Deep Sea-derived Fungus Aspergillus Research Articles

Antitumor aspochalasin and antiviral benzofuran derivatives from a marine-derived fungus Aspergillus sp. SCSIO41032

Chemical investigation of the EtOAc extract of a deep-sea derived fungus Aspergillus sp. SCSIO41032 resulted in the isolation of ten known compounds, including eight aspochalasins. Their structures were elucidated by using extensive NMR spectroscopic, mass spectrometric and single crystal X-ray diffraction analysis. The detailed crystallographic data for structures 1, 2, and 4, along with the relative configurations of aspochalasin E (3) determined by its acetonide derivative were reported for the first time. The results of antitumor and antiviral activities showed that 3 displayed moderate antitumor activities against 22Rv1, PC-3, A549, and HCT-15 cell lines with IC50 values ranged from 5.9 ± 0.8 to 19.0 ± 7.7 μM, and 9 exhibited moderate antiviral activities against HSV-1/2 with EC50 values of 9.5 ± 0.5 and 5.4 ± 0.6 μM, respectively. Plate clone formation assays results indicated that 3 inhibited the 22Rv1, PC-3 cells growth in a dose-dependent manner.

Secondary metabolites from the deep-sea derived fungus Aspergillus terreus MCCC M28183.

Aspergillus fungi are renowned for producing a diverse range of natural products with promising biological activities. These include lovastatin, itaconic acid, terrin, and geodin, known for their cholesterol-regulating, anti-inflammatory, antitumor, and antibiotic properties. In our current study, we isolated three dimeric nitrophenyl trans-epoxyamides (1-3), along with fifteen known compounds (4-18), from the culture of Aspergillus terreus MCCC M28183, a deep-sea-derived fungus. The structures of compounds 1-3 were elucidated using a combination of NMR, MS, NMR calculation, and ECD calculation. Compound 1 exhibited moderate inhibitory activity against human gastric cancer cells MKN28, while compound 7 showed similar activity against MGC803 cells, with both showing IC50 values below 10 μM. Furthermore, compound 16 exhibited moderate potency against Vibrio parahaemolyticus ATCC 17802, with a minimum inhibitory concentration (MIC) value of 7.8 μg/mL. This promising research suggests potential avenues for developing new pharmaceuticals, particularly in targeting specific cancer cell lines and combating bacterial infections, leveraging the unique properties of these Aspergillus-derived compounds.

New cyclic dipeptide discovered from deep-sea derived Aspergillus sp. HDN20-1401

A new alkaloid named aspergilalkaloid A (1) with pyridoindole hydroxymethyl piperazine dione structure along with six known compounds 2-7 were isolated from deep-sea derived fungus Aspergillus sp. HDN20-1401. The structure including absolute configuration was elucidated by extensive NMR analyses, HRESIMS, ECD calculation, and theoretical NMR calculation with DP4+ analysis. All isolated compounds were tested for antimicrobial and anticancer activity. Aspergilalkaloid A (1) showed inhibitive activity against Bacillus cereus with MIC value of 12.5 μM and weak activity against MRCNS.

New Ophiobolins from the Deep-Sea Derived Fungus Aspergillus sp. WHU0154 and Their Anti-Inflammatory Effects.

Deep-sea fungi have become a new arsenal for the discovery of leading compounds. Here five new ophiobolins 1–5, together with six known analogues 6–11, obtained from a deep-sea derived fungus WHU0154. Their structures were determined by analyses of IR, HR-ESI-MS, and NMR spectra, along with experimental and calculated electronic circular dichroism (ECD) analysis. Pharmacological studies showed that compounds 4 and 6 exhibited obvious inhibitory effects on nitric oxide (NO) production induced by lipopolysaccharide (LPS) in murine macrophage RAW264.7 cells. Mechanical study revealed that compound 6 could inhibit the inducible nitric oxide synthase (iNOS) level in LPS-stimulated RAW264.7 cells. In addition, compounds 6, 9, and 10 could significantly inhibit the expression of cyclooxygenase 2 (COX 2) in LPS-induced RAW264.7 cells. Preliminary structure-activity relationship (SAR) analyses revealed that the aldehyde group at C-21 and the α, β-unsaturated ketone functionality at A ring in ophiobolins were vital for their anti-inflammatory effects. Together, the results demonstrated that ophiobolins, especially for compound 6, exhibited strong anti-inflammatory effects and shed light on the discovery of ophiobolins as new anti-inflammatory agents.

Bioactive secondary metabolites from the deep-sea derived fungus Aspergillus sp. SCSIO 41029.

Two new compounds classified as one new lumazine peptide, penilumamide K (1) and one new sesquiterpene (2), were obtained from the deep-sea derived fungus Aspergillus sp. SCSIO 41029, together with eleven known compounds (3-13). The structures of 1-13 including absolute configurations were determined by detailed NMR spectroscopy, HR-ESI-MS, chemical derivatization, and optical rotation data. Among them, compound 1 represents the first lumazine peptide reported from deep-sea derived fungus. The bioactive assay exhibited that compounds 1, 3, 4, 5, 7 and 10 had significant potency against α-glucosidase with IC50 values ranging from 18.61 to 109.06 μΜ. In addition, compounds 4 and 9 showed strong antibacterial activity against Staphylococcus aureus with MIC values of 0.78 and 6.25 μg ml-1, respectively.

