Ochroborbone, A New Cytotoxic Indole Alkaloid from Ochrosia borbonica

A new monoterpenoid indole alkaloid, ochroborbone (1), along with five known alkaloids (2–6), were isolated from the stems and leaves of Ochrosia borbonica. Among them, ochroborbone (1) is a rare C17-nor monoterpenoid indole alkaloid, and the known compounds (2-6) were isolated from Ochrosia for the first time. These structures were established on the basis of extensive spectroscopic methods. All isolated compounds were evaluated for their cytotoxicities against five human cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7 and SW480 in vitro. Compounds 1 and 2 exhibited inhibitory effects with IC50 values comparable with those of cisplatin.

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Three New Cytotoxic Monoterpenoid Bisindole Alkaloids from Tabernaemontana bufalina

Planta Medica ◽

10.1055/a-0608-4988 ◽

2018 ◽

Vol 84 (15) ◽

pp. 1127-1133 ◽

Cited By ~ 4

Author(s):

Si-Yuan Zhou ◽

Ting-Lan Zhou ◽

Guofu Qiu ◽

Xiajuan Huan ◽

Ze-Hong Miao ◽

...

Keyword(s):

Human Cancer ◽

Spectroscopic Methods ◽

Human Cancer Cell ◽

Inhibitory Effects ◽

Human Cancer Cell Lines ◽

Human Cancer Cells ◽

Aerial Parts ◽

Ic50 Values ◽

Circular Dichroic ◽

Mcf 7

AbstractThree new bisindole alkaloids, 3′-(2-oxopropyl)-19,20-dihydrotabernamine (1), 3′-(2-oxopropyl)-ervahanine B (2), 19,20-dihydrovobparicine (3), and 20 known compounds were isolated from the aerial parts of Tabernaemontana bufalina. The structures of these alkaloids were elucidated using spectroscopic methods. The absolute configurations of 1–3 were determined by the circular dichroic exciton chirality method. Compounds 1–23 were screened for their cytotoxicity against two human cancer cell lines, A-549 and MCF-7. Ten compounds (1–3, 10, 14, 16, 17, 19, 22, and 23) exhibited inhibitory effects against the two human cancer cells with IC50 values of 1.19 ~ 6.13 µM.

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Discovery of New Pyrazolopyridine, Furopyridine, and Pyridine Derivatives as CDK2 Inhibitors: Design, Synthesis, Docking Studies, and Anti-Proliferative Activity

Molecules ◽

10.3390/molecules26133923 ◽

2021 ◽

Vol 26 (13) ◽

pp. 3923

Author(s):

Adel A.-H. Abdel-Rahman ◽

Amira K. F. Shaban ◽

Ibrahim F. Nassar ◽

Dina S. EL-Kady ◽

Nasser S. M. Ismail ◽

...

Keyword(s):

