Iridoid Glycosides from Lagotis alutacea

One new iridoid glycoside, lagotisoside F (1), was isolated from Lagotis alutacea, along with three known analogs, lagotisoside D (2), 6-O-α-L-(4″-O-(E)-cinnamoyl) rhamnopyranosyl-catapol (3) and globularin (4). Their structures were elucidated by extensive spectroscopic analysis and by comparison with data reported in the literature. Compounds 1-4were evaluated for cytotoxic activity against HL-60, MCF-7, A549, SW480, and SMMC-7721 cells and exhibited no appreciable activity with IC50 values above 40 μM.

Download Full-text

Nine Unique Iridoids and Iridoid Glycosides From Patrinia scabiosaefolia

Frontiers in Chemistry ◽

10.3389/fchem.2021.657028 ◽

2021 ◽

Vol 9 ◽

Author(s):

Zhenhua Liu ◽

Yun Niu ◽

Li Zhou ◽

Lijun Meng ◽

Sitan Chen ◽

...

Keyword(s):

Spectroscopic Analysis ◽

Chemical Constituents ◽

Iridoid Glycosides ◽

Chinese Herb ◽

2D Nmr ◽

Iridoid Glycoside ◽

Cytotoxic Activities ◽

Medicinal Value ◽

Patrinia Scabiosaefolia ◽

Mcf 7

Patrinia scabiosaefolia is a medical and edible Chinese herb with high nutritional and medicinal value. The continuing study of its chemical constituents led to the discovery of nine unique iridoids and iridoid glycosides, including three new iridoids (1-3) and six previously unknown irioid glycosides (5-10), and one known compound (4). Among them, compound 1 was a deformed iridoid, while compounds 3, 5-7, and 10 formed a new ring in their skeletons which was uncommon in this genus. For compound 3, the new ring existed between C-3 and C-10, while a 1,3-dioxane appeared between C-7 and C-10 in compounds 5-7 and 10. Moreover, compound 10 was a bis-iridoid glycoside, which was the first reported in P. scabiosaefolia. And the sugar of irioid glycosides (5-10) was glucose at C-11, except in 9 which had a 5-deoxyglucose moiety. All their structures were confirmed based on the extensive spectroscopic analysis, including IR, UV, HR-ESI-MS, ECD, and 1D- and 2D-NMR experiments. Their cytotoxic activities against HL-60, A-549, SMMC-7721, MCF-7, SW480 were also tested.

Download Full-text

Cytotoxic activity and anti-cancer potential of Ontario grown onion extracts against breast cancer cell lines

Functional Foods in Health and Disease ◽

10.31989/ffhd.v8i3.408 ◽

2018 ◽

Vol 8 (3) ◽

pp. 159 ◽

Cited By ~ 1

Author(s):

Meghan Fragis ◽

Abdulmonem I. Murayyan ◽

Suresh Neethirajan

Keyword(s):

Breast Cancer ◽

Cytotoxic Activity ◽

Cell Lines ◽

Cancer Cell ◽

Breast Cancer Cell ◽

Cancer Cell Lines ◽

Breast Cancer Cell Lines ◽

Cytotoxic Activities ◽

Cancer Line ◽

Mcf 7

Background: Breast cancer is the most commonly diagnosed cancer and the second leading cause of cancer deaths among Canadian women. Cancer management through changes in lifestyle, such as increased intake of foods rich in dietary flavonoids, have been shown to decrease the risk associated with breast, liver, colorectal, and upper-digestive cancers in epidemiologic studies. Onions are high in flavonoid content and one of the most common vegetables. Additionally, onions are used in most Canadian cuisines.Methods: We investigated the effect of five prominent Ontario grown onion (Stanley, Ruby Ring, LaSalle, Fortress, and Safrane) extracts on two subtypes of breast cancer cell lines: a triple negative breast cancer line MDA-MB-231 and an ER+ breast cancer line MCF-7.Results: These onion extracts elicited strong anti-proliferative, anti-migratory, and cytotoxic activities on both the cancer cell lines. Flavonoids present in these onion extracts induced apoptosis, cell cycle arrest in the G2/M phase, and a reduction in mitochondrial membrane potential at dose-dependent concentrations. Onion extracts were more effective against MDA-MB-231 compared to the MCF-7 cell line. Conclusion: In this study, we investigated the extracts synthesized from Ontario-grown onion varieties in inducing anti-migratory, cytostatic, and cytotoxic activities in two sub-types of human breast cancer cell lines. Anti-tumor activity of these extracts depends upon the varietal and can be formulated into nutraceuticals and functional foods for the wellbeing of cancer patients. Overall, the results suggest that onion extracts are a good source of flavonoids with anti-cancerous properties.Keywords: onion extracts; flavonoids; anti-proliferative; breast cancer; cytotoxic activity

