Sesquiterpenoids From the Antarctic Fungus Pseudogymnoascus sp. HSX2#-11

The fungal strains Pseudogymnoascus are a kind of psychrophilic pathogenic fungi that are ubiquitously distributed in Antarctica, while the studies of their secondary metabolites are infrequent. Systematic research of the metabolites of the fungus Pseudogymnoascus sp. HSX2#-11 led to the isolation of six new tremulane sesquiterpenoids pseudotremulanes A–F (1–6), combined with one known analog 11,12-epoxy-12β-hydroxy-1-tremulen-5-one (7), and five known steroids (8–12). The absolute configurations of the new compounds (1–6) were elucidated by their ECD spectra and ECD calculations. Compounds 1–7 were proved to be isomeride structures with the same chemical formula. Compounds 1/2, 3/4, 1/4, and 2/3 were identified as four pairs of epimerides at the locations of C-3, C-3, C-9, and C-9, respectively. Compounds 8 and 9 exhibited cytotoxic activities against human breast cancer (MDA-MB-231), colorectal cancer (HCT116), and hepatoma (HepG2) cell lines. Compounds 9 and 10 also showed antibacterial activities against marine fouling bacteria Aeromonas salmonicida. This is the first time to find terpenoids and steroids in the fungal genus Pseudogymnoascus.

Download Full-text

New Polyketides from the Antarctic Fungus Pseudogymnoascus sp. HSX2#-11

Marine Drugs ◽

10.3390/md19030168 ◽

2021 ◽

Vol 19 (3) ◽

pp. 168

Author(s):

Ting Shi ◽

Yan-Yan Yu ◽

Jia-Jia Dai ◽

Yi-Ting Zhang ◽

Wen-Peng Hu ◽

...

Keyword(s):

Pathogenic Fungus ◽

Diphenyl Ether ◽

Antibacterial Activities ◽

Systematic Research ◽

Metabolic Profiles ◽

X Ray Diffraction ◽

Molecular Networking ◽

X Ray ◽

The Antarctic ◽

First Time

The species Pseudogymnoascus is known as a psychrophilic pathogenic fungus with a ubiquitous distribution in Antarctica. Meanwhile, the study of its secondary metabolites is infrequent. Systematic research of the metabolites of the fungus Pseudogymnoascus sp. HSX2#-11, guided by the method of molecular networking, led to the isolation of one novel polyketide, pseudophenone A (1), along with six known analogs (2–7). The structure of the new compound was elucidated by extensive spectroscopic investigation and single-crystal X-ray diffraction. Pseudophenone A (1) is a dimer of diphenyl ketone and diphenyl ether, and there is only one analog of 1 to the best of our knowledge. Compounds 1 and 2 exhibited antibacterial activities against a panel of strains. This is the first time to use molecular networking to study the metabolic profiles of Antarctica fungi.

Download Full-text

Microbial Transformation of neo-Clerodane Diterpenoid, Scutebarbatine F, by Streptomyces sp. CPCC 205437

Frontiers in Microbiology ◽

10.3389/fmicb.2021.662321 ◽

2021 ◽

Vol 12 ◽

Author(s):

Dewu Zhang ◽

Xiaoyu Tao ◽

Guowei Gu ◽

Yujia Wang ◽

Wenxia Zhao ◽

...

Keyword(s):

