Browse
Submit Data
Databases
API
Help

Dataset Information

15 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

An Overview of Bioactive 1,3-Oxazole-Containing Alkaloids from Marine Organisms.

ABSTRACT: 1,3-Oxazole chemicals are a unique class of five-membered monocyclic heteroarenes, containing a nitrogen atom and an oxygen. These alkaloids have attracted extensive attention from medicinal chemists and pharmacologists owing to their diverse arrays of chemical structures and biological activities, and a series of 1,3-oxazole derivatives has been developed into therapeutic agents (e.g., almoxatone, befloxatone, cabotegravir, delpazolid, fenpipalone, haloxazolam, inavolisib). A growing amount of evidence indicates that marine organisms are one of important sources of 1,3-oxazole-containing alkaloids. To improve our knowledge regarding these marine-derived substances, as many as 285 compounds are summarized in this review, which, for the first time, highlights their sources, structural features and biological properties, as well as their biosynthesis and chemical synthesis. Perspective for the future discovery of new 1,3-oxazole compounds from marine organisms is also provided.

SUBMITTER: Chen J

PROVIDER: S-EPMC8706051 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Bioactive Indole Diketopiperazine Alkaloids from the Marine Endophytic Fungus Aspergillus sp. YJ191021.

Project description:Six new prenylated indole diketopiperazine alkaloids, asperthrins A-F (1-6), along with eight known analogues (7-14), were isolated from the marine-derived endophytic fungus Aspergillus sp. YJ191021. Their planar structures and absolute configurations were elucidated by HR-ESI-MS, 1D/2D NMR data, and time-dependent density functional theory (TDDFT)/ECD calculation. The isolated compounds were assayed for their inhibition against three agricultural pathogenic fungi, four fish pathogenic bacteria, and two agricultural pathogenic bacteria. Compound 1 exhibited moderate antifungal and antibacterial activities against Vibrioanguillarum, Xanthomonas oryzae pv. Oryzicola, and Rhizoctoniasolani with minimal inhibitory concentration (MIC) values of 8, 12.5, and 25 μg/mL, respectively. Furthermore, 1 displayed notable anti-inflammatory activity with IC50 value of 1.46 ± 0.21 μM in Propionibacteriumacnes induced human monocyte cell line (THP-1).

| S-EPMC8002477 | biostudies-literature

Marine alkaloids as bioactive agents against protozoal neglected tropical diseases and malaria.

Project description:Covering: 2000 up to 2021Natural products are an important resource in drug discovery, directly or indirectly delivering numerous small molecules for potential development as human medicines. Among the many classes of natural products, alkaloids have a rich history of therapeutic applications. The extensive chemodiversity of alkaloids found in the marine environment has attracted considerable attention for such uses, while the scarcity of these natural materials has stimulated efforts towards their total synthesis. This review focuses on the biological activity of marine alkaloids (covering 2000 to up to 2021) towards Neglected Tropical Diseases (NTDs) caused by protozoan parasites, and malaria. Chemotherapy represents the only form of treatment for Chagas disease, human African trypanosomiasis, leishmaniasis and malaria, but there is currently a restricted arsenal of drugs, which often elicit severe adverse effects, show variable efficacy or resistance, or are costly. Natural product scaffolds have re-emerged as a focus of academic drug discovery programmes, offering a different resource to discover new chemical entities with new modes of action. In this review, the potential of a range of marine alkaloids is analyzed, accompanied by coverage of synthetic efforts that enable further studies of key antiprotozoal natural product scaffolds.

| S-EPMC8672869 | biostudies-literature

Repurposing bioactive aporphine alkaloids as efflux pump inhibitors

Project description:In the current study, RNA sequencing was used to investigate the synergistic effects of the berberine and roemerine on Bacillus subtilis cells.

2020-10-09 | GSE106296 | GEO

2,4,5-Tris(pyridin-4-yl)-4,5-dihydro-1,3-oxazole.

Project description:In the title compound, C(18)H(14)N(4)O, the mol-ecules are disordered about a crystallographic twofold axis, leading to 50:50 disorder of the O- and N-atom sites within the oxazole ring. As a consequence, symmetry-related oxazole C-N and C-O bonds are averaged. The oxazole ring makes a dihedral angle of 6.920?(1)° with the pyridyl ring in the 2-position and 60.960?(2)° with the pyridyl rings in the 4- and 5-positions.

| S-EPMC3379436 | biostudies-literature

4-(5-tert-Butyl-1,3-dithian-2-yl)-5-chloro-2-phenyl-1,3-oxazole.

