Labdane and Abietane Diterpenoids from Juniperus oblonga and Their Cytotoxic Activity

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.

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Bioactivities of essential oils from different parts of Spiranthera odoratissima (Rutaceae)

Rodriguésia ◽

10.1590/2175-7860202071050 ◽

2020 ◽

Vol 71 ◽

Author(s):

Fernando Duarte Cabral ◽

Cassia Cristina Fernandes ◽

Arthur Barcelos Ribeiro ◽

Iara Squarisi Squarisi ◽

Denise Crispim Tavares ◽

...

Keyword(s):

Tumor Cell ◽

Cell Lines ◽

Normal Cell ◽

Human Tumor ◽

Tumor Cell Lines ◽

Human Tumor Cell ◽

Human Tumor Cell Lines ◽

Ic50 Values ◽

Mcf 7

Abstract This paper aims to investigate, for the first time, in vitro antitubercular, antileishmanial and antiproliferative activities of essential oils (EOs) from S. odoratissima leaves and flowers - grown in midwestern Brazil - against Mycobacterium tuberculosis, promastigote forms of Leishmania amazonensis and human tumor cell lines. Antimycobacterial activity of EOs was evaluated in terms of the minimal inhibitory concentration (MIC). EOs from leaves and flowers showed to be active antimicrobials against M. tuberculosis, since MIC values were 150 µg/mL and 162.5 µg/mL, respectively. Both EOs exhibited significant activity against promastigote forms of L. amazonensis; IC50 values (50% growth inhibition) were 14.36 ± 2.02 (EOs from leaves) and 19.89 ± 2.66 µg/mL (EOs from flowers). Antiproliferative activity in normal (GM07492A, lung fibroblasts) and tumor (MCF-7, HeLa and M059J) cell lines was performed by the XTT assay; results were expressed as IC50 (50% cell growth inhibition) and the selective index was calculated. IC50 values of EOs from leaves and flowers obtained in normal cell lines for were 502.97 ± 40.33 µg/mL and 370.60 ± 2.01 µg/mL, respectively. Antiproliferative activity was observed against human tumor cell lines, whose IC50 values were significantly lower than those obtained in normal cell lines of MCF-7 cells (367.57 ± 4.46 µg/mL-EOs from leaves and 357.70 ± 1.85 µg/mL-EOs from flowers) and M059J cells (492.53 ± 56.67 µg/mL-EOs from leaves and 324.90 ± 6.72 µg/mL-EOs from flowers), thus, indicating selectivity. These in vitro results showed that EOs from S. odoratissima may be an antimycobacterial, antiparasitic and antitumor agent.

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Antiproliferative Phenanthrenes from Juncus tenuis: Isolation and Diversity-Oriented Semisynthetic Modification

Molecules ◽

10.3390/molecules25245983 ◽

2020 ◽

Vol 25 (24) ◽

pp. 5983

Author(s):

Csaba Bús ◽

Norbert Kúsz ◽

Annamária Kincses ◽

Nikoletta Szemerédi ◽

Gabriella Spengler ◽

...

Keyword(s):

Cell Lines ◽

Human Tumor ◽

2D Nmr ◽

Hypervalent Iodine ◽

Isolation And Purification ◽

Wide Range ◽

Ic50 Values ◽

Plant Families ◽

Derivatives Of ◽

Mcf 7

The occurrence of phenanthrenes is limited in nature, with such compounds identified only in some plant families. Phenanthrenes were described to have a wide range of pharmacological activities, and numerous research programs have targeted semisynthetic derivatives of the phenanthrene skeleton. The aims of this study were the phytochemical investigation of Juncus tenuis, focusing on the isolation of phenanthrenes, and the preparation of semisynthetic derivatives of the isolated compounds. From the methanolic extract of J. tenuis, three phenanthrenes (juncusol, effusol, and 2,7-dihydroxy-1,8-dimethyl-5-vinyl-9,10-dihydrophenanthrene) were isolated. Juncusol and effusol were transformed by hypervalent iodine(III) reagent, using a diversity-oriented approach. Four racemic semisynthetic compounds possessing an alkyl-substituted p-quinol ring (1–4) were produced. Isolation and purification of the compounds were carried out by different chromatographic techniques, and their structures were elucidated by means of 1D and 2D NMR, and HRMS spectroscopic methods. The isolated secondary metabolites and their semisynthetic analogues were tested on seven human tumor cell lines (A2780, A2780cis, KCR, MCF-7, HeLa, HTB-26, and T47D) and on one normal cell line (MRC-5), using the MTT assay. The effusol derivative 3, substituted with two methoxy groups, showed promising antiproliferative activity on MCF-7, T47D, and A2780 cell lines with IC50 values of 5.8, 7.0, and 8.6 µM, respectively.

