Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Astataricusones A-D and astataricusol A, five new anti-HBV shionane-type triterpenes from Aster tataricus L. f.

ABSTRACT: Five new shionane-type triterpenes, astataricusones A-D (compounds 1-4) and astataricusol A (5), together with one known shionane-type triterpene 6 were obtained from the roots and rhizomes of Aster tataricus L. f. Their structures were elucidated on the basis of spectroscopic data, mainly NMR and MS data. The absolute configurations of 1 and 4 was determined by single crystal X-ray diffraction and CD analysis. Compound 2 showed inhibitory activity on HBsAg secretion with an IC50 value of 23.5 ?M, while 2 and 6 showed inhibitory activities on HBeAg secretion with IC50 values of 18.6 and 40.5 ?M, and cytotoxicity on HepG 2.2.15 cells with CC50 values of 172.4 and 137.7 ?M, respectively. Compounds 2 and 6 also exhibited inhibitory activities on HBV DNA replication with IC50 values of 2.7 and 30.7 ?M, respectively.

SUBMITTER: Zhou WB

PROVIDER: S-EPMC6270206 | biostudies-other | 2013

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

Astataricusones A-D and astataricusol A, five new anti-HBV shionane-type triterpenes from Aster tataricus L. f.

Zhou Wen-Bing WB Zeng Guang-Zhi GZ Xu Hui-Min HM He Wen-Jun WJ Tan Ning-Hua NH

Molecules (Basel, Switzerland) 20131125 12

Five new shionane-type triterpenes, astataricusones A-D (compounds 1-4) and astataricusol A (5), together with one known shionane-type triterpene 6 were obtained from the roots and rhizomes of Aster tataricus L. f. Their structures were elucidated on the basis of spectroscopic data, mainly NMR and MS data. The absolute configurations of 1 and 4 was determined by single crystal X-ray diffraction and CD analysis. Compound 2 showed inhibitory activity on HBsAg secretion with an IC50 value of 23.5 μ ...[more]

PMID: 24287992

Similar Datasets

Five new taraxerene-type triterpenes from the branch barks of Davidia involucrata.

Project description:Five new taraxerene-type triterpenes, 2-nor-D-friedoolean-14-en-28-ol (1), 2-nor-d-friedoolean-14-en-3?,28-diol (2), 6?-hydroxy-2-nor-D-friedoolean-14-en-3,21-dione (3), 6?,11?,29-trihydroxy-D-friedoolean-14-en-3,16,21-trione (4), and 6?,23,29-trihydroxy-D-friedoolean-14-en-3,16,21-trione (5), were isolated from the MeOH extract of the branch barks of Davidia involucrata, together with five known compounds. Their structures were elucidated by means of various spectroscopic analyses. Five of the identified compounds showed moderate cytotoxicities against the cell proliferation of SGC-7901, MCF-7, and BEL-7404.

| S-EPMC6271488 | biostudies-literature

Three new multiflorane-type triterpenes from pumpkin (Cucurbita maxima) seeds.

Project description:Three new multiflorane-type triterpenes; 7a-methoxymultiflor-8-ene-3a,29-diol 3-acetate-29-benzoate (1), 7-oxomultiflor-8-ene-3a,29-diol 3-acetate-29-benzoate (2), and multiflora-7,9(11)-diene-3a,29-diol 3-p-hydroxybenzoate-29-benzoate (3), were isolated from seeds of Cucurbita maxima, along with three known compounds. Compound 3 and multiflora-7,9(11)-diene-3a-29-diol 3-benzoate (5) exhibited potent inhibitory effects on melanogenesis, with low cytotoxicities, and 2 exhibited single-digit micromolar cytotoxicity against HL-60 and P388 cells.

| S-EPMC6270121 | biostudies-literature

Anti-Inflammatory Oleanolic Triterpenes from Chinese Acorns.

Project description:Acorns play an important role in human history and are a source of food and recipes for many cultures around the world. In this study, eleven oleanolic triterpenes, one of which was novel, were isolated from Chinese acorns (Quercus serrata var. brevipetiolata). The chemical structure of the novel triterpene, which was identified as 2?,3?,19?-trihydroxy-24-oxo-olean-12-en-28-oic acid (1), was established based on the interpretation of chemical and spectroscopic analyses, including IR, HR-ESI-MS, and NMR experiments (¹H, (13)C NMR, DEPT, ¹H-¹H COSY, HSQC, HMBC, and NOESY). All isolated compounds were tested for their inhibitory effects on LPS-induced nitric oxide (NO) production in RAW 264.7 macrophages. Compared with the positive control drug indomethacin (IC50 = 47.4 ?M), compounds 1, 3, 6 and 8 exhibited remarkable anti-inflammatory activities with IC50 values of 5.4, 7.8, 4.0 and 8.9 ?M, respectively. Besides, compounds 2, 4, 7 and 9 also showed moderate anti-inflammatory activities with IC50 values of 10.1, 13.0, 20.1 and 17.2 ?M, respectively. Furthermore, Compound 1 could inhibit TNF-?-induced IL-6 and IL-8 production in MH7A cells.