A new steroid with 7β,8β-epoxidation from the deep sea-derived fungus Aspergillus penicillioides SD-311

7β,8β-epoxy-(22E,24R)-24-methylcholesta-4,22-diene-3,6-dione (1), a new steroid, along with five known analogues (2–6), was isolated from the deep sea-derived fungus, Aspergillus penicillioides SD-311. Strikingly, 1 possessed a rare 7,8-epoxidation moiety. Meanwhile, this is the first time to report natural products from this fungus species. The structures were established by extensive spectroscopic analysis. The absolute configuration was determined by X-ray diffraction experiments. Compound 1 showed antibacterial activity against Vibrio anguillarum with MIC value of 32.0 µg/mL, while 2 displayed inhibitions against Edwardsiella tarda and Micrococcus luteus with MIC values both of 16 µg/mL.

Antioxidant CPA-type indole alkaloids produced from the deep-sea derived fungus Aspergillus sp. SCSIO 41024

Twelve indole alkaloids, including α-cyclopiazonic acid (CPA) (1), nine 2-oxo indole CPA derivatives (2–10), and two open-ring indole CPA derivatives (11 and 12), were isolated from the fermentation broth of a deep-sea derived fungus Aspergillus sp. SCSIO 41024. Their structures and absolute configurations were elucidated mainly by using extensive NMR spectroscopic, mass spectrometric and single crystal X-ray diffraction analysis. To the best of our knowledge, the crystallographic data of 3 and 7 were firstly reported, and the absolute configuration of 3 was confirmed for the first time by the single crystal X-ray diffraction analysis. Most isolated compounds were tested for their antimicrobial, antitumor and radical scavenging activities. In addition, compounds 1, 2 and 11 showed moderate antioxidative activity against DPPH with IC50 values of 190.1, 31.9, 228.4 μg/mL, respectively.

Asperpentenone A, A novel polyketide isolated from the deep-sea derived fungus Aspergillus sp. SCSIO 41024

Asperpentenone A (1), a novel polyketide with a rare cyclopentenone-tetrahydrofuran moiety, was isolated along with eight known compounds (2–9) from the deep-sea derived fungus Aspergillus sp. SCSIO 41024. Their structures including absolute configurations were determined by extensive analysis of their spectroscopic analysis and X-ray crystallography. Biological evaluation results revealed that kojic acid (3) showed weak antibacterial activities against Bacillus thuringiensis and Acinetobacter baumannii with MIC values of 32 and 128 μg/mL, respectively. Furthermore, griseofamine A (9) exhibited weak antibacterial activity with an MIC value of 64 μg/mL against Escherichia coli. The results of antibacterial experiments and especially the large yield of kojic acid (3) indicated that kojic acid might represent a candidate precursor for the development of antimicrobial agents.

New quinoline alkaloid and bisabolane-type sesquiterpenoid derivatives from the deep-sea-derived fungus Aspergillus sp. SCSIO06786

One new quinoline alkaloid (1), two new bisabolane-type sesquiterpene derivatives (2 and 3), and a new natural product (4) along with ten known compounds (514) were isolated from the deep sea-derived fungus Aspergillus sp. SCSIO06786 which cultured on solid rice medium. Three new structures were elucidated by analysis of 1D/2D NMR data and HR-ESI-MS. The absolute configurations of 2 and 3 were established by comparison of the experimental and reported ECD values. Compounds 11–13 exhibited moderate selective inhibitory activities against the tested pathogenic bacteria with MIC values among 3.13–12.5 μg/mL.

Aspterrics A and B, New Sesquiterpenes from Deep Sea-derived Fungus Aspergillus terreus YPGA10

Aspterrics A and B, New Sesquiterpenes from Deep Sea-derived Fungus Aspergillus terreus YPGA10

Butenolide Derivatives with α-Glucosidase Inhibitions from the Deep-Sea-Derived Fungus Aspergillus terreus YPGA10.

Three new butenolide derivatives, namely aspernolides N–P (1–3), together with six known analogues (4–9), were isolated from the ethyl acetate (EtOAc) extract of the deep sea-derived fungus Aspergillus terreus YPGA10. The structures of compounds 1–3 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 and 2 were determined by comparisons of experimental electronic circular dichroism (ECD) with calculated ECD spectra. Compound 1 represents the rare example of Aspergillus-derived butenolide derivatives featured by a monosubstituted benzene ring. Compounds 6–9 exhibited remarkable inhibitory effects against α-glucosidase with IC50 values of 3.87, 1.37, 6.98, and 8.06 μM, respectively, being much more active than the positive control acarbose (190.2 μM).

