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.

scholarly journals Unusual derivatives from Hypericum scabrum

2020 ◽  
Vol 10 (1) ◽  
Author(s):  
Sara Soroury ◽  
Mostafa Alilou ◽  
Thomas Gelbrich ◽  
Marzieh Tabefam ◽  
Ombeline Danton ◽  
...  
Keyword(s):  
Trypanosoma Brucei ◽  
2D Nmr ◽  
Moderate Activity ◽  
Trypanosoma Brucei Rhodesiense ◽  
L6 Cells ◽  
Aerial Parts ◽  
Hypericum Scabrum ◽  
New Compounds ◽  
Absolute Structure

AbstractThree new compounds (1–3) with unusual skeletons were isolated from the n-hexane extract of the air-dried aerial parts of Hypericum scabrum. Compound 1 represents the first example of an esterified polycyclic polyprenylated acylphloroglucinol that features a unique tricyclo-[4.3.1.11,4]-undecane skeleton. Compound 2 is a fairly simple MPAP, but with an unexpected cycloheptane ring decorated with prenyl substituents, and compound 3 has an unusual 5,5-spiroketal lactone core. Their structures were determined by extensive spectroscopic and spectrometric techniques (1D and 2D NMR, HRESI-TOFMS). Absolute configurations were established by ECD calculations, and the absolute structure of 2 was confirmed by a single crystal determination. Plausible biogenetic pathways of compounds 1–3 were also proposed. The in vitro antiprotozoal activity of the compounds against Trypanosoma brucei rhodesiense and Plasmodium falciparum and cytotoxicity against rat myoblast (L6) cells were determined. Compound 1 showed a moderate activity against T. brucei and P. falciparum, with IC50 values of 3.07 and 2.25 μM, respectively.

scholarly journals Six New 3,5-Dimethylcoumarins from Chelonopsis praecox, Chelonopsis odontochila and Chelonopsis pseudobracteata

2021 ◽  
Author(s):  
Chang-An Geng ◽  
Zhen-Tao Deng ◽  
Qian Huang ◽  
Chun-Lei Xiang ◽  
Ji-Jun Chen
Keyword(s):  
Protein Tyrosine Phosphatase ◽  
Tyrosine Phosphatase ◽  
2D Nmr ◽  
Cell Protein ◽  
Protein Tyrosine Phosphatase 1B ◽  
Protein Tyrosine ◽  
Aerial Parts ◽  
Spectroscopic Analyses ◽  
New Compounds

AbstractTen 3,5-dimethylcoumarins (1–6 and 8‒11) involving six new ones (1–6), together with a known 3-methylcoumarin (7), were isolated from the aerial parts of three Chelonopsis plants, C. praecox, C. odontochila, and C. pseudobracteata. The structures of the new compounds were determined by extensive HRESIMS, 1D and 2D NMR spectroscopic analyses. According to the substitution at C-5, these coumarins were classified into 5-methyl, 5-hydroxymethyl, 5-formyl, and 5-nor types. All the isolates were assayed for their inhibition on α-glucosidase, protein tyrosine phosphatase 1B, and T-cell protein tyrosine phosphatase in vitro. Graphic Abstract

scholarly journals Cyclic Peroxides from a Two-Sponge Association of Plakortis communis-Agelas mauritiana

2013 ◽  
Vol 8 (6) ◽  
pp. 1934578X1300800
Author(s):  
Pinus Jumaryatno ◽  
Lynette K. Lambert ◽  
John N. A. Hooper ◽  
Joanne T. Blanchfield ◽  
Mary J. Garson
Keyword(s):  
2D Nmr ◽  
Side Chain ◽  
Relative Configuration ◽  
Carboxylic Acid Groups ◽  
Rp Hplc ◽  
Chemical Shift Data ◽  
New Compounds ◽  
Cyclic Peroxide ◽  
Related Compounds ◽  
Shift Data

