LAMA-1: A Cerebroside Isolated from the Deep-Sea-Derived Fungus Penicillium chrysogenum

Chemical investigation of the ethyl acetate extract of Penicillium chrysogenum strain S003, a fungus isolated from Red Sea deep sediment, led to the isolation of a cerebroside molecular species LAMA (1) along with three other known compounds, ergosterol (2), epidioxyergosterol (3), and kojic acid (4). The structures of the isolated compounds were elucidated by interpretation of spectral data, including detailed 1D and 2D NMR (One and two dimensional Nuclear Magnetic Resonance) and mass spectrometry. The cytotoxic activities of isolated compounds 1–4 against five human carcinoma cells were evaluated using sulforhodamine B (SRB) assay. Compounds 2 and 3 displayed promising cytotoxic profiles against lung cancer (A-549), prostate (DU-145), breast adenocarcinoma (MCF-7), and hepatocellular (HepG2) cell lines, with IC50 values of 21.26, 19.3; 1.50, 6.10; 16.95, 13.6; and 2.89, 3.07 µM, respectively, while they were inactive against HeLa cells. Compounds 1 and 4 showed weak cytotoxic profiles against all cell lines under investigation.

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Chemical Constituents of Tibetan Herbal Medicine Pulicaria insignis and Their in vitro Cytotoxic Activities

Records of Natural Products ◽

10.25135/rnp.193.20.06.1692 ◽

2020 ◽

Vol 15 (2) ◽

pp. 91-102

Author(s):

Xinzhu Wang ◽

Peilei Hou ◽

Yanbo Qu ◽

Rizhen Huang ◽

Yan Feng ◽

...

Keyword(s):

Herbal Medicine ◽

Cell Lines ◽

Hepg2 Cells ◽

Chemical Constituents ◽

2D Nmr ◽

Cytotoxic Activities ◽

Hela Cell Lines ◽

Ic50 Values ◽

Hepg2 Cell Lines

One new phenolic derivative, 1-(4',5'-dihydroxy-2'-methylphenyl)-pentane-1,4-dione (1), along with eighteen known compounds including eight sesquiterpenoids (2–9), one triterpenoid (10), one bisdpoxylignan (11), one coumarin (12), and seven flavonoids (13–19) were isolated from the dried inflorescence of Tibetan herbal medicine Pulicaria insignis. The structure of 1 was established by spectroscopic methods, including HRESIMS, IR, 1D, and 2D NMR. All isolates were assessed for the cytotoxic activities against MGC-803, T24, HepG2, and HeLa cell lines using the MTT assay. The results showed that compound 1 displayed moderate cytotoxicity against Hela and HepG2, and compounds 3, 4, 5, 6, and 13 exhibited potential cytotoxic activities against the four cell lines with IC50 values ranging from 3.05 to 14.37 μM. Notably, compound 5 exhibited significant anti-proliferative activities against HepG2 cell lines with the IC50 values of 3.05 ± 0.36 μM. Further bioactivity investigation showed that compound 5 could block HepG2 cells in the G1 phase of the cell cycle, thereby inhibiting the growth of HepG2 cells and inducing apoptosis in HepG2 cells.

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Piperine Inhibits TGF-β Signaling Pathways and Disrupts EMT-Related Events in Human Lung Adenocarcinoma Cells

Medicines ◽

10.3390/medicines7040019 ◽

2020 ◽

Vol 7 (4) ◽

pp. 19 ◽

Cited By ~ 3

Author(s):

Leonardo Marques da Fonseca ◽

Lucas Rodrigues Jacques da Silva ◽

Jhenifer Santos dos Reis ◽

Marcos André Rodrigues da Costa Santos ◽

Victoria de Sousa Chaves ◽

...

Keyword(s):