Influenza A ◽

Microbial Transformation ◽

Cancer Cell Line ◽

Antibacterial Activities ◽

Positive Control ◽

Cytotoxic Activities ◽

Ionization Mass ◽

Nmr Data ◽

First Time ◽

New Metabolites

Biotransformation of the neo-clerodane diterpene, scutebarbatine F (1), by Streptomyces sp. CPCC 205437 was investigated for the first time, which led to the isolation of nine new metabolites, scutebarbatine F1–F9 (2–10). Their structures were determined by extensive high-resolution electrospray ionization mass spectrometry (HRESIMS) and NMR data analyses. The reactions that occurred included hydroxylation, acetylation, and deacetylation. Compounds 2–4 and 8–10 possess 18-OAc fragment, which were the first examples of 13-spiro neo-clerodanes with 18-OAc group. Compounds 7–10 were the first report of 13-spiro neo-clerodanes with 2-OH. Compounds 1–10 were biologically evaluated for the cytotoxic, antiviral, and antibacterial activities. Compounds 5, 7, and 9 exhibited cytotoxic activities against H460 cancer cell line with inhibitory ratios of 46.0, 42.2, and 51.1%, respectively, at 0.3 μM. Compound 5 displayed a significant anti-influenza A virus activity with inhibitory ratio of 54.8% at 20 μM, close to the positive control, ribavirin.

Download Full-text

Anthraquinone Derivatives from a Marine-Derived Fungus Sporendonema casei HDN16-802

Marine Drugs ◽

10.3390/md17060334 ◽

2019 ◽

Vol 17 (6) ◽

pp. 334 ◽

Cited By ~ 3

Author(s):

Xueping Ge ◽

Chunxiao Sun ◽

Yanyan Feng ◽

Lingzhi Wang ◽

Jixing Peng ◽

...

Keyword(s):

Chlorine Atom ◽

Anticoagulant Activity ◽

Antitubercular Activity ◽

Antibacterial Activities ◽

Cytotoxic Activities ◽

Spectroscopic Techniques ◽

Addition Compound ◽

Anthraquinone Derivatives ◽

Ic50 Values ◽

First Time

Five new anthraquinone derivatives, auxarthrols D–H (1–5), along with two known analogues (6–7), were obtained from the culture of the marine-derived fungus Sporendonema casei. Their structures, including absolute configurations, were established on the basis of NMR, HRESIMS, and circular dichroism (CD) spectroscopic techniques. Among them, compound 4 represents the second isolated anthraquinone derivative with a chlorine atom, which, with compound 6, are the first reported anthraquinone derivatives with anticoagulant activity. Compounds 1 and 3 showed cytotoxic activities with IC50 values from 4.5 μM to 22.9 μM, while compounds 1, 3–4, and 6–7 showed promising antibacterial activities with MIC values from 12.5 μM to 200 μM. In addition, compound 7 was discovered to display potential antitubercular activity for the first time.

Download Full-text

Synthesis of Silver Abietate as an Antibacterial Agent for Textile Applications

Bioinorganic Chemistry and Applications ◽

10.1155/2015/215354 ◽

2015 ◽

Vol 2015 ◽

pp. 1-5 ◽

Cited By ~ 6

Author(s):

A. Yıldız ◽

M. Değirmencioğlu

Keyword(s):

Textile Industry ◽

Antibacterial Agent ◽

Abietic Acid ◽

Antibacterial Activities ◽

Test Method ◽

Gram Positive Bacteria ◽

H Nmr ◽

Agar Diffusion Test ◽

New Compounds ◽

First Time

This study explored the potential use of new silver abietate obtained from abietic acid as an antibacterial agent for textile applications. Synthesis, structure, and antibacterial studies of silver abietate compound are reported. Silver complex was obtained reacting abietic acid with silver. The new compounds were characterized by1H NMR,13C NMR, DEPT, IR, UV, and ESI-MS techniques which support the proposed structures. The new Ag abietate complex has no environmental hazard, its antibacterial activities were evaluated after being applied to cotton fabric by padding process according to the JIS L 1902-2008 agar diffusion test method and against three Gram-negative and three Gram-positive bacteria, respectively. Stability of antibacterial effect after repeated washings (3, 5, 10, and 20) was also tested which indicated that the synthesized silver abietate compound could be used as a new antibacterial agent in textile industry. In this way, the compound has been synthesized the first time in the literature and the applications have been investigated.

