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Cytotoxic activity of guaiane-type sesquiterpene lactone (deoxycynaropicrin) isolated from the leaves of Centaurothamnus maximus

  • Fahd A. Nasr EMAIL logo , Nasir Ali Siddiqui , Ali A. ElGamal , Shaza M. Al-Massarani , Omer A. Basudan , Wael M. Abdel-Mageed , Mohammed R. Alhuzani and Ali S. Alqahtani EMAIL logo
Published/Copyright: May 19, 2022
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Open Chemistry
From the journal Open Chemistry Volume 20 Issue 1

Abstract

Guaianolide is a type of naturally occurring sesquiterpene lactone compounds that have attracted attention due to their diverse biological properties. In this work, a guaiane-type sesquiterpene lactone identified as deoxycynaropicrin (compound 1) was isolated and reported for the first time from the leaves of Centaurothamnus maximus with two known flavonoid derivatives namely luteolin 6-O-methyl ether (compound 2) and quercetin 3-methyl ether 5-O-glucopyranoside (compound 3). The cytotoxic activity of all the three compounds was evaluated against the THP-1 human leukemia cell lines. Moreover, flow cytometry was employed to explore the cell cycle arrest and apoptosis induction for the active compound. We found that compound 1 (deoxycynaropicrin) exerted the highest cytotoxicity while compounds 2 and 3 showed no activity. Cell cycle analysis showed that compound 1 arrested the cells’ population at the G2/M phase. Furthermore, THP-1 cells treated with compound 1 exhibited a marked increase in the apoptotic cells compared to the control. Overall, this study showed that deoxycynaropicrin induces cytotoxicity against human leukemia cell lines and provided an important insight into its potential therapeutic effects against leukemia cells.

Keywords: Centaurothamnus maximus ; guaianolide; leukemia; THP-1 cells

1 Introduction

Centaurothamnus is a Centaurea monotypic genus indigenous to the southwestern Arabian Peninsula’s mountains [1,2,3]. The genus of Centaurothamnus is represented by around 200 species, is highly restricted in Saudi Arabia and grows in rare places of cliffs and steep hillsides [4]. Centaurothamnus maximus Wagentz and Dittri (Asteraceae) (Figure 1) is one of the most important species in this genus that is characterized by a branched leafy shrub of about 1.5 m in height. The plant also possesses a densely white-tomentose stem having lanceolate-elliptic leaves arranged in an alternating manner. The flowers are in magenta with faint sweet odor and thistle-like shape with a size of 3–4 cm long situated at the end of the branches. It is a paleoendemic species that grows in Yemen and has not possessed any traditional usage. [1]. The phytochemical survey of C. maximus revealed the presence of guaianolides, edusamanolides, germacranolides and elemanolides [5,6,7,8,9]. Some flavonoids [10], acetylenes [11,12], oxygenated homoditerpenoids [13] and an aliphatic ester [14] have been reported previously. The present literature also reports on guaianolide sesquiterpene lactones chlorojanerin, janerin and cynaropicrin isolated from C. maximus [15]. As we know, the family Asteraceae is a good source of guaianolides. Most of the guaianolides are known for their antimicrobial, antitumor, anthelmintic, antischistosomal and contraceptive properties [16]. The wide spectrum of activities makes guaianolides the compounds of interest for the discovery of new leads, but their toxicity made some restrictions, and because of this, no drug has come to the market at present. Lately, however, the guaianolide thapsigargin and prodrugs have recently provided novel drug discovery possibilities [17]. This again makes guaianolides interesting synthetic and biosynthetic targets because the natural source is often limited and cannot be used as a sustainable source for isolating the compound on a large (kilogram) scale [18].

