scholarly journals Isolation, Structure Elucidation and Apoptosis-inducing Activity of New Compounds from the Edible Fungus Lentinus Striguellus

2009 ◽  
Vol 4 (4) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Yongbiao Zheng ◽  
Baobing Zhao ◽  
Chunhua Lu ◽  
Xinjian Lin ◽  
Zhonghui Zheng ◽  
...  
Keyword(s):  
Cell Cycle ◽  
Mtt Assay ◽  
Structure Elucidation ◽  
2D Nmr ◽  
Fungal Strain ◽  
Mass Spectrometric ◽  
Morphological Observation ◽  
Edible Fungus ◽  
New Compounds ◽  
Tof Ms

Three new natural compounds, striguellolide A (1), striguellol A (2) and striguellone A (6), together with three known ones, 3,4- trans-dihydroxy-6-methoxy-2,2-dimethylchroman (3), 3-hydroxy-6- methoxy-2,2-dimethylchroman-4-one (4) and 3-hydroxy-6- methoxy-2,2-dimethylchroman (5), were isolated from the agar cultures of the edible fungal strain Lentinus striguellus. Their structures were elucidated by spectroscopic and mass spectrometric analyses, including 1D-, 2D-NMR and HR-ESI-Q-TOF-MS, and chemical reactions. Striguellone A showed cytotoxicity against HeLa cells by MTT assay and was found to be an activator of apoptosis, assessed by morphological observation and cell cycle analysis using the flow cytometer.

Two Ceramides from Tanacetum artemesioides

2004 ◽  
Vol 59 (3) ◽  
pp. 329-333 ◽  
Author(s):  
Viqar U. Ahmad ◽  
Javid Hussain ◽  
Hidayat Hussain ◽  
Umar Farooq ◽  
Erum Akber ◽  
...  
Keyword(s):  
Inhibitory Activity ◽  
Structure Elucidation ◽  
2D Nmr ◽  
Nmr Analysis ◽  
New Compounds

Two new ceramides have been isolated from Tanacetum artemisioides, besides the known constituents β -sitosterol and β -sitosterol glycoside. The structure elucidation of the isolated new compounds was based primarily on 1D and 2D NMR analysis, including COSY, HMQC, HMBC correlations. The compound 1 and 2 showed inhibitory activity against acetylcholinesterase

scholarly journals Two New Compounds from Artemisia sacrorum

2016 ◽  
Vol 11 (4) ◽  
pp. 1934578X1601100
Author(s):  
Qinghu Wang ◽  
Rongjun Wu ◽  
Narenchaoketu Han ◽  
Nayintai Dai ◽  
Jiesi Wu
Keyword(s):  
Structure Elucidation ◽  
2D Nmr ◽  
Etoac Extract ◽  
First Report ◽  
Esi Ms ◽  
New Compounds

Two new compounds, named as sacric acid A (1) and sacric acid B (2), were isolated from the EtOAc extract of Artemisia sacrorum Ledeb. This is the first report on the structure elucidation of these compounds based on UV, IR, and extensive 1D and 2D NMR spectroscopic, and ESI-MS techniques.

scholarly journals New 3-Hydroxyquinaldic Acid Derivatives from Cultures of the Marine Derived Actinomycete Streptomyces cyaneofuscatus M-157

Marine Drugs ◽  
2018 ◽  
Vol 16 (10) ◽  
pp. 371 ◽  
Author(s):  
Francisco Ortiz-López ◽  
Elsa Alcalde ◽  
Aida Sarmiento-Vizcaíno ◽  
Caridad Díaz ◽  
Bastien Cautain ◽  
...  
Keyword(s):  
Nmr Spectra ◽  
2D Nmr ◽  
Two Dimensional ◽  
Amino Acid Residues ◽  
Trace Level ◽  
One Dimensional ◽  
2D Nmr Spectra ◽  
Ic50 Values ◽  
New Compounds ◽  
Tof Ms

