scholarly journals Diketopiperazine and Diphenylether Derivatives from Marine Algae-Derived Aspergillus versicolor OUCMDZ-2738 by Epigenetic Activation

Marine Drugs ◽  
2018 ◽  
Vol 17 (1) ◽  
pp. 6 ◽  
Author(s):  
Wen Liu ◽  
Liping Wang ◽  
Bin Wang ◽  
Yanchao Xu ◽  
Guoliang Zhu ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Specific Rotation ◽  
Crystallographic Analysis ◽  
Aspergillus Versicolor ◽  
X Ray ◽  
Naturally Occurring ◽  
Ic50 Values ◽  
New Compounds ◽  
First Time ◽  
Optically Pure

A chemical-epigenetic method was used to enhance the chemodiversity of a marine algicolous fungus. Apart from thirteen known compounds, (+)-brevianamide R ((+)-3), (‒)-brevianamide R ((‒)-3), (+)-brevianamide Q ((+)-4), (‒)-brevianamide Q ((‒)-4), brevianamide V ((+)-5), brevianamide W ((‒)-5), brevianamide K (6), diorcinol B (7), diorcinol C (8), diorcinol E (9), diorcinol J (10), diorcinol (11), 4-methoxycarbonyldiorcinol (12), two new compounds, (+)- and (‒)-brevianamide X ((+)- and (‒)- 2)), as well as a new naturally occurring one, 3-[6-(2-methylpropyl)-2-oxo-1H-pyrazin-3-yl]propanamide (1), were isolated from chemical-epigenetic cultures of Aspergillus versicolor OUCMDZ-2738 with 10 µM vorinostat (SAHA). Compared to cultures in the same medium without SAHA, compounds 1–4, 8, 9, 11, and 12 were solely observed under SAHA condition. The structures of these compounds were elucidated based on spectroscopic analysis, specific rotation analysis, ECD, and X-ray crystallographic analysis. (±)-3, (±)-4, and (±)-5 were further resolved into the corresponding optically pure enantiomers and their absolute configurations were determined for the first time. Compounds 11 and 12 showed selective antibacterial against Pseudomonas aeruginosa with a minimum inhibitory concentration (MIC) of 17.4 and 13.9 μM, respectively. Compound 10 exhibited better α-glucosidase inhibitory activity than the assay control acarbose with IC50 values of 117.3 and 255.3 μM, respectively.

scholarly journals Highly Substituted Benzophenone Aldehydes and Eremophilane Derivatives from the Deep-Sea Derived Fungus Phomopsis lithocarpus FS508

Marine Drugs ◽  
2018 ◽  
Vol 16 (9) ◽  
pp. 329 ◽  
Author(s):  
Jian-Lin Xu ◽  
Hong-Xin Liu ◽  
Yu-Chan Chen ◽  
Hai-Bo Tan ◽  
Heng Guo ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
A549 Cell ◽  
Marine Sediment ◽  
Deep Sea ◽  
Crystallographic Analysis ◽  
X Ray ◽  
Naturally Occurring ◽  
Ic50 Values ◽  
New Compounds

Five new benzophenone derivatives named tenellones D–H (1–5), sharing a rare naturally occurring aldehyde functionality in this family, and a new eremophilane derivative named lithocarin A (7), together with two known compounds (6 and 8), were isolated from the deep marine sediment-derived fungus Phomopsis lithocarpus FS508. All of the structures for these new compounds were fully characterized and established on the basis of extensive spectroscopic interpretation and X-ray crystallographic analysis. Compound 5 exhibited cytotoxic activity against HepG-2 and A549 cell lines with IC50 values of 16.0 and 17.6 μM, respectively.

scholarly journals Cycloartane and Oleanane Glycosides from the Tubers of Eranthis cilicica

Molecules ◽  
2018 ◽  
Vol 24 (1) ◽  
pp. 69 ◽  
Author(s):  
Kazuki Watanabe ◽  
Yoshihiro Mimaki ◽  
Haruhiko Fukaya ◽  
Yukiko Matsuo
Keyword(s):  
Spectroscopic Analysis ◽  
Apoptotic Cell ◽  
2D Nmr ◽  
Phytochemical Analysis ◽  
X Ray ◽  
C 23 ◽  
The Family ◽  
Ic50 Values ◽  
Cycloartane Glycosides ◽  
New Compounds

Phytochemical analysis of the tubers of Eranthis cilicica was performed as part of our continuous study on the plants of the family Ranunculaceae, which resulted in the isolation of eleven new cycloartane glycosides (1–11) and one new oleanane glycoside (13), together with one known oleanane glycoside (12). The structures of the new compounds were determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR, and enzymatic hydrolysis followed by either X-ray crystallographic or chromatographic analysis. The aglycone (1a) of 2 and its C-23 epimer (8a), and the oleanane glycosides (12 and 13) showed cytotoxic activity against HL-60 leukemia cells with IC50 values ranging from 10.6 μM to 101.6 μM. HL-60 cells were much more sensitive to 8a (IC50 14.8 μM) than 1a (IC50 101.1 μM), indicating that the C-23 configuration is associated with the cytotoxicity of these cycloartane derivatives. Compound 12 was revealed so as to partially induce apoptotic cell death in HL-60 cells, as was evident from morphology of HL-60 cells treated with 12.

