Polyprenylated Phloroglucinols from Hypericum maculatum

2015 ◽  
Vol 10 (7) ◽  
pp. 1934578X1501000
Author(s):  
Paraskev T. Nedialkov ◽  
Georgi Momekov ◽  
Zlatina K. Kokanova-Nedialkova ◽  
Jörg Heilmann
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Spectral Methods ◽  
Tumor Cell Lines ◽  
Aerial Parts ◽  
Phytochemical Investigation ◽  
Phloroglucinol Derivatives ◽  
New Compounds ◽  
First Time

A detailed phytochemical investigation of the dichloromethane extract of the aerial parts of Hypericum maculatum Crantz. led to the isolation of four new (2-5) and six known (1a/b, 6-10) polyprenylated phloroglucinol derivatives. The new compounds were identified by means of spectral methods (MS, NMR, IR, UV) as ( E)-4-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-2-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl isobutyrate (2), ( E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-4-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl isobutyrate (3), ( E)-4-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-2-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylbutanoate (4) and ( E)-2-(3,7-dimethylocta-2,6-dien-1-yl)-5-hydroxy-4-(3-methylbut-2-en-1-yl)-3,6-dioxocyclohexa-1,4-dien-1-yl 2-methylbutanoate (5). The known compounds have been identified as hyperpolyphyllirin/hyperibine J (1a/b), erectquione A (6), ( E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylpropan-1-one (7), ( E)-1-(3-(3,7-dimethylocta-2,6-dien-1-yl)-2,4,6-trihydroxyphenyl)-2-methylbutan-1-one (8), 1-(5,7-dihydroxy-2-methyl-2-(4-methylpent-3-en-1-yl)chroman-8-yl)-2-methylpropan-1-one (9) and 1-(6,8-dihydroxy-1,1,4a-trimethyl-2,3,4,4a,9,9a-hexahydro-1H-xanthen-5-yl)-2-methylpropan-1-one (10). The stereochemistry of 1a is described for the first time. The cytotoxicity of 1-6 on SKW-3, BV-173 and K-562 tumor cell lines was determined using MTT based assays.

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 A New Sulfated Triterpene Saponin from Gypsophila trichotoma

2013 ◽  
Vol 8 (6) ◽  
pp. 1934578X1300800 ◽  
Author(s):  
Ilina Krasteva ◽  
Maya Yotova ◽  
Kristina Jenett-Siems ◽  
Petranka Zdraveva ◽  
Stefan Nikolov
Keyword(s):  
Cell Proliferation ◽  
Tumor Cell ◽  
Cell Lines ◽  
Spectral Methods ◽  
Human Tumor ◽  
Malignant Cell ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
Dependent Inhibition

A new sulfated triterpeniod saponin, 3- O-sulfooleanolic acid 28- O-[ β-glucopyranosyl-(1→3)]-[ β-glucopyranosyl-(1→6)]- β-glucopyranosyl ester (1), along with three known Δ7-sterols: stigmast-7-en-3 β-ol (2), stigmast-7-en-3- O-β-D-glucopyranoside (3) and stigmast-7-en-3-on (4) were isolated from the roots of Gypsophila trichotoma Wend. (Caryophyllaceae). Their structures were elucidated by chemical and spectral methods. Compound 1 caused concentration-dependent inhibition of malignant cell proliferation against different human tumor cell lines.

scholarly journals New Dammarane-type Saponins from Gynostemma pentaphyllum

Molecules ◽  
2019 ◽  
Vol 24 (7) ◽  
pp. 1375 ◽  
Author(s):  
Po-Yen Chen ◽  
Chih-Chao Chang ◽  
Hui-Chi Huang ◽  
Li-Jie Zhang ◽  
Chia-Ching Liaw ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Human Tumor ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
Gynostemma Pentaphyllum ◽  
Antiproliferative Effects ◽  
Aerial Parts

Six new dammarane-type saponins, gypenosides CP1-6 (16), along with 19 known compounds 7–25, were isolated and characterized from the aerial parts of Gynostemma pentaphyllum. Among these compounds, eight dammarane-type saponins, 2, 5, 6, 7, 11, 12, 13, and 15, exhibited the greatest antiproliferative effects against two human tumor cell lines (A549 and HepG2).

scholarly journals Biological Effects of EF24, a Curcumin Derivative, Alone or Combined with Mitotane in Adrenocortical Tumor Cell Lines

