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During the search for natural fungicides, 14 new australifungin analogues cladrioides A-S ( 1 - 14 ) and two known ones ( 15 and 16 ) were obtained from Cladosporium cladosporioides LD-8. Their structures were elucidated by comprehensive analysis of NMR and HRESIMS data, as well as ECD calculations. Compounds 1 and 2 possess a novel 6/6/5-fused tricyclic scaffold. Most of the compounds exhibited remarkable antifungal activities against the tested phytopathogenic fungi. Among them, compounds 7 , 10 , and 16 showed excellent activities with IC 50 values ranging from 1.71 to 16.63 μg/mL. Their inhibitory activities against A . brassicicola and A . alternata were higher than that of the commercial fungicide hymexazol. Compound 16 displayed potent in vivo antifungal activity against A . solani at 100 μg/mL with an inhibitory rate of 96.82%. The structure-activity relationship of antifungal australifungin analogues was analyzed for the first time. Therefore, our study provides promising candidates for the development of new fungicides for plant protection.

Four new compounds, including one drimane sesquiterpene lactone (1), one isocoumarin (2), one coumarin (3), and a new natural product (4), as well as fourteen known compounds were obtained from a deep-sea derived Cladosporium sp. SCSIO 41318. The structures of the new compounds were determined using extensive NMR and HRESIMS spectroscopic analysis, electronic circular dichroism calculations, and single-crystal X-ray diffraction measurements. Biological assays showed that compounds (1, 6, 7, 9-12, 14, 15, 17, 18) exhibited varying degrees of antimicrobial activity against the tested human pathogenic bacteria and plant pathogenic fungi. Besides, penicitrinone A (11) and penicitrinol A (12) displayed weak antitumor activities against the 22Rv1 cell line., (© 2024 Wiley-VHCA AG, Zurich, Switzerland.)

A new cladosporol derivative xylophilum A ( 1 ), together with 10 known compounds ( 2 - 11 ), were isolated from the rice fermentation of the fungus Cladosporium xylophilum . Their structures were established by extensive spectroscopic methods and comparison of their NMR data with literatures. The antimicrobial activity of compound 1 against 11 kinds of pathogenic microbial was evaluated, but no significant activity was found (MIC >100 μg/ml).

Fungal contamination poses a serious threat to public health and food safety because molds can grow under stressful conditions through melanin accumulation. Although ultraviolet (UV) irradiation is popular for inhibiting microorganisms, its effectiveness is limited by our insufficient knowledge about UV tolerance in melanin-accumulating molds. In this study, we first confirmed the protective effect of melanin by evaluating the UV sensitivity of young and mature spores. Additionally, we compared UV sensitivity between spores with accumulated melanin and spores prepared with melanin biosynthesis inhibitors. We found that mature spores were less UV-sensitive than young spores, and that reduced melanin accumulation by inhibitors led to reduced UV sensitivity. These results suggest that melanin protects cells against UV irradiation. To determine the most effective wavelength for inhibition, we evaluated the wavelength dependence of UV tolerance in a yeast (Rhodotorula mucilaginosa) and in molds (Aspergillus fumigatus, Cladosporium halotolerans, Cladosporium sphaerospermum, Aspergillus brasiliensis, Penicillium roqueforti, and Botrytis cinerea). We assessed UV tolerance using a UV-light emitting diode (LED) irradiation system with 13 wavelength-ranked LEDs between 250 and 365 nm, a krypton chlorine (KrCl) excimer lamp device, and a low pressure (LP) Hg lamp device. The inhibition of fungi peaked at around 270 nm, and most molds showed reduced UV sensitivity at shorter wavelengths as they accumulated pigment. Absorption spectra of the pigments showed greater absorption at shorter wavelengths, suggesting greater UV protection at these wavelengths. These results will assist in the development of fungal disinfection systems using UV, such as closed systems of air and water purification., (© 2024. The Author(s).)

Two new compounds, cladospolides I ( 1 ) and J ( 2 ), together with two new naturally occurring ones, methyl 11-hydroxy-4-oxododecanoate ( 3 ) and 11-hydroxy-4-oxododecanoic acid ( 4 ), were isolated from the culture extract of the cold-seep sediment-derived fungus Cladosporium cladosporioides 8-1. Their structures and configurations were established by analysis of 1D/2D NMR, MS, ECD, and specific optical rotation data. Compound 3 was possibly formed by methyl esterification of 4 during the purification process due to the utilization of methanol. All compounds were evaluated for inhibition of four marine phytoplankton species and five marine-derived bacteria.

A new polyketide, cladoic acid, was isolated from a fungus of the genus Cladosporium . The structure of the highly oxygenated trans -decalin ring with an all- E triene side chain was elucidated by extensive spectroscopic analysis. The unique chair/twist-boat conformation of the trans -decalin core and the flexibility of the B-ring were demonstrated by computer-aided conformational analysis. Cladoic acid was active against Trypanosoma cruzi and inhibited the proliferation of amastigotes and epimastigotes with IC 50 values of 27 and 46 μM, respectively, but it did not show any appreciable activity against P388 murine leukemia cells, bacteria, or fungi, indicating it is a potential candidate for drug development against Chagas disease.

Two undescribed cladosporol derivatives, cladosporols J-K (1-2), and three previously unreported spirobisnaphthalenes, urnucratins D-F (3-5), as well as eleven known cladosporols (6-16), were characterized from Cladosporium cladosporioides (Cladosporiaceae), a common plant pathogen isolated from the skin of Chinese toad. Cladosporols J-K (1-2) with a single double bond have been rarely reported, while urnucratins D-F (3-5) featured an unusual benzoquinone bisnaphthospiroether skeleton, contributing to an expanding category of undiscovered natural products. Their structures and absolute configurations were determined using extensive spectroscopic methods, including NMR, HRESIMS analyses, X-ray single crystal diffraction, as well as through experimental ECD analyses. Biological assays revealed that compounds 1 and 2 exhibited inhibitory activity against A549 cells, with IC 50 values of 30.11 ± 3.29 and 34.32 ± 2.66 μM, respectively., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2024 Elsevier Ltd. All rights reserved.)

