Mangostanaxanthone VII, a new cytotoxic xanthone from Garcinia mangostana

2018 ◽  
Vol 73 (5-6) ◽  
pp. 185-189 ◽  
Author(s):  
Sabrin R.M. Ibrahim ◽  
Gamal A. Mohamed ◽  
Mahmoud A. Elfaky ◽  
Mohamed F. Zayed ◽  
Amal A. El-Kholy ◽  
...  
Keyword(s):  
Cell Lines ◽  
Mcf7 Cell ◽  
2D Nmr ◽  
Garcinia Mangostana ◽  
Spectral Techniques ◽  
Sulforhodamine B ◽  
Agar Disc ◽  
Diffusion Assay ◽  
Agar Disc Diffusion Assay ◽  
Mcf 7

Abstract Garcinia mangostana L. (the queen of fruits, mangosteen, family Guttiferae) is a wealthy source of xanthones. The CHCl3 soluble fraction of the air-dried pericarps of G. mangostana provided a new xanthone: mangostanaxanthone VII (5), along with four known xanthones: mangostanaxanthones I (1) and II (2), gartanin (3) and γ-mangostin (4). The structural verification of these metabolites was achieved by different spectral techniques, including UV, IR, 1D and 2D NMR and HRESIMS. The new metabolite was assessed for cytotoxic potential, using sulforhodamine B (SRB) assay towards the A549 and MCF-7 cancer cell lines. Moreover, its antimicrobial effects were evaluated against various bacterial and fungal strains, using agar disc diffusion assay. Mangostanaxanthone VII showed moderate cytotoxic activity against the A549 and MCF7 cell lines with IC50s 26.1 and 34.8 μM, respectively, compared with doxorubicin (0.74 and 0.41 μM, respectively).

scholarly journals Phytochemical Analysis of Anvillea garcinii Leaves: Identification of Garcinamines F–H and Their Antiproliferative Activities

Plants ◽  
2021 ◽  
Vol 10 (6) ◽  
pp. 1130
Author(s):  
Hanan Y. Aati ◽  
Shagufta Perveen ◽  
Raha Orfali ◽  
Areej M. Al-Taweel ◽  
Jiangnan Peng ◽  
...  
Keyword(s):  
Cell Lines ◽  
Liver Diseases ◽  
Mcf7 Cell ◽  
Sesquiterpene Lactones ◽  
2D Nmr ◽  
Phytochemical Analysis ◽  
Antidiabetic Agent ◽  
Arab Region ◽  
New Compounds ◽  
Acid Unit

Anvillea garcinii is a medicinal plant used in the Arab region for intestinal diseases, lung and liver diseases, digestive problems, and as an antidiabetic agent. Repeated chromatographic purifications of A. garcinii leaves led to the isolation of three undescribed guaiane sesquiterpene derivatives, named garcinamines F–H, characterized by the presence of an amino acid unit, along with five known sesquiterpene lactones (garcinamines B–E and 9β-hydroxyparthenolide). The structures of the new compounds were established using spectroscopic (1D and 2D NMR) and spectrometric methods (ESIMS). Garcinamine H possesses a double bond at the Δ1,10 position, a structural feature rarely reported in guaianolide-type sesquiterpenes. The antiproliferative activity of the isolated sesquiterpenes was screened against three different cancer cell lines, and 9β-hydroxyparthenolide and garcinamines C and D displayed significant effects against lung carcinoma (A549), colon carcinoma (LoVo), and breast carcinoma (MCF7) cell lines.

scholarly journals Labdane and Abietane Diterpenoids from Juniperus oblonga and Their Cytotoxic Activity

Molecules ◽  
2019 ◽  
Vol 24 (8) ◽  
pp. 1561 ◽  
Author(s):  
Qiao ◽  
Khutsishvili ◽  
Alizade ◽  
Atha ◽  
Borris
Keyword(s):  
Cell Lines ◽  
Human Tumor ◽  
2D Nmr ◽  
Human Tumor Cell Lines ◽  
Abietane Diterpenoids ◽  
Whole Plant ◽  
Phytochemical Investigation ◽  
Ic50 Values ◽  
First Time ◽  
Mcf 7

