLC-ESI-qTOF-MS/MS) method. Quantitative analysis results indicated that gallic acid, ellagic acid and astragalin were the predominant free phenolics, while gallic acid and syringetin-3-O-glucoside were dominant in bound phenolic fractions. In contrast, higher contents of phenolics were observed in FM-RTF. The results also confirmed that FM-RTF exhibited higher antioxidant activities and digestive enzymes inhibitory activities than UM-RTF. Strong inhibitory ability on α-glucosidase was found in RTF, while bound phenolics showed a stronger α-amylase inhibitory effect than free phenolics. Moreover, the interaction between the main phenolic compounds and α-glucosidase/α-amylase was preliminary explored by molecular docking analysis. The results provided valuable data about the chemical compositions and biological potential of R. tomentosa fruits in both maturation stages studied.

| S-EPMC9311718 | biostudies-literature

Rhodomyrtone as a New Natural Antibiotic Isolated from Rhodomyrtus tomentosa Leaf Extract: A Clinical Application in the Management of Acne Vulgaris.

Project description:Rhodomyrtone, a plant-derived principal compound isolated from Rhodomyrtus tomentosa (Myrtaceae) leaf extract, was assessed as a potential natural alternative for the treatment of acne vulgaris. The clinical efficacy of a 1% liposomal encapsulated rhodomyrtone serum was compared with a marketed 1% clindamycin gel. In a randomized and double-blind controlled clinical trial, 60 volunteers with mild to moderate acne severity were assigned to two groups: rhodomyrtone serum and clindamycin gel. The volunteers were instructed to apply the samples to acne lesions on their faces twice daily. A significant reduction in the total numbers of acne lesions was demonstrated in both treatment groups between weeks 2 and 8 (p < 0.05). Significant differences in acne numbers compared with the baseline were evidenced at week 2 onwards (p < 0.05). At the end of the clinical trial, the total inflamed acne counts in the 1% rhodomyrtone serum group were significantly reduced by 36.36%, comparable to 34.70% in the clindamycin-treated group (p < 0.05). Furthermore, a commercial prototype was developed, and a clinical assessment of 45 volunteers was performed. After application of the commercial prototype for 1 week, 68.89% and 28.89% of volunteers demonstrated complete and improved inflammatory acne, respectively. All of the subjects presented no signs of irritation or side effects during the treatment. Most of the volunteers (71.11%) indicated that they were very satisfied. Rhodomyrtone serum was demonstrated to be effective and safe for the treatment of inflammatory acne lesions.

| S-EPMC7912151 | biostudies-literature

Biomimetic Synthesis of Meroterpenoids by Dearomatization-Driven Polycyclization.

Project description:A biomimetic route to farnesyl pyrophosphate and dimethyl orsellinic acid (DMOA)-derived meroterpenoid scaffolds has yet to be reported despite great interest from the chemistry and biomedical research communities. A concise synthetic route with the potential to access DMOA-derived meroterpenoids is highly desirable to create a library of related compounds. Herein, we report novel dearomatization methodology followed by polyene cyclization to access DMOA-derived meroterpenoid frameworks in six steps from commercially available starting materials. Furthermore, several farnesyl alkene substrates were used to generate structurally novel, DMOA-derived meroterpenoid derivatives. DFT calculations combined with experimentation provided a rationale for the observed thermodynamic distribution of polycyclization products.

| S-EPMC6814491 | biostudies-literature

Biomimetic Synthesis and Chemical Proteomics Reveal the Mechanism of Action and Functional Targets of Lysine-Reactive Phloroglucinol Meroterpenoids

Project description:Natural products have long been an enduring source of drug leads and chemical probes that have led to the development of numerous medicines. Despite their scarcity, the discovery of natural products that modulate protein function through covalent interactions with lysine residues holds immense potential to unlock new therapeutic interventions and advance our understanding of the intricate biological processes governed by these modifications. Phloroglucinol meroterpenoids comprise one of the largest classes of natural products displaying a vast array of biological activities. However, their mechanism of action and molecular targets have remained largely unexplored. In this study, we present an in-depth experimental and computational investigation into the synthesis, physicochemical and kinetic parameters, molecular mechanism of action, and functional cellular targets of selected phloroglucinol meroterpenoids. We leverage synthetic clickable analogues of natural products to observe disparate proteome-wide reactivity by in-gel fluorescence scanning and cell imaging. By implementing sample multiplexing and a redesigned desthiobiotin-based probe, we streamline a quantitative activity-based protein profiling protocol for mapping proteome-wide reactivity and ligandability of proteinaceous lysines directly in human cells. Using this platform, we identify numerous lysine-phloroglucinol meroterpenoid interactions in breast cancer cells that occur at functional sites on proteins from diverse structural and functional classes. Lastly, we demonstrate that phloroglucinol meroterpenoids perturb diverse biochemical functions through stereoselective and site-specific modification of lysines in proteins involved in glycolysis, lipid metabolism, and mitochondrial respiration. These findings underscore the broad potential of phloroglucinol meroterpenoids for targeting functional lysines in the human proteome.

2024-05-23 | PXD045370 | Pride

Oxygen precursor to the reactive intermediate in methanol synthesis by Cu-ZSM-5.

Project description:The reactive oxidizing species in the selective oxidation of methane to methanol in oxygen activated Cu-ZSM-5 was recently defined to be a bent mono(?-oxo)dicopper(II) species, [Cu(2)O](2+). In this communication we report the formation of an O(2)-precursor of this reactive site with an associated absorption band at 29,000 cm(-1). Laser excitation into this absorption feature yields a resonance Raman (rR) spectrum characterized by (18)O(2) isotope sensitive and insensitive vibrations, ?O-O and ?Cu-Cu, at 736 (?(18)O(2) = 41 cm(-1)) and 269 cm(-1), respectively. These define the precursor to be a ?-(?(2):?(2)) peroxo dicopper(II) species, [Cu(2)(O(2))](2+). rR experiments in combination with UV-vis absorption data show that this [Cu(2)(O(2))](2+) species transforms directly into the [Cu(2)O](2+) reactive site. Spectator Cu(+) sites in the zeolite ion-exchange sites provide the two electrons required to break the peroxo bond in the precursor. O(2)-TPD experiments with (18)O(2) show the incorporation of the second (18)O atom into the zeolite lattice in the transformation of [Cu(2)(O(2))](2+) into [Cu(2)O](2+). This study defines the mechanism of oxo-active site formation in Cu-ZSM-5.

| S-EPMC2974621 | 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