The biotransformation of patchouli alcohol by Cladosporium cladosporioides afforded 31 products, including 21 new ones ( 1 - 3 , 5 , 6 , 8 - 14 , and 17 - 25 ). Their structures were determined by extensive spectroscopic data analysis ( 1 H and 13 C NMR, HSQC, HMBC, 1 H- 1 H COSY, ROESY, and HRESIMS), and the absolute configuration of compounds 1 , 2 , 8 , 9 , and 17 was determined by single-crystal X-ray diffraction using Cu Kα radiation. Structurally, compounds 21-24 were patchoulol-type norsesquiterpenoids without Me-12. Among them, a Δ 3(4) double bond existed in compounds 21 and 22 ; a three-membered ring was formed between C-4, C-5, and C-6 in compound 23 ; an epoxy moiety appeared between C-3 and C-4 in compound 24 . Furthermore, the biotransformation products 9 , 10 , 12, and 25 showed potent anti-influenza virus activity with EC 50 values of 2.11, 7.94, 20.87, and 3.45 μ M, respectively.

Two new compounds ( R )-6-((8 S )-hydroxypropyl)-2-methyl-5,6-dihydro-4 H -pyran-4-one ( 1 ) and ( R )-6-((8 R )-hydroxypropyl)-2-methyl-5,6-dihydro-4 H -pyran-4-one ( 2 ), together with four known compounds were isolated from the marine-derived fungus Cladosporium halotolerans FS702. The structures of these compounds were determined on the basis of extensive spectroscopic analysis including 1D/2D NMR, IR, UV, HRESIMS, ECD calculations as well as the modified Mosher's method. Cytotoxic assay results showed that compound 2 had significant cytotoxic activity against SF-268, MCF-7, HepG-2, and A549 cells lines with IC 50 values of 0.16, 0.47, 0.33 and 0.23 µM, respectively.

A new ceramide, named cladamide ( 1 ), in addition to cinnamic acid ( 2 ), para -coumaric acid ( 3 ), stigmasterol-3- O - β -D-glucoside ( 4 ), and uracil ( 5 ), was isolated from the white beans culture of Cladosporium cladosporioides , a marine-derived endohpytic fungus isolated from the leaves of the mangrove, Avicennia marina (Forssk.) Vierh. Structure elucidation of compound 1 was established on the basis of extensive 1D and 2D NMR spectroscopic techniques in combination with HR-ESI-MS. The ability of the isolated compounds to inhibit acetylcholine esterase was evaluated. Compound 3 showed the highest acetylcholine esterase inhibitory activity (IC 50  = 0.057 ± 0.003 µM), followed by compound 4 (IC 50  = 0.068 ± 0.003 µM) and compound 1 (IC 50  = 0.099 ± 0.005 µM) compared to donepezil, the positive control, (IC 50  = 0.044 ± 0.002 µM). Compounds 2 and 5 showed lower activity (IC 50  = 0.182 ± 0.009 and 0.236 ± 0.012 µM, respectively). The results were further validated by molecular docking study.

The Cladosporium fungi, one of the largest genera of dematiaceous hyphomycetes, could produce various bioactive secondary metabolites. From the AcOEt-soluble extract of Cladosporium oxysporum 170103, three new secopatulolides (1-3) and thirteen known compounds (4-16) were obtained. Their structures were established by detailed analysis of the NMR and HR-ESI-MS data. All sixteen compounds were tested for antibacterial activity against Vibrio parahemolyticus, ergosterol (10) presented moderate effect with the minimum inhibitory concentration (MIC) of 32 μM. It can destruct the membrane integrity of Vibrio parahemolyticus to change the cell shape., (© 2022 Wiley-VHCA AG, Zurich, Switzerland.)

Cladoxanthones A ( 1 ) and B ( 2 ), two xanthone-derived metabolites featuring a new spiro[cyclopentane-1,2'-[3,9a]ethanoxanthene]-2,4',9',11'(4a' H )-tetraone skeleton, were isolated from cultures of the ascomycete fungus Cladosporium sp., together with the known mangrovamide J ( 3 ). Their structures were elucidated primarily by NMR experiments. The absolute configurations of 1 and 2 were assigned by X-ray crystallography using Cu Kα radiation. Compound 1 could be generated from the hypothetical precursors related to α-methylene ketone and dihydro-xanthone via a Diels-Alder reaction, while 2 could be an oxidative coupling product resulting from 1 and 3 . Compounds 1 and 2 showed weakly cytotoxic effects.

Two new (cladosporioles A and B, 1 and 2) and fourteen known (3-16) compounds were isolated from the deep-sea-derived fungus Cladosporium cladosporioides 170056. The relative structures of the new compounds were elucidated mainly by detailed analysis of their NMR and HR-ESI-MS spectroscopic data. Their absolute configurations were determined by comparison of the experimental and calculated electronic circular dichroism (ECD) spectra. All isolates were tested for antimicrobial activity against Vibrio parahaemolyticus. Compound 15 exhibited weak effect with the MIC value of 156.25 μg/mL., (© 2022 Wiley-VHCA AG, Zurich, Switzerland.)

Cladosporine A ( 1 ), a new indole diterpenoid alkaloid, was isolated from the extract of a fungal strain Cladosporium sp. JNU17DTH12-9-01. Its structure was elucidated by extensive spectroscopic analysis, and the absolute configurations were determined by electronic circular dichroism (ECD) experiments. This is the first report of the presence of indole diterpenoid alkaloid in the genus Cladosporium . The antimicrobial activities against Staphylococcus aureus 209P, Escherichia coli ATCC0111, Aspergillus niger R330, and Candida albicans FIM709 were evaluated. Compound 1 showed MICs of 4 μg/mL and 16 μg/mL against S . aureus 209P and C . albicans FIM709, respectively.