Cell Lines ◽

Cancer Cell ◽

Human Cancer ◽

Cancer Cell Lines ◽

Human Cancer Cell ◽

Molecular Docking Study ◽

Human Cancer Cell Lines ◽

Hct 116 ◽

Mcf 7

New pyridine, pyrazoloyridine, and furopyridine derivatives substituted with naphthyl and thienyl moieties were designed and synthesized starting from 6-(naphthalen-2-yl)-2-oxo-4-(thiophen-2-yl)-1,2-dihydropyridine-3-carbonitrile (1). The chloro, methoxy, cholroacetoxy, imidazolyl, azide, and arylamino derivatives were prepared to obtain the pyridine-−C2 functionalized derivatives. The derived pyrazolpyridine-N-glycosides were synthesized via heterocyclization of the C2-thioxopyridine derivative followed by glycosylation using glucose and galactose. The furopyridine derivative 14 and the tricyclic pyrido[3′,2′:4,5]furo[3,2-d]pyrimidine 15 were prepared via heterocyclization of the ester derivative followed by a reaction with formamide. The newly synthesized compounds were evaluated for their ability to in vitro inhibit the CDK2 enzyme. In addition, the cytotoxicity of the compounds was tested against four different human cancer cell lines (HCT-116, MCF-7, HepG2, and A549). The CDK2/cyclin A2 enzyme inhibitory results revealed that pyridone 1, 2-chloro-6-(naphthalen-2-yl)-4-(thiophen-2-yl)nicotinonitrile (4), 6-(naphthalen-2-yl)-4-(thiophen-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-amine (8), S-(3-cyano-6-(naphthaen-2-yl)-4-(thiophen-2-yl)pyridin-2-yl) 2-chloroethanethioate (11), and ethyl 3-amino-6-(naphthalen-2-yl)-4-(thiophen-2-yl)furo[2,3-b]pyridine-2-carboxylate (14) are among the most active inhibitors with IC50 values of 0.57, 0.24, 0.65, 0.50, and 0.93 µM, respectively, compared to roscovitine (IC50 0.394 μM). Most compounds showed significant inhibition on different human cancer cell lines (HCT-116, MCF-7, HepG2, and A549) with IC50 ranges of 31.3–49.0, 19.3–55.5, 22.7–44.8, and 36.8–70.7 μM, respectively compared to doxorubicin (IC50 40.0, 64.8, 24.7 and 58.1 µM, respectively). Furthermore, a molecular docking study suggests that most of the target compounds have a similar binding mode as a reference compound in the active site of the CDK2 enzyme. The structural requirements controlling the CDK2 inhibitory activity were determined through the generation of a statistically significant 2D-QSAR model.

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Synthesis, Characterization, and Preliminary In Vitro Cytotoxic Evaluation of a Series of 2-Substituted Benzo [d] [1,3] Azoles

Molecules ◽

10.3390/molecules26092780 ◽

2021 ◽

Vol 26 (9) ◽

pp. 2780

Author(s):

Ozvaldo Linares-Anaya ◽

Alcives Avila-Sorrosa ◽

Francisco Díaz-Cedillo ◽

Luis Ángel Gil-Ruiz ◽

José Correa-Basurto ◽

...

Keyword(s):

Binding Site ◽

In Silico ◽

Cytotoxic Effect ◽

Human Cancer ◽

Cytotoxic Activities ◽

Human Cancer Cell ◽

Inhibitory Effects ◽

Reference Drug ◽

Human Cancer Cell Lines

A series of benzo [d] [1,3] azoles 2-substituted with benzyl- and allyl-sulfanyl groups were synthesized, and their cytotoxic activities were in vitro evaluated against a panel of six human cancer cell lines. The results showed that compounds BTA-1 and BMZ-2 have the best inhibitory effects, compound BMZ-2 being comparable in some cases with the reference drug tamoxifen and exhibiting a low cytotoxic effect against healthy cells. In silico molecular coupling studies at the tamoxifen binding site of ERα and GPER receptors revealed affinity and the possible mode of interaction of both compounds BTA-1 and BMZ-2.

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Cytotoxic constituents of Alocasia macrorrhiza

Zeitschrift für Naturforschung C ◽

10.1515/znc-2015-0157 ◽

2017 ◽

Vol 72 (1-2) ◽

pp. 21-25 ◽

Cited By ~ 4

Author(s):

Marwa Elsbaey ◽

Kadria F.M. Ahmed ◽

Mahmoud F. Elsebai ◽

Ahmed Zaghloul ◽

Mohamed M.A. Amer ◽

...

Keyword(s):

Acetic Acid ◽

Spectroscopic Data ◽

Human Cancer ◽

Indole Alkaloid ◽

Acid Methyl Ester ◽

2D Nmr ◽

Human Cancer Cell ◽

Human Cancer Cell Lines ◽

Acid Methyl ◽

First Time

AbstractAn indole alkaloid, 2-(5-hydroxy-1H-indol-3-yl)-2-oxo-acetic acid (1) isolated for the first time from nature, in addition to the nine known compounds 5-hydroxy-1H-indole-3-carboxylic acid methyl ester (2), alocasin B (3), hyrtiosin B (4), α-monopalmitin (5), 1-O-β-D-glucopyranosyl-(2S, 3R, 4E, 8Z)-2-[(2(R)-hydroctadecanoyl) amido]-4,8-octadecadiene-1,3-diol (6), 3-epi-betulinic acid (7), 3-epi-ursolic acid (8),β-sitosterol (9) andβ-sitosterol 3-O-β-D-glucoside (10) were isolated from the rhizomes ofAlocasia macrorrhiza(Araceae). Their structures were elucidated by 1D and 2D NMR spectroscopic data. Of these compounds,6exhibited the strongest cytotoxicity against the four tested human cancer cell lines (IC50of about 10 µM against Hep-2 larynx cancer cells).

