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 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 Abietane Diterpenoids Isolated from Clerodendrum bracteatum and Their Antioxidant and Cytotoxic Activities

Molecules ◽  
2021 ◽  
Vol 26 (16) ◽  
pp. 4870
Author(s):  
Pingting Li ◽  
Lingling Li ◽  
Qin Zhu ◽  
Mingfeng Xu
Keyword(s):  
Antioxidant Activities ◽  
Radical Scavenging ◽  
Cytotoxic Activities ◽  
Dpph Radical ◽  
Mtt Method ◽  
Extensive Analysis ◽  
Abietane Diterpenoids ◽  
New Compounds ◽  
Dpph Radical Scavenging

Two new abietane diterpenoids (1,2), along with five known diterpenoids (3–7), were first isolated and purified from the stems of Clerodendrum bracteatum. The structures of the new compounds were established by extensive analysis of mass spectrometric and 1-D, 2-D NMR spectroscopic data. Their antioxidant activities were determined on DPPH radical scavenging and ABTS. The in vitro cytotoxic activities of the compounds were evaluated against the HL-60 and A549 cell lines by the MTT method.

scholarly journals New Antiproliferative Cembrane Diterpenes from the Red Sea Sarcophyton Species

Marine Drugs ◽  
2019 ◽  
Vol 17 (7) ◽  
pp. 411 ◽  
Author(s):  
Hossam M. Hassan ◽  
Mostafa E. Rateb ◽  
Marwa H. Hassan ◽  
Ahmed M. Sayed ◽  
Samah Shabana ◽  
...  
Keyword(s):  
Red Sea ◽  
Antiproliferative Activity ◽  
High Resolution Mass Spectrometry ◽  
Cancer Cell Line ◽  
2D Nmr ◽  
Future Design ◽  
Chemical Structures ◽  
New Compounds ◽  
Mcf 7

The combination of liquid chromatography coupled to high resolution mass spectrometry (LC-HRESMS)-based dereplication and antiproliferative activity-guided fractionation was applied on the Red Sea-derived soft coral Sarcophyton sp. This approach facilitated the isolation of five new cembrane-type diterpenoids (1–5), along with two known analogs (6 and 7), as well as the identification of 19 further, known compounds. The chemical structures of the new compounds were elucidated while using comprehensive spectroscopic analyses, including one-dimensional (1D) and two-dimensional (2D) NMR and HRMS. All of the isolated cembranoids (1–7) showed moderate in vitro antiproliferative activity against a human breast cancer cell line (MCF-7), with IC50 ranging from 22.39–27.12 µg/mL. This class of compounds could thus serve as scaffold for the future design of anticancer leads.

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.

scholarly journals Pestalotiones A–D: Four New Secondary Metabolites from the Plant Endophytic Fungus Pestalotiopsis Theae

Molecules ◽  
2020 ◽  
Vol 25 (3) ◽  
pp. 470 ◽  
Author(s):  
Longfang Guo ◽  
Jie Lin ◽  
Shubin Niu ◽  
Shuchun Liu ◽  
Ling Liu
Keyword(s):  
Endophytic Fungus ◽  
Diphenyl Ether ◽  
2D Nmr ◽  
Hela Cell Line ◽  
Dpph Radical ◽  
Xanthone Derivatives ◽  
Ic50 Value ◽  
Ic50 Values ◽  
New Compounds ◽  
Mcf 7

Two new xanthone derivatives, pestalotiones A (1) and B (2), one new diphenyl ketone riboside, pestalotione C (7), and one new diphenyl ether, pestalotione D (8), along with five known compounds isosulochrin dehydrate (3), 3,8-dihydroxy-6-methyl-9-oxo-9H-xanthene-1-carboxylate (4), isosulochrin (5), chloroisosulochrin (6), and pestalotether D (9), were isolated from the crude extract of the plant endophytic fungus Pestalotiopsis theae (N635). The structures of the new compounds were unambiguously deduced by HRESIMS and 1D/2D-NMR spectroscopic data. Compound 6 showed modest cytotoxicity against the HeLa cell line with an IC50 value of 35.2 μM. Compound 9 also showed cytotoxic to the HeLa and MCF-7 cell lines, with IC50 values of 60.8 and 22.6 μM, respectively. Additionally, compounds 1 and 2 exhibited antioxidant activity in scavenging DPPH radical with IC50 values of 54.2 and 59.2 μg/mL, respectively.

