Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Tetra-, penta-, and hexa-nor-lanostane triterpenes from the medicinal fungus Ganoderma australe.

ABSTRACT: Chemical investigation on the medicinal fungus Ganoderma australe led to the identification of ten new nor-lanostane triterpenes, namely two hexa-nor ones, ganoaustratetraenones A (1) and B (2), five penta-nor ones, ganoaustraldehydes A-E (3-7), and three tetra-nor ones ganoaustrenoic acids A-C (8-10). The chemical structures along with the absolute configurations were determined by extensive spectroscopic analysis of 1D & 2D NMR and HRESIMS data. The postulated biosynthesis pathways of these compounds were proposed. Ganoaustraldehydes A (3) and B (4) showed moderate inhibition against nitric oxide production in RAW264.7 macrophage cells with the respective IC₅₀ values of 32.5, 34.2 µM (the IC₅₀ of positive control pyrrolidine dithiocarbamate was 20.0 µM).

SUBMITTER: Zhou L

PROVIDER: S-EPMC9378796 | biostudies-literature | 2022 Aug

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Tetra-, penta-, and hexa-nor-lanostane triterpenes from the medicinal fungus Ganoderma australe.

Zhou Lin L Akbar Subiy S Wang Meng-Xi MX Chen He-Ping HP Liu Ji-Kai JK

Natural products and bioprospecting 20220816 1

Chemical investigation on the medicinal fungus Ganoderma australe led to the identification of ten new nor-lanostane triterpenes, namely two hexa-nor ones, ganoaustratetraenones A (1) and B (2), five penta-nor ones, ganoaustraldehydes A-E (3-7), and three tetra-nor ones ganoaustrenoic acids A-C (8-10). The chemical structures along with the absolute configurations were determined by extensive spectroscopic analysis of 1D & 2D NMR and HRESIMS data. The postulated biosynthesis pathways of these co ...[more]

PMID: 35970939

Similar Datasets

[20(22)E]-Lanostane Triterpenes from the Fungus Ganoderma australe.

Project description:Twelve new lanostane triterpenoids (1-5, 7-13) were isolated from the fruiting bodies of the fungus Ganoderma australe. The structures of the new compounds were elucidated by extensive 1D and 2D NMR, and HRESIMS spectroscopic analysis. All the triterpenes are featured by 20(22)E configurations which are uncommon in the Ganoderma triterpene family. The absolute configuration of the C-25 of compounds 1, 2, and 6 were determined by the phenylglycine methyl ester (PGME) method. A postulated biosynthetic pathway for compound 1 was discussed. This study opens new insights into the secondary metabolites of the chemically underinvestigated fungus G. australe.

| S-EPMC9145439 | biostudies-literature

Ganoaustralins A and B, Unusual Aromatic Triterpenes from the Mushroom Ganoderma australe.

Project description:Two triterpenes, ganoaustralins A (1) and B (2), featuring unprecedented 6/6/6/5/6 scaffolds were isolated from the fruiting bodies of the mushroom Ganoderma australe. The structures were determined by extensive NMR and HRESIMS spectroscopic analysis. The absolute configuration of the C-25 in ganoaustralin A was assigned by the phenylglycine methyl ester (PGME) method. The relative and absolute configurations of the polycyclic backbones were determined by NMR and ECD calculations, respectively. The plausible biosynthetic pathways of ganoaustralins A and B were proposed. Ganoaustralin B showed weak inhibition against β-secretase 1.

| S-EPMC9785556 | biostudies-literature

Anti-Adipogenic Lanostane-Type Triterpenoids from the Edible and Medicinal Mushroom Ganoderma applanatum.

Project description:Our previous research has shown that lanostane triterpenoids from Ganoderma applanatum exhibit significant anti-adipogenesis effects. In order to obtain more structurally diverse lanostane triterpenoids to establish a structure-activity relationship, we continued the study of lanostane triterpenoids from the fruiting bodies of G. applanatum, and forty highly oxygenated lanostane-type triterpenoinds (1-40), including sixteen new compounds (1-16), were isolated. Their structures were elucidated using NMR spectra, X-ray crystallographic analysis, and Mosher's method. In addition, some of their parts were evaluated to determine their anti-adipogenesis activities in the 3T3-L1 cell model. The results showed that compounds 16, 22, 28, and 32 exhibited stronger anti-adipogenesis effects than the positive control (LiCl, 20 mM) at the concentration of 20 μM. Compounds 15 and 20 could significantly reduce the lipid accumulation during the differentiation process of 3T3-L1 cells, comparable to the untreated group. Their IC50 values were 6.42 and 5.39 μM, respectively. The combined results of our previous and present studies allow us to establish a structure-activity relationship of lanostane triterpenoids, indicating that the A-seco-23→26 lactone skeleton could play a key role in anti-adipogenesis activity.

| S-EPMC9028577 | biostudies-literature

Lanostane Triterpenoids from Fruiting Bodies of Ganoderma leucocontextum.

Project description:Six new lanostane-type triterpenoids, namely leucocontextins S-X (1-6), together with twelve known compounds, were isolated from the fruiting bodies of Ganoderma leucocontextum. Their structures were established by MS and NMR data.

| S-EPMC4805654 | biostudies-literature

Semisynthetic modifications of antitubercular lanostane triterpenoids from Ganoderma.