scholarly journals Alkaloids from an Endophytic Streptomyces sp. YIM66017

2013 ◽  
Vol 8 (10) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Hao Zhou ◽  
Yabin Yang ◽  
Jucheng Zhang ◽  
Tianfeng Peng ◽  
Lixing Zhao ◽  
...  
Keyword(s):  
Culture Filtrate ◽  
Spectroscopic Analysis ◽  
Crystallographic Analysis ◽  
Natural Source ◽  
Streptomyces Sp ◽  
X Ray ◽  
Alpinia Oxyphylla ◽  
Endophytic Streptomyces ◽  
First Time ◽  
Mcf 7

Three alkaloids, flavensomycinoic acid (1), a linear polyketide, alpiniamide (2), and cyclo (L-Trp-L-Ala) (3), were isolated from the culture filtrate of endophytic Streptomyces sp. YIM66017 from Alpinia oxyphylla. Their structures were elucidated by spectroscopic analysis and the structure of 1 was confirmed by X-ray crystallographic analysis. Compound 1 was isolated from a natural source for the first time, and compound 2 is a new compound. Compound 1 showed cytotoxicity to MCF-7 with an IC 50 value of 17.0 μM.

Synthesis of New Dialkyl 2,2′-[Carbonylbis(azanediyl)]dibenzoates via Curtius Rearrangement

Synthesis ◽  
2021 ◽  
Author(s):  
Mostafa Khouili ◽  
Maria Dolors Pujol ◽  
Hasna Yassine ◽  
Jamila Bouali ◽  
Asmaa Oumessaoud ◽  
...  
Keyword(s):  
Condensation Reaction ◽  
Crystallographic Analysis ◽  
Basic Medium ◽  
Urea Derivatives ◽  
1H And 13C Nmr ◽  
Curtius Rearrangement ◽  
X Ray ◽  
Alkyl Derivatives ◽  
New Compounds ◽  
First Time

AbstractThe 2-(alkylcarbonyl)benzoic acids obtained by esterification of phthalic anhydride are converted into azide derivatives: alkyl 2-[(azidocarbonyl)amino]benzoates and to ureas: dialkyl 2,2′-[carbonylbis(azanediyl)]dibenzoates. These transformations were carried out using classical Curtius rearrangement conditions in the presence of diphenylphosphoryl azide (DPPA) in a basic medium, followed by hydrolysis. Subsequently, a final condensation reaction of these urea derivatives enabled us to obtain, for the first time, the new alkyl derivatives, alkyl 2-[2,4-dioxo-1,2-dihydroquinazolin-3(4H)-yl]benzoates. All the new compounds obtained in satisfactory yields were characterized by 1H and 13C NMR, and by X-ray crystallographic analysis.

scholarly journals New 18(4→3)-Abeo-Abietanoids from Tripterygium wilfordii

Molecules ◽  
2018 ◽  
Vol 23 (10) ◽  
pp. 2467
Author(s):  
Lin Ni ◽  
Ying-da Zang ◽  
Jing-zhi Yang ◽  
Chuang-jun Li ◽  
Jie Ma ◽  
...  
Keyword(s):  
Spectroscopic Analysis ◽  
Crystallographic Analysis ◽  
No Production ◽  
Anomalous Scattering ◽  
Tripterygium Wilfordii ◽  
Raw 264.7 Macrophages ◽  
X Ray ◽  
Inhibitory Activities ◽  
New Compounds

Three 18(4→3)-abeo-abietanoids, a new natural product and two new compounds, named tripordolides A–C (1–3), were isolated from the leaves of Tripterygium wilfordii. Their structures were elucidated on the basis of their spectroscopic analysis, and the absolute configuration of compounds was confirmed by CD and X-ray crystallographic analysis using anomalous scattering of Cu Kα radiation. Compounds 1 and 3 showed moderate inhibitory activities against NO production in lipopolysaccharide-induced (LPS) RAW 264.7 macrophages in vitro.

scholarly journals HPLC-DAD-Guided Isolation of Diversified Chaetoglobosins from the Coral-Associated Fungus Chaetomium globosum C2F17

Molecules ◽  
2020 ◽  
Vol 25 (5) ◽  
pp. 1237 ◽  
Author(s):  
Xiao-Wei Luo ◽  
Cheng-Hai Gao ◽  
Hu-Mu Lu ◽  
Jia-Min Wang ◽  
Zi-Qi Su ◽  
...  
Keyword(s):  
Single Crystal ◽  
Cell Lines ◽  
Cancer Cell ◽  
Spectroscopic Analysis ◽  
Chaetomium Globosum ◽  
X Ray ◽  
X Ray Crystallography ◽  
Ic50 Values ◽  
First Time ◽  
Mcf 7