Lung Adenocarcinoma ◽

Cell Lines ◽

A549 Cell ◽

Epithelial Mesenchymal Transition ◽

Metastatic Cancer ◽

Breast Adenocarcinoma ◽

Mesenchymal Transition ◽

Ic50 Values ◽

Hepg2 Cell Lines ◽

Tgf Β1

Background: Piperine, an amide extracted from the Piper spices, exhibits strong anti-tumor properties. However, its effect on the epithelial–mesenchymal transition (EMT) process has never been investigated. Herein, we evaluate the toxic effect of piperine on lung adenocarcinoma (A549), breast adenocarcinoma (MDA-MB-231) and hepatocellular carcinoma (HepG2) cell lines, as well as its ability to inhibit EMT-related events induced by TGF-β1 treatment. Methods: The cell viability was investigated by MTT assay. Protein expression was evaluated by Western blot. Gene expression was monitored by real-time PCR. Zymography assay was employed to detect metalloproteinase (MMP) activity in conditioned media. Cell motility was assessed by the wound-healing and phagokinetic gold sol assays. Results: The results revealed that piperine was cytotoxic in concentrations over 100 µM, showing IC50 values for HepG2, MDA-MB-231 and A549 cell lines of 214, 238 and 198 µM, respectively. In order to investigate whether piperine would reverse the TGF-β1 induced-EMT, the A549 cell line was pretreated with sublethal concentrations of the natural amide followed by the addition of TGF-β1. Besides disrupting EMT-related events, piperine also inhibited both ERK 1/2 and SMAD 2 phosphorylation. Conclusions: These results suggest that piperine might be further used in therapeutic strategies for metastatic cancer and EMT-related disorders.

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Cytotoxic Secondary Metabolites Isolated from the Marine Alga-Associated Fungus Penicillium chrysogenum LD-201810

Marine Drugs ◽

10.3390/md18050276 ◽

2020 ◽

Vol 18 (5) ◽

pp. 276

Author(s):

Lin-Lin Jiang ◽

Jin-Xiu Tang ◽

Yong-Heng Bo ◽

You-Zhi Li ◽

Tao Feng ◽

...

Keyword(s):

Circular Dichroism ◽

Cell Lines ◽

Penicillium Chrysogenum ◽

Marine Alga ◽

2D Nmr ◽

Ionization Mass ◽

Human Carcinoma ◽

Hydroxyphenylacetic Acid ◽

The Absolute ◽

Circular Dichroïsm

A new pentaketide derivative, penilactonol A (1), and two new hydroxyphenylacetic acid derivatives, (2’R)-stachyline B (2) and (2’R)-westerdijkin A (3), together with five known metabolites, bisabolane-type sesquiterpenoids 4–6 and meroterpenoids 7 and 8, were isolated from the solid culture of a marine alga-associated fungus Penicillium chrysogenum LD-201810. Their structures were elucidated based on extensive spectroscopic analyses, including 1D/2D NMR and high resolution electrospray ionization mass spectra (HRESIMS). The absolute configurations of the stereogenic carbons in 1 were determined by the (Mo2(OAc)4)-induced circular dichroism (CD) and comparison of the calculated and experimental electronic circular dichroism (ECD) spectra, while the absolute configuration of the stereogenic carbon in 2 was established using single-crystal X-ray diffraction analysis. Compounds 2 and 3 adapt the 2’R-configuration as compared to known hydroxyphenylacetic acid-derived and O-prenylated natural products. The cytotoxicity of 1–8 against human carcinoma cell lines (A549, BT-549, HeLa, HepG2, MCF-7, and THP-1) was evaluated. Compound 3 exhibited cytotoxicity to the HepG2 cell line with an IC50 value of 22.0 μM. Furthermore, 5 showed considerable activities against A549 and THP-1 cell lines with IC50 values of 21.2 and 18.2 μM, respectively.

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Monarubins A–C from the Marine Shellfish-Associated Fungus Monascus ruber BB5

Marine Drugs ◽

10.3390/md18020100 ◽

2020 ◽

Vol 18 (2) ◽

pp. 100

Author(s):

Yan-Qin Ran ◽

Wen-Jian Lan ◽

Yi Qiu ◽

Qi Guo ◽

Gong-Kan Feng ◽

...

Keyword(s):

Cell Lines ◽

Cancer Cell ◽

Carcinoma Cell ◽

2D Nmr ◽

Cancer Cell Lines ◽

Cytotoxic Activities ◽

Monascus Ruber ◽

Carcinoma Cell Lines ◽

Ic50 Values ◽

New Compounds

Three new compounds, monarubins A–C (1, 6 and 13), together with ten known compounds, including four alkaloids (2–5), two isocoumarins (7 and 8) and four polyketides (9–12), were isolated from marine shellfish-associated fungus Monascus ruber BB5. The structures were determined on the basis of the 1D and 2D NMR, MS, UV and IR data. The absolute configurations of compounds 3, 6 and 13 were determined by ECD calculations. The NMR data of compounds deoxyhydroxyaspergillic acid (3) and 2-hydroxy-6-(1-hydroxy-1-methylpropyl)-3-sec-buthylpyrazine (4) were first reported. All of the isolated compounds were evaluated for their cytotoxic activities against human nasopharyngeal carcinoma cell lines CNE1, CNE2, SUNE1 and HONE1 and hepatocellular carcinoma cell lines QGY7701 and HepG2. Monarubin B (6) displayed potent cytotoxicities against the cancer cell lines HepG2 and QGY7701 with IC50 values of 1.72 and 0.71 μΜ, respectively; lunatinin (7) showed moderate cytotoxic activities against the cancer cell lines HepG2, QGY7701 and SUNE1 with the IC50 values of 9.60, 7.12 and 28.12 μΜ, respectively.

