Bioactive compounds from Matricaria chamomilla: structure identification, in vitro antiproliferative, antimigratory, antiangiogenic, and antiadenoviral activities

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Mohamed Shaaban ◽  
Ali M. El-Hagrassi ◽  
Abeer F. Osman ◽  
Maha M. Soltan
Keyword(s):  
2D Nmr ◽  
Structure Identification ◽  
Matricaria Chamomilla ◽  
Cell Type ◽  
Chromatographic Purification ◽  
Aerial Parts ◽  
Stem Extract ◽  
Infectivity Titer ◽  
Mcf 7

Abstract During our exploring the anticancer activity of some medicinal plants and their major metabolites, the aerial parts of the Egyptian Matricaria chamomilla (flowers and stems) were studied. GC–MS analysis of the organic soluble extracts of the flowers and stems fractions revealed the presence of 43 and 45 compounds, respectively. Individual chromatographic purification of the flowers and stems’ extracts afforded three major compounds. Structures of these compounds were identified by 1D- and 2D-NMR and HRESI-MS spectroscopic data as bisabolol oxide A (1) and (E)-tonghaosu (2) (as mixture of ratio 2:1) from the flowers extract, meanwhile apigenin-7-β-d-glucoside (3) from the stems fraction. Biologically, the chamomile extracts announced significant antiproliferative activities exceeded in potency by ∼1.5 fold in case of the stem, recording GI50 13.16 and 17.04 μg/mL against Caco-2 and MCF-7, respectively. Both fractions were approximately equipotent against the migration of the same cell type down to 10 μg/mL together, compounds 1, 2 but not 3, showed considerable growth inhibition of the same cells at GI50 13.36 and 11.83 μg/mL, respectively. Interestingly, they were able to suppress Caco-2 colon cancer cells migration at 5.8 μg/mL and potently inactivate the VEGFR2 angiogenic enzyme (1.5-fold relative to sorafenib. The obtained compounds and corresponding chamomile extracts were evaluated against Adeno-7 virus, revealing that both chamomiles’ extracts (flowers and stems) and their corresponding obtained compounds (1–3) were potent in their depletion to the Adeno 7 infectivity titer, however, the flower extract and compounds 1–2 were more effective than those of the stem extract and its end-product (3).

Halo-phenolic metabolites and their in vitro antioxidant and cytotoxic activities from the Red Sea alga Avrainvillea amadelpha

2021 ◽  
Vol 76 (5-6) ◽  
pp. 213-218
Author(s):  
Usama W. Hawas ◽  
Lamia T. Abou El-Kassem ◽  
Radwan Al-farawati ◽  
Fekri M. Shaher
Keyword(s):  
2D Nmr ◽  
Cytotoxic Activities ◽  
Dpph Radical ◽  
Srb Assay ◽  
Phenolic Metabolites ◽  
2D Nmr Spectra ◽  
New Compounds ◽  
Benzaldehyde Derivatives ◽  
Mcf 7

Abstract From the green alga Avrainvillea amadelpha, two new naturally halo-benzaldehyde derivatives were isolated by various chromatographic methods along with 10 known metabolites of bromophenols, sulfonoglycolipid, and steroids. Based on the 1D and 2D NMR spectra as well as on MS data, the structures of the new compounds were identified as 5-bromo-2-(3-bromo-4-hydroxybenzyl)-3,4-dihydroxybenzaldehyde named avrainvilleal (1), and 3-iodo-4-hydroxy-benzaldehyde (2). Using SRB assay, both compounds showed mild and weak cytotoxic activity against HeLa and MCF-7 cancer cell lines, compared to the good activity of their extract (IC50 values 3.1 and 4.3 μg/mL, respectively). However, avrainvilleal (1) displayed an effective scavenged DPPH radical activity with IC50 value 3.5 μM, compared to the antioxidant quercetin with IC50 value 1.5 μM.