Cytochalasans have continuously aroused considerable attention among the chemistry and pharmacology communities due to their structural complexities and pharmacological significances. Sixteen structurally diverse chaetoglobosins, 10-(indol-3-yl)-[13]cytochalasans, including a new one, 6-O-methyl-chaetoglobosin Q (1), were isolated from the coral-associated fungus Chaetomium globosum C2F17. Their structures were accomplished by extensive spectroscopic analysis combined with single-crystal X-ray crystallography and ECD calculations. Meanwhile, the structures and absolute configurations of the previously reported compounds 6, 12, and 13 were confirmed by single-crystal X-ray analysis for the first time. Chaetoglobosins E (6) and Fex (11) showed significant cytotoxicity against a panel of cancer cell lines, K562, A549, Huh7, H1975, MCF-7, U937, BGC823, HL60, Hela, and MOLT-4, with the IC50 values ranging from 1.4 μM to 9.2 μM.

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

Marine Drugs ◽  
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.

scholarly journals Microbialite-like structures in Cladophora sp. (Ulvophyceae) mats from a subtropical Andean basin: ecological implications

2019 ◽  
Vol 67 (1) ◽  
Author(s):  
Hugo R. Fernández ◽  
Ana Lucia Gonzalez Achem ◽  
Marcela Correa ◽  
Virginia H. Albarracín
Keyword(s):  
Organic Pollution ◽  
Biological Factors ◽  
X Ray Diffraction ◽  
Calcite Precipitation ◽  
Annual Cycles ◽  
X Ray ◽  
Naturally Occurring ◽  
Ecological Implications ◽  
First Time ◽  
Solubility Equilibrium

The solubility equilibrium of calcite is influenced by physicochemical, climatic and biological factors. Annual cycles of exceptionally prolonged drought, in conjunction with naturally occurring diffuse organic pollution, generate the unique conditions for the precipitation of lithified carbonate structures (microbialites). The aim of this article is to analyze the possible implications of calcite precipitation produced in mats of Cladophora sp. in an Andean subtropical basin, considering it is the first time this phenomenon is described for the region. We collected samples from selected sites at the Lules River Basin, in four sampling dates between the years 2003 and 2004, within a monitoring work of 15 years. Samples were analyzed using an electron microscope and X-ray diffraction analysis. We found that Gomphonema sp. attached to Cladophora sp. contributes to precipitation of calcite and formation of microbialite like structures, in the studied area. This work presents an initial discussion of the discovery of microbialites-like structures attached to Cladophora sp. mats in a subtropical Andean stream and the environmental conditions that lead to their production, as well as the possible ecological implications of these microbialites.

scholarly journals Benzyl Furanones and Pyrones from the Marine-Derived Fungus Aspergillus terreus Induced by Chemical Epigenetic Modification

Molecules ◽  
2020 ◽  
Vol 25 (17) ◽  
pp. 3927
Author(s):  
Jing-Shuai Wu ◽  
Xiao-Hui Shi ◽  
Ya-Hui Zhang ◽  
Chang-Lun Shao ◽  
Xiu-Mei Fu ◽  
...  
Keyword(s):  
Aspergillus Terreus ◽  
Epigenetic Modification ◽  
2D Nmr ◽  
Etoac Extract ◽  
One Dimensional ◽  
X Ray ◽  
Deacetylase Inhibitor ◽  
Ic50 Values ◽  
First Time ◽  
Mic Value

Chemical epigenetic modification on a marine-derived fungus Aspergillus terreus RA2905 using a histone deacetylase inhibitor, suberoylanilide hydroxamic acid (SAHA), resulted in a significantly changed metabolic profile. A chemical investigation of its ethyl acetate (EtOAc) extract led to the isolation of a racemate of benzyl furanone racemate (±)-1, which further separated chirally as a pair of new enantiomers, (+)- and (−)-asperfuranone (1), together with two new benzyl pyrones, asperpyranones A (2) and B (3). Their structures were elucidated by analysis of the comprehensive spectroscopic data, including one-dimensional (1D) and two-dimensional (2D) NMR, and HRESIMS. The absolute configurations were determined by electronic circular dichroism (ECD) calculation and single-crystal X-ray crystallographic experiment. The structures with benzyl furanone or benzyl pyrone skeletons were discovered from natural products for the first time. Compounds (±)-1, (+)-1, (−)-1, and 2 displayed the antifungal activities against Candida albicans with MIC values of 32, 16, 64, and 64 μg/mL and PTP1B inhibitory activities with the IC50 values of 45.79, 17.32, 35.50, and 42.32 μM, respectively. Compound 2 exhibited antibacterial activity against Pseudomonas aeruginosa with the MIC value of 32 μg/mL.

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