Figure 1 C. maximus and its various parts collected from Aqabaat Al-Makhwah, Saudi Arabia.
Figure 1

C. maximus and its various parts collected from Aqabaat Al-Makhwah, Saudi Arabia.

In the present investigation, a guaiane-type sesquiterpene lactone (deoxycynaropicrin) was isolated and reported for the first time along with two known flavonoid derivatives luteolin 6-O-methyl ether (compound 2) and quercetin 3-methyl ether 5-O-glucopyranoside (compound 3) from the leaves of C. maximus. The chemical structure of deoxycynaropicrin (compound 1) was established with the help of spectroscopic techniques including UV, IR, NMR and MS. In addition, we showed that deoxycynaropicrin exerted promising cytotoxic and apoptotic effects against THP-1 leukemic cells.

2 Materials and methods

2.1 Plant material

Leaves of C. maximus were collected from Aqabaat Al-Makhwah, after tunnel # 13, Kingdom of Saudi Arabia, in 2016 and identified by Field Taxonomist at the Pharmacognosy Department, College of Pharmacy, King Saud University. A voucher specimen (Voucher # 15024) was deposited at the Pharmacognosy Department, College of Pharmacy, King Saud University.

2.2 Extraction and isolation

The air-dried powdered leaves (750 g) of C. maximus were extracted with 96% ethanol at room temperature, filtered and concentrated under reduced pressure to afford 60 g of dried extracts of the leaves. The obtained dried extract was defatted using MeOH. The MeOH soluble part (50 g) was suspended in 40% H2O/EtOH and successively partitioned with n-hexane (n-Hex.), chloroform (CHCl3) and n-butanol (n-BuOH) to afford the corresponding fractions. The chloroform fraction (10 g) was chromatographed over a silica gel column, starting with CHCl3 as a mobile system, and gradually increasing polarity with MeOH. The eluted fractions were monitored with TLC and similar fractions were combined to end up with 12 main fractions (CH.1-12). Fraction CH.1, eluted with 5% MeOH/CHCl3, was purified using two successive chromatographic steps including CC (10% EtOAc/CHCl3 and Rp-18 CC (25% H2O/MeOH) to obtain compound-1 in the pure form. Compound 2 was precipitated from fraction CH.3 and also eluted with 5% MeOH/CHCl3 after Sephadex LH-20 CC purification with 10% H2O/MeOH as solvent system. Fraction CH.11 eluted with 30% MeOH/CHCl3 was passed through Sephadex LH-20 CC (10% H2O/MeOH) to afford pure compound 3.

2.3 Cell viability (MTT) assay

To test the cytotoxic effect of isolated compounds, an MTT assay was performed as previously described [19]. Before treatment, 5 × 104 THP-1 cells were plated per well in a 24-well plate. Thereafter, cells were treated with various concentrations of each compound (5, 2.5, 1.25 and 0.625 µg/mL), while wells without treatment were used as a control. Following 24 h of treatment, 0.01 mL of MTT was added to each well. Then, wells were incubated at 37°C in 5% CO2 for 4 h to MTT reduction. Isopropanol (1 mL) with acidified HCL was then added and mixed thoroughly to solubilize the formazan product. After 10 min of plate shaking, growth was measured through absorbance measurement with an ELISA plate reader at 570 nm wavelength. Using OriginPro 8.5 software, the IC50 values were calculated from the dose–response curve.

2.4 Cell cycle analysis

As previously documented [19], a flow cytometric study of cell cycle distribution based on DNA content was performed. In brief, THP-1 cells at 1 × 105 cells were cultured in 12-well plates in the presence of compound 1 (2.5 and 5 μg/mL) for 24 h. After treatment, the cells were washed, centrifuged and fixed with 70% ethanol at 4°C for 4 h. After fixing, the cells were washed, centrifuged and then resuspended in 500 μL phosphate-buffered saline (PBS) containing PI (50 μg/mL) and RNase A (100 μg/mL) and incubated for a further 30 min in the dark. Finally, the cells were analyzed by flow cytometry (Cytomics FC 500; Beckman Coulter, CA, USA).