A fungal metabolite, isocladosporin was isolated from natural fungus, Cladosporium cladosporioides in the mid of 90s. Due to the lack of optical rotation of isolated natural product sample, the absolute configuration of the natural product remained undetermined for more than two decades. Herein, we demonstrated an SAR study of enantiomers of isocladosporin in herbicidal bio-assay against wheat coleoptile. Using this study as a comparative tool we further proposed the plausible absolute configuration of natural isocladosporin for the first time. The assigned configuration was also supported through biogenetic precursors.

Four new cyclohexene derivatives cladoscyclitols A-D (1-4) and one new ribofuranose phenol derivative 4-O-α-D-ribofuranose-2-pentyl-3-phemethylol (5) were obtained from the EtOAC extract of the mangrove-derived endophytic fungus Cladosporium sp. JJM22. The structures were elucidated by extensive NMR and MS analysis, while the absolute configurations of the stereogenic carbons were established based on quantum-chemical electronic circular dichroism calculations or comparison of the optical rotations with those of related compounds. Compounds 2 and 5 displayed potent inhibitory activity against α-glucosidase with the IC 50 values of 2.95 and 2.05 μM, respectively., (Copyright © 2021 Elsevier B.V. All rights reserved.)

The hyphae of Cladosporium sp. strain F1 (CFGR 2020-301-00084) were heavily encrusted with pre-synthesized uranium phosphate minerals under a wide range of pH conditions. SEM and TEM images showed that nanorods and nanoplates of uranium phosphate minerals at pH 4 and 5 and at pH 6, 7, and 8, respectively, were tightly adsorbed along the hyphae of Cladosporium sp. strain F1, while only a few uranium phosphate minerals were observed on the hyphae of Aspergillus niger VKMF 1119. Based on the physical mobility and chemical stability of uranium phosphate minerals under in situ oxidizing environmental conditions, the application of Cladosporium sp. strain F1 has potential as a novel strategy for the remediation of uranium contamination in sediments and aquifers under a wide range of pH conditions where larger amounts of phosphate are present in the environment.

A simple but previously undescribed macrolide with unprecedented bicyclo 5/9 ring system, namely, cladocladosin A (1), along with two new sulfur-containing macrolides, namely, thiocladospolides F and G (2 and 3), were characterized from the mangrove-derived endophytic fungus Cladosporium cladosporioides MA-299. The structures of these compounds were established on the basis of spectroscopic interpretation, and the absolute configurations of compounds 1-3 were determined by X-ray crystallographic analysis, Mosher's method, and by a biogenetic point of view. The possible biogenetic pathway for compounds 1-3 as well as their congeners thiocladospolides A-D and pandangolide 3 was proposed, providing a role in distinguishing the position of sulfur substitution in thiomacrolides. Compounds 1-3 were evaluated for antimicrobial activities against human-, aquatic-, and plant-pathogenic microbes., (Copyright © 2020 Elsevier Inc. All rights reserved.)

Plants trigger immune responses upon recognition of fungal cell wall chitin, followed by the release of various antimicrobials, including chitinase enzymes that hydrolyze chitin. In turn, many fungal pathogens secrete LysM effectors that prevent chitin recognition by the host through scavenging of chitin oligomers. We previously showed that intrachain LysM dimerization of the Cladosporium fulvum effector Ecp6 confers an ultrahigh-affinity binding groove that competitively sequesters chitin oligomers from host immune receptors. Additionally, particular LysM effectors are found to protect fungal hyphae against chitinase hydrolysis during host colonization. However, the molecular basis for the protection of fungal cell walls against hydrolysis remained unclear. Here, we determined a crystal structure of the single LysM domain-containing effector Mg1LysM of the wheat pathogen Zymoseptoria tritici and reveal that Mg1LysM is involved in the formation of two kinds of dimers; a chitin-dependent dimer as well as a chitin-independent homodimer. In this manner, Mg1LysM gains the capacity to form a supramolecular structure by chitin-induced oligomerization of chitin-independent Mg1LysM homodimers, a property that confers protection to fungal cell walls against host chitinases., Competing Interests: The authors declare no conflict of interest exists.

A unique polyketide cladosporactone A along with eight known compounds were isolated from the deep-sea-derived Cladosporium cladosporioides. The structure of cladosporactone A was established by spectroscopic analyses, and the absolute configuration was clarified by the theoretical ECD calculation. Cladosporactone A is the first member of polyketide with the 7-methylisochromen-3-one skeleton., (© 2020 Wiley-VHCA AG, Zurich, Switzerland.)

Background: Endophytic fungi are largely underexplored in the discovery of natural bioactive products though being rich sources of novel compounds with promising pharmaceutical potential. In this study, Taxus wallichiana, which has huge medicinal value, was investigated for its endophytic diversity and capability to produce bioactive secondary metabolites by analyzing antioxidant, antimicrobial and cytotoxic properties. Methods: The endophytes were identified by ITS-PCR using genomic DNA samples. The secondary metabolites were extracted by solvent extraction method using ethyl acetate. The antioxidant activity was analyzed by Thin Layer Chromatography, Total Phenol Content (TPC), Total Flavonoid Content (TFC) and DPPH assay, and the antimicrobial activity was analyzed by agar-well diffusion method. Brine shrimp lethality assay was used to analyze the cytotoxicity of the fungal extracts. Results: Out of 16 different Taxus trees sampled from different locations of Dhorpatan, 13 distinctive endophytic fungi were isolated and grouped into 9 different genera: Bjerkandera, Trichoderma, Preussia, Botrytis, Arthrinium, Alternaria, Cladosporium, Sporormiella and Daldinia . The ethyl acetate extracts isolated from three endophytic fungi: Alternaria alternata , Cladosporium cladosporioides and Alternaria brassicae showed significant TPC values of 204±6.144, 312.3±2.147 and 152.7±4.958µg GAE/mg of dry extract, respectively, and TFC values of 177.9±2.911, 644.1±4.202 and 96.38±3.851µg RE/mg of dry extract, respectively. Furthermore, these three extracts showed a dose dependent radical scavenging activity with IC 50 concentration of 22.85, 22.15 and 23.001 µg/ml, respectively. The extracts of C. cladosporioides and A. brassicae also showed promising antimicrobial activity against Escherichia coli , Staphylococcus aureus and Bacillus subtilis with a minimum inhibitory concentration of 250μg/ml for all bacteria. Both the samples showed cytotoxic property against shrimp nauplii with LC 50 of 104.2 and 125.9µg/ml, respectively. Conclusions: The crude fungal extracts obtained from endophytes: A. alternata , C. cladosporioides and A. brassicae upon purification and further identification of the bioactive compounds can be a fascinating source for novel pharmaceutical agents., Competing Interests: No competing interests were disclosed., (Copyright: © 2020 Gauchan DP et al.)