Download Full-text

One-Pot Synthesis of 5-(Het)Aryl 8-Aminoquinoline Amide Derivatives as Potential Antibacterial / Cytotoxic Agents

Current Bioactive Compounds ◽

10.2174/1573407214666180910130225 ◽

2020 ◽

Vol 16 (2) ◽

pp. 142-151

Author(s):

Zanjam Spandana ◽

Tadigiri M. Rekha ◽

Mandava V.B. Rao ◽

Manojit Pal

Keyword(s):

Hepg2 Cell ◽

Cell Lines ◽

Antibacterial Activities ◽

Cytotoxic Agents ◽

Hek293 Cells ◽

Cytotoxic Activities ◽

Quinoline Derivatives ◽

One Pot ◽

Hepg2 Cell Lines

Background: The 8-Aminoquinoline (8-AQ) framework has attracted particular attention in the discovery and development of antimalarial and anti-bacterial agents or drugs. However, the clinical uses of 8-AQ based drugs are often associated with toxic side effects such as methemoglobinemia and hemolytic anemia with deficiency in Glucose-6-Phosphate Dehydrogenase (G6PD) Activity. The 4-aryl- 8-amino(acetamido)quinoline derivatives, on the other hand, have shown antiproliferative activities against cancer cell lines. These reports prompted us to assess the antibacterial and cytotoxic activities of a series of compounds based on 5-aryl 8-aminoquinoline amide scaffold. Methods: A series of compounds based on 5-(het)aryl 8-aminoquinoline amide scaffold was synthesized via a one-pot ultrasound-assisted method using a C-5 selective halogenation of quinoline derivatives followed by Pd/C-catalyzed Suzuki-Miyaura coupling with (het)aryl boronic acids. All these compounds were evaluated for their in vitro antibacterial activities against representative Gram-(+) and Gram-(-) strains including Escherichia coli, Pseudomonas aeruginosa, Klebsiella species and Staphylococcus aureus. Three compounds were further tested for cytotoxicities in vitro against breast adenocarcinoma (MCF7) and Hepatocellular Carcinoma (HepG2) along with non-cancerous human embryonic kidney (HEK293) cell lines. Results: All these compounds demonstrated moderate to good antibacterial activities against the four organisms used. In vitro assay results revealed that three compounds showed good activities against Gram-(+) strains and Gram-(-) strains and one was comparable to ciprofloxacin and pefloxacin. These three compounds were further tested for their cytotoxic properties against MCF7 and HepG2 cell lines. One of them showed IC50 value comparable to doxorubicin when tested against HepG2 cell lines. However, none of these compounds showed any significant effects when tested against HEK293 cells indicating their selectivity towards the growth inhibition of cancer cells. Conclusion: A series of compounds based on 5-(het)aryl 8-aminoquinoline amide scaffold was synthesized and evaluated for antibacterial and cytotoxic activities. Several of these compounds showed promising antibacterial and cytotoxic activities when tested in vitro suggesting that the present class of compounds may be of interest for the identification of new and potential antibacterial / cytotoxic agents.

Download Full-text

Resorcylic Acid Lactones Produced by an Endophytic Penicillium ochrochloron Strain from Kadsura angustifolia

Planta Medica ◽

10.1055/a-1326-2600 ◽

2020 ◽

Author(s):

Hong Chuan Song ◽

Dan Qin ◽

Hai Yang Liu ◽

Jin Yan Dong ◽

Chuan You ◽

...

Keyword(s):

