Rhytidhyesters A – D, 4 New Chlorinated Cyclopentene Derivatives from the Endophytic Fungus Rhytidhysteron sp. BZM-9

AbstractFour new chlorinated cyclopentene derivatives, rhytidhyesters A – D (1 – 4), were isolated from Rhytidhysteron sp. BZM-9, an endophytic fungus from Leptospermum brachyandrum. The planar structures of compounds 1 – 4 were mainly elucidated by 1D, 2D NMR, and HRESIMS data. Their absolute configurations were established by X-ray crystallographic analysis, quantum chemical 13C NMR, and electronic circular dichroism calculations. Compounds 1 and 2 are a pair of epimers. Moreover, all the isolated compounds were evaluated for cytotoxic activities against 3 human colon cancer cell lines (SW620, HT29, SW480) and antimicrobial activity against Staphylococcus aureus. All compounds exhibited weak to moderate antiproliferative activities with IC50 values ranging from 15.4 to 37.7 µM but were inactive against S. aureus.

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Mono- and Dimeric Xanthones with Anti-Glioma and Anti-Inflammatory Activities from the Ascidian-Derived Fungus Diaporthe sp. SYSU-MS4722

Marine Drugs ◽

10.3390/md20010051 ◽

2022 ◽

Vol 20 (1) ◽

pp. 51

Author(s):

Senhua Chen ◽

Heng Guo ◽

Minghua Jiang ◽

Qilin Wu ◽

Jing Li ◽

...

Keyword(s):

High Resolution Mass Spectrometry ◽

2D Nmr ◽

Crystallographic Analysis ◽

Selective Cytotoxicity ◽

X Ray ◽

Planar Structures ◽

Spectroscopic Analyses ◽

Ic50 Values ◽

Anti Inflammatory ◽

Resolution Mass

Seven new xanthones, diaporthones A−G (1−7), together with 13 known analogues, including five mono- (8−14) and six dimeric xanthones (15−20), were obtained from the ascidian-derived fungus Diaporthe sp. SYSU-MS4722. Their planar structures were established by extensive spectroscopic analyses, including 1D and 2D NMR and high-resolution mass spectrometry (HR-ESIMS). The absolute configurations of 1−7 were clearly identified by X-ray crystallographic analysis and calculation of the ECD Spectra. Compounds 15−20 showed significant anti-inflammatory activity with IC50 values between 6.3 and 8.0 μM. In addition, dimeric xanthones (15−20) showed selective cytotoxicity against T98G cell lines with IC50 values ranging from 19.5 to 78.0 μM.

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New Cardenolides from Biotransformation of Gitoxigenin by the Endophytic Fungus Alternaria eureka 1E1BL1: Characterization and Cytotoxic Activities

Molecules ◽

10.3390/molecules26103030 ◽

2021 ◽

Vol 26 (10) ◽

pp. 3030

Author(s):

Erdal Bedir ◽

Çiğdem Karakoyun ◽

Gamze Doğan ◽

Gülten Kuru ◽

Melis Küçüksolak ◽

...

Keyword(s):

Endophytic Fungus ◽

2D Nmr ◽

Dimethyl Acetal ◽

Nerium Oleander ◽

Cytotoxic Activities ◽

Hek 293 ◽

Natural Product Library ◽

Ic50 Values ◽

Biotransformation Products ◽

Ft Ir

Microbial biotransformation is an important tool in drug discovery and for metabolism studies. To expand our bioactive natural product library via modification and to identify possible mammalian metabolites, a cytotoxic cardenolide (gitoxigenin) was biotransformed using the endophytic fungus Alternaria eureka 1E1BL1. Initially, oleandrin was isolated from the dried leaves of Nerium oleander L. and subjected to an acid-catalysed hydrolysis to obtain the substrate gitoxigenin (yield; ~25%). After 21 days of incubation, five new cardenolides 1, 3, 4, 6, and 8 and three previously- identified compounds 2, 5 and 7 were isolated using chromatographic methods. Structural elucidations were accomplished through 1D/2D NMR, HR-ESI-MS and FT-IR analysis. A. eureka catalyzed oxygenation, oxidation, epimerization and dimethyl acetal formation reactions on the substrate. Cytotoxicity of the metabolites were evaluated using MTT cell viability method, whereas doxorubicin and oleandrin were used as positive controls. Biotransformation products displayed less cytotoxicity than the substrate. The new metabolite 8 exhibited the highest activity with IC50 values of 8.25, 1.95 and 3.4 µM against A549, PANC-1 and MIA PaCa-2 cells, respectively, without causing toxicity on healthy cell lines (MRC-5 and HEK-293) up to concentration of 10 µM. Our results suggest that A. eureka is an effective biocatalyst for modifying cardenolide-type secondary metabolites.

