Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Bioactive pregnane steroids from a South China Sea gorgonian Carijoa sp.

ABSTRACT: A new pregnane steroid, 1, and three known analogues 2-4, have been isolated from a gorgonian Carijoa sp. collected from the South China Sea. The planar structure and relative configuration of 1 were elucidated from comprehensive spectroscopic data. Its absolute configuration was determined by application of the modified Mosher method. Compounds 1, 3 and 4 exhibited cytotoxicity against the human hepatoma cell line Bel-7402, with IC50 values of 9.33, 11.02 and 18.68 µM, respectively. Additionally, compound 1 exhibited promising antibacterial activity against Pseudomona puido, with a MIC value of 31 nM, which is approximately 5-fold more potent than ciprofloxacin (MIC = 156 nM).

SUBMITTER: Zhao HY

PROVIDER: S-EPMC6270022 | biostudies-literature | 2013 Mar

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Bioactive pregnane steroids from a South China Sea gorgonian Carijoa sp.

Zhao Hong-Ying HY Shao Chang-Lun CL Li Zhi-Yong ZY Han Lei L Cao Fei F Wang Chang-Yun CY

Molecules (Basel, Switzerland) 20130315 3

A new pregnane steroid, 1, and three known analogues 2-4, have been isolated from a gorgonian Carijoa sp. collected from the South China Sea. The planar structure and relative configuration of 1 were elucidated from comprehensive spectroscopic data. Its absolute configuration was determined by application of the modified Mosher method. Compounds 1, 3 and 4 exhibited cytotoxicity against the human hepatoma cell line Bel-7402, with IC50 values of 9.33, 11.02 and 18.68 µM, respectively. Additionall ...[more]

PMID: 23503119

Similar Datasets

Bioactive polyoxygenated steroids from the South China sea soft coral, Sarcophyton sp.

Project description:Seven new polyoxygenated steroids (1-7) were isolated together with seven known analogues (8-14) from the South China Sea soft coral, Sarcophyton sp. The structures of the new compounds were identified on the basis of extensive spectroscopic analysis and comparison with reported data. All the steroids are characterized with 3?,5?,6?-hydroxy moiety, displaying carbon skeletons of cholestane, ergostane, gorgostane and 23,24-dimethyl cholestane. In the in vitro bioassay, metabolites exhibited different levels of antimicrobial activity against bacterial species Escherichia coli and Bacillus megaterium, and fungal species Microbotryum violaceum and Septoria tritici. No inhibition was detected towards microalga Chlorella fusca. Preliminary structure-activity analysis suggests that the 11?-acetoxy group may increase both antibacterial and antifungal activities. The terminal-double bond and the cyclopropane moiety at the side chain may also contribute to the bioactivity.

| S-EPMC3705369 | biostudies-literature

Bioactive (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids from the South China Sea gorgonian Dichotella gemmacea.

Project description:Six new (3Z,5E)-11,20-epoxybriara-3,5-dien-7,18-olide diterpenoids, gemmacolides N-S (1-6), were isolated together with four known analogues, juncenolide D, and juncins R, S and U (7-10), from the South China Sea gorgonian Dichotella gemmacea. The structures of the new compounds were elucidated by the detailed analysis of spectroscopic data in combination with the comparison with reported data. The absolute configuration of 1 was determined by a TDDFT calculation of its solution ECD spectrum, affording the determination of absolute configuration of other analogues by simply comparing their ECD spectra with that of 1. The cytotoxic and antimicrobial activities of these compounds were evaluated. In preliminary in vitro bioassays, compounds 4, 5, 6, 8 and 9 showed cytotoxicity against A549 and MG63, while compounds 1, 2, 4, 7-10 showed antimicrobial activity against the fungus Septoria tritici and the bacterium Escherichia coli.

| S-EPMC3164382 | biostudies-literature

Six new tetraprenylated alkaloids from the South China Sea gorgonian Echinogorgia pseudossapo.

Project description:Six new tetraprenylated alkaloids, designated as malonganenones L-Q (1-6), were isolated from the gorgonian Echinogorgia pseudossapo, collected in Daya Bay of Guangdong Province, China. The structures of 1-6 featuring a methyl group at N-3 and a tetraprenyl chain at N-7 in the hypoxanthine core were established by extensive spectroscopic analyses. Compounds 1-6 were tested for their inhibitory activity against the phosphodiesterases (PDEs)-4D, 5A, and 9A, and compounds 1 and 6 exhibited moderate inhibitory activity against PDE4D with IC₅₀ values of 8.5 and 20.3 µM, respectively.

| S-EPMC3944508 | biostudies-literature

Polyhydroxylated steroids from the South China Sea soft coral Sarcophyton sp. and their cytotoxic and antiviral activities.