| S-EPMC6272836 | biostudies-other

Five new mexicanolide type limonoids from Heynea trijuga

Project description:Five new mexicanolide-type limonoids, heytrijunolides A–E (1–5) were isolated from the branches and leaves of Heynea trijuga. The structures of these new compounds were elucidated on the basis of extensive spectroscopic analysis. Compound 3 showed weak cytotoxicity against HL-60, SMMC-7721 and A-549 human tumor cell lines with the IC50 values of 21.88, 20.66 and 12.70 µM, respectively. Electronic Supplementary Material Supplementary material is available for this article at 10.1007/s13659-012-0040-1 and is accessible for authorized users.

| S-EPMC4131624 | biostudies-literature

Development of anti-HBV agents targeting HBV capsid proteins.

Project description:Hepatitis B is a viral hepatitis, which is caused by infection of hepatitis B virus (HBV). This disease progresses to chronic hepatitis, cirrhosis and liver cancer. To treat hepatitis B, exclusion of virus and covalently closed circular DNA (cccDNA) that is formed in hepatocyte nucleus is necessary. A hepatitis B capsid protein (HBc) is an indispensable protein, which forms the capsid that encapsulates viral DNA. Since HBc is correlated to the transcriptional regulation of cccDNA, this protein would be an attractive target for complete cure of hepatitis B. By in silico screening of a library of compounds, a small compound, Cpd4 (1), which binds to a hydrophobic cavity located in the inner pocket on the tetramer interface of HBc proteins, was identified. In anti-HBV assays, this synthetic compound, Cpd4 (1) decreased the amount of HBV core related antigen (HBcrAg), which has been correlated with the proliferation of HBV, and decreased the amount of HBV surface antigen (HBsAg), which is correlated with the amount of cccDNA. Based on Cpd4 (1) as a lead compound, 20 derivatives of 1 were designed and synthesized and their structure-activity relationships were examined. As a result, specific interactions between each compound and amino acid residues of the target protein appeared to be unimportant but the shape/size of compounds which can bind to the hydrophobic cavity might be important in the expression of high anti-HBV activity, and a more potent derivative, TKB-HBV-CA-001 (3b), was discovered. These results will be useful in the development of novel anti-HBV agents for a complete cure of hepatitis B.

| S-EPMC10583812 | biostudies-literature

Anti-Inflammatory Activity of Triterpenes Isolated from Protium paniculatum Oil-Resins.

Project description:Protium is the main genus of the Burseraceae family and one of the most common genera in South America, with an important species called "breu." Gum and oil-resins of this species are used as tonic and stimulant and for the treatment of ulcers and inflammation. The present study aims to isolate and investigate the anti-inflammatory activity of triterpene compounds isolated from oil-resin of Protium paniculatum. The pentacyclic triterpenes ?,?-amyrin, acetylated ?,?-amyrin, ?,?-amyrone, and brein/maniladiol did not alter the viability of murine J774 macrophages (IC50 > 20?µg/mL), with the exception of mixture of brein/maniladiol which showed moderate cytotoxic activity. Also it was observed that compounds at 10?µg/mL inhibited more than 80% of production of NO(•), although only ?,?-amyrin was able to inhibit the production of TNF-? (52.03 ± 2.4%). The compounds inhibited the production of IL-6 and induced the production of IL-10 in murine J774 macrophages stimulated by LPS. ?,?-Amyrone inhibited the expression of COX-2 and also inhibited the formation of paw or ear edema in rats and mice, having a quick and immediate effect. This study may provide the basis for future investigations on the therapeutic role of ?,?-amyrone in treating inflammation.

| S-EPMC4806667 | biostudies-literature

Design, Synthesis, and Anti-HBV Activity of New Bis(l-amino acid) Ester Tenofovir Prodrugs.