A phytochemical investigation of the whole plant of Juniperus oblonga led to the isolationof one previously undescribed labdane diterpenoid, (4R,5S,9S,10R)‐13‐des‐ethyl‐13‐oxolabda‐8(17),11E‐dien‐19‐oic acid (1), together with nine known diterpenoids (2–3, 6–12), two lignans (4, 5),and a coumarin (13). The structures of all the compounds were elucidated on the basis ofspectrometric data, primarily one‐dimensional (1D)‐ and two‐dimensional (2D)‐NMR and massspectrometry. Electronic circular dichroism (ECD) calculations determined the absoluteconfiguration of 1. In addition, the isolated compounds were evaluated for their cytotoxic activityagainst three human tumor cell lines (HepG2, MCF‐7, and HeLa). 6,12‐Dihydroxyabieta‐5,8,11,13‐tetraen‐7‐one (6) showed moderate cytotoxicity against all three cell lines with IC50 values rangingfrom 24.41 μM to 58.39 μM and trilobinone (10) showed weaker activity with IC50 values rangingfrom 56.93 μM to 79.98 μM. None of the isolated diterpenoids have been previously reported fromJuniperus oblonga, and five compounds are here reported from the genus Juniperus for the first time.

scholarly journals A New Triterpene Glucoside from Genista numidica

2018 ◽  
Vol 13 (9) ◽  
pp. 1934578X1801300
Author(s):  
Feryal Benayache ◽  
Massimiliano D'Ambola ◽  
Roberta Cotugno ◽  
Massika Chaouche ◽  
Samir Benayache ◽  
...  
Keyword(s):  
Ethyl Acetate ◽  
Cell Lines ◽  
Oleanolic Acid ◽  
Hela Cells ◽  
Antiproliferative Activity ◽  
Mcf7 Cell ◽  
2D Nmr ◽  
Aerial Parts ◽  
Ethyl Acetate Extracts

A new oleanolic acid triterpene glucoside, 3- O-β-D-glucopyranosyl-3β,21β,28-trihydroxy-olean-12-en-27-oic acid (1), has been isolated together with twelve known compounds from the chloroform and ethyl acetate extracts of Genista numidica Spach (Fabaceae) aerial parts. The structures were elucidated by spectroscopic and spectrometric analyses, mainly 1D-, 2D-NMR and MS data, and comparison with the literature. The antiproliferative activity of isolates was investigated on Jurkat, HeLa, and MCF7 cell lines. The most active triterpene, 3- O-β-D-glucopyranosyl-olean-12-en-3β,27,28,29-tetraol, showed activity in all cell lines. Further studies revealed that this compound induced in HeLa cells a cytostatic response.

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

Metabolites ◽  
2020 ◽  
Vol 10 (2) ◽  
pp. 75
Author(s):  
Samah O. Alshehri ◽  
Rania T. Malatani ◽  
Hanin A. Bogari ◽  
Ahmad O. Noor ◽  
Amany K. Ibrahim ◽  
...  
Keyword(s):  
Cell Lines ◽  
Penicillium Chrysogenum ◽  
2D Nmr ◽  
Carcinoma Cells ◽  
Breast Adenocarcinoma ◽  
Cytotoxic Activities ◽  
Human Carcinoma ◽  
Sulforhodamine B ◽  
Ic50 Values ◽  
Hepg2 Cell Lines

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.

scholarly journals Synthesis and Anti-Proliferative Assessment of Triazolo-Thiadiazepine and Triazolo-Thiadiazine Scaffolds

Molecules ◽  
2019 ◽  
Vol 24 (24) ◽  
pp. 4471 ◽  
Author(s):  
Ahmed T. A. Boraei ◽  
Hazem A. Ghabbour ◽  
Mohamed S. Gomaa ◽  
El Sayed H. El Ashry ◽  
Assem Barakat
Keyword(s):  
Single Crystal ◽  
Cell Lines ◽  
Cancer Cell ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Docking Studies ◽  
X Ray ◽  
Cytotoxicity Activity ◽  
Human Liver Cancer ◽  
Mcf 7