scholarly journals Five New Cucurbitane-Type Triterpenoid Glycosides from the Rhizomes of Hemsleya penxianensis with Cytotoxic Activities

Molecules ◽  
2019 ◽  
Vol 24 (16) ◽  
pp. 2937
Author(s):  
De-Li Chen ◽  
Xu-Dong Xu ◽  
Rong-Tao Li ◽  
Bo-Wen Wang ◽  
Meng Yu ◽  
...  
Keyword(s):  
Human Cancer ◽  
Normal Liver ◽  
2D Nmr ◽  
Cytotoxic Activities ◽  
Human Cancer Cell Lines ◽  
Ic50 Value ◽  
Low Cytotoxicity ◽  
Triterpenoid Glycosides ◽  
New Compounds

Five new cucurbitane-typetriterpenoid glycosides, named Xuedanoside F–J (1–5), were obtained from the rhizomes of Hemsleya penxianensis (Xue dan), which belongs to the family of Cucurbitaceae. These new compounds were elucidated byspectroscopic analysis, including 1D, 2D NMR, and HR-ESI-MS spectra. Additionally, all the isolates were evaluated for cytotoxicity against three human cancer cell lines (Hela, MCF-7, and A-549) with the IC50 ranging from 2.25 to 49.44 µM in vitro with treatment 48 h and showed low cytotoxicity in human normal liver L-02 cells (IC50 > 50 µM). Compound 5 showed the most significant cytotoxic activity with the IC50 value of 2.25, 4.72, and 5.33 µM in 48 h, respectively.

scholarly journals In Vitro Cytotoxic Effects of Secondary Metabolites Present in Sarcopoterium Spinosum L.

2021 ◽  
Vol 11 (11) ◽  
pp. 5300
Author(s):  
Jozef Hudec ◽  
Jan Mojzis ◽  
Marta Habanova ◽  
Jorge A. Saraiva ◽  
Pavel Hradil ◽  
...  
Keyword(s):  
Mammary Gland ◽  
Ethyl Acetate ◽  
Cytotoxic Activity ◽  
Cell Lines ◽  
Benzalkonium Chloride ◽  
Ethanol Extract ◽  
Cytotoxic Activities ◽  
Sarcopoterium Spinosum ◽  
Mcf 7

Sarcopoterium spinosum (L.) is a medicinal plant traditionally used for the treatment of various diseases including cancer in the Near- and Middle East. The fractions and constituents of the ethanol extract of S. spinosum were screened for in vitro cytotoxic activities on Jurkat (acute T-lymphoblastic leukemia), HeLa (cervical adenocarcinoma), MCF-7 (mammary gland adenocarcinoma), Caco-2 (human colorectal adenocarcinoma), and MDA-MB-231 (mammary gland adenocarcinoma) cell lines using the MTT (3-(dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide) assay. The ethanol extract was subsequently re-extracted with ethyl acetate and in its sub-fraction obtained by column chromatography three compounds (stachydrine, benzalkonium chloride and rutine) were the first time identified by nuclear magnetic resonance (NMR) analyses. The most active subfraction showed cytotoxic activity against HeLa, MCF-7, and Caco-2 cell lines. The three compounds mentioned, as standards of high-performance liquid chromatography (HPLC) quality, were studied individually and in combination. Cytotoxic activity observed might be due to the presence of benzalkonium chloride and rutin. Benzalkonium chloride showed the strongest growth suppression effect against HeLa cells (IC50 8.10−7 M) and MCF-7 cells (IC50 5.10−6 M). The mixture of stachydrine and benzalkonium chloride allowed a synergistic cytotoxic effect against all tested cancer and normal cells to be obtained. Anti-cancer activity of the plant extract of S. spinosum remains under-investigated, so this research describes how the three major compounds identified in the ethyl acetate extract can exert a significant dose dependent in vitro cytotoxicity.

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 In vitro antioxidant and cytotoxic activities of polyherbal extracts from Vetiveria zizanioides, Trichosanthes cucumerina, and Mollugo cerviana on HeLa and MCF-7 cell lines

2020 ◽  
Vol 27 (6) ◽  
pp. 1475-1481
Author(s):  
Vidya Devanathadesikan Seshadri ◽  
P. Vijayaraghavan ◽  
Y.-O. Kim ◽  
H.-J. Kim ◽  
Abdullah Ahmed Al-Ghamdi ◽  
...  
Keyword(s):  
Cell Lines ◽  
Cytotoxic Activities ◽  
Vetiveria Zizanioides ◽  
Mcf 7
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