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New Cytotoxic Cycloartane Triterpenes from the Aerial Parts of Actaea heracleifolia (syn. Cimicifuga heracleifolia)

Planta Medica ◽

10.1055/a-0733-7229 ◽

2018 ◽

Vol 85 (02) ◽

pp. 154-159

Author(s):

Qiang-Qiang Shi ◽

Wei-Hua Wang ◽

Jing Lu ◽

Da-Shan Li ◽

Lin Zhou ◽

...

Keyword(s):

Cell Lines ◽

Human Tumor ◽

Human Tumor Cell ◽

Human Tumor Cell Lines ◽

Chemical Structures ◽

Aerial Parts ◽

Ic50 Values ◽

Weak Activity ◽

Mcf 7

AbstractOne new 15,16-seco-cycloartane triterpene (1), three new cycloartane triterpene glycosides (2–4), and five known compounds (5–9) were isolated from the aerial parts of Actaea heracleifolia. The chemical structures of these compounds were determined on the basis of NMR analysis, HRTOF-ESIMS data, and other spectroscopic methods. Selected compounds were evaluated for their cytotoxicity against human tumor cell lines (HL-60, SMMC-7721, A549, MCF-7, and SW480) in vitro. Compounds 3 and 4 showed weak activity against the HL-60, A-549, and MCF-7 cell lines with IC50 values ranging from 21.34 to 36.98 µM.

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Phytochemical Constituents of Annona reticulata and their Cytotoxic Activity

Letters in Organic Chemistry ◽

10.2174/1570178616666190724123004 ◽

2020 ◽

Vol 17 (3) ◽

pp. 206-210

Author(s):

Ty Viet Pham ◽

Thang Quoc Le ◽

Anh Tuan Le ◽

Hung Quoc Vo ◽

Duc Viet Ho

Keyword(s):

Cytotoxic Activity ◽

Cell Lines ◽

Structural Determination ◽

Phytochemical Investigation ◽

Ic50 Values ◽

Phytochemical Constituents ◽

First Time ◽

Annona Reticulata

A phytochemical investigation of the leaves of Annona reticulata led to the isolation and structural determination of β-sitosterol (1), ent-pimara-8(14),15-dien-19-oic acid (2), ent-pimara- 8(14),15-dien-19-ol (3), quercetin (4), quercetin 3-O-α-L-arabinopyranoside (5), and a mixture of quercetin 3-O-β-D-galactopyranoside (6a) and quercetin 3-O-β-D-glucopyranoside (6b). Of these, compounds 2 and 3 were isolated from the genus Annona for the first time. Compound 3 showed strong cytotoxicity against SK-LU-1 and SW626 cell lines with IC50 values of 17.64 ± 1.07 and 19.79 ± 1.41 μg mL-1, respectively.

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Diorganotin(iv) benzyldithiocarbamate complexes: synthesis, characterization, and thermal and cytotoxicity study

Open Chemistry ◽

10.1515/chem-2020-0037 ◽

2020 ◽

Vol 18 (1) ◽

pp. 453-462

Author(s):

Jerry O. Adeyemi ◽

Damian C. Onwudiwe ◽

Nirasha Nundkumar ◽

Moganavelli Singh

Keyword(s):

Cell Lines ◽

Human Tumor ◽

Complexation Reaction ◽

Spectroscopic Techniques ◽

X Ray Diffraction ◽

Human Tumor Cell Lines ◽

H Nmr ◽

Cytotoxicity Studies ◽

Final Residue ◽

Mcf 7

AbstractAmmonium benzyldithiocarbamate, represented as NH4L, was prepared and used in the complexation reaction involving three organotin(iv) salts, represented as R2SnCl2 (R = CH3, C4H9, and C6H5). The structures of the synthesized complexes [(CH3)2SnL2] (1), [(C4H9)2SnL2] (2), and [(C6H5)2SnL2] (3) were established using various spectroscopic techniques (Fourier transform infrared spectroscopy, 1H NMR, 13C NMR, and 119Sn NMR) and elemental analysis. Thermal decomposition of the complexes using thermogravimetric analysis under nitrogen showed no definite pathway in the pattern of the complexes even though they are structurally related. X-ray diffraction studies of the final residue showed a common diffraction pattern for the complexes and confirmed SnS as the product of the thermal treatment. Cytotoxicity studies of these complexes against the human tumor cell lines (HeLa and MCF-7) compared favorably with the used standard 5-fluorouracil drug, with complexes 2 and 3 showing very good activity toward the used cell lines.

