Browse
Submit Data
Databases
API
Help

Dataset Information

19 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

Three New Indole Diterpenoids from the Sea-Anemone-Derived Fungus Penicillium sp. AS-79.

ABSTRACT: Three new indolediterpenoids, namely, 22-hydroxylshearinine F (1), 6-hydroxylpaspalinine (2), and 7-O-acetylemindole SB (3), along with eight related known analogs (4-11), were isolated from the sea-anemone-derived fungus Penicillium sp. AS-79. The structures and relative configurations of these compounds were determined by a detailed interpretation of the spectroscopic data, and their absolute configurations were determined by ECD calculations (1 and 2) and single-crystal X-ray diffraction (3). Some of these compounds exhibited prominent activity against aquatic and human pathogenic microbes.

SUBMITTER: Hu XY

PROVIDER: S-EPMC5450543 | biostudies-literature | 2017 May

REPOSITORIES: biostudies-literature

ACCESS DATA

Json Xml

Publications

Three New Indole Diterpenoids from the Sea-Anemone-Derived Fungus Penicillium sp. AS-79.

Hu Xue-Yi XY Meng Ling-Hong LH Li Xin X Yang Sui-Qun SQ Li Xiao-Ming XM Wang Bin-Gui BG

Marine drugs 20170512 5

Three new indolediterpenoids, namely, 22-hydroxylshearinine F (1), 6-hydroxylpaspalinine (2), and 7-O-acetylemindole SB (3), along with eight related known analogs (4-11), were isolated from the sea-anemone-derived fungus Penicillium sp. AS-79. The structures and relative configurations of these compounds were determined by a detailed interpretation of the spectroscopic data, and their absolute configurations were determined by ECD calculations (< ...[more]

PMID: 28498358

Similar Datasets

Cytotoxic Indole-Diterpenoids from the Marine-Derived Fungus Penicillium sp. KFD28.

Project description:Four new indole-diterpenoids, named penerpenes K-N (1-4), along with twelve known ones (5-16), were isolated from the fermentation broth produced by adding L-tryptophan to the culture medium of the marine-derived fungus Penicillium sp. KFD28. The structures of the new compounds were elucidated extensively by 1D and 2D NMR, HRESIMS data spectroscopic analyses and ECD calculations. Compound 4 represents the second example of paxilline-type indole diterpene bearing a 1,3-dioxepane ring. Three compounds (4, 9, and 15) were cytotoxic to cancer cell lines, of which compound 9 was the most active and showed cytotoxic activity against the human liver cancer cell line BeL-7402 with an IC50 value of 5.3 μM. Moreover, six compounds (5, 7, 10, 12, 14, and 15) showed antibacterial activities against Staphylococcus aureus ATCC 6538 and Bacillus subtilis ATCC 6633.

| S-EPMC8619218 | biostudies-literature

Anti-Vibrio Indole-Diterpenoids and C-25 Epimeric Steroids From the Marine-Derived Fungus Penicillium janthinellum.

Project description:A systematic chemical exploration of the marine-derived fungus Penicillium janthinellum led to the isolation of four indole-diterpenoid derivatives (1-4), including new penijanthines C and D (1 and 2), and a pair of new steroidal epimers, penijanthoids A and B (5 and 6). The calculated ECD spectra and Snatzke's method for the new compound 1 were carried out to determine its absolute configuration. The absolute configuration of 3 was established by X-ray diffraction and calculated ECD methods for the first time. DP4plus approach was used to elucidate the absolute configurations of the C-25 epimeric steroids 5 and 6. 25-Epimeric 5 and 6 represent the first examples of steroids forming a five-membered lactone between C-23 and C-27 from marine fungi. Compounds 1, 2, 5, and 6 displayed significant anti-Vibrio activity (Minimum inhibitory concentration, MIC values ranging from 3.1 to 50.0 μM) against three pathogenic Vibrio spp.

| S-EPMC6413715 | biostudies-literature

Peniginsengins B?E, New Farnesylcyclohexenones from the Deep Sea-Derived Fungus Penicillium sp. YPGA11.

Project description:Chemical examination of the EtOAc extract of the deep sea-derived fungus Penicillium sp. YPGA11 resulted in the isolation of four new farnesylcyclohexenones, peniginsengins B?E (1?4), and a known analog peniginsengin A (5). The structures of compounds 1?4 were determined on the basis of comprehensive analyses of the nuclear magnetic resonance (NMR) and mass spectroscopy (MS) data, and the absolute configurations of 1, 2, and 4 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compounds 1?5, characterized by a highly oxygenated 1-methylcyclohexene unit and a (4E,8E)-4,8-dimethyldeca-4,8-dienoic acid side chain, are rarely found in nature. Compounds 2?4 exhibited antibacterial activity against Staphylococcus aureus.

| S-EPMC6213461 | biostudies-literature

Xanthones and Quinolones Derivatives Produced by the Deep-Sea-Derived Fungus Penicillium sp. SCSIO Ind16F01.

Project description:Chemical investigation of the fungus Penicillium sp. SCSIO Ind16F01 derived from deep-sea sediment sample afforded a new xanthone, 3,8-dihydroxy-2-methyl-9-oxoxanthene-4-carboxylic acid methyl ester (1) and a new chromone, coniochaetone J (2), together with three known xanthones, 8-hydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ester (3), 7,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylic acid methyl ester (4), 1,6,8-trihydroxy-3-(hydroxymethyl)anthraquinone (5), three known chromones, coniochaetone B (6), citrinolactones B (7), epiremisporine B (8), and four reported rare class of N-methyl quinolone lactams: quinolactacins B (9), C1 (10), and C2 (11), and quinolonimide (12). The structures of new compounds were determined by analysis of the NMR and MS spectroscopic data. Those isolated compounds were evaluated for their antiviral (EV71 and H3N2) and cytotoxic activities.

| S-EPMC6149711 | biostudies-literature

Phenalenones from a Marine-Derived Fungus Penicillium Sp.