Molecules ◽  
2019 ◽  
Vol 24 (12) ◽  
pp. 2202 ◽  
Author(s):  
Loris Bertazza ◽  
Susi Barollo ◽  
Maria Elena Mari ◽  
Irene Faccio ◽  
Maira Zorzan ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Biological Effects ◽  
Adrenocortical Tumor ◽  
Tumor Cell Lines ◽  
Adrenocortical Cancer ◽  
Reference Drug ◽  
Enhanced Solubility ◽  
H295r Cells ◽  
First Time

Background: Curcumin has numerous properties and is used in many preclinical conditions, including cancer. It has low bioavailability, while its derivative EF24 shows enhanced solubility. However, its effects have never been explored in adrenocortical tumor cell models. The efficacy of EF24 alone or combined with mitotane (reference drug for adrenocortical cancer) was evaluated in two adrenocortical tumor cell lines, SW13 and H295R. Method and Results: EF24 reduced cell viability with an IC50 (half maximal inhibitory concentration) of 6.5 ± 2.4 μM and 4.9 ± 2.8 μM for SW13 and H295R cells, respectively. Combination index (EF24 associated with mitotane) suggested an additivity effect in both cell lines. Cell cycle analysis revealed an increase in subG0/G1 phase, while motility assay showed a decrease in migratory cell capacity, and similarly, clonogenic assay indicated that EF24 could reduce colony numbers. Furthermore, Wnt/β-catenin, NF-κB, MAPK, and PI3k/Akt pathways were modulated by Western blot analysis when treating cells with EF24 alone or combined with mitotane. In addition, intracellular reactive oxygen species levels increased in both cell lines. Conclusion: This work analyzed EF24 in adrenocortical tumor cell lines for the first time. These results suggest that EF24 could potentially impact on adrenocortical tumors, laying the foundation for further research in animal models.

Synthesis of New Galanthamine-Peptide Derivatives Designed for Prevention and Treatment of Alzheimer’s Disease

2019 ◽  
Vol 16 (3) ◽  
pp. 183-192 ◽  
Author(s):  
Lyubomir T. Vezenkov ◽  
Daniela S. Tsekova ◽  
Ivanka Kostadinova ◽  
Rositsa Mihaylova ◽  
Nikolay G. Vassilev ◽  
...  
Keyword(s):  
Alzheimer’S Disease ◽  
Alzheimer's Disease ◽  
Acute Toxicity ◽  
Tumor Cell ◽  
Cell Lines ◽  
Tumor Cell Lines ◽  
Cytotoxicity Studies ◽  
Peptide Derivatives ◽  
New Compounds ◽  
Derivatives Of

Background: Although no effective treatment for the Alzheimer’s disease currently exist, some drugs acting as Acetylcholinesterase inhibitors, like galanthamine have positively affected such patients. β- and/or γ-secretase inhibitors are another type of potential drugs. Here we report synthesis of new peptide-galanthamine derivatives, with expected inhibitory activity against both Acetylcholinesterase and β-secretase. The aim of this work is obtaining new peptide derivatives of galanthamine with decreased Objectives: toxicity compared to galanthamine. Methods: Syntheses were conducted in solution using fragment condensation approach. The new derivatives were characterized by melting points, angle of optical rotation, NMR and Mass spectra. Acute toxicity was determined on mice, according to a Standard protocol. All new compounds were tested in vitro for cytotoxic activity in a panel of human (HEP-G2, BV-173) and murine (Neuro-2a) tumor cell lines via a standard MTT-based colorimetric method. Results: New derivatives of galanthamine containing shortened analogues of β-secretase inhibitor (Boc- Asn-Leu-Ala-Val-OH) and either nicotinic or isonicotinic residue, both connected with a linker (L-Asp) to position 11 of galanthamine were obtained. In vivo toxicity of some new compounds was found up to 1000 mg/kg. Cell toxicity screening against the tumor cell lines showed negligible growth-inhibiting properties of the galanthamine derivatives. Conclusion: Synthesis of new galanthamine derivatives comprising peptide moiety and nicotinic acid or isonicotinic acid is reported. Acute toxicity studies reveal they are about 100 times less toxic than galanthamine. This effect is due to the peptide fragment. Cytotoxicity studies show good correlation with low toxicity results. These results are encouraging for the application of this class compounds as medicines.</P>

Parvifloracin and parviflorin: cytotoxic bistetrahydrofuran acetogenins with 35 carbons from Asimina parviflora (Annonaceae)