A cyclic peroxide 1 with an unusual phenethenyl side chain, together with the known peroxide 2 with a C4-sidechain have been isolated from a two-sponge association of Plakortis communis – Agelas mauritiana (Carter, 1883) collected near Mooloolaba, South-East Queensland, Australia. Metabolite purification was complicated by the presence of the free carboxylic acid groups in 1 and 2; therefore, diazomethane treatment was undertaken to afford methyl ester 3. Following RP-HPLC purification, the ring-opened analogues 4 and 5 were also obtained. The structures of the new compounds were elucidated on the basis of their 1D and 2D NMR and MS data, and by comparison with literature data. The relative configuration of the isolated peroxides was determined by the interpretation of JH-H values and comparison of the 13C chemical shift data with literature data for related compounds. The bromopyrrole alkaloid longamide (6) was also isolated.

scholarly journals Four New Pterosins from Pteris cretica and Their Cytotoxic Activities

Molecules ◽  
2019 ◽  
Vol 24 (15) ◽  
pp. 2767
Author(s):  
Jian Lu ◽  
Caiying Peng ◽  
Shuang Cheng ◽  
Jianqun Liu ◽  
Qinge Ma ◽  
...  
Keyword(s):  
Human Tumor ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Aerial Parts ◽  
Pteris Cretica ◽  
Phytochemical Investigation ◽  
Hct 116 ◽  
Hct 116 Cells ◽  
New Compounds

Phytochemical investigation of the aerial parts of Pteris cretica led to the isolation and elucidation of nine pterosins, including four new pterosins, creticolacton A (1), 13-hydroxy-2(R),3(R)-pterosin L (2), creticoside A (3), and spelosin 3-O-β-d-glucopyranoside (4), together with five known pterosins 5–9. Their structures were identified mainly on the basis of 1D and 2D NMR spectral data, ESI-MS and literature comparisons. Compounds 1 and 3 were new type of petrosins with a six membered ring between C-14 and C-15. The new compounds were tested in vitro for their cytotoxic activities against four human tumor cell lines (SH-SY5Y, SGC-7901, HCT-116, Lovo). Results showed that compounds 1 and 2 exhibited cytotoxic activity against HCT-116 cells with IC50 value of 22.4 μM and 15.8 μM, respectively.

scholarly journals Three New Cytotoxic Withanolides from the Chinese Folk Medicine Physalis angulata

2015 ◽  
Vol 10 (12) ◽  
pp. 1934578X1501001 ◽  
Author(s):  
Cai-Yun Gao ◽  
Ting Ma ◽  
Jun Luo ◽  
Ling-Yi Kong
Keyword(s):  
Cell Line ◽  
Folk Medicine ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Spectroscopic Techniques ◽  
Aerial Parts ◽  
Physalis Angulata ◽  
The Absolute ◽  
New Compounds

Physagulides M-O, three new withanolides (1–3), were isolated from the aerial parts of Physalis angulata L. Their structures were elucidated through extensive spectroscopic techniques, including 1D and 2D NMR, and HRESIMS. The absolute configurations (22- R) of these new compounds were determined by CD analysis. Compounds 1 and 3 showed significant selective cytotoxic activities on the MG-63 cell line, with IC50 values of 4.28 and 5.44 μM, respectively.

scholarly journals Mutagenesis of the pRB Pocket Reveals that Cell Cycle Arrest Functions Are Separable from Binding to Viral Oncoproteins

2000 ◽  
Vol 20 (10) ◽  
pp. 3715-3727 ◽  
Author(s):  
Frederick A. Dick ◽  
Elizabeth Sailhamer ◽  
Nicholas J. Dyson
Keyword(s):  
Cell Cycle ◽  
Binding Site ◽  
Cell Cycle Arrest ◽  
Binding Proteins ◽  
Tumor Cell Line ◽  
T Antigen ◽  
Viral Oncoproteins ◽  
Adenovirus E1a ◽  
Cycle Arrest ◽  
A Cell