Project description:Six new phenalenone derivatives (1?6), along with five known compounds (7?11) of the herqueinone class, were isolated from a marine-derived fungus Penicillium sp. The absolute configurations of these compounds were assigned based on chemical modifications and their specific rotations. 4-Hydroxysclerodin (6) and an acetone adduct of a triketone (7) exhibited moderate anti-angiogenetic and anti-inflammatory activities, respectively, while ent-peniciherqueinone (1) and isoherqueinone (9) exhibited moderate abilities to induce adipogenesis without cytotoxicity.

| S-EPMC6470642 | biostudies-literature

Four new chloro-eremophilane sesquiterpenes from an Antarctic deep-sea derived fungus, Penicillium sp. PR19N-1.

Project description:A new chloro-trinoreremophilane sesquiterpene 1, three new chlorinated eremophilane sesquiterpenes 2-4, together with a known compound, eremofortine C (5), were isolated from an Antarctic deep-sea derived fungus, Penicillium sp. PR19N-1. Structures were established using IR, HRMS, 1D and 2D NMR techniques. In addition, the plausible metabolic network of these isolated products is proposed. Compound 1 showed moderate cytotoxic activity against HL-60 and A549 cancer cell lines.

| S-EPMC3705411 | biostudies-literature

Antibacterial Polyketides from Antarctica Sponge-Derived Fungus Penicillium sp. HDN151272.

Project description:Three new polyketides, ketidocillinones A-C (1-3), were discovered from the extract of an Antarctica sponge-derived fungus Penicillium sp. HDN151272. All the structures were deduced by spectroscopic data, including NMR and HRESIMS. The absolute configuration of compound 3 was established by using ECD calculation. Compounds 1-3 can be slowly oxidized to quinone form when exposed to air. Ketidocillinones B and C (2 and 3) exhibited potent antibacterial activity against Pseudomonas aeurigenosa, Mycobacterium phlei, and MRCNS (methicillin-resistant coagulase-negative staphylococci) with MIC values ranging from 1.56 to 25.00 µg/mL.

| S-EPMC7073682 | biostudies-literature

Three New Quinazoline-Containing Indole Alkaloids From the Marine-Derived Fungus Aspergillus sp. HNMF114.

Project description:By feeding tryptophan to the marine-derived fungus Aspergillus sp. HNMF114 from the bivalve mollusk Sanguinolaria chinensis, 3 new quinazoline-containing indole alkaloids, named aspertoryadins H-J (1-3), along with 16 known ones (4-19), were obtained. The structures of the new compounds were elucidated by the analysis of spectroscopic data combined with quantum chemical calculations of nuclear magnetic resonance (NMR) chemical shifts and electron capture detector (ECD) spectra. Structurally, compound 3 represents the first example of this type of compound, bearing an amide group at C-3. Compounds 10 and 16 showed potent α-glucosidase inhibitory activity with IC50 values of 7.18 and 5.29 μM, and compounds 13 and 14 showed a clear activation effect on the ryanodine receptor from Spodoptera frugiperda (sfRyR), which reduced the [Ca2+] ER by 37.1 and 36.2%, respectively.

| S-EPMC8206283 | biostudies-literature

Bioactive Lactones from the Mangrove-Derived Fungus Penicillium sp. TGM112.

Project description:Three new lactones penicilactones A-C (1-3) were obtained from the mangrove-derived fungus Penicillium sp. TGM112. Their structures and absolute configurations were determined by detailed NMR, MS spectroscopic data, Mo2(OAc)4-induced electronic circular dichroism (ECD), and circular dichroism (CD) spectroscopy. Compound 1 showed antibacterial activity against Staphylococcus aureus with an MIC value of 6.25 ?g/mL. Compound 2 showed insecticidal activity against newly hatched larvae of Culex quinquefasciatus with the LC50 value of 78.5 (±0.58) ?g/mL.

| S-EPMC6722761 | biostudies-literature

Bioactive Metabolites from the Mariana Trench Sediment-Derived Fungus Penicillium sp. SY2107.

Project description:Mariana Trench sediments are enriched in microorganisms, however, the structures and bioactivities of their secondary metabolites are not very known. In this study, a fungus Penicillium sp. SY2107 was isolated from a sample of Mariana Trench sediment collected at a depth of 11000 m and an extract prepared from the culture of this fungus in rice medium showed antimicrobial activities. Chemical investigation on this active extract led to the isolation of 16 compounds, including one novel meroterpenoid, named andrastone C. Structure of the new compound was elucidated based on high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses and a single crystal X-ray diffraction. The crystal structure of a known meroterpenoid andrastone B was also reported in this study. Both andrastones B and C exhibited antimicrobial activities against methicillin-resistant Staphylococcus aureus (MRSA), Escherichia coli, and Candida albicans with minimum inhibitory concentration (MIC) values in a range from 6 to 13 g/mL.

| S-EPMC7281598 | biostudies-literature

OmicsDI is part of the ELIXIR infrastructure

OmicsDI is an Elixir interoperability service. Learn more ›

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