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Benzylated Dihydroflavones and Isoquinoline-Derived Alkaloids from the Bark of Diclinanona calycina (Annonaceae) and Their Cytotoxicities

Molecules ◽

10.3390/molecules26123714 ◽

2021 ◽

Vol 26 (12) ◽

pp. 3714

Author(s):

Emmanoel V. Costa ◽

Liviane do N. Soares ◽

Jamal da Silva Chaar ◽

Valdenizia R. Silva ◽

Luciano de S. Santos ◽

...

Keyword(s):

Cytotoxic Activity ◽

Cell Lines ◽

2D Nmr ◽

Cytotoxic Activities ◽

2D Nmr Spectroscopy ◽

Cancerous Cell ◽

Ic50 Value ◽

Ic50 Values ◽

Low Cytotoxicity ◽

First Time

Diclinanona calycina R. E. Fries popularly known as “envira”, is a species of the Annonaceae family endemic to Brazil. In our ongoing search for bioactive compounds from Annonaceae Amazon plants, the bark of D. calycina was investigated by classical chromatography techniques that yielded thirteen compounds (alkaloids and flavonoids) described for the first time in D. calycina as well as in the genus Diclinanona. The structure of these isolated compounds were established by extensive analysis using 1D/2D-NMR spectroscopy in combination with MS. The isolated alkaloids were identified as belonging to the subclasses: simple isoquinoline, thalifoline (1); aporphine, anonaine (2); oxoaporphine, liriodenine (3); benzyltetrahydroisoquinolines, (S)-(+)-reticuline (4); dehydro-oxonorreticuline (3,4-dihydro-7-hydroxy-6-methoxy-1-isoquinolinyl)(3-hydroxy-4-methoxyphenyl)-methanone) (5); (+)-1S,2R-reticuline Nβ-oxide (6); and (+)-1S,2S-reticuline Nα-oxide (7); tetrahydroprotoberberine, coreximine (8); and pavine, bisnorargemonine (9). While the flavonoids belong to the benzylated dihydroflavones, isochamanetin (10), dichamanetin (11), and a mixture of uvarinol (12) and isouvarinol (13). Compound 5 is described for the first time in the literature as a natural product. The cytotoxic activity of the main isolated compounds was evaluated against cancer and non-cancerous cell lines. Among the tested compounds, the most promising results were found for the benzylated dihydroflavones dichamanetin (10), and the mixture of uvarinol (12) and isouvarinol (13), which presented moderate cytotoxic activity against the tested cancer cell lines (<20.0 µg·mL−1) and low cytotoxicity against the non-cancerous cell line MRC-5 (>25.0 µg·mL−1). Dichamanetin (11) showed cytotoxic activity against HL-60 and HCT116 with IC50 values of 15.78 µg·mL−1 (33.70 µmol·L−1) and 18.99 µg·mL−1 (40.56 µmol·L−1), respectively while the mixture of uvarinol (12) and isouvarinol (13) demonstrated cytotoxic activity against HL-60, with an IC50 value of 9.74 µg·mL−1, and HCT116, with an IC50 value of 17.31 µg·mL−1. These cytotoxic activities can be attributed to the presence of one or more hydroxybenzyl groups present in these molecules as well as the position in which these groups are linked. The cytotoxic activities of reticuline, anonaine and liriodenine have been previously established, with liriodenine being the most potent compound.

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ISOLATION OF BIOACTIVE COMPOUNDS FROM CENTAUREA AEGYPTIACA

International Journal of Pharmacy and Pharmaceutical Sciences ◽

10.22159/ijpps.2018v10i4.17528 ◽

2018 ◽

Vol 10 (4) ◽

pp. 1

Author(s):

Hanan G. Sary ◽

Nahla A. Ayoub ◽

Abdel Nasser B. Singab ◽

Mickey Vinodh ◽

Khaled Y. Orabi

Keyword(s):