Project description:A series of bis(l-amino acid) ester prodrugs of tenofovir (TFV) were designed and synthesized as new anti-HBV agents in this work. Four compounds 11, 12a, 12d, and 13b displayed better anti-HBV activity (IC50: 0.71-4.22 ?M) than the parent drug TFV. The most active compound 11 (IC50: 0.71 ?M), a bis(l-valine) ester prodrug of TFV, was found to have obviously greater AUC0-?, C max, and F% than tenofovir disoproxil fumarate (TDF), and potent in vivo efficacy which is not inferior to TDF in a duck HBV (DHBV) model and a HBV DNA hydrodynamic mouse model, and it may serve as a promising lead compound for further anti-HBV drug discovery.

| S-EPMC6580537 | biostudies-literature

Three new ring-A modified ursane triterpenes from Davidia involucrata.

Project description:Three new ursane triterpenes, 3?,19?-dihydroxy-2-nor-urs-12-en-23,28-dioic acid-23-methyl ester (1), 19?,23-dihydroxy-3-oxo-2-nor-urs-12-en-28-oic acid (2), and 2,3-seco-3-methoxy-3,19?,23-trihydroxy-urs-12-en-2-al-28-oic acid (3), were isolated from the MeOH extract of the branch barks of Davidia involucrata, together with six known compounds. Their structures were elucidated by means of various spectroscopic analyses. The isolated triterpenes provide important evolutionary and chemotaxonomic knowledge about the monotypic genus Davidia. Five of the identified compounds showed moderate cytotoxicities against the cell proliferation of SGC-7901, MCF-7, and BEL-7404 with IC50 range from 7.26 to 47.41 ?M.

| S-EPMC6271727 | biostudies-literature

Structure Identification and Anti-Cancer Pharmacological Prediction of Triterpenes from Ganoderma lucidum.

Project description:Ganoderma triterpenes (GTs) are the major secondary metabolites of Ganoderma lucidum, which is a popularly used traditional Chinese medicine for complementary cancer therapy. In the present study, systematic isolation, and in silico pharmacological prediction are implemented to discover potential anti-cancer active GTs from G. lucidum. Nineteen GTs, three steroids, one cerebroside, and one thymidine were isolated from G. lucidum. Six GTs were first isolated from the fruiting bodies of G. lucidum, including 3?,7?,15?-trihydroxy-11,23-dioxo-lanost-8,16-dien-26-oic acid methyl ester (1), 3?,7?,15?-trihydroxy-11,23-dioxo-lanost-8,16-dien-26-oic acid (2), 3?,7?,15?,28-tetrahydroxy-11,23-dioxo-lanost-8,16-dien-26-oic acid (3), ganotropic acid (4), 26-nor-11,23-dioxo-5?-lanost-8-en-3?,7?,15?,25-tetrol (5) and (3?,7?)-dihydroxy-lanosta-8,24-dien- 11-one (6). (4E,8E)-N-d-2'-hydroxypalmitoyl-l-O-?-d-glucopyranosyl-9-methyl-4,8-spingodienine (7), and stigmasta-7,22-dien-3?,5?,6?-triol (8) were first reported from the genus Ganodema. By using reverse pharmacophoric profiling of the six GTs, thirty potential anti-cancer therapeutic targets were identified and utilized to construct their ingredient-target interaction network. Then nineteen high frequency targets of GTs were selected from thirty potential targets to construct a protein interaction network (PIN). In order to cluster the pharmacological activity of GTs, twelve function modules were identified by molecular complex detection (MCODE) and gene ontology (GO) enrichment analysis. The results indicated that anti-cancer effect of GTs might be related to histone acetylation and interphase of mitotic cell cycle by regulating general control non-derepressible 5 (GCN5) and cyclin-dependent kinase-2 (CDK2), respectively. This research mode of extraction, isolation, pharmacological prediction, and PIN analysis might be beneficial to rapidly predict and discover pharmacological activities of novel compounds.

| S-EPMC6273610 | biostudies-literature

Anti-inflammatory and Cytotoxic Triterpenes from the Rot Roots of Panax notoginseng.

Project description:Four new protopanaxatriol-type triterpenes (1-2) and glucosides (3-4), were isolated from the rot roots of Panax notoginseng (Burk.) Chen, along with four known ones (5-8). Their structures were elucidated on the basis of extensive spectroscopic analysis (HRESIMS, NMR, UV, IR, and OR) and acidic hydrolysis. The possible transformation pathway of these compounds were also speculated from ginsenoside Rg1. Compound 1, with a unique ?,?-unsaturated ketene in its side chain, showed significant inhibitory effects against NO production on Murine macrophage cells (IC50?=?4.12?±?0.20 ?M) and comparable cytotoxicities against five human cancer cell lines (myeloid leukemia HL-60, lung cancer A-549 cells, hepatocellular carcinoma SMMC7721, breast cancer MCF-7, and colon cancer SW480) to positive control, cisplatin (DDP).

| S-EPMC6646631 | 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