Fractionation of the bioactive extract of a culture of the marine derived actinomycete Streptomyces cyaneofuscatus M-157 led to the isolation of the known 3-hydroxyquinaldic acid (4), its amide (5) and three new derivatives (1–3) containing different amino acid residues. The structures of the new molecules (1–3), including their absolute configuration, were determined by the analysis of their ESI-TOF MS and one-dimensional (1D) and two-dimensional (2D) NMR spectra and advanced Marfey’s analysis of their hydrolyzation products. Compound 3 spontaneously dimerized in solution to give the disulfide derivative 6. Unfortunately, none of the new compounds isolated confirmed the antimicrobial activity found in the bacterial extract, perhaps indicating that such antibacterial activity might be due to presence in the extract at the trace level of larger bioactive 3-hydroxyquinaldic acid derivatives from which compounds 1–3 are biosynthetic precursors. Cytotoxicity tests confirmed the moderate and weak IC50 values of 15.6 and 51.5 µM for compounds 5 and 1, respectively.

scholarly journals Secondary Metabolites of Aeromonas veronii Strain A134 Isolated from a Microcystis aeruginosa Bloom

Metabolites ◽  
2019 ◽  
Vol 9 (6) ◽  
pp. 110 ◽  
Author(s):  
Gad Weiss ◽  
Dimitry Kovalerchick ◽  
Omer Murik ◽  
Assaf Sukenik ◽  
Aaron Kaplan ◽  
...  
Keyword(s):  
Secondary Metabolites ◽  
Microcystis Aeruginosa ◽  
Structure Elucidation ◽  
Large Scale ◽  
Culture Media ◽  
2D Nmr ◽  
X Ray ◽  
Aeromonas Veronii ◽  
Large Scale Culture ◽  
New Compounds

Aeromonas veronii strain A134 was isolated from Microcystis aeruginosa colonies collected from Lake Kinneret (Sea of Galilee), Israel. The Aeromonas culture media inhibited the growth of M. aeruginosa (strain MGK). The crude extract of a large-scale culture of A. veronii A134 was separated in a few chromatographic steps to yield three new secondary metabolites, 9-chlorolumichrome (1), veronimide (2) and veronipyrazine (3), along with a known lumichrome and several known diketopiperazines. The structures of the new compounds were established by analyses of the data from 1D and 2D NMR experiments and HRMS data of the compounds, as well as a single-crystal X-ray analysis of synthetic 1. The structure elucidation and proposed biogenesis of the new compounds are described below.

scholarly journals Isolation, Structure Determination of Sesquiterpenes from Neurolaena lobata and Their Antiproliferative, Cell Cycle Arrest-Inducing and Anti-Invasive Properties against Human Cervical Tumor Cells

Pharmaceutics ◽  
2021 ◽  
Vol 13 (12) ◽  
pp. 2088
Author(s):  
Andrea Vasas ◽  
Ildikó Lajter ◽  
Norbert Kúsz ◽  
Sándor Balázs Király ◽  
Tibor Kovács ◽  
...  
Keyword(s):  
Cell Cycle ◽  
Tumor Cell Line ◽  
2D Nmr ◽  
Chiral Hplc ◽  
Cervical Tumor ◽  
Relative Configuration ◽  
Cycle Arrest ◽  
Aerial Parts ◽  
Hpv Status ◽  
New Compounds

Seven new germacranolides (1–3, 5–8), among them a heterodimer (7), and known germacranolide (4), eudesmane (9) and isodaucane (10) sesquiterpenes were isolated from the aerial parts of Neurolaena lobata. Their structures were determined by using a combination of different spectroscopic methods, including HR-ESIMS and 1D and 2D NMR techniques supported by DFT-NMR calculations. The enantiomeric purity of the new compounds was investigated by chiral HPLC analysis, while their absolute configurations were determined by TDDFT-ECD and OR calculations. Due to the conformationally flexible macrocycles and difficulties in assigning the relative configuration, 13C and 1H NMR chemical shift and ECD and OR calculations were performed on several stereoisomers of two derivatives. The isolated compounds (1–10) were shown to have noteworthy antiproliferative activities against three human cervical tumor cell line with different HPV status (HeLa, SiHa and C33A). Additionally, lobatolide C (6) exhibited substantial antiproliferative properties, antimigratory effect, and it induced cell cycle disturbance in SiHa cells.