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 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 High performance thin-layer chromatography and in vitro cytotoxic studies on ethanol extract of Matricaria chamomilla L (Asteraceae) flowers

2021 ◽  
Vol 18 (9) ◽  
pp. 1969-1976
Author(s):  
Mohammed Al Bratty ◽  
Lalitha K. Govindaram ◽  
Lalitha K. Govindaram ◽  
Neelaveni Thangavel ◽  
Hassan A. Alhazmi ◽  
...  
Keyword(s):  
Thin Layer ◽  
Thin Layer Chromatography ◽  
Mtt Assay ◽  
High Performance ◽  
Cytotoxic Effect ◽  
Ethanol Extract ◽  
Matricaria Chamomilla ◽  
Layer Chromatography ◽  
Mcf 7

Purpose: To develop a high performance thin-layer chromatography (HPTLC procedure for quantitation of apigenin in ethanol extract of Matricaria chamomilla (Babunaj) flowers, and to evaluate the extract for in vitro cytotoxic effect on MCF-7 cell lines. Methods: Quantification of apigenin was carried out using a CAMAG TLC system. A combination of toluene, ethyl acetate and formic acid (4.5:3.5:0.2 v/v/v) was used as mobile phase, with densitometry detection at 336 nm. The HPTLC procedure was subjected to validation as per ICH guidelines. The cytotoxicity of the extract was assessed by 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyl tetrazolium bromide (MTT) assay. Results: A sharp apigenin band at Rf of 0.51 was obtained, and the content of apigenin in the extract was 0.062 % w/w. The detection limit (LOD) and quantification limit (LOQ) were 0.19 and 0.57 ng/band, respectively. MTT assay results indicate that M. chamomilla was cytotoxic to Michigan Cancer Foundation-7 (MCF-7) cells, with half-maximal concentration (IC50) of 74 µg/mL. Conclusion: The developed HPTLC method is linear, precise, accurate and specific for the determination of apigenin. M. chamomilla exerts cytotoxic effect on MCF-7 cell line via induction of apoptosis.

scholarly journals Diterpenoid Alkaloids from Delphinium aemulans

2018 ◽  
Vol 13 (11) ◽  
pp. 1934578X1801301
Author(s):  
Nurfida Ablajan ◽  
Bo Zhao ◽  
Wenjuan Xue ◽  
Zukela Ruzi ◽  
Jiangyu Zhao ◽  
...  
Keyword(s):  
2D Nmr ◽  
Diterpenoid Alkaloids ◽  
Diterpenoid Alkaloid ◽  
Esi Ms ◽  
Mtt Method ◽  
Naturally Occurring ◽  
Spectroscopic Analyses ◽  
Type C ◽  
Mcf 7

A new naturally occurring lycoctonine-type C19-diterpenoid alkaloid aemulansine (1), together with ten known alkaloids (2–11), were isolated from the whole herb of Delphinium aemulans Navski. Their structures were elucidated by extensive spectroscopic analyses, including 1D, 2D NMR and HR-ESI-MS. Compounds 1–10 were also evaluated in vitro for cytotoxicity against A549, Hela and MCF-7 cells using the MTT method.

scholarly journals Chemical Composition and Nutraceutical Potential of Indian Borage (Plectranthus amboinicus) Stem Extract

2013 ◽  
Vol 2013 ◽  
pp. 1-7 ◽  
Author(s):  
Praveena Bhatt ◽  
Gilbert Stanley Joseph ◽  
Pradeep Singh Negi ◽  
Mandyam Chakravarthy Varadaraj
Keyword(s):  
Radical Scavenging ◽  
Reducing Power ◽  
Food Ingredients ◽  
Antiplatelet Aggregation ◽  
Total Antioxidant ◽  
Stem Extract ◽  
Reducing Power Assay ◽  
Plectranthus Amboinicus ◽  
Mcf 7