Ethyl Acetate ◽

Cell Lines ◽

Hepg2 Cells ◽

Sesquiterpene Lactones ◽

Cytotoxic Activities ◽

Isolation And Identification ◽

Cytotoxic Effects ◽

Ic50 Values ◽

Hepg2 Cell Lines ◽

Ethyl Acetate Extracts

Objective: In a previous study, Centaurea aegyptiaca ethanol and ethyl acetate extracts showed potent cytotoxic effects against laryngeal (HEP2) and hepatic (HEPG2) carcinoma cell lines. Additionally, two novel compounds were isolated and identified. The aim of this study is to continue isolating and identifying another compound (s) that may, also, be responsible for this potent biological activity.Methods: C. aegyptiaca dried aerial parts were extracted with ethanol and ethyl acetate. Both extracts were chromatographed separately to afford seven guaianolides that were identified using different spectroscopic methods. Moreover, compounds 1-7 were evaluated for their cytotoxicity (IC50, µM) against HEP2 and HEPG2 cells in comparison to the normal fibroblasts (BHK) using sulforhodamine B assay. Doxorubicin was used as a positive control.Results: Seven sesquiterpene lactones, centaurepensin, also known as chlorohyssopifolin A (1), 8α-hydroxy-11α, 13-dihydrozaluzanin C (2), chlorohyssopifolin B (3), desacylcynaropicrin (4), chlorohyssopifolin C, acroptilin (5), subluteolide (6), and solstitiolide (7) were isolated from C. aegyptiaca extracts and identified. This is the first report on the occurrence of 2, 4, 5 and 6 in C. aegyptiaca. Compounds 1-4 and 6 exhibited selective cytotoxic effects against HEP2 and HEPG2 cells. However, compounds 1 and 7 showed the highest activities against HEP2 with IC50 values of 10.6±0.02 and 10.9±0.03 µM, respectively. Moreover, compound 3 was the most potent one against HEPG2 cells with IC50value of 13.8±0.05 µM.Conclusions: Chemical investigation of C. aegyptiaca ethanol and ethyl acetate extracts led to the isolation and identification of seven guaianolides. These compounds exhibited good cytotoxic activities against HEP2 and HEPG2 cell lines.

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Chemical constituents of the lichen Dendriscosticta platyphylloides, Lobariaceae

Science and Technology Development Journal ◽

10.32508/stdj.v22i1.1219 ◽

2019 ◽

Vol 22 (1) ◽

pp. 165-172

Author(s):

Dung Thi My Nguyen ◽

Lien Thi My Do ◽

Huynh Thi Ngoc Tuyet ◽

Minh Ky Quang Ho ◽

Hai Tuan Nguyen ◽

...

Keyword(s):

Cell Lines ◽

Chemical Constituents ◽

2D Nmr ◽

Human Lung Cancer ◽

Cytotoxic Activities ◽

Tropical Regions ◽

Sulforhodamine B ◽

The Family ◽

Liver Hepatocellular Carcinoma ◽

First Time

Introduction: Dendriscosticta is a new genus belong the Sticta wrightii group of the family Lobariaceae. This genus of foliose lichen is widely distributed in tropical regions worldwide. The lichen Dendriscosticta platyphylloides is very abundant in Bidoup forest, Lam Dong province, Vietnam. Methods: The structure of these compounds was elucidated through the interpretation of their 1D and 2D-NMR and HR-MS data. The cytotoxic activities of these compounds against liver hepatocellular carcinoma (HepG2), human lung cancer (NCI-H460), human epithelial carcinoma (HeLa) and human breast cancer (MCF-7) cell lines was performed at the concentration of 100 mg/mL using the sulforhodamine B (SRB) assay. Results: In this paper, we reported the isolation of six known compounds, including (1) 15a-acetoxyhopan-22-ol (2) hopane-15a,22-diol, (3) zeorin, (4) cerevisterol, (5) salvigenin, and (6) 5-hydroxy-3',4',7-trimethoxyflavone. Conclusion: This is the first time that these compounds are isolated from Dendriscosticta genus. These compounds showed no cytotoxic activity against four cell lines.

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Isolation of New Glycosides from Anemarrhena Asphodeloides Rhizome and Screening of their Anticancer Activity

Letters in Organic Chemistry ◽

10.2174/1570178615666181102125553 ◽

2019 ◽

Vol 16 (6) ◽

pp. 474-477 ◽

Cited By ~ 1

Author(s):

Pham Van Khang ◽

Nguyen Thi Hien Lan ◽

Le Quang Truong ◽

Mai Thi Minh Chau ◽

Mai Xuan Truong ◽

...