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Cytotoxic Activities of (Graptophyllum pictum (L.) Griff) Ethanolic Extract and Its Fractions on Human Colon Cancer Cell WiDr

Majalah Obat Tradisional ◽

10.22146/mot.48189 ◽

2020 ◽

Vol 25 (1) ◽

pp. 29

Author(s):

Azizah Amin ◽

Andayana Puspitasari Gani ◽

Retno Murwanti

Keyword(s):

Colon Cancer ◽

Ethyl Acetate ◽

Cytotoxic Activity ◽

Ethanolic Extract ◽

Human Colon ◽

Cytotoxic Activities ◽

Human Colon Cancer ◽

Water Fraction ◽

Cancerous Cell ◽

Ic50 Values

Colon cancer is the third most common cancer in the world. Treatments for colon cancer might cause major side effects, hence increase opportunities for the development of new cancer drugs. One of the plants that potential to develop as an anticancer agent is daun ungu (Graptophyllum pictum (L.) Griff). From previous studies, G.pictum had cytotoxic activity against several cancerous cell lines. Traditionally, G.pictum leaves have been used for hemorrhoid treatment. The purpose of this study was to determine the cytotoxic activity of G.pictum ethanolic extract and its fractions on human colon cancer WiDr cells and to elucidate the compounds contained in most active extracts/fractions. G.pictum was extracted using 70% ethanol and fractionated using n-hexane, chloroform, and ethyl acetate, respectively. The yield of the extract obtained was 18.9%. The yield of hexane, chloroform, ethyl acetate, and ethanol-water fractions were 1.07%, 2.93%, 10.26%, and 84.82%, respectively. The cytotoxic activity was carried out on WiDr cells using the MTT assay. Cytotoxic activity was determined based on IC50 values. IC50 value of extract, hexane, chloroform, ethyl acetate and ethanol-water fraction obtained on WiDr cells were 1527,58; 143,97; 507,19; 3538,67 and 3186,60 μg/mL. The hexane fraction containing terpenoids and phenolics showed the highest cytotoxic activities against WiDr colon cancer cells.

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Triterpene Saponins from Cyclamen persicum

Natural Product Communications ◽

10.1177/1934578x1000500707 ◽

2010 ◽

Vol 5 (7) ◽

pp. 1934578X1000500 ◽

Cited By ~ 3

Author(s):

Ghezala Mihci-Gaidi ◽

David Pertuit ◽

Tomofumi Miyamoto ◽

Jean-François Mirjolet ◽

Olivier Duchamp ◽

...

Keyword(s):

Human Colon ◽

2D Nmr ◽

Colon Cancer Cell ◽

Human Colon Cancer Cell ◽

Triterpene Saponins ◽

Cyclamen Persicum ◽

Human Colon Cancer ◽

Colon Cancer Cell Lines ◽

Hct 116 ◽

Ht 29

A new triterpene saponin 3- O-β-D-glucopyranosyl-(1→4)-α-L-arabinopyranosyl-16α-hydroxy-13β,28-epoxy-oleanan-30-al (1), along with four known triterpene glycosides (2-5) were isolated from Cyclamen persicum. Their structures were characterized by a combination of 1D- and 2D-NMR (1H-1H COSY, TOCSY, NOESY, HSQC, and HMBC) and MS spectrocopic data. The cytotoxicity of compounds 2 and 4 was evaluated using two human colon cancer cell lines HT-29 and HCT 116.

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Fusarins G–L with Inhibition of NO in RAW264.7 from Marine-Derived Fungus Fusarium solani 7227

Marine Drugs ◽

10.3390/md19060305 ◽

2021 ◽

Vol 19 (6) ◽

pp. 305

Author(s):

Guangyuan Luo ◽

Li Zheng ◽

Qilin Wu ◽

Senhua Chen ◽

Jing Li ◽

...

Keyword(s):

Fusarium Solani ◽

2D Nmr ◽

Inflammatory Activity ◽

Raw264.7 Cells ◽

Spectroscopic Methods ◽

X Ray ◽

X Ray Crystallography ◽

Structure Activity ◽

Ic50 Values ◽

New Compounds

Six new fusarin derivatives, fusarins G–L (1–6), together with five known compounds (5–11) were isolated from the marine-derived fungus Fusarium solani 7227. The structures of the new compounds were elucidated by means of comprehensive spectroscopic methods (1D and 2D NMR, HRESIMS, ECD, and ORC) and X-ray crystallography. Compounds 5–11 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide, with IC50 values ranging from 3.6 to 32.2 μM. The structure–activity relationships of the fusarins are discussed herein.