Andrographolide Inhibits Proliferation of Colon Cancer SW-480 Cells via Downregulating Notch Signaling Pathway.

2020 ◽  
Vol 20 ◽  
Author(s):  
Imran Khan ◽  
Sadaf Mahfooz ◽  
Mohd Saeed ◽  
Irfan Ahmad ◽  
Irfan A. Ansari
Keyword(s):  
Cell Cycle ◽  
Colon Cancer ◽  
Notch Signaling ◽  
Signaling Pathway ◽  
Mtt Assay ◽  
Annexin V ◽  
Notch Signaling Pathway ◽  
Phase Cell ◽  
Ros Generation ◽  
Notch 1

Background: Recently Notch signaling pathway has gained attention as a potential therapeutic target for chemotherapeutic intervention. However, the efficacy of previously known Notch inhibitors in colon cancer is still unclear. The purpose of this study was to investigate the effect of andrographolide on aberrantly activated Notch signaling in SW-480 cells in vitro. Methods: The cytostatic potential of andrographolide on SW-480 cells was evaluated by 3-(4,5-dimethylthiazol-2-yl)-2, 5-diphenyl tetrazolium bromide (MTT) assay, morphology assessment and colony formation assay. The apoptotic activity was evaluated by FITC Annexin V assay, 4′,6-diamidino-2-phenylindole (DAPI), Hoechst, Rhodamine 123 and Mito Tracker CMXRos staining. Scratch assay for migratory potential assessment. 7’-Dichlorodihydrofluorescein Diacetate (DCFH-DA) staining was used to evaluate the Reactive Oxygen Species (ROS) generation. Relative mRNA expression of Bax, Bcl2, NOTCH 1 and JAGGED 1 was estimated by Real-Time Quantitative Reverse Transcription PCR (qRT-PCR). Cell cycle phase distribution was evaluated Annexin V-FITC/PI staining. Results: MTT assay demonstrated dose and time dependent cytoxicity of andrographolide on SW-480 cells. It also inhibited the migratory and colony forming potential of SW-480 cells. Furthermore, andrographolide also showed disruption of mitochondrial membrane potential and induced apoptosis through nuclear condensation. Flow cytometric evaluation showed andrographolide enhanced early and late apoptotic cells and induced upregulation of proapoptotic (Bax and Bad) and downregulation of antiapoptotic Bcl2 in treated SW-480 cells. Andrographolide augmented intracellular ROS generation and induced G0/G1 phase cell cycle arrest in colon cancer SW480 cells. Furthermore, andrographolide repressed the Notch signaling by decreasing the expression of NOTCH 1 and JAGGED 1. Conclusion: Our findings suggested that andrographolide constraint the growth of SW-480 cells through the inhibition of Notch signaling pathway.

A Cytotoxic Natural Product from Patrinia villosa Juss

2019 ◽  
Vol 19 (11) ◽  
pp. 1399-1404 ◽  
Author(s):  
Yangcheng Liu ◽  
Wei Liu ◽  
Changlan Chen ◽  
Zheng Xiang ◽  
Hongwei Liu
Keyword(s):  
Cell Cycle ◽  
Cell Lines ◽  
Silica Gel ◽  
Column Chromatography ◽  
Bioactive Compound ◽  
Antitumor Agent ◽  
2D Nmr ◽  
Preparative Hplc ◽  
Dependent Manner ◽  
2D Nmr Spectra