Background: Endophytic fungi are largely underexplored in the discovery of natural bioactive products though being rich sources of novel compounds with promising pharmaceutical potential. In this study, Taxus wallichiana, which has huge medicinal value, was investigated for its endophytic diversity and capability to produce bioactive secondary metabolites by analyzing antioxidant, antimicrobial and cytotoxic properties. Methods: The endophytes were identified by ITS-PCR using genomic DNA samples. The secondary metabolites were extracted by solvent extraction method using ethyl acetate. The antioxidant activity was analyzed by Thin Layer Chromatography, Total Phenol Content (TPC), Total Flavonoid Content (TFC) and DPPH assay, and the antimicrobial activity was analyzed by agar-well diffusion method. Brine shrimp lethality assay was used to analyze the cytotoxicity of the fungal extracts. Results: Out of 16 different Taxus trees sampled from different locations of Dhorpatan, 13 distinctive endophytic fungi were isolated and grouped into 9 different genera: Bjerkandera, Trichoderma, Preussia, Botrytis, Arthrinium, Alternaria, Cladosporium, Sporormiella and Daldinia . The ethyl acetate extracts isolated from three endophytic fungi: Alternaria alternata , Cladosporium cladosporioides and Alternaria brassicae showed significant TPC values of 204±6.144, 312.3±2.147 and 152.7±4.958µg GAE/mg of dry extract, respectively, and TFC values of 177.9±2.911, 644.1±4.202 and 96.38±3.851µg RE/mg of dry extract, respectively. Furthermore, these three extracts showed a dose dependent radical scavenging activity with IC 50 concentration of 22.85, 22.15 and 23.001 µg/ml, respectively. The extracts of C. cladosporioides and A. brassicae also showed promising antimicrobial activity against Escherichia coli , Staphylococcus aureus and Bacillus subtilis with a minimum inhibitory concentration of 250μg/ml for all bacteria. Both the samples showed cytotoxic property against shrimp nauplii with LC 50 of 104.2 and 125.9µg/ml, respectively. Conclusions: The crude fungal extracts obtained from endophytes: A. alternata , C. cladosporioides and A. brassicae upon purification and further identification of the bioactive compounds can be a fascinating source for novel pharmaceutical agents., Competing Interests: No competing interests were disclosed., (Copyright: © 2020 Gauchan DP et al.)

During the course of our search for novel bioactive compounds from marine fungi, four new citrinin derivatives, cladosporins A-D ( 1-4 ) were isolated from a culture broth of the deep-sea-derived fungus Cladosporium sp. SCSIO z015. Their complete structural assignments were elucidated by the extensive spectroscopic investigation. The absolute configurations of 1 - 3 were established by quantum chemical calculations of the electronic circular dichroism (ECD) spectra. Compounds 1-4 showed weak toxicity towards brine shrine naupalii with LC 50 values of 72.0, 81.7, 49.9 and 81.4 μM, respectively. And 4 also showed significant antioxidant activity against ɑ,α-diphenyl-picrylhydrazyl (DPPH) radicals with an IC 50 value of 16.4 μM.

The endophytic fungus Cladosporium sphaerospermum WBS017 was obtained from healthy bulbs of Fritillaria unibracteata var. wabuensis. Fermentation of C. sphaerospermum on solid rice medium yielded three new hybrid polyketides, cladosins L-N (1-3), and a known derivative cladodionen (4). Further cultivation of this fungus on white bean medium afforded an additional new hybrid polyketide, cladosin O (5) along with three known analogues (6-8). The structures of the new compounds were elucidated using a combination of NMR and HRESIMS data. The absolute configurations of compounds 2 and 3 were determined by Mosher's method and TDDFT-ECD calculations. All isolated compounds were evaluated for their cytotoxic and antimicrobial activities. Cladodionen (4) exhibited cytotoxicity against the mouse lymphoma cell line L5178Y with an IC 50 value of 3.7 μM, and also exhibited antifungal activity against Ustilago maydis and Saccharomyces cerevisiae, while cladosin L (1) displayed week antibacterial activity against Staphylococcus aureus ATCC 29213 and S. aureus ATCC 700699 with MIC values of 50 and 25 μM, respectively., Competing Interests: Declaration of competing interest The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this paper., (Copyright © 2020 Elsevier Masson SAS. All rights reserved.)

Introduction: Infectious diseases represent one of the leading causes of death worldwide. Considering the growing global challenge of antimicrobial resistance, research into new sources of potentially effective antimicrobial agents from natural origins is of great importance for world health. Objective: To evaluate the antimicrobial activity of endophytic fungi from Mammea americana and Moringa oleifera upon Staphylococcus aureus (ATCC 29213), S. aureus (resistant strain USb003), Escherichia coli (ATCC 25922), and E. coli (resistant strain USb007). Materials and methods: We isolated endophytic fungi from the leaves, seeds, and stems of the two plants under study. We evaluated their antimicrobial activity through the formation of sensitivity haloes in dual tests in vitro, as well as in trials using crude ethanolic extracts from the endophytes. The minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and cytotoxicity o the substances were analyzed. Results: Three ethanolic extracts of Penicillium sp., Cladosporium (001), and Cladosporium (002) exhibited the greatest inhibition halos in sensitive and resistant strains of E. coli and S. aureus. The MIC and CBM found were statistically significant (p≤0.05) compared with the gentamicin control. Furthermore, the cytotoxicity test results of CC50>1,000 demonstrated that the endophytic fungi studied exhibit bactericidal characteristics without causing unintended damage. Conclusion: The endophytic fungi M. oleifera and M. americana represent a source of active secondary metabolites with antimicrobial and non-toxic properties. In light of these findings, further research should proceed with chemical identification of the compounds and the study of their mechanisms of action, especially given the paucity of current scientific knowledge concerning the isolation of endophytes in these plants.