Spectroscopic Analysis ◽

Tumor Cell Line ◽

Antibacterial Activities ◽

Preparative Hplc ◽

Solid Culture ◽

Ic50 Value ◽

Resorcylic Acid Lactones ◽

New Compounds ◽

First Time

AbstractFour new β-resorcylic acid lactones, including penochrochlactone A (2), 4-O-desmethyl-aigialomycin B (4), and penochrochlactones C and D (5 and 6), two compounds isolated from a natural source for the first time, 5α, 6β-acetonide-aigialomycin B (1) and penochrochlactone B (3), together with six known compounds, aigialomycin F (7), aigialomycins A, B, and D (8–10), zeaenol (11), and oxozeaenol (12), were isolated from a mycelial solid culture of the endophytic fungus Penicillium ochrochloron SWUKD4.1850 from the medicinal plant Kadsura angustifolia by sequential purification over silica gel, Sephadex LH-20 column chromatography, and preparative HPLC. Their structures were elucidated by extensive spectroscopic analysis and chemical conversions. In addition, all the new compounds were evaluated for their cytotoxic and antibacterial activities in vitro. Penochrochlactone C (5) displayed moderate cytotoxicity against the HeLa tumor cell line with an IC50 value of 9.70 µM. In the antibacterial assays, compounds 4 – 6 exhibited moderate activities against Staphylococcus aureus, Bacillus subtilis, Escherichia coli, and Pseudomonas aeruginosa with MIC values between 9.7 and 32.0 µg/mL.

Download Full-text

Antifungal and Antibacterial Activities of Araucaria araucana (Mol.) K. Koch Heartwood Lignans

Zeitschrift für Naturforschung C ◽

10.1515/znc-2006-1-207 ◽

2006 ◽

Vol 61 (1-2) ◽

pp. 35-43 ◽

Cited By ~ 40

Author(s):

Carlos L. Céspedes ◽

J. Guillermo Avila ◽

Ana M. Garcıá ◽

José Becerra ◽

Cristian Flores ◽

...

Keyword(s):

Micrococcus Luteus ◽

Pathogenic Fungi ◽

Trichophyton Mentagrophytes ◽

Antibacterial Activities ◽

Antimicrobial Activities ◽

Fusarium Spp ◽

Meoh Extract ◽

Penicillium Notatum ◽

Araucaria Araucana ◽

First Time

Abstract Five lignans (secoisolariciresinol, pinoresinol, eudesmin, lariciresinol, and lariciresinol-4- methyl ether) were isolated from an MeOH extract from Araucaria araucana (Mol.) K. Koch wood for the first time in this species and their structures determined with spectroscopic methods. The antimicrobial activities of these compounds were determined for the bacteria Citrobacter sp., Bacillus subtilis, Escherichia coli, Micrococcus luteus, Staphylococcus aureus, and Pseudomonas aeruginosa, and for the white rooting and staining fungi Mucor miehei, Paecilomyces variotii, Ceratocystis pilifera, Trametes versicolor, and Penicillium notatum, and in addition, the MeOH extract was evaluated against Aspergillus niger, Candida albicans, Fusarium moniliforme, F. sporotrichum and Trichophyton mentagrophytes. The most sensitive bacteria against pinoresinol were the Gram-positive. However, secoisolariciresinol exhibited a significant antifungal activity on fungi of white rooting and wood staining and this compound completely inhibited the mycelial growth of T. versicolor and C. pilifera at 300 and 400 μg per disc, respectively, whereas pinoresinol showed a moderate inhibitory activity. On the other hand, the MeOH extract had the highest activity against rooting and staining and pathogenic fungi as well as T. versicolor, Fusarium spp. and Trichophyton mentagrophytes, inhibiting completely the growth at 400 μg per disc

Download Full-text

Secondary Metabolites with Antimicrobial Activities from Chamaecyparis obtusa var. formosana

Molecules ◽

10.3390/molecules27020429 ◽

2022 ◽

Vol 27 (2) ◽

pp. 429

Author(s):

Ming-Der Wu ◽

Ming-Jen Cheng ◽

Jih-Jung Chen ◽

Nanthaphong Khamthong ◽

Wen-Wei Lin ◽

...

Keyword(s):