Secondary metabolites isolated from the deep sea-derived fungus Aspergillus sydowii C1-S01-A7

Two novel compounds, 2-hydroxy-6-formyl-vertixanthone (1) and 12-O-acetyl-sydowinin A (2), were obtained from the culture of a deep sea-derived fungus Aspergillus sydowii C1-S01-A7, together with twenty-two known compounds (3–24). Their structures were elucidated based on extensive spectroscopic methods. Compounds 4, 8 and 12 showed antibacterial activities against Vibrio rotiferianus and Vibrio vulnificus. Compounds 1, 2, 7, 8, 11 and 12 exhibited antibacterial activity against methicillin-resistant Staphylococcus aureus. Remarkably, compound 8 displayed selectively cytotoxic activity against A549 and strongest cytotoxic activities for both A549 and HepG2 in comparison to the remaining compounds.

Bioactive Novel Indole Alkaloids and Steroids from Deep Sea-Derived Fungus Aspergillus fumigatus SCSIO 41012.

Two new alkaloids, fumigatosides E (1) and F (2), and a new natural product, 3, 7-diketo-cephalosporin P1 (6) along with five known compounds (3–5, 7, 8) were isolated from deep-sea derived fungal Aspergillus fumigatus SCSIO 41012. Their structures were determined by extensive spectroscopic data analysis, including 1D, 2D nuclear magnetic resonance (NMR) and mass spectrometry (MS), and comparison between the calculated and experimental electronic circular dichroism (ECD) spectra. In addition, all compounds were tested for antibacterial and antifungal inhibitory activities. Compound 1 showed significant antifungal activity against Fusarium oxysporum f. sp. momordicae with MIC at 1.56 µg/mL. Compound 4 exhibited significant higher activity against S. aureus (16,339 and 29,213) with MIC values of 1.56 and 0.78 µg/mL, respectively, and compound 2 exhibited significant activity against A. baumanii ATCC 19606 with a MIC value of 6.25 µg/mL.

Antituberculosis compounds from a deep-sea-derived fungus Aspergillus sp. SCSIO Ind09F01

Eleven diketopiperazine and fumiquinazoline alkaloids (1–11) together with a tetracyclic triterpenoid helvolic acid (12) were obtained from the cultures of a deep-sea derived fungus Aspergillus sp. SCSIO Ind09F01. The structures of these compounds (1–12) were determined mainly by the extensive NMR, ESIMS spectra data and by comparison with previously described compounds. Besides, anti-tuberculosis, cytotoxic, antibacterial, COX-2 inhibitory and antiviral activities of these compounds were evaluated. Gliotoxin (3), 12,13-dihydroxy-fumitremorgin C (11) and helvolic acid (12) exhibited very strong anti-tuberculosis activity towards Mycobacterium tuberculosis with the prominent MIC50 values of <0.03, 2.41 and 0.894 μM, respectively, which was here reported for the first time. Meanwhile gliotoxin also displayed significant selective cytotoxicities against K562, A549 and Huh-7 cell lines with the IC50 values of 0.191, 0.015 and 95.4 μM, respectively.

20-Nor-isopimarane cycloethers from the deep-sea sediment-derived fungus Aspergillus wentii SD-310

Five new 20-nor-isopimaranes, asperethers A–E (1–5), were isolated from the deep-sea derived fungus Aspergillus wentii SD-310. These compounds possess a unique 6/6/6/5 tetracyclic system and exhibited cytotoxicity against several tumor cell lines.

Westerdijkin A, a new hydroxyphenylacetic acid derivative from deep sea fungus Aspergillus westerdijkiae SCSIO 05233

A new methyl 2-(4-((2-hydroxy-3-methylbut-3-en-1-yl)oxy)phenyl) acetate 1, together with five known compounds 2–6, was isolated from the culture of the deep sea-derived fungus Aspergillus westerdijkiae SCSIO 05233. The new structure was determined by NMR (1H and 13C NMR, HSQC, HMBC and MS) and optical rotation analysis. Compound 5 displayed weak inhibitory activities towards K562 and promyelocytic HL-60 with IC50 values of 25.8 and 44.9 μM, and compound 6 showed strong antifouling activity with EC50 value 8.81 μg/mL.

Secondary metabolites of a deep sea derived fungus Aspergillus versicolor CXCTD-06-6a and their bioactivity

In order to obtain novel secondary metabolites, a deep sea inhabiting fungus Aspergillus versicolor CXCTD-06-6a was investigated. One new diketopiperazine brevianamide W (1a), as well as five known diketopiperazine alkaloids, diketopiperazine V (1b), brevianamide Q (2), brevianamide R (3), brevianamide K (4), and brevianamide E (5), were isolated from the EtOAc extract of the fermentation broth. Their structures were elucidated by spectroscopy techniques (NMR, MS). The six compounds exhibited moderate radical scavenging activity against DPPH with clearance ratio of 55.0% (1a and 1b), 53.7% (2), 46.2% (3), 61.4% (4) and 19.3% (5) at a concentration of 13.9 μmol L−1, respectively; while the positive control ascorbic acid showed a ratio of 70.3% at the concentration of 28.4 μmol L−1.