Download Full-text

Cytotoxic Constituents from the Bark of Erythrina poeppigiana Against the MCF-7 Breast Cancer Cell Lines

The Natural Products Journal ◽

10.2174/2210315509666191115152811 ◽

2020 ◽

Vol 10 (3) ◽

pp. 257-261

Author(s):

Tati Herlina ◽

Merlin ◽

Mohd. Azlan ◽

Unang Supratman

Keyword(s):

Breast Cancer ◽

Cytotoxic Activity ◽

Chemical Structure ◽

Breast Cancer Cell Lines ◽

Erythrina Poeppigiana ◽

Structure Activity ◽

Cancer Line ◽

Cytotoxic Compounds ◽

Ic50 Values ◽

Mcf 7

Background: Erythrina poeppigiana (Leguminosae) is a high-growing plant with an orange flower that is widely distributed in tropical and subtropical countries. This particular plant is widely used in traditional medicine for gynecological complications and the treatment of various diseases. There exists no previous information regarding cytotoxic compounds from this plant. Objective: This research is to isolate cytotoxic compounds from E. poeppigiana. Methods: The isolation step was carried out using a combination of chromatographic techniques to obtain isolated three compounds (1, 2, and 3). Results: The chemical structure of isolated compounds was elucidated by spectroscopic methods and identified as β-erythroidine (1), 8-oxo-β-erythroidine (2), and 8-oxo-α-erythroidine (3). Compounds (1-3) showed cytotoxic activity against MCF-7 breast cancer line with IC50 values of 36.8, 60.8 and 875.4 μM, respectively. Conclusion: Three compounds have been successfully isolated from Erythrina poeppigiana (Leguminosae), showing cytotoxic properties against MCF-7 breast cancer line. Structure-activity relationship studies showed that the presence of enone moiety on compound 1 can reduce its cytotoxic activity towards MCF-7 breast cancer line.

Download Full-text

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

Applied Sciences ◽

10.3390/app11115300 ◽

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.

Download Full-text

Chemical Constituents of the Marine Sponge Aaptos aaptos (Schmidt, 1864) and Their Cytotoxic Activity

Natural Product Communications ◽

10.1177/1934578x21993345 ◽

2021 ◽

Vol 16 (2) ◽

pp. 1934578X2199334

Author(s):

Do Thi Trang ◽

Bui Huu Tai ◽

Dan Thuy Hang ◽

Pham Hai Yen ◽

Phan Thi Thanh Huong ◽

...

Keyword(s):

Cytotoxic Activity ◽

Spectral Data ◽

Absolute Configuration ◽

Marine Sponge ◽

Chemical Constituents ◽

2D Nmr ◽

Extensive Analysis ◽

First Time ◽

Tddft Method ◽

Mcf 7

Seven compounds (1-7) were isolated from the marine sponge Aaptos aaptos living in the Vietnamese sea. Their structures were determined as 2 hours, 5 H,7 H,9 H-9 S-hydroxy-imidazo[1,5- α]pyridine-1,3-dione (1), 3-([9-methylhexadecyl]oxy)propane-1,2-diol 2, 2,3-dihydro-2,3-dioxoaaptamine (3), indol-3-aldehyde (4), methyl indole-3-carboxylate (5) 4-hydroxy-5-(indole-3-yl)−5-oxo-pentan-2-one (6), and thymidine (7) by extensive analysis of HR-ESI-MS, 1D, and 2D NMR spectral data, as well as by comparison of the spectral data with those reported in the literature. In addition, the absolute configuration of 1 was determined from the experimental ECD spectrum and comparison of this with the theoretical ECD calculations using the TDDFT method. Compounds 1 and 2 were isolated from nature for the first time. Compound 3 induced cytotoxic activity against SK-LU-1, MCF-7, HepG2, and SK-Mel-2 cell lines with IC50 values of 41.27 ± 2.63, 40.70 ± 2.65, 34.31 ± 3.43, and 36.63 ± 1.40 µM, respectively.

Download Full-text

In Vitro Antitumor Activity of Endophytic Fungi Isolated From the Mexican Cactus Pachycereus Marginatus (DC.) Britton & Ros

10.21203/rs.3.rs-426788/v1 ◽

2021 ◽

Author(s):

Jesica M. Ramírez-Villalobos ◽

César I. Romo-Sáenz ◽

Karla S. Morán Santibañez ◽

Patricia Tamez-Guerra ◽

Ramiro Quintanilla-Licea ◽

...