1994 ◽  
Vol 72 (2) ◽  
pp. 287-293 ◽  
Author(s):  
Sunil Ratnayake ◽  
Zhe-Ming Gu ◽  
Laura R. Miesbauer ◽  
David L. Smith ◽  
Karl V. Wood ◽  
...  
Keyword(s):  
Tumor Cell ◽  
Cell Lines ◽  
Test Data ◽  
Solid Tumor ◽  
Brine Shrimp ◽  
Tumor Cell Lines ◽  
Brine Shrimp Lethality ◽  
Human Solid Tumor ◽  
First Time

Using lethality to brine shrimp, activity-directed fractionation of extracts of Asimina parviflora (Michx.) Dunal. (Annonaceae) has led to the isolation of two new and four known acetogenins (1–6). Compound 1, parvifloracin, is the first nonadjacent bistetrahydrofuran acetogenin with 35 carbons. Compound 2, parviflorin, is an unusual adjacent bistetrahydrofuran acetogenin with 35 carbons. Bullatacin (3), molvizarin (4), annonacin (5), and goniothalamicin (6) are also reported for the first time from this plant. Brine shrimp lethality test data and comparative cytotoxicities of 1–6 against three human solid tumor cell lines are presented.

scholarly journals New Indole Glycosides from Aesculus chinensis var. chekiangensis and Their Neuroprotective Activities

Molecules ◽  
2019 ◽  
Vol 24 (22) ◽  
pp. 4063 ◽  
Author(s):  
Nan Zhang ◽  
Shijie Cao ◽  
Weixing Huang ◽  
Pan Li ◽  
Ning Kang ◽  
...  
Keyword(s):  
Chinese Medicine ◽  
Traditional Chinese Medicine ◽  
Tumor Cell ◽  
Human Tumor ◽  
2D Nmr ◽  
Tumor Cell Lines ◽  
Human Tumor Cell ◽  
Human Tumor Cell Lines ◽  
New Compounds ◽  
First Time

The dried seeds of Aesculus chinensis Bge. var. chekiangensis (Hu et Fang) Fang, called “Suo Luo Zi”, have been used in traditional Chinese medicine. Nevertheless, most studies have been focused on components of less polarity fractions. In this research, twelve indoles, including six new indole glycosides (1–6) as well as six known analogs were isolated from the polar portion which has been seldom studied. This is the first description of N-glucosylated indoles obtained from the genus of Aesculus. Structures of the new compounds (1–6) were elucidated based on comprehensive interpretation of HRESIMS, 1D and 2D NMR. Additionally, the neuroprotective activities of the N-glucosylated indoles were evaluated for the first time indicating that compounds 1–5 and 9–10 exhibited moderate neuroprotective activities. Further cytotoxicity tests of isolates 1–10 on three human tumor cell lines suggested that none of these compounds were cytotoxic (IC50 > 50 μM).

Interaction of Human Tumor Cells with Human Platelets and the Coagulation System

1983 ◽  
Vol 50 (03) ◽  
pp. 726-730 ◽  
Author(s):  
Hamid Al-Mondhiry ◽  
Virginia McGarvey ◽  
Kim Leitzel
Keyword(s):  
Tumor Cell ◽  
Tumor Cells ◽  
Cell Lines ◽  
Human Tumor ◽  
Human Platelets ◽  
Factor Vii ◽  
Coagulation System ◽  
Breast Adenocarcinoma ◽  
Activate Factor ◽  
Tumor Cell Lines

SummaryThis paper reports studies on the interaction between human platelets, the plasma coagulation system, and two human tumor cell lines grown in tissue culture: Melanoma and breast adenocarcinoma. The interaction was monitored through the use of 125I- labelled fibrinogen, which measures both thrombin activity generated by cell-plasma interaction and fibrin/fibrinogen binding to platelets and tumor cells. Each tumor cell line activates both the platelets and the coagulation system simultaneously resulting in the generation of thrombin or thrombin-like activity. The melanoma cells activate the coagulation system through “the extrinsic pathway” with a tissue factor-like effect on factor VII, but the breast tumor seems to activate factor X directly. Both tumor cell lines activate platelets to “make available” a platelet- derived procoagulant material necessary for the conversion of prothrombin to thrombin. The tumor-derived procoagulant activity and the platelet aggregating potential of cells do not seem to be inter-related, and they are not specific to malignant cells.

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