Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Topsensterols A-C, Cytotoxic Polyhydroxylated Sterol Derivatives from a Marine Sponge Topsentia sp.

ABSTRACT: Three new polyhydroxylated sterol derivatives topsensterols A-C (1-3) have been isolated from a marine sponge Topsentia sp. collected from the South China Sea. Their structures were elucidated by detailed analysis of the spectroscopic data, especially the NOESY spectra. Topsensterols A-C (l-3) possess novel 2?,3?,4?,6?-tetrahydroxy-14?-methyl ?(9(11)) steroidal nuclei with unusual side chains. Compound 2 exhibited cytotoxicity against human gastric carcinoma cell line SGC-7901 with an IC50 value of 8.0 ?M. Compound 3 displayed cytotoxicity against human erythroleukemia cell line K562 with an IC50 value of 6.0 ?M.

SUBMITTER: Chen M

PROVIDER: S-EPMC4999907 | biostudies-other | 2016 Aug

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Topsensterols A-C, Cytotoxic Polyhydroxylated Sterol Derivatives from a Marine Sponge Topsentia sp.

Chen Min M Wu Xu-Dong XD Zhao Qing Q Wang Chang-Yun CY

Marine drugs 20160801 8

Three new polyhydroxylated sterol derivatives topsensterols A-C (1-3) have been isolated from a marine sponge Topsentia sp. collected from the South China Sea. Their structures were elucidated by detailed analysis of the spectroscopic data, especially the NOESY spectra. Topsensterols A-C (l-3) possess novel 2β,3α,4β,6α-tetrahydroxy-14α-methyl Δ(9(11)) steroidal nuclei with unusual side chains. Compound 2 exhibited cytotoxicity against human gastric carcinoma cell line SGC-7901 with an IC50 value ...[more]

PMID: 27490555

Similar Datasets

Callyspongiolide, a cytotoxic macrolide from the marine sponge Callyspongia sp.

Project description:A novel macrolide, callyspongiolide, whose structure was determined by comprehensive analysis of the NMR and HRMS spectra, was isolated from the marine sponge Callyspongia sp. collected in Indonesia. The compound features a carbamate-substituted 14-membered macrocyclic lactone ring with a conjugated structurally unprecedented diene-ynic side chain terminating at a brominated benzene ring. Callyspongiolide showed strong cytotoxicity against human Jurkat J16 T and Ramos B lymphocytes.

| S-EPMC4900817 | biostudies-literature

Papuamides E and F, Cytotoxic Depsipeptides from the Marine Sponge Melophlus sp.

Project description:Two known papuamides C (1) and D (2) together with two new depsipeptides, papuamides E (3) and F (4), were isolated from an undescribed sponge of the genus Melophlus collected in the Solomon Islands. The planar structures of the compounds were elucidated on the basis of spectroscopic studies. Papuamides C-F (1-4) showed cytotoxicity against brine shrimp with LD(50) values between 92 and 106 ?g/mL.

| S-EPMC3192506 | biostudies-literature

New Cytotoxic Cyclic Peptide from the Marine Sponge-Associated Nocardiopsis sp. UR67.

Project description:A new cyclic hexapeptide, nocardiotide A (1), together with three known compounds-tryptophan (2), kynurenic acid (3), and 4-amino-3-methoxy benzoic acid (4)-were isolated and identified from the broth culture of Nocardiopsis sp. UR67 strain associated with the marine sponge Callyspongia sp. from the Red Sea. The structure elucidation of the isolated compounds were determined based on detailed spectroscopic data including ¹D and ²D nuclear magnetic resonance (NMR) experimental analyses in combination with high resolution electrospray ionization mass spectrometry (HR-ESI-MS), while the absolute stereochemistry of all amino acids components of nocardiotide A (1) was deduced using Marfey's method. Additionally, ten known metabolites were dereplicated using HR-ESI-MS analysis. Nocardiotide A (1) displayed significant cytotoxic effects towards the murine CT26 colon carcinoma, human HeLa cervix carcinoma, and human MM.1S multiple myeloma cell lines. The results obtained revealed sponge-associated Nocardiopsis as a substantial source of lead natural products with pronounced pharmacological activities.

| S-EPMC6174345 | biostudies-literature

Structure elucidation and cytotoxic evaluation of new polyacetylenes from a marine sponge Petrosia sp.

Project description:The sponge Petrosia sp. yielded five polyacetylenic compounds (1-5), including two new polyacetylenes, petrosianynes A (1) and B (2). The structures of these compounds were elucidated by detailed spectroscopic analysis and by comparison with the physical and spectral data of related known analogues. Compounds 1-5 exhibited significant cytotoxic activity against a limited panel of cancer cell lines.

| S-EPMC4200862 | biostudies-literature

Carpatamides A-C, cytotoxic arylamine derivatives from a marine-derived Streptomyces sp.

