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 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 Tersone A-G, New Pyridone Alkaloids from the Deep-Sea Fungus Phomopsis tersa

Marine Drugs ◽  
2019 ◽  
Vol 17 (7) ◽  
pp. 394 ◽  
Author(s):  
Shan-Chong Chen ◽  
Zhao-Ming Liu ◽  
Hai-Bo Tan ◽  
Yu-Chan Chen ◽  
Sai-Ni Li ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
A549 Cell ◽  
Deep Sea ◽  
X Ray Diffraction ◽  
X Ray ◽  
Spectroscopic Analyses ◽  
Ic50 Values ◽  
Mic Value ◽  
Mcf 7

Four phenylfuropyridone racemates, (±)-tersones A-C and E (1–3, 5), one phenylpyridone racemate, (±)-tersone D (4), one new pyridine alkaloid, tersone F (6), single new phenylfuropyridone, tersone G (7) and two known analogs 8 and 9 were isolated from the deep-sea fungus Phomopsis tersa. Their structures and absolute configurations were characterized on the basis of comprehensive spectroscopic analyses, single-crystal X-ray diffraction experiments, and electronic circular dichroism (ECD) calculations. Moreover, compounds 1–9 were evaluated for in vitro antimicrobial and cytotoxic activity. Compounds 5b and 8b exhibited antibacterial activity against S. aureus with the MIC value of 31.5 μg/mL, while compound 5b showed cytoxic activities against SF-268, MCF-7, HepG-2 and A549 cell lines with IC50 values of 32.0, 29.5, 39.5 and 33.2 μM, respectively.

Phytochemical Constituents of Annona reticulata and their Cytotoxic Activity

2020 ◽  
Vol 17 (3) ◽  
pp. 206-210
Author(s):  
Ty Viet Pham ◽  
Thang Quoc Le ◽  
Anh Tuan Le ◽  
Hung Quoc Vo ◽  
Duc Viet Ho
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
Structural Determination ◽  
Phytochemical Investigation ◽  
Ic50 Values ◽  
Phytochemical Constituents ◽  
First Time ◽  
Annona Reticulata

A phytochemical investigation of the leaves of Annona reticulata led to the isolation and structural determination of β-sitosterol (1), ent-pimara-8(14),15-dien-19-oic acid (2), ent-pimara- 8(14),15-dien-19-ol (3), quercetin (4), quercetin 3-O-α-L-arabinopyranoside (5), and a mixture of quercetin 3-O-β-D-galactopyranoside (6a) and quercetin 3-O-β-D-glucopyranoside (6b). Of these, compounds 2 and 3 were isolated from the genus Annona for the first time. Compound 3 showed strong cytotoxicity against SK-LU-1 and SW626 cell lines with IC50 values of 17.64 ± 1.07 and 19.79 ± 1.41 μg mL-1, respectively.

Pyrrolizines as Potential Anticancer Agents: Design, Synthesis, Caspase-3 activation and Micronucleus (MN) Induction

2019 ◽  
Vol 18 (15) ◽  
pp. 2124-2130
Author(s):  
Amany Belal
Keyword(s):  
Cancer Cells ◽  
Cell Lines ◽  
Anticancer Agents ◽  
Caspase 3 ◽  
Assay Method ◽  
Breast Adenocarcinoma ◽  
Compound I ◽  
Design Synthesis ◽  
Ic50 Values ◽  
New Compounds

Background: For further exploration of the promising pyrrolizine scaffold and in continuation of our previous work, that proved the potential anticancer activity of the hit compound I, a new series of pyrrolizines 2-5 and 7-9 were designed and synthesized. Methods: Structures of the new compounds were confirmed by IR, 1H-NMR, 13C-NMR and elemental analysis. Antitumor activity for the prepared compounds against human breast adenocarcinoma (MCF-7), liver (HEPG2) and colon (HCT116) cancer cell lines was evaluated using SRB assay method. Result: Compounds 2, 3 and 5 were the most potent on colon cancer cells, their IC50 values were less than 5 µM. Compounds 2, 3 and 8 were the most potent on liver cancer cells, their IC50 values were less than 10 µM. As for MCF7, compounds 2, 7, 8 and 9 were the most active with IC50 values less than 10 µM. We can conclude that combining pyrrolizine scaffold with urea gave abroad spectrum anticancer agent 2 against the three tested cell lines. Micronucleus assays showed that compounds 2, 3, 8 are mutagenic and can induce apoptosis. In addition, caspase-3 activation was evaluated and compound 2 showed increase in the level of caspase-3 (9 folds) followed by 3 (8.28 folds) then 8 (7.89 folds). Conclusion: The obtained results encourage considering these three compounds as novel anticancer prototypes.