ABSTRACT The pocket domain of pRB is required for pRB to arrest the cell cycle. This domain was originally defined as the region of the protein that is necessary and sufficient for pRB's interaction with adenovirus E1A and simian virus s40 large T antigen. These oncoproteins, and other pRB-binding proteins that are encoded by a variety of plant and animal viruses, use a conserved LXCXE motif to interact with pRB. Similar sequences have been identified in multiple cellular pRB-binding proteins, suggesting that the viruses have evolved to target a highly conserved binding site of pRB that is critical for its function. Here we have constructed a panel of pRB mutants in which conserved amino acids that are predicted to make close contacts with an LXCXE peptide were altered. Despite the conservation of the LXCXE binding site throughout evolution, pRB mutants that lack this site are able to induce a cell cycle arrest in a pRB-deficient tumor cell line. This G1 arrest is overcome by cyclin D-cdk4 complexes but is resistant to inactivation by E7. Consequently, mutants lacking the LXCXE binding site were able to induce a G1 arrest in HeLa cells despite the expression of HPV-18 E7. pRB mutants lacking the LXCXE binding site are defective in binding to adenovirus E1A and human papillomavirus type 16 E7 protein but exhibit wild-type binding to E2F or DP, and they retain the ability to interact with CtIP and HDAC1, two transcriptional corepressors that contain LXCXE-like sequences. Consistent with these observations, the pRB mutants are able to actively repress transcription. These observations suggest that viral oncoproteins depend on the LXCXE-binding site of pRB for interaction to a far greater extent than cellular proteins that are critical for cell cycle arrest or transcriptional repression. Mutation of this binding site allows pRB to function as a cell cycle regulator while being resistant to inactivation by viral oncoproteins.

scholarly journals New Benzophenone O-Glucoside from Hypericum Ellipticum

2009 ◽  
Vol 4 (4) ◽  
pp. 1934578X0900400 ◽  
Author(s):  
Elyse Petrunak ◽  
Andrew C. Kester ◽  
Yunbao Liu ◽  
Camile S. Bowen-Forbes ◽  
Muraleedharan G. Nair ◽  
...  
Keyword(s):  
Lipid Peroxidation ◽  
Tumor Cell ◽  
Cell Line ◽  
Spectroscopic Data ◽  
Tumor Cell Line ◽  
2D Nmr ◽  
Acetone Extract ◽  
In Vitro Assays ◽  
Aerial Parts

Examination of the acetone extract of the aerial parts of Hypericum ellipticum afforded a new acetylated benzophenone glucoside (3′- O-β-D-3″,4″,6″-triacetylglucopyranosyl-2,4,5′,6-tetrahydroxybenzophenone) together with catechin and epicatechin. The structure of the benzophenone glucoside was determined by 2D NMR spectroscopic data. The compound inhibited the proliferation of CNS tumor cell line (SF-268) and lipid peroxidation in in vitro assays.

scholarly journals Triterpenoids from Aerial Parts of Glochidion eriocarpum

2010 ◽  
Vol 5 (3) ◽  
pp. 1934578X1000500 ◽  
Author(s):  
Vu Kim Thu ◽  
Phan Van Kiem ◽  
Pham Hai Yen ◽  
Nguyen Xuan Nhiem ◽  
Nguyen Huu Tung ◽  
...  
Keyword(s):  
Spectroscopic Data ◽  
2D Nmr ◽  
Chromatographic Separations ◽  
Triterpenoid Saponins ◽  
Fticr Ms ◽  
Aerial Parts ◽  
New Compounds

From the aerial parts of Glochidion eriocarpum, a new triterpene, glochieriol (1), three new triterpenoid saponins, glochieriosides C - E (2 - 4), together with four known triterpenes (glochidonol, glochidiol, lupeol, and 3- epi-lupeol) were isolated by using combined chromatographic separations. The structures of the new compounds were elucidated on the basis of spectroscopic data, including FTICR-MS, 1D and 2D NMR.

scholarly journals New Flavonoids from Baeckea Frutescens and their Antioxidant Activity