Keyword(s):

Cytotoxic Activity ◽

Endophytic Fungi ◽

Human Tumor ◽

Tumor Cell Lines ◽

Human Tumor Cell ◽

Normal Cells ◽

Human Tumor Cell Lines ◽

Ht 29 ◽

Mcf 7

Abstract Background: Arid zone plants such as cacti are known to harbor diverse groups of endophytic fungi, which represent potential sources of new compounds with anticancer properties. In the present study we isolated, identified, and characterized Pachycereus marginatus (DC.) Britton & Ros endophytic fungi with cytotoxic activity against murine and human tumor cell lines.Methods: Endophytic fungi were isolated from P. marginatus stems. Methanol extracts were then obtained from fungi liquid cultures and their cytotoxic activity at concentrations ranging from 31 µg/ml to 250 µg/ml against murine L5178Y-R lymphoma, human colorectal adenocarcinoma HT-29, and human breast cancer MCF-7 was evaluated by the colorimetric 3-(4, 5-dimethylthiazol-2-yl)-2, 5-diphenyltetrazolium bromide reduction assay, using the normal cells Macacus rhesus monkey epitelial kidney MA-104 and human peripheral blood mononuclear cells (PBMC) as controls. IC50 values were obtained and the selectivity index (SI) was calculated from the IC50 ratio of cancer cells and normal cells. Furthermore, molecular identification of fungi showing cytotoxic activity was determined by the internal transcribed spacer molecular marker.Results: The Cladosporium sp. PME-H008 strain showed significant (P < 0.01) 94.3% and 36.8% cytotoxicity against L5178Y-R and HT-29 cells, respectively. The highest SI was observed by L5178Y-R cells with 2.4 and 2.9 for MA-104 and PBMC respectively. In addition, the Metarhizium anisopliae PME-H007 strain was more effective against MCF-7 with 55.8% cytotoxicity. The lowest IC50 was obtained with the Aspergillus sp. PME-H005 strain at 95.21 µg/ml against the MCF-7 cell line, followed by PME-H008 strain at 101 µg/ml against L5178Y-R cells.Conclusion: P. marginatus endophytic fungi showed in vitro cytotoxic activity against murine and human tumor cell lines, without affecting normal cells.

Download Full-text

Synthesis and Biological Screening of New Thiadiazolopyrimidine-based Polycyclic Compounds

10.21203/rs.3.rs-606990/v1 ◽

2021 ◽

Author(s):

Alaa M. Alqahtani

Keyword(s):

Cytotoxic Activity ◽

Fibroblast Cell ◽

Docking Studies ◽

Normal Fibroblast ◽

Polycyclic Compounds ◽

Gram Positive Bacteria ◽

Standard Normal ◽

Structural Activity Relationship ◽

Cyclic Compounds ◽

Mcf 7

Abstract New tri- and tetra-cyclic compounds based on the thiadiazolopyrimidine ring system were prepared and their antimicrobial activity were estimated. The achieved results evidenced that pyrano-thiadiazolopyrimidine compounds 8a-b and 9a-b have substantial efficiencies toward the two strains of Gram-positive bacteria (S. aureus and B. cereus). While tetracyclic derivatives pyrazolopyrimido-thiadiazolopyrimidine derivatives 16a-b and 17a-b displayed prominent efficiencies toward the two strains of Gram-negative bacteria (E. coli and P. aeruginosa). In addition, compounds 8a-b and 9a-b presented good efficacy toward C. albicans. The activity of antiquorum-sensing (anti-QS) inhibition of the new synthesized thiadiazolopyrimidine-based compounds was tested toward C. violaceum, where derivatives 16a-b, 17a-b, 8b and 9a displayed satisfactory activity. Cytotoxic activity of the same derivatives was screened toward various cancer cell lines (MCF-7, PC3, Hep-2 and HepG2) and standard normal fibroblast cell (WI38) by utilizing the MTT assay. The pyrazolopyrimido-thiadiazolopyrimidine derivatives 16a, 16b, 17a and 17b recorded potent cytotoxic efficacy against MCF-7 cells with IC50 values ranging from 5.69 to 9.36 µM. Also, the endorsed structural activity relationship (SAR) for the inspected thiadiazolopyrimidine derivatives provided an awareness concerning the chemical structure connected to anticancer efficiency. In silico docking studies were implemented toward silence hormone signaling in breast (PDB Code-5NQR). The results are consistent and supportive to the cytotoxic activity.