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Arylsulfonamides From the Roots and Rhizomes of Tupistra chinensis Baker

Natural Product Communications ◽

10.1177/1934578x20921665 ◽

2020 ◽

Vol 15 (4) ◽

pp. 1934578X2092166

Author(s):

Yue Xu ◽

Xiaofei Liang ◽

Yuze Li ◽

Zhuofei Liang ◽

Wenli Huang ◽

...

Keyword(s):

Benzoic Acid ◽

Cell Lines ◽

Human Cancer ◽

Acid Methyl Ester ◽

Spectroscopic Methods ◽

Tumor Cell Lines ◽

Human Cancer Cell Lines ◽

Acid Methyl ◽

Amino Benzoic Acid

One new arylsulfonamide (1) and a novel natural product (2) were isolated from the roots and rhizomes of Tupistra chinensis Baker. Their structures were characterized by physicochemical properties and spectroscopic methods, as 2-[2-([1,1′-biphenyl]-4-ylsulfonylamino)-benzoylamino]-benzoic acid methyl ester (1), 2-[([1,1′-biphenyl]-4-ylsulfonyl)amino]-benzoic acid (2), respectively. Additionally, the cytotoxic activity of 1-2 was evaluated on human HCT116, HT29, A549, and H1299 tumor cell lines in vitro, respectively. Whereas, the result showed that these compounds displayed weak cytotoxicity in the human cancer cell lines.

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Four New ent-Kaurane Diterpene Glycosides from Isodon henryi

Molecules ◽

10.3390/molecules24152736 ◽

2019 ◽

Vol 24 (15) ◽

pp. 2736 ◽

Cited By ~ 4

Author(s):

Liu ◽

Zhang ◽

Wu ◽

Chen ◽

Li ◽

...

Keyword(s):

Cell Lines ◽

Human Cancer ◽

Spectroscopic Methods ◽

Human Cancer Cell ◽

Human Cancer Cell Lines ◽

Aerial Parts ◽

Ic50 Values ◽

Hct 116 ◽

Relationship Of ◽

First Time

To obtain diterpene glycosides from an aqueous extract of the aerial parts of Isodon henryi and further investigate their cytotoxicities, in this study, a total of seven compounds were isolated, including six ent-kaurane diterpene glycosides (1–6) and one diterpene aglycon (7). Among the seven ent-kaurane diterpenes obtained, four were novel compounds, including ent-7,20-epoxy- kaur-16-en-1α,6β,7β,15β-tetrahydroxyl-11-O-β-d-glucopyranoside (1), ent-7,20-epoxy-kaur-16-en- 6β,7β,14β,15β-tetrahydroxyl-1-O-β-d-glucopyranoside (2), ent-7,20-epoxy-kaur-16-en-6β,7β,15β- trihydroxyl-1-O-β-d-glucopyranoside (3), and ent-7,20-epoxy-kaur-16-en-7β,11β,14α,15β-tetrahydr- oxyl-6-O-β-d-glucopyranoside (4), and three were isolated from this plant for the first time (5–7). Their structures were elucidated by utilizing spectroscopic methods and electronic circular dichroism analyses. Furthermore, the cytotoxicities of all seven compounds were investigated in four human cancer cell lines, including A2780, BGC-823, HCT-116, and HepG2. The IC50 values of these diterpenes ranged from 0.18 to 2.44 mM in the tested cell lines. In addition, the structure–cytotoxicity relationship of diterpene glycosides was also evaluated to study the effect of glycosylation on the cytotoxicity of diterpene compounds.

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Bioactive Components of Fissistigma cupreonitens

Natural Product Communications ◽

10.1177/1934578x1801300607 ◽

2018 ◽

Vol 13 (6) ◽

pp. 1934578X1801300 ◽

Cited By ~ 1

Author(s):

I-Hsiao Chen ◽

Ming-Yi Yang ◽

Shin-Hun Juang ◽

Chia-Lin Lee ◽

Tran-Dinh Thang ◽

...