A series of triazolo-thiadiazepines 4a–k were synthesized with excellent yields using dehydrated PTSA as a catalyst in toluene. Two triazolo-thiadiazines were obtained; 8a was formed directly by reflux in ethanol, whereas, PTSA promoted the formation of 8b. The molecular structure of the formed triazolo-thiadiazepines is identical to the imine-form 4a–k and not the enamine-tautomer 6a–k. The structures of the newly synthesized triazolo-thiadiazepines 4a–k and triazolo-thiadiazines 8a–b were elucidated using NMR (1H, and 13C), 2D NMR, HRMS, and X-ray single crystal. Furthermore, 4a was deduced using X-ray single crystal diffraction analysis. These new thiadiazepine hits represent an optimized series of previously synthesized indole-triazole derivatives for the inhibition of EGFR. The cytotoxicity activity against two cancer cell lines including human liver cancer (HEPG-2) and breast cancer (MCF-7) was promising, with IC50 between 12.9 to 44.6 µg/mL and 14.7 to 48.7 µg/mL for the tested cancer cell lines respectively, compared to doxorubicin (IC50 4.0 µg/mL). Docking studies revealed that the thiadiazepine scaffold presented a suitable anchor, allowing good interaction of the various binding groups with the enzyme binding regions and sub-pockets.

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.

Cytotoxic and Pro-apoptotic Activities of Diterpenoids from Zhumeria Majdae

2020 ◽  
Vol 17 ◽  
Author(s):  
Abolfazl Shakeri ◽  
Samira Navabi Nejad ◽  
Javad Asili ◽  
Milena Masullo ◽  
Mansoor Saeidi ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cytotoxic Effect ◽  
Therapeutic Agent ◽  
2D Nmr ◽  
Etoac Extract ◽  
Chemical Structures ◽  
Ic50 Value ◽  
Cytotoxic Compounds ◽  
First Time ◽  
Mcf 7

Abstract:: Since the ethylacetate (EtOAc) extract of the roots of Zhumeria majdae had the potent cytotoxic effect (IC50 < 50 μg/ml) on three cancer cell lines; MCF-7, PC3 and MDA-MB-231, therefore the purpous of this study is to isolation of the responcible cytotoxic compounds from the plant. Isolation of the extract led to the identification of four diterpenoids named as lanugon Q (1), 12,16-dideoxy aegyptinone B (2), 12-deoxy-salvipisone (3) and manool (4). The chemical structures have been determined on the basis of 1D and 2D NMR experiments. Compound 1 is reported for the first time in the plants of Zhumeria genus. The results of cytotoxic and apoptotic evaluation revealed that compound 2 had the strong cytotoxic effect with the IC50 value of 15.90 μg/ml against MCF-7 cell lines. Sub-G1 peak in flow cytometry histogram of cells treated with EtOAc axtract and compound 2 showed the induction of apoptosis. Changes in the Bax/Bcl-2 ratio and cleavage of PARP were observed. It is to be noted that owing to strong cytotoxic effect, Z. majdae extract could be represented as therapeutic agent against cancer.

scholarly journals Sesquiterpene Quinones and Diterpenes from Smenospongia cerebriformis and Their Cytotoxic Activity

2017 ◽  
Vol 12 (4) ◽  
pp. 1934578X1701200
Author(s):  
Le Thi Huyen ◽  
Dan Thuy Hang ◽  
Nguyen Xuan Nhiem ◽  
Bui Huu Tai ◽  
Hoang Le Tuan Anh ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Human Cancer ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Cytotoxic Activities ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Nmr Data ◽  
Mcf 7

