Browse
Submit Data
Databases
API
Help

Dataset Information

0 Views

0 Connections

0 Citations

0 Reanalyses

0 Downloads

Omics score: 0

A New Macrodiolide and Two New Polycyclic Chromones from the Fungus Penicillium sp. SCSIO041218.

ABSTRACT: A new macrodiolide, mangrovlide A (1) and two new polycyclic chromones, penixanthones C (2) and D (3), as well as four other known compounds (4-7), have been isolated from the mangrove sediment derived fungus Penicillium sp. SCSIO041218, cultured in the 0.25% NaCl rice substrate. The structures of the new compounds were determined by analysis of the NMR and MS spectroscopic data. Compound 1 possesses a 10-membered macrodiolide unit, while 2 and 3 are chromones with an unprecedented 6/6/6/5 polycyclic skeleton. Compounds 1-7 were evaluated for their cytotoxicities, while all the compounds displayed weak or no activity.

SUBMITTER: Huang J

PROVIDER: S-EPMC6539008 | biostudies-other | 2019 Apr

REPOSITORIES: biostudies-other

ACCESS DATA

Json Xml

Publications

A New Macrodiolide and Two New Polycyclic Chromones from the Fungus Penicillium sp. SCSIO041218.

Huang Jingxia J She Jianglian J Yang Xiliang X Liu Juan J Zhou Xuefeng X Yang Bin B

Molecules (Basel, Switzerland) 20190430 9

A new macrodiolide, mangrovlide A (1) and two new polycyclic chromones, penixanthones C (2) and D (3), as well as four other known compounds (4-7), have been isolated from the mangrove sediment derived fungus Penicillium sp. SCSIO041218, cultured in the 0.25% NaCl rice substrate. The structures of the new compounds were determined by analysis of the NMR and MS spectroscopic data. Compound 1 possesses a 10-membered macrodiolide unit, while 2 ...[more]

PMID: 31052174

Similar Datasets

New Andrastin-Type Meroterpenoids from the Marine-Derived Fungus Penicillium sp.

Project description:Three new andrastin-type meroterpenoids penimeroterpenoids A-C (1-3) together with two known analogs (4 and 5) were isolated from the cultures of the marine-derived Penicillium species (sp.). The structures of the new compounds were elucidated on the basis of 1- and 2-dimensional (1D/2D) Nuclear Magnetic Resonance (NMR) spectroscopic and mass spectrometric analysis. The absolute configurations of 1-3 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra. Compound 1 showed moderate cytotoxicity against A549, HCT116, and SW480 cell lines.

| S-EPMC8066695 | biostudies-literature

Two New Alkaloids and a New Butenolide Derivative from the Beibu Gulf Sponge-Derived Fungus Penicillium sp. SCSIO 41413.

Project description:Marine sponge-derived fungi have been proven to be a prolific source of bioactive natural products. Two new alkaloids, polonimides E (1) and D (2), and a new butenolide derivative, eutypoid F (11), were isolated from the Beibu Gulf sponge-derived fungus, Penicillium sp. SCSIO 41413, together with thirteen known compounds (3-10, 12-16). Their structures were determined by detailed NMR, MS spectroscopic analyses, and electronic circular dichroism (ECD) analyses. Butenolide derivatives 11 and 12 exhibited inhibitory effect against the enzyme PI3K with IC50 values of 1.7 μM and 9.8 μM, respectively. The molecular docking was also performed to understand the inhibitory activity, while 11 and 12 showed obvious protein/ligand-binding effects to the PI3K protein. Moreover, 4 and 15 displayed obvious inhibitory activity against LPS-induced NF-κB activation in RAW264.7 cells at 10 µM.

| S-EPMC9864330 | biostudies-literature

Four New Insecticidal Xanthene Derivatives from the Mangrove-Derived Fungus Penicillium sp. JY246.

Project description:Four new xanthene derivatives, penicixanthenes A-D (1-4), and one known compound 5 were isolated from a marine mangrove endophytic fungus Penicillium sp. JY246 that was obtained from the stem of Ceriops tagal. Their structures were determined by detailed NMR, MS spectroscopic data, modified Mosher's method, and calculated electronic circular dichroism data. All of the isolated compounds were examined for insecticidal activity. Compounds 2 and 3 showed growth inhibition activity against newly hatched larvae of Helicoverpa armigera Hubner with the IC50 values 100 and 200 μg/mL, respectively, and compounds 1, 3, and 4 showed insecticidal activity against newly hatched larvae of Culex quinquefasciatus with LC50 values of 38.5 (±1.16), 11.6 (±0.58), and 20.5 (±1) μg/mL, respectively. The four xanthene derivatives have the potential to be developed as new biopesticides.

| S-EPMC6950184 | biostudies-literature

New Alkaloids and Polyketides from the Marine Sponge-Derived Fungus Penicillium sp. SCSIO41015.