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Synthesis of Exosome-Based Fluorescent Gold Nanoclusters for Cellular Imaging Applications

International Journal of Molecular Sciences ◽

10.3390/ijms22094433 ◽

2021 ◽

Vol 22 (9) ◽

pp. 4433

Author(s):

Eun Sung Lee ◽

Byung Seok Cha ◽

Seokjoon Kim ◽

Ki Soo Park

Keyword(s):

Photoelectron Spectroscopy ◽

Low Cost ◽

Stokes Shift ◽

Gold Nanoclusters ◽

Human Colon ◽

Cellular Imaging ◽

Metal Nanoclusters ◽

Human Colon Cancer ◽

X Ray ◽

High Concentrations

In recent years, fluorescent metal nanoclusters have been used to develop bioimaging and sensing technology. Notably, protein-templated fluorescent gold nanoclusters (AuNCs) are attracting interest due to their excellent fluorescence properties and biocompatibility. Herein, we used an exosome template to synthesize AuNCs in an eco-friendly manner that required neither harsh conditions nor toxic chemicals. Specifically, we used a neutral (pH 7) and alkaline (pH 11.5) pH to synthesize two different exosome-based AuNCs (exo-AuNCs) with independent blue and red emission. Using field-emission scanning electron microscopy, energy dispersive X-ray microanalysis, nanoparticle tracking analysis, and X-ray photoelectron spectroscopy, we demonstrated that AuNCs were successfully formed in the exosomes. Red-emitting exo-AuNCs were found to have a larger Stokes shift and a stronger fluorescence intensity than the blue-emitting exo-AuNCs. Both exo-AuNCs were compatible with MCF-7 (human breast cancer), HeLa (human cervical cancer), and HT29 (human colon cancer) cells, although blue-emitting exo-AuNCs were cytotoxic at high concentrations (≥5 mg/mL). Red-emitting exo-AuNCs successfully stained the nucleus and were compatible with membrane-staining dyes. This is the first study to use exosomes to synthesize fluorescent nanomaterials for cellular imaging applications. As exosomes are naturally produced via secretion from almost all types of cell, the proposed method could serve as a strategy for low-cost production of versatile nanomaterials.

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In vitro antiproliferative activity against human colon cancer cell lines of representative 4-thiazolidinones. Part I

Bioorganic & Medicinal Chemistry Letters ◽

10.1016/j.bmcl.2005.05.093 ◽

2005 ◽

Vol 15 (17) ◽

pp. 3930-3933 ◽

Cited By ~ 92

Author(s):

Rosaria Ottanà ◽

Stefania Carotti ◽

Rosanna Maccari ◽

Ida Landini ◽

Giuseppa Chiricosta ◽

...

Keyword(s):

Colon Cancer ◽

Cell Lines ◽

Cancer Cell ◽

Antiproliferative Activity ◽

Human Colon ◽

Colon Cancer Cell ◽

Human Colon Cancer Cell ◽

Human Colon Cancer ◽

Colon Cancer Cell Lines

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Bile salt-induced apoptosis in human colon cancer cell lines involves the mitochondrial transmembrane potential but not the CD95 (Fas/Apo-1) receptor

International Journal of Colorectal Disease ◽

10.1007/s00384-004-0616-2 ◽

2004 ◽

Vol 20 (2) ◽

pp. 103-113 ◽

Cited By ~ 22

Author(s):

Frank-Peter Wachs ◽

Ren� C. Krieg ◽

Cecilia M. P. Rodrigues ◽

Helmut Messmann ◽

Frank Kullmann ◽

...

Keyword(s):

Colon Cancer ◽

Bile Salt ◽

Cell Lines ◽

Transmembrane Potential ◽

Human Colon ◽

Colon Cancer Cell ◽

Human Colon Cancer Cell ◽

Human Colon Cancer ◽

Colon Cancer Cell Lines ◽

Induced Apoptosis

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Secondary Metabolites with Nitric Oxide Inhibition from Marine-Derived Fungus Alternaria sp. 5102

Marine Drugs ◽

10.3390/md18080426 ◽

2020 ◽

Vol 18 (8) ◽

pp. 426 ◽

Cited By ~ 1

Author(s):

Senhua Chen ◽

Yanlian Deng ◽

Chong Yan ◽

Zhenger Wu ◽

Heng Guo ◽

...

Keyword(s):

Secondary Metabolites ◽

2D Nmr ◽

X Ray ◽

X Ray Crystallography ◽

Spectroscopic Analyses ◽

Structure Activity ◽

Ic50 Values ◽

Alternaria Sp ◽

Modified Mosher’S Method ◽

Oxide Inhibition

Two new benzofurans, alternabenzofurans A and B (1 and 2) and two new sesquiterpenoids, alternaterpenoids A and B (3 and 4), along with 18 known polyketides (5−22), were isolated from the marine-derived fungus Alternaria sp. 5102. Their structures were elucidated on the basis of extensive spectroscopic analyses (1D and 2D NMR, HR-ESIMS, and ECD) and X-ray crystallography, as well as the modified Mosher’s method. Compounds 2, 3, 5, 7, 9–18, and 20–22 exhibited potent anti-inflammatory activity by inhibiting the production of NO in RAW264.7 cells activated by lipopolysaccharide with IC50 values in the range from 1.3 to 41.1 μM. Structure-activity relationships of the secondary metabolites were discussed.

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