Project description:In the title mol-ecule, C(17)H(20)ClNOS(2), the phenyl and oxazole rings are nearly coplanar with an average deviation of 0.022?Å from the mean plane (M). The 1,3-dithiane ring adopts a chair conformation and is twisted in such a way that the C-C(Bu) fragment lies in M (deviations are 0.031 and 0.010?Å, respectively, for the two C atoms).

| S-EPMC2960807 | biostudies-literature

1,3-Oxazin-6-one Derivatives and Bohemamine-Type Pyrrolizidine Alkaloids from a Marine-Derived Streptomyces spinoverrucosus.

Project description:Two new 1,3-oxazin-6-one derivatives (1 and 2) and six new bohemamine-type pyrrolizidine alkaloids (3-8) were isolated from the marine-derived Streptomyces spinoverrucosus strain SNB-048. Their structures including the absolute configurations were fully elucidated on the basis of spectroscopic analysis, ECD spectra, quantum chemical calculations, and chemical methods. Compounds 1 and 2 possess a γ-lactam moiety and a 1,3-oxazin-6-one system.

| S-EPMC5435457 | biostudies-literature

2-(2-Methoxy-phen-yl)-4,4-dimethyl-4,5-dihydro-1,3-oxazole.

Project description:In the title mol-ecule, C(12)H(15)NO(2), the oxazole ring adopts an envelope conformation. Overall, the mol-ecule is approximately planar, the dihedral angle between the mean plane through all but the methyl-ene C atom of the five-membered ring and the aromatic ring being 8.6?(1)°. A weak C-H?O inter-action contributes to the stabilization of the crystal structure.

| S-EPMC2915019 | biostudies-literature

2-(3-Methyl-2-nitro-phen-yl)-4,5-dihydro-1,3-oxazole.

Project description:In the title compound, C(10)H(10)N(2)O(3), an inter-mediate in the synthesis of anthranilamide insecticides, all the non-H atoms except the nitro-group O atom lie on a crystallographic mirror plane. The H atoms of the methyl group are disordered over two sets of sites with equal occupancies. In the crystal structure, C-H⋯N links lead to chains of mol-ecules propagating in [100].

| S-EPMC2967968 | biostudies-literature

Marine Bioactive Peptides-An Overview of Generation, Structure and Application with a Focus on Food Sources.

Project description:The biggest obstacles in the application of marine peptides are two-fold, as in the case of non-marine plant and animal-derived bioactive peptides: elucidating correlation between the peptide structure and its effect and demonstrating its stability in vivo. The structures of marine bioactive peptides are highly variable and complex and dependent on the sources from which they are isolated. They can be cyclical, in the form of depsipeptides, and often contain secondary structures. Because of steric factors, marine-derived peptides can be resistant to proteolysis by gastrointestinal proteases, which presents an advantage over other peptide sources. Because of heterogeneity, amino acid sequences as well as preferred mechanisms of peptides showing specific bioactivities differ compared to their animal-derived counterparts. This review offers insights on the extreme diversity of bioactivities, effects, and structural features, analyzing 253 peptides, mainly from marine food sources. Similar to peptides in food of non-marine animal origin, a significant percentage (52.7%) of the examined sequences contain one or more proline residues, implying that proline might play a significant role in the stability of bioactive peptides. Additional problems with analyzing marine-derived bioactive peptides include their accessibility, extraction, and purification; this review considers the challenges and proposes possible solutions.

| S-EPMC7460072 | biostudies-literature

5-(4-Fluoro-phen-yl)-2-[2-(5-phenyl-1,3-oxazol-2-yl)phen-yl]-1,3-oxazole.

Project description:In the title compound, C(24)H(15)FN(2)O(2), the dihedral angles between the central benzene ring and the oxazole rings are 10.7 (6) and 64.1 (5)°. The dihedral angles between the oxazole rings and their pendant rings are 2.0 (3) and 24.3 (2)°. The F atoms are disordered over two sites with occupancies of 0.627 (3) and 0.373 (3) in the phenyl-ene-oxazol-yl-phenyl and in oxazol-yl-phenyl fragments, respectively. In the crystal structure, mol-ecules are linked through a network of C-H⋯F and weak π-π stacking inter-actions.

| S-EPMC3007962 | 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