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 Synthesis, Cytotoxic Activity, Crystal Structure, DFT Studies and Molecular Docking of 3-Amino-1-(2,5-dichlorophenyl)-8-methoxy-1H-benzo[f]chromene-2-carbonitrile

Crystals ◽  
2021 ◽  
Vol 11 (2) ◽  
pp. 184
Author(s):  
Menna El Gaafary ◽  
Tatiana Syrovets ◽  
Hany M. Mohamed ◽  
Ahmed A. Elhenawy ◽  
Ahmed M. El-Agrody ◽  
...  
Keyword(s):  
Cytotoxic Activity ◽  
Cell Lines ◽  
Cancer Cell ◽  
Dna Methyltransferase ◽  
Human Cancer ◽  
Theoretical Calculations ◽  
Cancer Cell Lines ◽  
Molecular Structures ◽  
Cytotoxic Activities ◽  
X Ray

The target compound 3-amino-1-(2,5-d ichlorophenyl)-8-methoxy-1H-benzo[f]-chromene-2-carbonitrile (4) was synthesized via a reaction of 6-methoxynaphthalen-2-ol (1), 2,5-dichlorobenzaldehyde (2), and malononitrile (3) in ethanolic piperidine solution under microwave irradiation. The newly synthesized β-enaminonitrile was characterized by FT-IR, 1H NMR, 13C NMR, mass spectroscopy, elemental analysis and X-ray diffraction data. Its cytotoxic activity was evaluated against three different human cancer cell lines MDA-MB-231, A549, and MIA PaCa-2 in comparison to the positive controls etoposide and camptothecin employing the XTT cell viability assay. The analysis of the Hirshfeld surface was utilized to visualize the reliability of the crystal package. The obtained results confirmed that the tested molecule revealed promising cytotoxic activities against the three cancer cell lines. Furthermore, theoretical calculations (DFT) were carried out with the Becke3-Lee-Yang-parr (B3LYP) level using 6-311++G(d,p) basis. The optimization geometry for molecular structures was in agreement with the X-ray structure data. The HOMO-LUMO energy gap of the studied system was discussed. The intermolecular-interactions were studied through analysis of the topological-electron-density(r) using the QTAIM and NCI methods. The novel compound exhibited favorable ADMET properties and its molecular modeling analysis showed strong interaction with DNA methyltransferase 1.

Antitumor Agents. 192. Antitubulin Effect and Cytotoxicity of C(7)-Oxygenated Allocolchicinoids

1999 ◽  
Vol 64 (2) ◽  
pp. 217-228 ◽  
Author(s):  
Jian Guan ◽  
Xiao-Kang Zhu ◽  
Arnold Brossi ◽  
Yoko Tachibana ◽  
Kenneth F. Bastow ◽  
...  
Keyword(s):  
Cell Lines ◽  
Antitumor Agents ◽  
Human Tumor ◽  
Crystallographic Analysis ◽  
Antitumor Activities ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
X Ray ◽  
Tubulin Binding ◽  
Marked Resistance

Two allocolchicinoids 6 and 8, prepared from colchicine, together with allo compounds 9-11, made from 6 by reduction and regiodemethylation, were evaluated for antitubulin and antitumor activities. Structures of 6, 8, and 10 were confirmed by X-ray crystallographic analysis. Compounds 6, 8, and 9 have high tubulin binding affinity and display potent inhibitory activities against tubulin polymerization and solid human tumor cell lines. Particularly, drug-resistant KB cell lines, including KB-7d, KB-VCR, and KB-CPT, do not show marked resistance to these compounds.

scholarly journals Antibacterial and Cytotoxic Phenolic Polyketides from Two Marine-Derived Fungal Strains of Aspergillus unguis

2022 ◽  
Vol 15 (1) ◽  
pp. 74
Author(s):  
Cao Van Anh ◽  
Joo-Hee Kwon ◽  
Jong Soon Kang ◽  
Hwa-Sun Lee ◽  
Chang-Su Heo ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Detailed Analysis ◽  
Cell Lines ◽  
Spectroscopic Data ◽  
Bacterial Activity ◽  
Tumor Cell Lines ◽  
Fungal Strains ◽  
Aspergillus Unguis ◽  
Ic50 Values ◽  
New Compounds

A chemical investigation on the EtOAc extracts from two marine-derived fungal strains of Aspergillus unguis resulted in the isolation of three previously undescribed phenolic polyketides including unguidepside C (1), aspersidone B (3), and agonodepside C (12), and their 14 known congeners. The structures of the new compounds were determined based on detailed analysis and comparison of their spectroscopic data with literature values, as well as Snatzke’s method. The new compounds (1, 3, and 12) displayed a significant anti-Gram-positive bacterial activity, with MIC values ranging from 5.3 to 22.1 µM. Additionally, the isolated compounds (1–11 and 13–16) were evaluated for their cytotoxicity against a panel of tumor cell lines. Most of them (except for 9) displayed cytotoxicity against all the tested cell lines, with IC50 values ranging from 2.5 to 46.9 µM.

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.

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