Five new perylenequinone derivatives, altertoxins VIII-XII ( 1 - 5 ), as well as one known compound cladosporol I ( 6 ), were isolated from the fermentation broth of the marine-derived fungus Cladosporium sp. KFD33 from a blood cockle from Haikou Bay, China. Their structures were determined based on spectroscopic methods and ECD spectra analysis along with quantum ECD calculations. Compounds 1 - 6 exhibited quorum sensing inhibitory activities against Chromobacterium violaceum CV026 with MIC values of 30, 30, 20, 30, 20 and 30 μg/well, respectively.

Five hybrid polyketides ( 1a , 1b , and 2 - 4 ) containing tetramic acid core including a new hybrid polyketide, cladosin L ( 1 ), were isolated from the marine fungus Cladosporium sphaerospermum SW67, which was isolated from the marine hydroid polyp of Hydractinia echinata . The hybrid polyketides were isolated as a pair of interconverting geometric isomers. The structure of 1 was determined based on 1D and 2D NMR spectroscopic and HR-ESIMS analyses. Its absolute configuration was established by quantum chemical electronic circular dichroism (ECD) calculations and modified Mosher's method. Tetramic acid-containing compounds are reported to be derived from a hybrid PKS-NRPS, which was also proved by analyzing our 13 C-labeling data. We investigated whether compounds 1 - 4 could prevent cell damage induced by cisplatin, a platinum-based anticancer drug, in LLC-PK1 cells. Co-treatment with 2 and 3 ameliorated the damage of LLC-PK1 cells induced by 25 μM of cisplatin. In particular, the effect of compound 2 at 100 μM (cell viability, 90.68 ± 0.81%) was similar to the recovered cell viability of 88.23 ± 0.25% with 500 μM N -acetylcysteine (NAC), a positive control.

One new pentenoic acid derivative, named 1,1'-dioxine-2,2'-dipropionic acid (1) and a new natural product, named 2-methylacetate-3,5,6-trimethylpyrazine (2), along with six known compounds (3-8), were obtained from the Cladosporium sp. JS1-2, an endophytic fungus isolated from the mangrove Ceriops tagal collected in South China Sea. Their structures were elucidated by detailed analysis of comprehensive spectroscopic data, and the structure of 1 was further determined by X-ray diffraction analyses. 13 C NMR chemical shifts of structure 2 was further determined by GIAO based 13 C NMR chemical shifts calculations. Compounds 1-4 and 6 showed growth inhibition activities against newly hatched larvae of Helicoverpa armigera Hubner with the IC 50 values ranging from 100 to 150 μg ml -1 . Compounds 1, 2, 4, 6 and 7 showed moderate antibacterial activities against Staphylococcus aureus with the MIC values of 25.0, 12.5, 6.25, 1.25, and 6.25 μg ml -1 , respectively.

Chemical investigation of the mangrove endophytic fungus Cladosporium sp. SCNU-F0001 resulted in the isolation and identification of a new macrolide compound named thiocladospolide E (1) and a novel macrolide lactam named cladospamide A (2), along with the known cladospolide B (3). The structures were elucidated based on spectroscopic methods, and the absolute configurations were determined by X-ray diffraction and HPLC analysis after chemical derivatization. All compounds were tested for their antibacterial and cytotoxic activity., (Copyright © 2019 Elsevier B.V. All rights reserved.)

Four new 12-membered macrolides, thiocladospolides A-D (1-4), each possessing a sulfur substitution at C-2, along with the known congener pandangolide 3 (5) and the possible hydrolysis product seco-patulolide C (6), were isolated and identified from the culture extract of Cladosporium cladosporioides MA-299, an endophytic fungus obtained from the leaves of the mangrove plant Bruguiera gymnorrhiza. Their structures were established by interpretation of the NMR spectroscopic and mass spectrometric data. X-ray crystallographic analysis of compound 1, which represents the first crystal structure described for a sulfur-containing 12-membered macrolide, confirmed its structure and absolute configuration. The proposed sulfur side chain at C-3 in pandangolide 3 (5) was revised to be at C-2 by detailed analysis of the NMR data and by a comparison with data for thiocladospolide A (1). The structures for pandangolides 2 and 4 should also be considered for revisions. The isolated compounds were evaluated for the antimicrobial activities against aquatic bacteria and plant pathogens.

Five new polyketides, namely, 5 R -hydroxyrecifeiolide ( 1 ), 5 S -hydroxyrecifeiolide ( 2 ), ent -cladospolide F ( 3 ), cladospolide G ( 4 ), and cladospolide H ( 5 ), along with two known compounds ( 6 and 7 ), were isolated from the endophytic fungal strain Cladosporium cladosporioides MA-299 that was obtained from the leaves of the mangrove plant Bruguiera gymnorrhiza. The structures of these compounds were established by extensive analysis of 1D/2D NMR data, mass spectrometric data, ECDs and optical rotations, and modified Mosher's method. The structures of 3 and 6 were confirmed by single-crystal X-ray diffraction analysis and this is the first time for reporting the crystal structures of these two compounds. All of the isolated compounds were examined for antimicrobial activities against human and aquatic bacteria and plant pathogenic fungi as well as enzymatic inhibitory activities against acetylcholinesterase. Compounds 1 - 4 , 6 , and 7 exhibited antimicrobial activity against some of the tested strains with MIC values ranging from 1.0 to 64 μg/mL, while 3 exhibited enzymatic inhibitory activity against acetylcholinesterase with the IC 50 value of 40.26 μM.

