Browse
Submit Data
Databases
API
Help

Dataset Information

22 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Anti-HIV Tigliane Diterpenoids from Wikstroemia scytophylla.

ABSTRACT: During a chemical investigation of Wikstroemia scytophylla, three new [wikstrocins A-C (1-3)] and three known tigliane diterpenoids (4-6) were isolated. The structures of the new compounds were elucidated from extensive physiochemical and spectroscopic analysis. The correlations between the ECD Cotton effects and B ring structures of tiglianes were also evaluated. The isolated compounds were assessed for their anti-HIV activity against HIV-1 infection of MT4 cells, and two compounds (4 and 6) showed potent anti-HIV activity with IC₅₀ values of 3.8 and 12.8 nM, respectively.

SUBMITTER: Otsuki K

PROVIDER: S-EPMC8176626 | biostudies-literature |

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Similar Datasets

Anti-HIV tigliane diterpenoids from Reutealis trisperma.

Project description:Bioassay-guided fractionation of the n-butanol extract from the branches and leaves of Reutealis trisperma resulted in the isolation of six undescribed (crotignoids L ~ Q) together with two known (12-deoxyphorbol-13-hexadecanoate and 12-deoxyphorbol-13-myristate) tigliane diterpenoids. Their structures, especially the absolute configurations, were determined from extensive spectroscopic studies, including 2D NMR spectra, CD data analysis and electronic circular dichroism (ECD) calculations. All isolates were tested for anti-HIV activity against HL4-3 virus in MT4 cells. Except for crotignoid Q, the remaining seven tigliane diterpenoids exhibited potent anti-HIV activity with IC50 values ranging from 0.0023 to 4.03 μM.

| S-EPMC7238976 | biostudies-literature

Isolation, structure determination, and anti-HIV evaluation of tigliane-type diterpenes and biflavonoid from Stellera chamaejasme.

Project description:Five novel tigliane-type diterpenes, stelleracins A-E (3-7), a novel flavanone dimer, chamaeflavone A (8), and six known compounds were isolated from the roots of Stellera chamaejasme. Their structures were elucidated by extensive spectroscopic analyses. The isolated compounds were evaluated for anti-HIV activity in MT4 cells. New compounds 3-5 showed potent anti-HIV activity (EC90 0.00056-0.0068 ?M) and relatively low or no cytotoxicity (IC50 4.4-17.2 ?M). These new compounds represent promising new leads for development into anti-AIDS clinical trial candidates.

| S-EPMC3715147 | biostudies-literature

Identification of Daphnane Diterpenoids from Wikstroemia indica Using Liquid Chromatography with Tandem Mass Spectrometry.

Project description:Liquid chromatography coupled with tandem mass spectrometry (LC-MS/MS) has emerged as a powerful tool for the rapid identification of compounds within natural resources. Daphnane diterpenoids, a class of natural compounds predominantly found in plants belonging to the Thymelaeaceae and Euphorbiaceae families, have attracted much attention due to their remarkable anticancer and anti-HIV activities. In the present study, the presence of daphnane diterpenoids in Wikstroemia indica, a plant belonging to the Thymelaeaceae family, was investigated by LC-MS/MS analysis. As a result, 21 daphnane diterpenoids (1-21) in the stems of W. indica were detected. Among these, six major compounds (12, 15, 17, 18, 20, and 21) were isolated and their structures were unequivocally identified through a comprehensive analysis of the MS and NMR data. For the minor compounds (1-11, 13, 14, 16, and 19), their structures were elucidated by in-depth MS/MS fragmentation analysis. This study represents the first disclosure of structurally diverse daphnane diterpenoids in W. indica, significantly contributing to our understanding of bioactive diterpenoids in plants within the Thymelaeaceae family.

| S-EPMC10609749 | biostudies-literature

Stelleralides A-C, novel potent anti-HIV daphnane-type diterpenoids from Stellera chamaejasme L.

Project description:Three novel 1-alkyldaphnane-type diterpenes, stelleralides A-C (4-6), and five known compounds were isolated from the roots of Stellera chamaejasme L. The structures of 4-6 were elucidated by extensive spectroscopic analyses. Several isolated compounds showed potent anti-HIV activity. Compound 4 showed extremely potent anti-HIV activity (EC(90) 0.40 nM) with the lowest cytotoxicity (IC(50) 4.3 ?M) and appears to be a promising compound for development into anti-AIDS clinical trial candidates.

| S-EPMC3109985 | biostudies-literature

Daphnepedunins A-F, Anti-HIV Macrocyclic Daphnane Orthoester Diterpenoids from Daphne pedunculata.