Keyword(s):

Cell Line ◽

Human Cancer ◽

Spectroscopic Methods ◽

Human Cancer Cell ◽

Bioactive Components ◽

Standard Drug ◽

Human Cancer Cell Lines ◽

Chemical Structures ◽

Phytochemical Investigation ◽

First Time

Phytochemical investigation of Fissistigma cupreonitens (Annonaceae) led to the isolation of 34 compounds. The chemical structures of all compounds were determined by spectroscopic methods. Among the isolates, compounds 20–27 and 31–34 were reported from this genus for the first time. From the results of the cytotoxicity assay against three human cancer cell lines (NCI-H226, NPC-TW01, and Jurkat E6–1), oxoaporphine compounds oxoxylopine (1), oxocrebanine (3), kuafumine (4) and lysicamine (5), and the flavonoid adunctin E (26) displayed significant cytotoxicity against NCI-H226 cell line, with IC50 values of 8.45, 8.10, 8.54, 12.83 and 12.00 μM, respectively, in comparison with the standard drug, cisplatin with IC50 of 13.37 μM.

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CYTOTOXIC ACTIVITY OF LUVUNGA SCANDENS AGAINST HUMAN CANCER CELL LINES

Jurnal Teknologi ◽

10.11113/jt.v78.7328 ◽

2016 ◽

Vol 78 (10) ◽

Author(s):

Putri Nur Hidayah Al-Zikri ◽

Muhammad Taher ◽

Deny Susanti ◽

Solachuddin Jauhari Arief Ichwan

Keyword(s):

Cytotoxic Activity ◽

Cell Line ◽

Cell Lines ◽

A549 Cell ◽

Human Cancer ◽

In Vitro Cytotoxicity ◽

Breast Adenocarcinoma ◽

Human Cancer Cell Lines ◽

Mcf 7

Luvunga scandens belongs to the family of Rutaceae which usually inhabit tropical and moist environment. This plant is known as ‘Mengkurat Jakun’ among locals and used traditionally to treat fever and fatigue via decoction. The aim of this study was to investigate the cytotoxic activity of the leaves and stems extracts of L. scandens extract. Extracts of the leaves and stems were obtained from sequential extraction procedures by various organic solvents. All extracts were subjected to cytotoxic study by 3-(4, 5-dimethylthaizol-2-yl)-2, 5-diphenyltetrazolium bromide (MTT) assay. In in vitro cytotoxicity assay, all L. scandens extracts exhibited cytotoxicity against human breast adenocarcinoma (MCF-7) and human lung adenocarcinoma (A549) cell lines. The IC50 values of dichloromethane and methanol extracts from the leaves of L. scandens against MCF-7 cell line were 62.5 µg/mL and 88.0 µg/mL, respectively, whereas IC50 of methanol extract from stem was 81.0 µg/mL. All extracts were less active against A549 cell line where IC50 value were not be determined. The present findings revealed the potential of L. scandens as a cytotoxic agent against MCF-7 cell line. However, further studies should be planned to evaluate role of the plant in cytotoxic activity.

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Chemical characterization and bioactive properties of Geranium molle L.: from the plant to the most active extract and its phytochemicals

Food & Function ◽

10.1039/c5fo01479d ◽

2016 ◽

Vol 7 (5) ◽

pp. 2204-2212 ◽

Cited By ~ 10

Author(s):

V. C. Graça ◽

Lillian Barros ◽

Ricardo C. Calhelha ◽

Maria Inês Dias ◽

Ana Maria Carvalho ◽

...

Keyword(s):

Antioxidant Activity ◽

Cell Lines ◽

Human Cancer ◽

Chemical Characterization ◽

Human Cancer Cell ◽

Human Cancer Cell Lines ◽

Bioactive Properties ◽

First Time ◽

Geranium Molle

The phytochemical characterization, antioxidant activity and in vitro cytotoxicity against human cancer cell lines of Geranium molle L. extracts are reported for the first time.

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