Two new compounds (1 and 2), together with six known compounds (3-8), were obtained from the Cladosporium sp. JJM22, an endophytic fungus isolated from the stem bark of the mangrove plant Ceriops tagal collected in South China Sea. Their structures were elucidated on the basis of detailed spectroscopic analysis. The absolute configurations of 1 and 2 were confirmed by the comparison of optical rotation and the CD data with those of known compounds. The inhibitory activities of the isolated compounds against six terrestrial pathogenic bacteria and human cervical carcinoma Hela cell line were evaluated. Compound 3 exhibited a broad spectrum of antibacterial activities.

Two new succinimide-containing derivatives, cladosporitins A ( 1 ) and B ( 2 ), were isolated from the fermentation cultures of the mangrove-derived fungus Cladosporium sp. HNWSW-1, along with a new pyrone, clapone ( 3 ), as well as the previously reported talaroconvolutin A ( 4 ) and anthraquinone ( 5 ). The structures of the isolated compounds were elucidated by 1D, 2D NMR, and HRMS spectral analysis. Compound 2 showed cytotoxicity against BEL-7042, K562 and SGC-7901 cell lines with IC 50 values of 29.4 ± 0.35 μM, 25.6 ± 0.47 μM, and 41.7 ± 0.71 μM, respectively, whereas compound 4 exhibited cytotoxicity against Hela and BEL-7042 cell lines with IC 50 values of 14.9 ± 0.21 μM and 26.7 ± 1.1 μM, respectively. In addition, compounds 4 and 5 displayed inhibitory activity against α-glycosidase, with IC 50 values of 78.2 ± 2.1 μM and 49.3 ± 10.6 μM, respectively.

This work presents a second-to-none method for Taxol isolation from the Endophytic fungus Cladosporium sphaerospermum (AUMC 6896) and the Entomopathogenic fungus Metarizium anisopliae (AUMC 5130). The extracts were analyzed by high performance liquid chromatography (HPLC) and Liquid chromatography coupled to tandem mass spectrometry (LC-MS/MS) using positive electrospray ionization (ESI) in the multiple reaction monitoring (MRM) mode. This is rapid, consistent, reproducible, accurate, and sensitive for quantifying Taxol across multiple samples. The yield of crude Taxol product obtained from Potato Dextrose broth (PDB) medium inoculated with Cladosporium sphaerospermu and Metarizium anisopliae was found to be 3.732, and 0.0023 μg L -1 respectively. The yield can be improved by adding ammonium acetate or salicylic acid to the culture broth. Addition of ammonium acetate (AA) (20 mg L -1 ) to culture media resulted in an increase of Taxol yield to 30.365 and 27.289 μg L -1 respectively. Production of Taxol was 29.844 and 67.254 μg L -1 for the two fungus species when ammonium acetate was substituted by 90 mg L -1 salicylic acid (SA). Adding both AA (20 mg L -1 ) and SA (90 mg L -1 ) to the culture media resulted in an increase of the Taxol yield to 4.054 and 116.373 μg L -1 respectively. Our proposed analytical method offers very fast (3 min) quantitation of Taxol in comparison with other published methods. These findings represent a new bioprospecting of the endophytic fungi that may serve as a potential material for the production of Taxol for anticancer treatment., (Copyright © 2018. Published by Elsevier B.V.)

Seven new unstable tetramic acid derivatives, cladosporiumins I-O ( 1 ⁻ 7 ), together with the known analogue cladodionen ( 8 ) were isolated from the extract of the deep-sea-derived fungus Cladosporium sphaerospermum EIODSF 008. Their structures were elucidated by spectroscopic analysis, quantum chemical calculations and ECD spectra. Compound 4 was a Mg complex of tetramic acid derivative. In acidic solvent, 4 could change to 1 and 6 , and 7 could change to 5 . In addition, 1 , 5 and 8 existed as two exchangeable isomers, respectively. The structures of cladosporiumins E-H were reassigned as their Na complexes. The antibacterial and cytotoxic activities of 1 ⁻ 8 were also evaluated. However, because of their instability, all of the isolated compounds did not show significant antibacterial activity as the preliminary EtOAc extracts of the fungal strain.

Four new tetramic acids, cladosins H-K (1-4), and a related known compound, cladodionen (5), were isolated from the culture of the Mariana Trench (depth 6562 m) sediment-derived fungus Cladosporium sphaerospermum L3P3 treated with the histone deacetylase inhibitor SAHA (suberanilohydroxamic acid). Interestingly, compounds 1-5 existed as equilibrium E/ Z mixtures and 1-4 were the first cases of tetramic acids containing aniline moieties. Their structures including absolute configurations were elucidated through a combination of NMR, MS, and Mosher's method, together with the consideration of biogenetic origins. Incubation experiments of exogenous aniline and N-phenyloctanamide revealed that the aniline moiety in cladosins H-K (1-4) is probably derived from the degradation of SAHA, indicating that the well-known histone deacetylase inhibitor SAHA could be metabolized by L3P3 and provide aniline as a precursor for biotransformation of chemically reactive polyketides. The cytotoxicity of 1-5 was evaluated against the PC-3, MGC-803, SH-SY5Y, HCT-116, K562, and HL-60 cell lines, and compound 2 showed promising cytotoxicity against the HL-60 cell line with an IC 50 value of 2.8 μM.

Cladosporamide A (1), a new protein tyrosine phosphatase (PTP) 1B inhibitor, was isolated together with a known prenylated flavanone derivative (2) from the culture broth of an Indonesian marine sponge-derived Cladosporium sp. TPU1507 by solvent extraction, ODS column chromatography, and preparative HPLC (ODS). The structure of 1 was elucidated based on 1D and 2D NMR data. Compound 1 modestly inhibited PTP1B and T-cell PTP (TCPTP) activities with IC 50 values of 48 and 54 μM, respectively. The inhibitory activity of 2 against PTP1B (IC 50  = 11 μM) was approximately 2-fold stronger than that against TCPTP (IC 50  = 27 μM).