Project description:Three new acylated arylamine derivatives (1-3), carpatamides A-C, were isolated from a marine-derived Streptomyces sp. based on activity screening against non-small-cell lung cancer (NSCLC). The structures of 1-3 were established on the basis of comprehensive spectroscopic analyses and chemical methods. Compounds 1 and 3 showed moderate cytotoxicity against NSCLC cell lines HCC366, A549, and HCC44 with IC50 values ranging from 2.2 to 8.4 μM.

| S-EPMC4035114 | biostudies-literature

A new 3-alkylpyridine alkaloid from the marine sponge Haliclona sp. and its cytotoxic activity.

Project description:A new alkaloid, 3-dodecyl pyridine containing a terminal cyano group (1), was isolated from the methanol extract of an Indonesia marine sponge Haliclona sp. Its chemical structure was determined by a combination of spectroscopic methods, including 1D and 2D NMR. Bioassay results indicated that compound 1 had moderate cytotoxity against tumour cell lines A549, MCF-7 and Hela with IC50 values of 41.8, 48.4 and 33.2 μM, respectively.

| S-EPMC5182040 | biostudies-literature

Cytotoxic Polyketide Metabolites from a Marine Mesophotic Zone Chalinidae Sponge-Associated Fungus Pleosporales sp. NBUF144.

Project description:Two new polyketide natural products, globosuxanthone F (1), and 2'-hydroxy bisdechlorogeodin (2), were isolated from the fungus Pleosporales sp. NBUF144, which was derived from a 62 m deep Chalinidae family sponge together with four known metabolites, 3,4-dihydroglobosuxanthone A (3), 8-hydroxy-3-methylxanthone-1-carboxylate (4), crosphaeropsone C (5), and 4-megastigmen-3,9-dione (6). The structures of these compounds were elucidated on the basis of extensive spectroscopic analysis, including 1D and 2D NMR and high-resolution electrospray ionization mass spectra (HRESIMS) data. The absolute configuration of 1 was further established by single-crystal X-ray diffraction studies. Compounds 1-5 were evaluated for cytotoxicity towards CCRF-CEM human acute lymphatic leukemia cells, and it was found that 1 had an IC50 value of 0.46 µM.

| S-EPMC8065988 | biostudies-literature

Structure and biological evaluation of novel cytotoxic sterol glycosides from the marine red alga Peyssonnelia sp.

Project description:Bioactivity-guided fractionation of the extract from a Fijian red alga Peyssonnelia sp. led to the isolation of two novel sterol glycosides 19-O-?-d-glucopyranosyl-19-hydroxy-cholest-4-en-3-one (1) and 19-O-?-d-N-acetyl-2-aminoglucopyranosyl-19-hydroxy-cholest-4-en-3-one (2), and two known alkaloids indole-3-carboxaldehyde (3) and 3-(hydroxyacetyl)indole (4). Their structures were characterized by 1D and 2D NMR and mass spectral analysis. The sterol glycosides inhibited cancer cell growth with mean IC?? values (for 11 human cancer cell lines) of 1.63 and 1.41?M for 1 and 2, respectively. The most sensitive cancer cell lines were MDA-MB-468 (breast) and A549 (lung), with IC??'s in of 0.71-0.97?M for 1 and 2. Modification of the sterol glycoside structures revealed that the ?,?-unsaturated ketone at C-3 and oxygenation at C-19 of 1 and 2 are crucial for anticancer activity, whereas the glucosidic group was not essential but contributed to enhanced activity against the most sensitive cell lines.

| S-EPMC2998995 | biostudies-literature

New Aromatic Bisabolane Derivatives with Lipid-Reducing Activity from the Marine Sponge Myrmekioderma sp.

Project description:The previously reported 1-(2,4-dihydroxy-5-methylphenyl)ethan-1-one (1), (1'Z)-2-(1',5'-dimethylhexa-1',4'-dieny1)-5-methylbenzene-1,4-diol (2), and 1,8-epoxy-1(6),2,4,7,10-bisaborapentaen-4-ol (5) together with four new structures of aromatic bisabolane-related compounds (3, 4, 6, 7) were isolated from the marine sponge Myrmekioderma sp. Compounds 1, 2, and 5 were identified based on spectral data available in the literature. The structures of the four new compounds were experimentally established by 1D and 2D-NMR and (-)-HRESIMS spectral analysis. Cytotoxic and lipid-reducing activities of the isolated compounds were evaluated. None of the isolated compounds were active against the tested cancer cell lines; however, lipid-reducing activity was found for compounds 2-5 and 7 in the zebrafish Nile red fat metabolism assay. This class of compounds should be further explored for their suitability as possible agents for the treatment of lipid metabolic disorders and obesity.

| S-EPMC6627430 | biostudies-literature

Cytotoxic sesterterpenoids from a sponge Hippospongia sp.

Project description:One new pentacyclic sesterterpene, hippospongide A (1), and one new scalarane sesterterpenoid, hippospongide B (2), along with six previously reported known scalarane-type sesterterpenes (3-8), were isolated from a sponge Hippospongia sp. The structures of these compounds were elucidated on the basis of their spectroscopic data and comparison of the NMR data with those of known analogues. These metabolites are the first pentacyclic sesterterpene and scalarane-type sesterterpenes to be reported from this genus. Compounds 3-5 exhibited significant cytotoxicity against DLD-1, HCT-116, T-47D and K562 cancer cell lines.

| S-EPMC3397461 | 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