Project description:Antitubercular lanostane triterpenoids isolated from mycelial cultures of the basidiomycete Ganoderma australe were structurally modified by semisynthesis. One of the synthetic compounds, named GA003 (9), showed more potent activity against Mycobacterium tuberculosis H37Ra than the lead natural lanostane (1). GA003 was also significantly active against the virulent strain (H37Rv) as well as extensively drug-resistant tuberculosis strains.

| S-EPMC8113785 | biostudies-literature

Dicarbon-yl(hexa-methyl-ene-1,3,5,7-tetra-mine-κN(1))(η(5)-penta-methyl-cyclo-penta-dien-yl)iron(II) tetra-fluoridoborate.

Project description:In the title compound, [Fe(C(10)H(15))(C(6)H(12)N(4))(CO)(2)]BF(4), the arrangement around the Fe(II) atom corresponds to a three-legged piano stool. The penta-methyl-cyclo-penta-dienyl (Cp*) ligand occupies three coordination sites, while two CO ligands and one N atom of the hexa-methyl-ene-tetra-mine ligand occupy the remaining coordination sites, completing a pseudo-octahedral geometry. Both the complex cation and the BF(4) (-) anion reside on crystallographic mirror planes. The Fe-N bond length is 2.069 (2) and the Fe-Cp*(centroid) distance is 1.7452 (3) Å.

| S-EPMC3393194 | biostudies-literature

Tetra-kis(1,3,4,6,7,9-hexa-aza-1H-phen-alen-6-ium) sodium(I) penta-kis(tetra-fluorido-borate).

Project description:In the title compound, Na(+)·4C(7)H(5)N(6) (+)·5BF(4) (-), the Na(+) ion lies on a fourfold rotation axis and one of the tetra-fluoridoborate ions lies on a site of symmetry . Each Na(+) ion is surrounded by four symmetry-related tetra-fluoridoborate ions, and is eight-coordinated by F atoms, the Na⋯F separation being 2.3956 (15) or 2.4347 (17) Å. The hexa-azaphenalenium ring system is essentially planar. In the crystal structure, the cations and anions are linked into a three-dimensional network by N-H⋯N and C-H⋯F hydrogen bonds.

| S-EPMC2959227 | biostudies-literature

Tris(3,4,7,8-tetra-methyl-1,10-phenanthrolin-1-ium) hexa-cyanidocobaltate(III) penta-hydrate.

Project description:The structure of the title compound, (C16H17N2)3[Co(CN)6]·5H2O, consists of three 3,4,7,8-tetra-methyl-1,10-phenanthrolin-1-ium cations, a [Co(CN)6](3-) anion and five water mol-ecules of crystallization, one of which is disordered over two sets of sites in a 0.587 (15):0.413 (15) ratio. The [Co(CN)6](3-) anion exhibits an octa-hedral geometry. In the structure, cations and anions are linked alternatively through O-H⋯O, O-H⋯N, N-H⋯O and N-H⋯N hydrogen bonds, π-π inter-actions [centroid-centroid distances = 3.523 (2)-4.099 (2) Å] and van der Waals forces, forming a three-dimensional supra-molecular network.

| S-EPMC3588511 | biostudies-literature

Characteristics of the Genome, Transcriptome and Ganoderic Acid of the Medicinal Fungus Ganoderma lingzhi.

Project description:Ganoderma (Ganodermaceae) is a genus of edible and medicinal mushrooms that create a diverse set of bioactive compounds. Ganoderma lingzhi has been famous in China for more than 2000 years for its medicinal properties. However, the genome information of G. lingzhi has not been characterized. Here, we characterized its 49.15-Mb genome, encoding 13,125 predicted genes which were sequenced by the Illumina and PacBio platform. A wide spectrum of carbohydrate-active enzymes, with a total number of 519 CAZymes were identified in G. lingzhi. Then, the genes involved in sexual recognition and ganoderic acid (GA, key bioactive metabolite) biosynthesis were characterized. In addition, we identified and deduced the possible structures of 20 main GA constituents by UPLC-ESI-MS/MS, including a new special ganochlearic acid A. Furthermore, 3996 novel transcripts were discovered, and 9276 genes were predicted to have the possibility of alternative splicing from RNA-Seq data. The alternative splicing genes were enriched for functional categories involved in protein processing, endocytosis, and metabolic activities by KEGG. These genomic, transcriptomic, and GA constituents’ resources would enrich the toolbox for biological, genetic, and secondary metabolic pathways studies in G. lingzhi.

| S-EPMC9784716 | biostudies-literature

Chromosome-level genome map provides insights into diverse defense mechanisms in the medicinal fungus Ganoderma sinense.

Project description:Fungi have evolved powerful genomic and chemical defense systems to protect themselves against genetic destabilization and other organisms. However, the precise molecular basis involved in fungal defense remain largely unknown in Basidiomycetes. Here the complete genome sequence, as well as DNA methylation patterns and small RNA transcriptomes, was analyzed to provide a holistic overview of secondary metabolism and defense processes in the model medicinal fungus, Ganoderma sinense. We reported the 48.96 Mb genome sequence of G. sinense, consisting of 12 chromosomes and encoding 15,688 genes. More than thirty gene clusters involved in the biosynthesis of secondary metabolites, as well as a large array of genes responsible for their transport and regulation were highlighted. In addition, components of genome defense mechanisms, namely repeat-induced point mutation (RIP), DNA methylation and small RNA-mediated gene silencing, were revealed in G. sinense. Systematic bioinformatic investigation of the genome and methylome suggested that RIP and DNA methylation combinatorially maintain G. sinense genome stability by inactivating invasive genetic material and transposable elements. The elucidation of the G. sinense genome and epigenome provides an unparalleled opportunity to advance our understanding of secondary metabolism and fungal defense mechanisms.

| S-EPMC4457147 | 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