2008 ◽  
Vol 3 (5) ◽  
pp. 1934578X0800300 ◽  
Author(s):  
Tran Hong Quang ◽  
Nguyen Xuan Cuong ◽  
Chau Van Minh ◽  
Phan Van Kiem
Keyword(s):  
Antioxidant Activity ◽  
Ethyl Acetate Extract ◽  
Radical Scavenging ◽  
2D Nmr ◽  
Flavonoid Glycosides ◽  
Dpph Radical ◽  
Aerial Parts ◽  
Baeckea Frutescens ◽  
New Compounds ◽  
Dpph Radical Scavenging

From the ethyl acetate extract of the aerial parts of Baeckea frutescens, a new flavonoid, 6,8-di- C-methylkaempferol (1), and three new flavonoid glycosides, 6,8-di- C-methylkaempferol 3- O-α-L-rhamnopyranoside (2), 6- C-methylquercetin 3- O-α-L-rhamnopyranoside (3), and 6- C-methylquercetin 4′- O-β-D-glucopyranoside (4), along with four known flavonoids were isolated. Their structures were elucidated by extensive spectroscopic methods including 1D and 2D NMR experiments, as well as ESI-MS analysis. All the new compounds were tested for their antioxidant activity in the 1,1-diphenyl-2-pecrylhydrazyl (DPPH) radical scavenging assay system. Compounds 3 and 4 showed potent activity with IC50 values of 12.1 ± 0.5 and 13.5 ± 0.9 (μM), respectively.

scholarly journals Unusual Secondary Metabolites of the Aerial Parts of Dionysia diapensifolia Bioss. (Primulaceae) and Their Anti-Inflammatory Activity

Biomolecules ◽  
2020 ◽  
Vol 10 (3) ◽  
pp. 438
Author(s):  
Mostafa Alilou ◽  
Stefania Marzocco ◽  
Hossein Batooli ◽  
Jakob Troppmair ◽  
Stefan Schwaiger ◽  
...  
Keyword(s):  
Diethyl Ether ◽  
2D Nmr ◽  
Inhibitory Effect ◽  
Inflammatory Activity ◽  
Relative Configuration ◽  
Aerial Parts ◽  
No Release ◽  
Cox 2 ◽  
Anti Inflammatory ◽  
First Time

The genus Dionysia, belonging to the Primulaceae family, encompasses more than 50 species worldwide with a center of diversity located in the arid Irano-Turanian mountains. In this study, a phytochemical investigation of the aerial parts of D. diapensifolia Bioss. led to the isolation of 24 phenolic compounds 1–7 and 9–25, and one sesquiterpenoid 8. Compound 1 was identified as new natural product, while isolation of 2 and 3, already known as synthetic products, from a natural source is reported for the first time in the present study. Isolation of compound 8 from a Dionysia species and indeed the whole Primulaceae family is reported for the first time too. Structure elucidation was performed by extensive spectroscopic analyses (1D-, 2D-NMR, and MS), and by comparison with reported literature data. Furthermore, DP4+ chemical shift probability calculations were performed to establish the relative configuration of compound 1. Additionally, subfractions obtained by liquid-liquid extraction of the methanolic extract of the plant, and subsequently the isolated new and selected known compounds 1–4, 6, 8–11 obtained from the diethyl ether subfraction were investigated for their inhibitory effect on NO release and iNOS and COX-2 expression in J774A.1 murine macrophages. The results showed a potential anti-inflammatory activity of the obtained subfractions, of which the diethyl ether subfraction was the most active one in inhibiting NO release and COX-2 expression (p < 0.001). Among the investigated isolated compounds, compound 4 significantly (p < 0.001) inhibited NO release and iNOS and COX-2 expression in a comparable manner like the used positive controls (L-NAME and indomethacin, respectively). Moreover, other isolated substances displayed moderate to high inhibitory activities, illustrating the potential anti-inflammatory activity of Dionysia diapensifolia.

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