The stem of Indian borage (Plectranthus amboinicus) was found to be an antioxidant rich fraction as evaluated byin vitromodels such as DPPH free radical scavenging, reducing power assay, superoxide anion radical scavenging, and total antioxidant capacity. The extract also exhibited antiplatelet aggregation ability, antibacterial activity, and antiproliferative effect against cancer cell lines: Caco-2, HCT-15, and MCF-7. Phytochemical evaluation of the extract revealed the occurrence of total phenolics (49.91 mg GAE/g extract), total flavonoids (26.6 mg RE/g extract), and condensed tannins (0.7 mg TAE/g extract). Among the major phenolics, rosmarinic acid (6.160 mg/g extract) was predominant, followed by caffeic acid (0.770 mg/g extract), rutin (0.324 mg/g extract), gallic acid (0.260 mg/g extract), quercetin (0.15 mg/g extract), andp-coumaric acid (0.104 mg/g extract). The appreciable biological activity and presence of biomolecules in the methanolic extract of stem indicate its potential application as functional food ingredients and nutraceuticals.

scholarly journals A New Xanthone from the Pericarp of Garcinia mangostana

2013 ◽  
Vol 8 (12) ◽  
pp. 1934578X1300801 ◽  
Author(s):  
Manqin Fu ◽  
Samuel X. Qiu ◽  
Yujuan Xu ◽  
Jijun Wu ◽  
Yulong Chen ◽  
...  
Keyword(s):  
Colorimetric Assay ◽  
Human Cancer ◽  
Ethanol Extract ◽  
2D Nmr ◽  
Hep G2 ◽  
Garcinia Mangostana ◽  
Human Cancer Cell Lines ◽  
Mtt Colorimetric Assay ◽  
Mcf 7

A new prenylxanthone, garcimangostanol (1), was isolated from the EtOAc-soluble partition of the ethanol extract of the pericarp of Garcinia mangostana L., along with three known compounds, namely 8-deoxygartanin (2), 1-isomangostin (3), and garcinone C (4). The structure of compound 1 was elucidated on the basis of its 1D, 2D NMR and MS data. Compounds 1–4 exhibited either significant or moderate cytotoxicity against MCF-7, A549, Hep-G2 and CNE human cancer cell lines in vitro with IC50 values from 4.0 ± 0.3 to 23.6 ± 1.5 μM by MTT colorimetric assay.

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.

Three new coumarin types from aerial parts of Ammi majus L. and their cytotoxic activity

2018 ◽  
Vol 73 (1-2) ◽  
pp. 1-7 ◽  
Author(s):  
Eman El-Sharkawy ◽  
Yasser Selim
Keyword(s):  
High Activity ◽  
Hct116 Cell ◽  
2D Nmr ◽  
In Vitro Cytotoxicity ◽  
Spectroscopic Methods ◽  
Aerial Parts ◽  
Western Asia ◽  
Ammi Majus ◽  
Diphenyl Tetrazolium Bromide

AbstractThree new coumarin types were isolated from the aerial parts of the wild medicinal plantAmmi majus, which was collected from western Asia (Saudi Arabia), including pyrano coumarin, namely, 5-isobutylcoumarin-6-C-glucoside(1); furanocoumarin, namely, 6,7,9-Trimethoxy-3-(8′-methoxy-2′-oxo-2H-chromen-3-yl)-2H-furo[3,2-g]chromen-2(3H)-one(2); and pyrone coumarin, namely, 6-hydroxy-3-(2-hydroxypropyl)-7-methoxy-4 methyl coumarin(3). The structures were determined by spectroscopic methods, mainly 1D- and 2D-NMR. In vitro cytotoxicity was evaluated by 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyl-tetrazolium bromide (MTT) assay. The results of cytotoxicity depending on their structure features showed that compound3had high activity on different cell lines, while compound1showed no activity against HCT116. Compound2had high activity towards HCT116 cell line.

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