Background and Purpose:: Patrinia villosa Juss is an important Chinese herbal medicine widely used for thousands of years, but few reports on the ingredients of the herb have been presented. In this study, we aim to isolate the bioactive compound from the plant. Material and Methods:: The air-dried leaves of P. villosa (15kg) were extracted three times with 70% EtOH under reflux. The condensed extract was suspended in H2O and partitioned with light petroleum, dichloromethane and n-BuOH. The dichloromethane portion was then subjected to normal-phase silica gel column chromatography, ODS silica gel column chromatography and semi-preparative HPLC to yield compound 1. Cytotoxicities of 1 were assayed on HepG2, A549 and A2780 cell lines. The mechanism of apoptosis and cell cycle on A549 was confirmed subsequently. Results: A new impecylone (Impecylone A) was isolated from the leaves of Patrinia villosa Juss, and its structures were established using 1D, 2D-NMR spectra and HR-ESI-MS. Impecylone A could selectivity inhibit HepG2 and A549 cell lines. The compound could induce apoptosis of A549 and arrest the cell cycle at G2/M phase in a dose-dependent manner. Conclusion: Impecylone A is a novel compound from Patrinia villosa Juss and could be a potential antitumor agent especially in the cell lines of A549.

scholarly journals 5-((8-Hydroxyquinolin-5-yl)diazenyl)-3-methyl-1H-pyrazole-4-carboxylic Acid

Molbank ◽  
10.3390/m1238 ◽  
2021 ◽  
Vol 2021 (2) ◽  
pp. M1238
Author(s):  
Ion Burcă ◽  
Valentin Badea ◽  
Calin Deleanu ◽  
Vasile-Nicolae Bercean
Keyword(s):  
Chemical Structure ◽  
Functional Group ◽  
Coupling Reaction ◽  
2D Nmr ◽  
Azo Coupling ◽  
2D Nmr Spectroscopy ◽  
Azo Compound ◽  
Ft Ir ◽  
New Compounds ◽  
Carboxylic Functional Group

A new azo compound was prepared via the azo coupling reaction between 4-(ethoxycarbonyl)-3-methyl-1H-pyrazole-5-diazonium chloride and 8-hydroxyquinoline (oxine). The ester functional group of the obtained compound was hydrolyzed and thus a new chemical structure with a carboxylic functional group resulted. The structures of the new compounds were fully characterized by: UV–Vis, FT-IR, 1D and 2D NMR spectroscopy, and HRMS spectrometry.

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

Marine Drugs ◽  
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.

scholarly journals New Diterpenoids and Isocoumarin Derivatives from the Mangrove-Derived Fungus Hypoxylon sp.

Marine Drugs ◽  
2021 ◽  
Vol 19 (7) ◽  
pp. 362
Author(s):  
Bolin Hou ◽  
Sushi Liu ◽  
Ruiyun Huo ◽  
Yueqian Li ◽  
Jinwei Ren ◽  
...  
Keyword(s):  
Nuclear Magnetic Resonance ◽  
Magnetic Resonance ◽  
Crude Extract ◽  
Mass Spectrometric ◽  
Spectrometric Analysis ◽  
Ic50 Values ◽  
Inhibitory Activities ◽  
The Absolute ◽  
Dpph Scavenging ◽  
New Compounds

Two new diterpenoids, hypoxyterpoids A (1) and B (2), and four new isocoumarin derivatives, hypoxymarins A–D (4–7), together, with seven known metabolites (3 and 8–13) were obtained from the crude extract of the mangrove-derived fungus Hypoxylon sp. The structures of the new compounds were elucidated on the basis of 1- and 2-dimensional (1D/2D) nuclear magnetic resonance (NMR) spectroscopic and mass spectrometric analysis. The absolute configurations of compounds 1, 2, 4, 5, and 7 were determined by comparison of experimental and calculated electronic circular dichroism (ECD) spectra, and the absolute configurations of C-4′ in 6 and C-9 in 7 were determined by [Rh2(OCOCF3)4]-induced ECD spectra. Compound 1 showed moderate α-glucosidase inhibitory activities with IC50 values of 741.5 ± 2.83 μM. Compounds 6 and 11 exhibited DPPH scavenging activities with IC50 values of 15.36 ± 0.24 and 3.69 ± 0.07 μM, respectively.

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