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Design, Synthesis, and Structural Characterization of Novel Diazaphenothiazines with 1,2,3-Triazole Substituents as Promising Antiproliferative Agents

Molecules ◽

10.3390/molecules24234388 ◽

2019 ◽

Vol 24 (23) ◽

pp. 4388 ◽

Cited By ~ 3

Author(s):

Morak-Młodawska ◽

Pluta ◽

Latocha ◽

Jeleń ◽

Kuśmierz

Keyword(s):

Anticancer Activity ◽

Cell Lines ◽

Human Fibroblasts ◽

Human Tumor ◽

Design Synthesis ◽

Human Tumor Cell Lines ◽

Ic50 Values ◽

Normal Human ◽

Low Cytotoxicity

A series of novel 1,2,3-triazole-diazphenothiazine hybrids was designed, synthesized, and evaluated for anticancer activity against four selected human tumor cell lines (SNB-19, Caco-2, A549, and MDA-MB231). The majority of the synthesized compounds exhibited significant potent activity against the investigated cell lines. Among them, compounds 1d and 4c showed excellent broad spectrum anticancer activity, with IC50 values ranging from 0.25 to 4.66 μM and 0.25 to 6.25 μM, respectively. The most promising compound 1d, possessing low cytotoxicity against normal human fibroblasts NHFF, was used for gene expression analysis using reverse transcription–quantitative real-time PCR (RT–qPCR). The expression of H3, TP53, CDKN1A, BCL-2, and BAX genes revealed that these compounds inhibited the proliferation in all cells (H3) and activated mitochondrial events of apoptosis (BAX/BCL-2).

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A Novel Sesquiterpene Polyol Ester from the Celastrus Rosthornianus with Anti-tumor Activities

Natural Product Communications ◽

10.1177/1934578x0600100704 ◽

2006 ◽

Vol 1 (7) ◽

pp. 1934578X0600100 ◽

Cited By ~ 1

Author(s):

Kuiwu Wang ◽

Yuanjiang Pan

Keyword(s):

Tumor Cell ◽

Cell Lines ◽

Human Tumor ◽

2D Nmr ◽

Spectroscopic Techniques ◽

Tumor Cell Lines ◽

Human Tumor Cell ◽

Polyol Ester ◽

Human Tumor Cell Lines ◽

Polyol Esters

A new (1) and a known (2) β-dihydroagarofuran sesquiterpene polyol esters were isolated from Celastrus rosthornianus and their structures were established by 1D- and 2D-NMR spectroscopic techniques. The two compounds exhibited anti-tumor activities against a panel of human tumor cell lines.

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Synthesis, Characterization and Antitumor Activity of 4-Ferrocenylpyridine-3, 5-Dicarbonitrile Derivatives and Sodium Polymeric Complexes Containing Carbanionic Ligands

MRS Proceedings ◽

10.1557/opl.2015.407 ◽

2015 ◽

Vol 1766 ◽

pp. 9-17

Author(s):

E. Klimova ◽

J. Sánchez ◽

M. Flores ◽

S. Cortez ◽

T. Ramírez ◽

...

Keyword(s):

Antitumor Activity ◽

Cell Lines ◽

Human Tumor ◽

X Ray Diffraction ◽

Human Tumor Cell ◽

Human Tumor Cell Lines ◽

Biological Specificity ◽

Polymeric Complexes ◽

Mcf 7

ABSTRACTThe reactions of 2-cyano-3-ferrocenylacrylonitrile with malononitrile in a ROH/H2O medium in the presence of Na2CO3 afforded 6-alkoxy-2-amino-4-ferrocenylpyridine-3,5-dicarbonitriles, 6-alkoxy-2-amino-4-ferrocenyl-3-ferrocenyl-methyl-3,4-dihydropyridine-3,5-dicarbonitriles and Na+ polymeric complexes: {[Na+(2-ferrocenyl(tetracyano)propenyl)−L]∞ and [Na+(2-amino-3,5-dicyano-4-ferrocenyl-6-pyridyl-dicyanomethyl)−L]∞ where L = ethanol, methanol. Complexes with L = acetonitrile (c), dimethylformamide (d), acetone (e), ethyl acetate (f) were prepared by recrystallization. The structures of the compounds 4b and Na+ polymeric complexes 5c and 6d, e were established by the spectroscopic data and X-ray diffraction analysis. Two compounds 3a and 4a were tested in vitro against six human tumor cell lines U-251, PC-3, K-562, HCT-15, MCF-7 and SKLU-1 to assess their in vitro antitumor activity. The results suggest biological specificity towards PC-3, K-562 and HCT-15 cells for compound 3a, and towards PC-3 cell for compound 4a at doses 50 μM, which are lower than Cisplatin IC50′s in the three cell lines.