Project description:From the whole plant of Daphne pedunculata, 12 macrocyclic daphnane diterpenoids, including six new compounds, daphnepedunins A-F (1-4, 9, and 10), were isolated. Their structures were elucidated by physiochemical and spectroscopic data analysis, the modified Mosher's method, and X-ray crystallography. The isolated compounds were evaluated for anti-HIV activity against HIV-1 infection in MT4 cells and showed significant anti-HIV activity with IC50 values of 36.3-994 nM. A consideration of the anti-HIV activity of these compounds provided further insight into the structure-activity relationships of macrocyclic daphnane diterpenoids.

| S-EPMC10131280 | biostudies-literature

Isolation, Structural Elucidation, and Anti-HIV Activity of Daphnane Diterpenoids from Daphne odora.

Project description:Five new [daphneodorins D-H (1, 5, and 10-12)] and seven known daphnane diterpenoids (2-4 and 6-9) were isolated from Daphne odora. The structures of the new compounds were elucidated by extensive physicochemical and spectroscopic analysis. The isolated compounds were evaluated for their anti-HIV activity against HIV-1 infection of MT4 cells. Nine daphnane diterpenoid orthoesters (1-9) showed potent anti-HIV activity with EC50 values of 1.5-7.7 nM.

| S-EPMC8176625 | biostudies-literature

Marine Diterpenoids as Potential Anti-Inflammatory Agents.

Project description:The inflammatory response is a highly regulated process, and its dysregulation can lead to the establishment of chronic inflammation and, in some cases, to death. Inflammation is the cause of several diseases, including rheumatoid arthritis, inflammatory bowel diseases, multiple sclerosis, and asthma. The search for agents inhibiting inflammation is a great challenge as the inflammatory response plays an important role in the defense of the host to infections. Marine invertebrates are exceptional sources of new natural products, and among those diterpenoids secondary metabolites exhibit notable anti-inflammatory properties. Novel anti-inflammatory diterpenoids, exclusively produced by marine organisms, have been identified and synthetic molecules based on those structures have been obtained. The anti-inflammatory activity of marine diterpenoids has been attributed to the inhibition of Nuclear Factor-κB activation and to the modulation of arachidonic acid metabolism. However, more research is necessary to describe the mechanisms of action of these secondary metabolites. This review is a compilation of marine diterpenoids, mainly isolated from corals, which have been described as potential anti-inflammatory molecules.

| S-EPMC4619941 | biostudies-literature

Wikstroemia sp.

Project description:Wikstroemia sp. Genome sequencing and assembly

| PRJNA1113815 | ENA

Diterpenoids from Blumea balsamifera and Their Anti-Inflammatory Activities

Project description:Six new diterpenoids, blusamiferoids A–F (1–6), including four pimarane-type diterpenoids, one rosane-type diterpenoid (3), and one rearranged abietane-type diterpenoid (6), were isolated from the dry aerial parts of Blumea balsamifera. Their structures were characterized by spectroscopic and computational methods. In particular, the structures of 1 and 4 were confirmed by X-ray crystallography. Compounds 5 and 6 were found to dose-dependently inhibit the production of TNF-α, IL-6, and nitrite oxide, and compound 5 also downregulated NF-κB phosphorylation in lipopolysaccharide (LPS)-induced RAW 264.7 cells.

| S-EPMC9100843 | biostudies-literature

Anti-Neuroinflammatory ent-Kaurane Diterpenoids from Pteris multifida Roots.

Project description:Activated microglia are known to be a major source of cellular neuroinflammation which causes various neurodegenerative diseases, including Alzheimer's disease. In our continuing efforts to search for new bioactive phytochemicals against neuroinflammatory diseases, the 80% methanolic extract of Pteris multifida (Pteridaceae) roots was found to exhibit significant NO inhibitory activity in lipopolysaccharide (LPS)-activated BV-2 microglia cells. Three new ent-kaurane diterpenoids, pterokaurane M₁ 2-O-β-d-glucopyranoside (4), 2β,16α-dihydroxy-ent-kaurane 2,16-di-O-β-d-glucopyranoside (10), and 2β,16α,17-trihydroxy-ent-kaurane 2-O-β-d-glucopyranoside (12), were isolated along with nine other known compounds from P. multifida roots. The chemical structures of the new compounds were determined by 1D- and 2D-NMR, HR-ESI-MS, and CD spectroscopic data analysis. Among the isolates, compounds 1 and 7 significantly inhibited NO production in LPS-stimulated BV-2 cells reducing the expression of the cyclooxygenase-2 (COX-2) protein and the level of pro-inflammatory mediators such as prostaglandin E₂ (PGE₂), tumor necrosis factor (TNF)-α, interleukin (IL)-1β, and IL-6. These results suggest that ent-kaurane diterpenes from P. multifida could be potential lead compounds that act as anti-neuroinflammatory agents.

| S-EPMC6155576 | 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