Project description:Chemical investigation on the soft coral Sarcophyton sp. collected from the South China Sea yielded three new polyhydroxylated steroids, compounds (1-3), together with seven known ones (4-10). Their structures were established by extensive spectroscopic methods and comparison of their data with those of the related known compounds. All the isolates possessed the 3β,5α,6β-trihydroxylated steroidal nucleus. The cytotoxicities against selected HL-60, HeLa and K562 tumor cell lines and anti-H1N1 (Influenza A virus (IAV)) activities for the isolates were evaluated. Compounds 2, 3 and 5-8 exhibited potent activities against K562 cell lines with IC₅₀ values ranging from 6.4 to 10.3 μM. Compounds 1, 6-8 potently inhibited the growth of HL-60 tumor cell lines, and 6 also showed cytotoxicity towards HeLa cell lines. In addition, preliminary structure-activity relationships for the isolates are discussed. The OAc group at C-11 is proposed to be an important pharmacophore for their cytotoxicities in the 3β,5α,6β-triol steroids. Compounds 4 and 9 exhibited significant anti-H1N1 IAV activity with IC₅₀ values of 19.6 and 36.7 μg/mL, respectively.

| S-EPMC3877887 | biostudies-literature

Chemistry and Bioactivity of Briaranes from the South China Sea Gorgonian Dichotella gemmacea.

Project description:Seven new briarane diterpenoids, gemmacolides AZ-BF (1-7), were isolated together with eight known analogues (8-15) from the South China gorgonian Dichotella gemmacea. Their structures were elucidated based on detailed spectroscopic analysis and a comparison with reported data. In an in vitro bioassay, these compounds exhibited different levels of growth inhibition activity against A549 and MG63 cells, giving continuous evidences about the biological contribution of functional groups at C-2, C-12, C-13, and C-16. These compounds were also evaluated for their antibacterial and antifungal activities. Compound 8 exhibited a potential antibacterial activity against both Gram-positive bacterium Bacillus megaterium and Gram-negative bacterium Escherichia coli.

| S-EPMC5128744 | biostudies-literature

South China Sea

Project description:South China Sea Genome sequencing

| PRJNA1057713 | ENA

Neorhizobium sp. CSC1952 strain:South China Sea | isolate:South China Sea

Project description:Neorhizobium sp. CSC1952 strain:South China Sea | isolate:South China Sea Genome sequencing

| PRJNA1031374 | ENA

Neorhizobium sp. CSC1952 strain:south China sea | isolate:south China sea

Project description:Neorhizobium sp. CSC1952 strain:south China sea | isolate:south China sea Genome sequencing

| PRJNA984414 | ENA

Unusual Inner-Salt Guaiazulene Alkaloids and bis-Sesquiterpene from the South China Sea Gorgonian Muriceides collaris.

Project description:Three new guaiazulene alkaloids muriceidines A-C (1-3) and one new bis-sesquiterpene muriceidone A (4), were isolated from the South China Sea gorgonian Muriceides collaris. Muriceidines are the first examples structurally architected by guaiazulene coupling with an inner-salt ? 1-pipecolic acid via a unique sp2 methine-bridged linkage, and the bis-sesquiterpene was comprised by a guaiazulene and a indene units linked through a unprecedented carbon-carbon ?-bond between the high steric bridgehead carbon C-10 of guaiazulene moiety and C-2' of indene moiety. The chiral compounds 2-4 were obtained initially as racemates and further separated by chiral HPLC methods. The inner-salt structures of 1-3 and absolute configurations of 2-4 were fully elucidated by calculated 13C NMR, ECD and OR with quantum chemical calculation methods. Compound 1 showed cytotoxicity against K562 cell lines with IC50 value of 8.4??M and antifouling activity against the larvae of the barnacle Balanus albicostatus with EC50 value of 11.9 ?g/mL and potent therapeutic index (LC50/EC50?=?3.66). Also the racemic (±)-3 showed cytotoxicities against both HL-60 and K562 cell lines with IC50 values of 2.2 and 3.7??M, respectively. A semisynthetic trial was performed to validate the proposed biosynthetic hypotheses.

| S-EPMC5550455 | biostudies-literature

Bioactive cembranoids from the South China Sea soft coral Sarcophyton elegans.

Project description:Four new cembranoids, sarcophelegans A-D (1-4) and six known analogues (5-10) were isolated from the South China Sea soft coral Sarcophyton elegans. Their structures were elucidated through detailed spectroscopic analysis, and the absolute conﬁguration of 1 was conﬁrmed by single-crystal X-ray diffraction. The antimigratory potential of compounds 1-10 were evaluated and compounds 2 and 6 were found to inhibit human breast tumor MDA-MB-231 cell migration at 10 μM.

| S-EPMC6331945 | 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