Keyword(s):

Anticancer Activity ◽

Spectral Data ◽

Cell Lines ◽

Cancer Cell ◽

Spectroscopic Analysis ◽

2D Nmr ◽

Ic50 Values ◽

Nmr Techniques ◽

Inhibitory Activities ◽

Anemarrhena Asphodeloides

In this report, two new steroidal glycosides were isolated and determined from n-butanol fraction of A.asphodeloides. The structures were confirmed in comparison with the spectral data of known compounds by using different spectroscopic analysis approaches including 1D & 2D-NMR techniques and HRMS. The anti-proliferation screening against cancer cell lines A549 and HeLa indicated that compound 1 exhibited good inhibitory activities with IC50 values of 0.79 and 0.55 µg/mL, respectively.

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Synthesis and Antitumor Activity Evaluation of New Phenanthrene-Based Tylophorine Derivatives

Letters in Organic Chemistry ◽

10.2174/1570178615666181025115513 ◽

2019 ◽

Vol 16 (6) ◽

pp. 462-467

Author(s):

Songtao Li ◽

Hongling Zhao ◽

Zhifeng Yin ◽

Shuhua Deng ◽

Yang Gao ◽

...

Keyword(s):

Antitumor Activity ◽

Cell Lines ◽

Antitumor Activities ◽

Human Carcinoma ◽

Carcinoma Cell Lines ◽

Structure Activity ◽

Human Carcinoma Cell ◽

Ic50 Values ◽

Relationship Of

A series of new phenanthrene-based tylophorine derivatives (PBTs) were synthesized in good yield and their structures were characterized by 1H-NMR spectroscopy and ESI MS. In vitro antitumor activity of these compounds against five human carcinoma cell lines, including HCT116 (colorectal), BGC-823 (gastric), HepG-2 (hepatic), Hela (cervical) and H460 (lung) cells, was evaluated by MTT assay. Among these PBTs, compound 6b showed the highest antitumor activities against HCT116 and HepG-2 cell lines with IC50 values of 6.1 and 6.4 μM, respectively, which were comparable to that of adriamycin hydrochloride. The structure-activity relationship of these compounds was also discussed based on the results of their antitumor activity.

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Naphthoquinone-based hydrazone hybrids: synthesis and potent activity against cancer cell lines

Medicinal Chemistry ◽

10.2174/1573406416666200817164308 ◽

2020 ◽

Vol 16 ◽

Author(s):

Délis Galvão Guimarães ◽

Arlan de Assis Gonsalves ◽

Larissa Araújo Rolim ◽

Edigênia Cavalcante Araújo ◽

Victória Laysna dos Anjos Santos ◽

...

Keyword(s):

Anticancer Activity ◽

Cell Lines ◽

Cancer Cell ◽

Biological Activities ◽

Supporting Electrolyte ◽

Cancer Cell Lines ◽

Molecular Structures ◽

Cytotoxic Activities ◽

Electrochemical Studies ◽

Ic50 Values

Background: Natural naphthoquinones have shown diversified biological activities including antibacterial, antifungal, antimalarial, and cytotoxic activities. However, they are also compounds with acute cytotoxicity, immunotoxicity, carcinogenesis, and cardio- and hepatotoxicity, then the modification at their redox center is an interesting strategy to overcome such harmful activity. Objective: In this study, four novel semisynthetic hydrazones, derived from the isomers α- and β-lapachones (α and β, respectively) and coupled with the drugs hydralazine (HDZ) and isoniazid (ACIL), were prepared, evaluated by electrochemical methods and assayed for anticancer activity. Method: The semisynthetic hydrazones were obtained and had their molecular structures established by NMR, IR, and MS. Anticancer activity was evaluated by cell viability determined by reduction of 3-(4,5-dimethyl-2-thiazol)-2,5-diphenyl-2H-tetrazolium bromide (MTT). The electrochemical studies, mainly cyclic voltammetry, were performed, in aprotic and protic media. Result: The study showed that the compounds 2, 3, and 4 were active against at least one of the cancer cell lines evaluated, being compounds 3 and 4 the most cytotoxic. Toward HL-60 cells, compound 3 was 20x more active than β-lapachone, and 3x more cytotoxic than doxorubicin. Furthermore, 3 showed an SI value of 39.62 for HL-60 cells. Compound 4 was active against all cancer cells tested, with IC50 values in the range 2.90–12.40 μM. Electrochemical studies revealed a profile typical of self-protonation and reductive cleavage, dependent on the supporting electrolyte. Conclusion: These results therefore indicate that compounds 3 and 4 are strong candidates as prototypes of new antineoplastic drugs.

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