Download Full-text

Synthesis and evaluation of new benzimidazole derivatives with hydrazone moiety as anticancer agents

Turkish Journal of Biochemistry ◽

10.1515/tjb-2017-0167 ◽

2018 ◽

Vol 43 (2) ◽

pp. 151-158 ◽

Cited By ~ 3

Author(s):

Ulviye Acar Çevik ◽

Begüm Nurpelin Sağlık ◽

Cankız Mina Ardıç ◽

Yusuf Özkay ◽

Özlem Atlı

Keyword(s):

Cytotoxic Activity ◽

Anticancer Agents ◽

Point Of View ◽

Current Therapy ◽

Benzimidazole Derivatives ◽

Anticancer Activities ◽

New Chemical Entities ◽

Nih 3T3 ◽

Mcf 7

Abstract Objectives: Cancer is one of the leading causes of death throughout the world. Current therapy options suffer from the major limitations of side effects and drug resistance. Thus, continuing search for newer and safer anticancer drugs remains critically important. From this point of view, in the present study benzimidazole-hydrazone derivatives were synthesized by aiming at the identification of new chemical entities as potent anticancer agents. Material and methods: A series of 12 new compounds of 4-(5(6)-substituted-1H-benzimidazol-2-yl)-N′thiophen/furan-2-yl-methylene) benzohydrazide derivatives were synthesized. The structures of the obtained compounds were elucidated using by IR, 1H NMR, 13C NMR, mass spectroscopy and elemental analyses. In vitro cytotoxic activity of the compounds against A549, MCF-7 and NIH/3T3 cell lines was evaluated by MTT assay. Results: Among the tested compounds, compound 3e showed higher cytotoxicity against MCF-7 human breast cancer cells when compared with cisplatin. Also, it has lower cytotoxicty against healthy cell line, NIH/3T3. Conclusions: It was determined that compound 3e showed inhibition towards MCF-7. Considering the substituent effect on cytotoxic activity, compound 3e bearing 2-methylthiophene has attracted attention with its higher anticancer activities.

Download Full-text

Caffeic Acid Versus Caffeic Acid Phenethyl Ester in the Treatment of Breast Cancer MCF-7 Cells: Migration Rate Inhibition

Integrative Cancer Therapies ◽

10.1177/1534735418801521 ◽

2018 ◽

Vol 17 (4) ◽

pp. 1247-1259 ◽

Cited By ~ 14

Author(s):

Agata Kabała-Dzik ◽

Anna Rzepecka-Stojko ◽

Robert Kubina ◽

Robert Dariusz Wojtyczka ◽

Ewa Buszman ◽

...

Keyword(s):

Breast Cancer ◽

Cell Migration ◽

Cytotoxic Activity ◽

Caffeic Acid ◽

Migration Rate ◽

Wound Closure ◽

Migration Inhibition ◽

Srb Assay ◽

Microscopic Evaluation ◽

Mcf 7

Epithelium mammary carcinoma is a cancer with a high death rate among women. One factor having a significant impact on metastasis is cell migration. The aim of this study was to compare migration rate inhibition of caffeic acid (CA) and its phenethyl ester (CAPE) on MCF-7 breast cancer cells. Microscopic evaluation was used to determine the morphology of carcinoma cells, before and after 24-hour treatment with CA and CAPE using a dose of 50 µM. The cytotoxic effect was measured by XTT-NR-SRB assay (tetrazolium hydroxide-neutral red-Sulforhodamine B) for 24-hour and 48-hour periods, using CA and CAPE, with doses of 50 and 100 µM. These doses were used to determine cell migration inhibition using a wound closure assay for 0-hour, 8-hour, 16-hour, and 24-hour periods. Both CA and CAPE treatments displayed cytotoxic activity in a dose- and time-dependent trend. CAPE displayed IC50 values more than twice as low as CA. IC50 values for the XTT assay were as follows: CA was 102.98 µM for 24 hours and 59.12 µM for 48 hours, while CAPE was 56.39 µM for 24 hours and 28.10 µM for 48 hours. For the NR assay: CA was 84.87 µM at 24 hours and 65.05 µM at 48 hours, while CAPE was 69.05 µM at 24 hours and 29.05 µM at 48 hours. For the SRB assay: At 24 hours, CA was 83.47 µM and 53.46 µM at 48 hours, while CAPE was 38.53 µM at 24 hours and 20.15 µM at 48 hours. Both polyphenols induced migration inhibition, resulting in practically halting the wound closure. CAPE produced better results than CA with the same doses and experiment times, though both CA and CAPE displayed cytotoxic activity against MCF-7 cells, as well as inhibited migration.

Download Full-text