Project description:The sponge-derived fungus Penicillium sp. SCSIO41015 cultured on solid rice medium yielded twenty-one compounds (1-21), including two new alkaloids (1 and 2) and one new pyrone derivative (3). Their structures were elucidated by analysis of 1D/2D NMR data and HR-ESI-MS. Their absolute configurations were established by single-crystal X-ray diffraction analysis and comparison of the experimental with reported specific rotation values. Compound 16 exhibited selective cytotoxic activity against the human gastric cancer cells MGC803, with IC50 value of 5.19 μM. Compounds 9 and 18 showed weak antibacterial activity against Staphylococcus aureus and Acinetobacter baumannii, respectively, both with MIC values of 57 μg/mL. Furthermore, compound 16 displayed potent antibacterial activity against S. aureus with an MIC value of 3.75 μg/mL.

| S-EPMC6669684 | biostudies-literature

A New Breviane Spiroditerpenoid from the Marine-Derived Fungus Penicillium sp. TJ403-1.

Project description:Marine-derived fungi are a promising and untapped reservoir for discovering structurally interesting and pharmacologically active natural products. In our efforts to identify novel bioactive compounds from marine-derived fungi, four breviane spiroditerpenoids, including a new compound, brevione O (1), and three known compounds breviones I (2), J (3), and H (4), together with a known diketopiperazine alkaloid brevicompanine G (5), were isolated and identified from an ethyl acetate extract of the fermented rice substrate of the coral-derived fungus Penicillium sp. TJ403-1. The absolute structure of 1 was elucidated by HRESIMS, one- and two-dimensional NMR spectroscopic data, and a comparison of its electronic circular dichroism (ECD) spectrum with the literature. Moreover, we confirmed the absolute configuration of 5 by single-crystal X-ray crystallography. All the isolated compounds were evaluated for isocitrate dehydrogenase 1 (IDH1) inhibitory activity and cytotoxicity, and compound 2 showed significant inhibitory activities against HL-60, A-549, and HEP3B tumor cell lines with IC50 values of 4.92 ± 0.65, 8.60 ± 1.36, and 5.50 ± 0.67 µM, respectively.

| S-EPMC5923397 | biostudies-literature

Two new chroman derivations from the endophytic Penicillium sp. DCS523.

Project description:Strain DCS523 was isolated from the branch tissue of Daphniphyllum longeracemosum and determined to be a Penicillium sp. according to the ITS sequence analysis. The extracts from the PDA solid fermentation media of Penicillium sp. DCS523 were purified to give two new chroman derivatives as well as six known compounds. Based on their spectral data the new compounds were identified as (Z)-6-acetyl- 3-(1,2-dihydroxypropylidene)-5-hydroxy-8-methylchroman-2-one and 6-acetyl-2?,5- dihydroxy-2-(2-hydroxypropyl)- 3?,8-dimethylchroman, respectively.

| S-EPMC6259220 | 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

New Eudesmane-Type Sesquiterpenoids from the Mangrove-Derived Endophytic Fungus Penicillium sp. J-54.

Project description:Four new eudesmane-type sesquiterpenoids, penicieudesmol A-D (1-4), were isolated from the fermentation broth of the mangrove-derived endophytic fungus Penicillium sp. J-54. Their structures were determined by spectroscopic methods, the in situ dimolybdenum CD method, and modified Mosher's method. The bioassays results showed that 2 exhibited weak cytotoxicity against K-562 cells.

| S-EPMC5923395 | biostudies-literature

New Antiproliferative Compounds against Glioma Cells from the Marine-Sourced Fungus Penicillium sp. ZZ1750.

Project description:Seven novel compounds, namely peniresorcinosides A-E (1-5), penidifarnesylin A (6), and penipyridinone A (7), together with the 11 known ones 8-17, were isolated from a culture of the marine-associated fungus Penicillium sp. ZZ1750 in rice medium. The structures of the new compounds were established based on their high-resolution electrospray ionization mass spectroscopy (HRESIMS) data, extensive nuclear magnetic resonance (NMR) spectroscopic analyses, chemical degradation, Mosher's method, 13C-NMR calculations, electronic circular dichroism (ECD) calculations, and single crystal X-ray diffraction. Peniresorcinosides A (1) and B (2) are rare glycosylated alkylresorcinols and exhibited potent antiglioma activity, with IC50 values of 4.0 and 5.6 µM for U87MG cells and 14.1 and 9.8 µM for U251 cells, respectively.

| S-EPMC8465473 | biostudies-literature

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

Project description: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.

| S-EPMC5450543 | biostudies-literature