A new pregnane, 3α-hydroxy-7-ene-6,20-dione (1), and five known steroids (2-6), along with one known steroidal glycoside (7) were obtained from the fungus Cladosporium sp. WZ-2008-0042 cultured from a gorgonian Dichotella gemmacea collected from the South China Sea. The structure and absolute configuration of the new compound (1) were elucidated by comprehensive spectroscopic data and X-ray diffraction data. The compound has a rare configuration of 3α-OH that is different from most of pregnanes. All of the isolated compounds were evaluated for their antiviral activities against respiratory syncytial virus (RSV). Among them, 1 exhibited potential antiviral activity with the IC 50 value of 0.12 mM.

A new hybrid polyketide, cladodionen ( 1 ), together with a new abscisic acid analogue, cladosacid ( 2 ), were isolated from the marine-derived fungus, Cladosporium sp. OUCMDZ-1635. Their structures, including the absolute configurations, were fully elucidated on the basis of spectroscopic analysis, ECD spectra, quantum chemical calculations, and chemical methods. Cladodionen ( 1 ) showed cytotoxic activities against MCF-7, HeLa, HCT-116, and HL-60 human cancer cell lines with IC 50 values of 18.7, 19.1, 17.9, and 9.1 µM., Competing Interests: The authors declare no conflict of interest.

Three new highly oxygenated sterols (1-3) and a new dihydroisocoumarin (7) together with six known compounds were isolated from the extracts of the culture of a sponge-derived fungus Cladosporium sp. SCSIO41007. The structures of all new compounds (1-3, 7) were determined by the extensive spectroscopic analysis including NMR, MS, IR, and UV. Their absolute configurations were determined by X-ray single-crystal and CD data analysis. Compound 2 exhibited weak inhibitory activity against H3N2 with the IC 50 value of 16.2 μM., (Copyright © 2017 Elsevier Inc. All rights reserved.)

Tomato leaf mold disease is caused by the biotrophic fungus Cladosporium fulvum. During infection, C. fulvum produces extracellular small secreted protein (SSP) effectors that function to promote colonization of the leaf apoplast. Resistance to the disease is governed by Cf immune receptor genes that encode receptor-like proteins (RLPs). These RLPs recognize specific SSP effectors to initiate a hypersensitive response (HR) that renders the pathogen avirulent. C. fulvum strains capable of overcoming one or more of all cloned Cf genes have now emerged. To combat these strains, new Cf genes are required. An effectoromics approach was employed to identify wild tomato accessions carrying new Cf genes. Proteomics and transcriptome sequencing were first used to identify 70 apoplastic in planta-induced C. fulvum SSPs. Based on sequence homology, 61 of these SSPs were novel or lacked known functional domains. Seven, however, had predicted structural homology to antimicrobial proteins, suggesting a possible role in mediating antagonistic microbe-microbe interactions in planta. Wild tomato accessions were then screened for HR-associated recognition of 41 SSPs, using the Potato virus X-based transient expression system. Nine SSPs were recognized by one or more accessions, suggesting that these plants carry new Cf genes available for incorporation into cultivated tomato.

Halotolerant fungus Cladosporium cladosporioides OUCMDZ-187 was isolated from the mangrove plant Rhizophora stylosa collected in Shankou, Guangxi Province of China. Three new fatty acid esters cladosporesters A-C (1-3) and 5 new fatty acids cladosporacids A-E (4-8) were isolated from the ethyl acetate extract of the fermentation broth of OUCMDZ-187 in a hypersaline (10% salt) medium. Their structures were elucidated by UV, IR, MS, specific rotation, and 1D and 2D NMR data., (Copyright © 2017 John Wiley & Sons, Ltd.)

Four new cladosporol derivatives, cladosporols F-I (1-4), the known cladosporol C (5), and its new epimer, cladosporol J (6), were isolated and identified from the marine algal-derived endophytic fungus Cladosporium cladosporioides EN-399. Their structures were determined by detailed interpretation of NMR and MS data, and the absolute configurations were established on the basis of TDDFT-ECD and OR calculations. The configurational assignment of cladosporols F (1) and G (2) showed that the previously reported absolute configuration of cladosporol A and all the related cladosporols need to be revised from (4'R) to (4'S). Compounds 1-6 showed antibacterial activity against Escherichia coli, Micrococcus luteus, and Vibrio harveyi with MIC values ranging from 4 to 128 μg/mL. Compound 3 showed significant cytotoxicity against A549, Huh7, and LM3 cell lines with IC 50 values of 5.0, 1.0, and 4.1 μM, respectively, and compound 5 showed activity against H446 cell line with IC 50 value of 4.0 μM.

Cladosin C is one of the few known enaminotetramic acids, isolated from extracts of the deep sea fungus Cladosporium sphaerospermum. It was synthesised in ten steps and 14% overall yield by a late-stage amination of the corresponding 3-acyltetramic acid. This was obtained by a Dieckmann condensation of an N-β-ketoacylaminoester derived from dehydrovalinate and the thioester-terminated side chain containing the stereogenic centre which stemmed from poly-(R)-3-hydroxybutyrate.

Three new isoaigialones, A, B, and C (1-3), along with aigialone (4), were isolated from the crude EtOAc extract of a Phaeoacremonium sp., an endophytic fungus obtained from the leaves of Senna spectabilis. The structures of these compounds were elucidated based on the analysis of spectroscopic data. Compounds 2 and 4 were active against the phytopathogenic fungi Cladosporium cladosporioides and C. sphaerospermum. This is the first report of metabolites produced by an Phaeoacremonium sp., associated with S. spectabilis.