Using various chromatographic methods, one new sesquiterpene quinone named smenohaimien F (1) and five known, neodactyloquinone (2), dactyloquinone C (3), dactyloquinone D (4), isoamijiol (5), and amijiol (6), were isolated from the marine sponge Smenospongia cerebriformis Duchassaing & Michelotti, 1864. Their structures were elucidated by 1D-, 2D-NMR spectroscopic analysis, HR-ESI-MS, and by comparing with the NMR data reported in the literature. The cytotoxic activities of the all compounds were evaluated on five human cancer cell lines, LU-1, HL-60, SK-Mel-2, HepG-2, and MCF-7. Compound 4 was found to exhibit significant cytotoxic activities on all tested human cancer cell lines with IC50 values ranging from 0.7 to 1.6 μg/mL.

scholarly journals Flavonoids from Twigs of Millettia pubinervis

2014 ◽  
Vol 9 (12) ◽  
pp. 1934578X1400901
Author(s):  
Zhi Na ◽  
Qi-Shi Song ◽  
Hua-Bin Hu
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
Spectroscopic Data ◽  
Human Cancer ◽  
Data Interpretation ◽  
2D Nmr ◽  
Human Cancer Cell ◽  
Human Cancer Cell Lines ◽  
Phytochemical Investigation ◽  
Mcf 7

A new flavone, 3-methoxy-5-hydroxy-[2”,3”:7,8] furanoflavone, pubinerone (1), was isolated from the twigs of Millettia pubinervis Kurz, together with ten known flavonoids, karanjin (2), kanjone (3), 3,6-dimethoxy-[2”,3”:7,8] furanoflavone (4), pongaglabrone (5), pongapin (6), pongaflavone (7), 3,6-dimethoxy-6”,6”-dimethylchromene-[2”,3”:7,8] flavone (8), pongachromene (9), 3,6-dimethoxy-3′,4′-methylenedioxy-6”,6”-dimethylchromene-[2”,3”:7,8] flavone (10) and demethoxykanugin (11). This is the first phytochemical investigation of this plant. The structure of compound 1 was elucidated on the basis of spectroscopic data interpretation, including 1D and 2D NMR and HREIMS analysis. The cytotoxicity of 1 against five human cancer cell lines, HL-60, SMMC-7721, A-549, MCF-7 and SW480, was evaluated, but it was inactive (IC50>40μM).

scholarly journals Six New Phenolic Glycosides and a New Ceramide from the Flowers of Wedelia biflora and Their Cytotoxicity Against Some Cancer Cell Lines

2013 ◽  
Vol 8 (3) ◽  
pp. 1934578X1300800
Author(s):  
Nguyen T. H. Thu ◽  
Le T. Ha ◽  
Vo T. Nga ◽  
Pham N. K. Tuyen ◽  
Ton T. Quang ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cancer Cell ◽  
2D Nmr ◽  
Cancer Cell Lines ◽  
Phenolic Glycosides ◽  
Cytotoxic Activities ◽  
2D Nmr Spectroscopy ◽  
New Compounds ◽  
Potential Use ◽  
Mcf 7

The plant Wedelia biflora has been used in traditional medicine in India and Vietnam to treat various symptoms. However, the chemical composition of its flowers remains mostly unknown. Therefore, we now report the isolation and structural elucidation of six new phenolic glycosides {wedebicoside A – F (1–6)} and one new ceramide [wedebiceramide (9)], together with six known compounds, 1- O-(2′,4′-diangeloyloxy- β-D-fucopyranosyl)-6-hydroxythymol (7), 1- O-[2′,4′-diangeloyloxy-3′-(3′'-angeloyloxy- β-D-fucopyranosyl)- β-D-fucopyranosyl]-6-hydroxythymol (8), anhydrosecoisolariciresinol (10), friedeline (11), epifriedelanol (12) and stigmasterol (13) from the flowers of Wedelia biflora. Their structures were established by 1D and 2D NMR spectroscopy, as well as by high resolution ESI–MS analysis and comparison with literature data. The cytotoxic activities against HeLa, MCF-7 and NCI–H460 were evaluated on some purified compounds at the concentration of 100 μg/mL. Compounds 1, 2, 3 and 5 showed strong cytotoxic activities against three surveyed cancer cell lines. Consequently, this study elucidated the phytochemical composition of W. biflora, as well as the potential use of some of the new compounds against some cancers.

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