Spectroscopic Analysis ◽

High Resolution Mass Spectrometry ◽

Chamaecyparis Obtusa ◽

Antibacterial Activities ◽

Antimicrobial Activities ◽

The Past ◽

Nmr Data ◽

The Mean ◽

New Compounds ◽

First Time

Seven new compounds, including one dimer novel skeleton, chamaecyformosanin A (1); three diterpenes, chamaecyformosanins B–D (2-4); one sesquiterpene, chamaecyformosanin E (5); and two monoterpenes, chamaecyformosanins F and G (6 and 7) were isolated from the methanol extract of the bark of Chamaecyparis obtusa var. formosana. Their structures were established by the mean of spectroscopic analysis and the comparison of NMR data with those of known analogues. Their structures were elucidated on the basis of physicochemical evidence, in-depth NMR spectroscopic analysis, and high-resolution mass spectrometry. Furthermore, the isolated compounds were subjected to an evaluation of their antimicrobial activity. Metabolites 1, 3, and 4 present antibacterial activities. It is worth mentioning that the chemical composition of the bark of C. obtusa var. formosana has never been studied in the past. This is the first time the barks from C. obtusa var. formosana were studied and two new skeleton compounds, 1 and 7, were obtained.

Download Full-text

New Acetophenones and Chromenes from the Leaves of Melicope barbigera A. Gray

Molecules ◽

10.3390/molecules26030688 ◽

2021 ◽

Vol 26 (3) ◽

pp. 688

Author(s):

Kim-Thao Le ◽

Jan J. Bandolik ◽

Matthias U. Kassack ◽

Kenneth R. Wood ◽

Claudia Paetzold ◽

...

Keyword(s):

Ovarian Cancer Cell Line ◽

Hawaiian Island ◽

Cancer Cell Line ◽

2D Nmr ◽

Cytotoxic Activities ◽

2D Nmr Spectroscopy ◽

Ic50 Values ◽

New Compounds ◽

First Time ◽

Modified Mosher’S Method

The dichloromethane extract from leaves of Melicope barbigera (Rutaceae), endemic to the Hawaiian island of Kaua’i, yielded four new and three previously known acetophenones and 2H-chromenes, all found for the first time in M. barbigera. The structures of the new compounds obtained from the dichloromethane extract after purification by chromatographic methods were unambiguously elucidated by spectroscopic analyses including 1D/2D NMR spectroscopy and HRESIMS. The absolute configuration was determined by modified Mosher’s method. Compounds 2, 4 and the mixture of 6 and 7 exhibited moderate cytotoxic activities against the human ovarian cancer cell line A2780 with IC50 values of 30.0 and 75.7 µM for 2 and 4, respectively, in a nuclear shrinkage cytotoxicity assay.

Download Full-text

The Embittered Mind

Journal of Individual Differences ◽

10.1027/1614-0001/a000208 ◽

2016 ◽

Vol 37 (4) ◽

pp. 213-222 ◽

Cited By ~ 4

Author(s):

Hansjörg Znoj ◽

Sandra Abegglen ◽

Ulrike Buchkremer ◽

Michael Linden

Keyword(s):

Emotional Reaction ◽

Control Group ◽

Systematic Research ◽

Roc Curve Analysis ◽

Confirmatory Factor Analyses ◽

Receiver Operating Characteristic Curves ◽

Confirmatory Factor ◽

Different Dimensions ◽

First Time ◽

Common Understanding

Abstract. There is a growing interest in embitterment as psychological concept. However, little systematic research has been conducted to characterize this emotional reaction. Still, there is an ongoing debate about the distinctiveness of embitterment and its dimensions. Additionally, a categorical and a dimensional perspective on embitterment have been developed independently over the last decade. The present study investigates the dimensions of embitterment by bringing these two different approaches together, for the first time. The Bern Embitterment Inventory (BEI) was given to 49 patients diagnosed with “Posttraumatic Embitterment Disorder (PTED)” and a matched control group of 49 patients with psychological disorders with other dominant emotional dysregulations. The ability to discriminate between the two groups was assessed by t-tests and Receiver Operating Characteristic Curves (ROC curve analysis). PTED patients scored significantly higher on the BEI than the patients of the control group. ROC analyses indicated diagnostic accuracy of the inventory. Further, we conducted Confirmatory Factor Analyses (CFA) to examine the different dimensions of embitterment and their relations. As a result, we found four characteristic dimensions of embitterment, namely disappointment, lack of acknowledge, pessimism, and misanthropy. In general, our findings showed a common understanding of embitterment as a unique but multidimensional emotional reaction to distressful life-events.

Download Full-text