Ethnopharmacological Relevance: Tinospora cordifolia (Willd. Hook. f. & Thomson; family: Menispermaceae), has a long history of use in various traditional medicinal systems including "Ayurveda". It is reported to possess anticancer, antidiabetic, antimicrobial, antispasmodic, and antiinflammatory activities. T. cordifolia has also been well documented for production of various bioactive metabolites and their antioxidant activity, but the microorganisms associated with it have been least explored for the same properties., Aim of the Study: Aim of the present study was to evaluate antioxidant and in vivo genoprotective potential of phenolic compounds produced by an endophytic fungus Cladosporium velox TN-9S isolated from T. cordifolia., Materials and Methods: The isolate of C. velox TN-9S was cultivated in malt extract medium and extracted with ethyl acetate. Total phenol content was determined by Folin Ciocalteu reagent. The antioxidant activity was measured in terms of DPPH and FRAP assay. The in vivo genoprotective activity was assessed using fish Channa punctatus as model. Identification of phenolic compounds was carried out using RP-HPLC. The fungal extract was evaluated for biosafety using Salmonella typhimurium His - strain and CHO cell lines for mutagenicity and cytotoxicity, respectively., Results: The total phenolic content in the ethyl acetate extract of the fungus was determined to be 730μg gallic acid equivalent/mL. The extract evinced significant antioxidant activity with IC 50 value of 22.5µg/mL in DPPH scavenging assay. The phenolic extract showed good in vivo genoprotective activity against the genetic damage induced in fish C. punctatus after treatment with a non-ionic surfactant 4-nonylphenol. RP-HPLC analysis revealed the presence of peaks corresponding to various phenolic compounds in the extract. Mutagenicity and cytotoxicity results revealed the extract to be nonmutagenic and non cytotoxic in nature., Conclusion: The results indicate the potential of an endophytic C. velox isolated from T. cordifolia as a producer of phenolic compounds with antioxidant and genoprotective activities which could be exploited in pharmaceutical industry. The ability of endophytes to produce similar compounds as the host, is also revealed in the present study., (Copyright © 2016 Elsevier Ireland Ltd. All rights reserved.)

To investigate contamination of ground red pepper with fungi and mycotoxin, we obtained 30 ground red pepper samples from 15 manufacturers in the main chili-pepper-producing areas in Korea. Fungal contamination was evaluated by spreading diluted samples on potato dextrose agar plates. The total fungi counts ranged from 0 to 7.3 × 10 3 CFU/g. In the samples, the genus Aspergillus had the highest incidence, while Paecilomyces was isolated most frequently. The next most frequent genera were Rhizopus, Penicillium, Cladosporium, and Alternaria. Within Aspergillus, A. ruber was predominant, followed by A. niger, A. amstelodami, A. ochraceus, A. terreus, A. versicolor, A. flavus, and A. fumigatus. The samples were analyzed for aflatoxins, ochratoxin A, and citrinin by ultra-perfomance liquid chromatography (UPLC) with a fluorescence detector. Ochratoxin A was detected from three samples at 1.03‒2.08 μg/kg, whereas no aflatoxins or citrinin were detected. To test the potential of fungal isolates to produce aflatoxin, we performed a PCR assay that screened for the norB-cypA gene for 64 Aspergillus isolates. As a result, a single 800-bp band was amplified from 10 A. flavus isolates, and one Aspergillus sp. isolate. UPLC analyses confirmed aflatoxin production by nine A. flavus isolates and one Aspergillus sp. isolate, which produced total aflatoxins at 146.88‒909.53 μg/kg. This indicates that continuous monitoring of ground red pepper for toxigenic fungi is necessary to minimize mycotoxin contamination.

A pair of new azaphilone epimers, perangustols A-B (1-2), and two new natural products (3-4), together with two known metabolites (5-6) were isolated from the culture of the marine sediment-derived fungus Cladosporium perangustum FS62. The structures of these compounds were established on the basis of extensive spectroscopic analysis. The isolated compounds (1-6) were evaluated for their cytotoxic activities against the SF-268, MCF-7, NCI-H460, and HepG-2 tumor cell lines. Nonetheless, no significant activity was observed.

. Natural antifungal agents are generally broad-spectrum compounds with low mammalian and environmental toxicity. Cladosporin is a naturally occurring fungal metabolite mainly isolated from the endophytic fungus Cladosporium cladosporioides. This review article summarizes the chemistry and biological - properties of cladosporin covering references published from 1971-2016, including the source, phytochemical characterization, biosynthesis, total synthesis, structure and activity (SAR), and biological activity of cladosporin. Cladosporin exhibited potent antibacterial, antifungal, insecticidal, and anti-inflammatory activities, as well as plant growth regulatory effects. More importantly, cladosporin was identified as having potent, nanomolar, antiparasitic activity against both Plasmodiumfalciparum blood and liver stages via specific inhibition of protein synthesis. This provides a new approach for the design of isocoumarin- based compounds for the treatment of malaria. Herbicidal activity and antifungal activity against Cryptococcus neoformans (C₅₀ value of 17.7 μg/mL) of cladosporin are also described here in the review for the first time. Cladosporin selectively inhibited the growth of a monocot (agostis) and showed no activity against a dicot (lettuce), which indicates its great potential as a selective herbicide for monocots in agriculture use. The above data suggest that cladosporin has great potential utility as a lead compound in the development of agrochemicals against certain plant pathogens and pharmaceuticals against drug-resistant bacteria and parasites.

The principal fungal species isolated from a contaminated library environment were tested for their microbial volatile organic compound (MVOC) production ability. Aspergillus creber, A. penicillioides, Cladosporium cladosporioides, Eurotium chevalieri, E. halophilicum, Penicillium brevicompactum and P. chrysogenum were cultivated on suitable culture media inside sample bottles specifically designed and created for direct MVOC injection to a GC-MS instrument. The fungal emissions were monitored over several weeks to detect changes with the aging of the colonies, monitored also by respirometric tests. A total of 55 different MVOCs were detected and isopropyl alcohol, 3-methyl-1-butanol and 2-butanone were the principal compounds in common between the selected fungal species. Moreover, 2,4-dimethylheptane, 1,4-pentadiene, styrene, ethanol, 2-methyl-1-butanol, acetone, furan and 2-methylfuran were the most detected compounds. For the first time, the MVOC production for particular fungal species was detected. The species A. creber, which belongs to the recently revised group Aspergillus section Versicolores, was characterized by the production of ethanol, furan and 1,4-pentadiene. For the xerophilic fungus E. halophilicum, specific production of acetone, 2-butanone and 1,4-pentadiene was detected, supported also by respirometric data. The results demonstrated the potential use of this method for the detection of fungal contamination phenomena inside Cultural Heritage's preservation environments., (Copyright © 2016 Elsevier B.V. All rights reserved.)