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Cytotoxic and Anti-Inflammatory Activities of Dihydroisocoumarin and Xanthone Derivatives from Garcinia picrorhiza

Molecules ◽

10.3390/molecules26216626 ◽

2021 ◽

Vol 26 (21) ◽

pp. 6626

Author(s):

Edwin R. Sukandar ◽

Sutin Kaennakam ◽

Pia Raab ◽

Xuehong Nöst ◽

Kitiya Rassamee ◽

...

Keyword(s):

2D Nmr ◽

Stem Bark ◽

No Production ◽

Hep G2 ◽

Pharmacological Studies ◽

Ic50 Values ◽

Hela S3 ◽

Anti Inflammatory ◽

First Time ◽

Mcf 7

Garcinia picrorhiza, a woody plant native to Sulawesi and Maluku Islands, Indonesia, has been traditionally used as a wound healing ointment. In our continuous search for bioactive compounds from this plant, 15 phenolic compounds were isolated from its stem bark, including a previously undescribed dihydroisocoumarin, 2′-hydroxyannulatomarin, and two undescribed furanoxanthones, gerontoxanthone C hydrate and 3′-hydroxycalothorexanthone. The structures of the new metabolites were elucidated on the basis of spectroscopic analysis, including 1D and 2D NMR and HRESIMS. Gerontoxanthone C hydrate possessed cytotoxicity against four cancer cells (KB, HeLa S3, MCF-7, and Hep G2) with IC50 values ranging from 5.6 to 7.5 µM. Investigation on the anti-inflammatory activities showed that 3′-hydroxycalothorexanthone inhibited NO production in RAW 264.7 and BV-2 cell lines with IC50 values of 16.4 and 13.8 µM, respectively, whereas only (−)-annulatomarin possessed inhibition activity on COX-2 enzyme over 10% at 20 µM. This work describes the presence of 3,4-dihydroisocoumarin structures with a phenyl ring substituent at C-3, which are reported the first time in genus Garcinia. These findings also suggest the potential of furanxanthone derivatives as cytotoxic and anti-inflammatory agents for further pharmacological studies.

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Phytochemical Investigation of Tradescantia Albiflora and Anti-Inflammatory Butenolide Derivatives

Molecules ◽

10.3390/molecules24183336 ◽

2019 ◽

Vol 24 (18) ◽

pp. 3336 ◽

Cited By ~ 2

Author(s):

Ping-Chen Tu ◽

Han-Chun Tseng ◽

Yu-Chia Liang ◽

Guan-Jhong Huang ◽

Te-Ling Lu ◽

...

Keyword(s):

2D Nmr ◽

Raw 264.7 Cells ◽

No Production ◽

Isolation And Characterization ◽

Whole Plant ◽

Phytochemical Investigation ◽

Ic50 Value ◽

Anti Inflammatory ◽

New Compounds ◽

First Time

Phytochemical investigation of the whole plant of Tradescantia albiflora Kunth led to the isolation and characterization of a butanolide, rosmarinosin B (1), that was isolated from natural sources for the first time, a new butenolide, 5-O-acetyl bracteanolide A (2), and a new apocarotenoid, 2β-hydroxyisololiolide (11), together with 25 known compounds (compounds 3–10 and 12–28). The structures of the new compounds were elucidated by analysis of their spectroscopic data, including MS, 1D, and 2D NMR experiments, and comparison with literature data of known compounds. Furthermore, four butenolides 4a–4d were synthesized as novel derivatives of bracteanolide A. The isolates and the synthesized derivatives were evaluated for their preliminary anti-inflammatory activity against lipopolysaccharide (LPS)-stimulated nitric oxide (NO) production in RAW 264.7 cells. Among them, the synthesized butenolide derivative n-butyl bracteanolide A (4d) showed enhanced NO inhibitory activity compared to the original compound, with an IC50 value of 4.32 ± 0.09 μg/mL.

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