2.5 Annexin V-FITC/PI apoptosis assay

The Annexin V-FITC/PI kit (Biolegend, USA) was used to perform the apoptosis detection for the most active compound (1) following the manufacturer’s guidelines. Briefly, treated and untreated cells were harvested, washed with PBS and resuspended with 100 µL of Annexin-binding buffer (1×). Then, cells were stained with both Annexin-FITC and PI (5 µL each) for 15 min in the dark. Then, 400 μL of binding buffer was added and the apoptotic cells were measured by a fluorescence-activated cell sorter analysis (Cytomics FC 500).

3 Results and discussion

The phytochemical study of C. maximus resulted in the identification and chemical characterization of three compounds (compounds 1–3) (Figure 2). The phytochemical study revealed that compound 1 belonged to a class of sesquiterpene lactone (NMR data, Table 1) and proved to be a therapeutically potent entity as far as human leukemia cell lines are concerned. Compound 2 (luteolin 6-O-methyl ether) and compound 3 (quercetin 3-methyl ether 5-O-glucopyranoside) belonged to the class of flavonoids and exhibited no response with human leukemia cell lines.

Figure 2 Chemical structure of the isolated compounds.
Figure 2

Chemical structure of the isolated compounds.

Table 1

1H NMR and 13C NMR data of compound 1

Position 1H δ H multi, J/Hz 13C δ C multi
1 2.87 m 45.1 CH
2 (a) 1.66 m 36.9 CH2
(b) 2.10 m
3 4.46 t, 7.6 73.4 CH
4 — 152.2 C
5 2.75 tr, 9.2 51.1 CH
6 4.19 q, 9.1 78.6 CH
7 3.11 m 47.4 CH
8 5.00 m 74.1 CH
9 (a) 2.29 dd, 4.7, 3.6 36.9 CH2
(b) 2.61 dd, 14.6, 5.2
10 — 141.9 C
11 — 137.5 C
12 — 169.3 C
13 (a) 5.53 d, 3.0 122.5 CH2
(b) 6.12 d, 3.3
14 (a) 4.86 s 118.0 CH2
(b) 5.07 s
15 (a) 5.29 s 113.2 CH2
(b) 5.40 s
16 — 166.4 C
17 — 135.9 C
18 1.92 s 18.2 CH3
19 (a) 5.62 s 126.6 CH2
(b) 6.12 s

Compound 1 showed a molecular ion peak at m/z 330 calculated for C19H22O5 with eight unsaturation numbers. A characteristic absorption bands appeared at 3,393, 1,753 and 1,710 cm−1 in the IR spectrum assigned for free hydroxyl group, γ lactone and ester functionalities, respectively. 1H NMR showed a characteristic signals for guaianolide-type sesquiterpene esterified with acrylate moiety. The γ lactone ring was confirmed by a lactonic proton at 4.19 ppm and a multiple proton at 3.11 ppm assigned for protons at C6 and C7. A carbonyl carbon that appeared at 169.0 ppm in 13C NMR also confirmed the cyclic ester structure [20]. The rest of 1H NMR spectral data for compound 1 showed six methylenes; four of them attributed for exomethylene groups, each appeared as two signals at 5.53 (d, J = 3.0 Hz), 6.12 (d, J = 3.3 Hz); 5.07 (s), 4.86 (s), 5.29 (s), 5.54 (s), 5.62 (s) and 6.12 (s) ppm assigned for positions 13, 14, 15 and 19. The other two methylenes were assigned for positions 2 and 9, resonating at 1.66–2.61 ppm. A singlet olefenic methyl appeared at 1.92 for position 18. Moreover, the 1H NMR displayed two oxygenated downfield protons at 4.46 (t, J = 7.6) and 5.00 (m) assigned for CH at C3 and C8, respectively. 13C NMR and DEPT experiments showed a total of 19 carbon atoms deduced to one methyl, six methylene, six methines and six quaternary carbons. 2DHSQC experiment was also useful to connect each carbon to its corresponding proton through one bond length. The exact positions for the exomethylene were confirmed by the HMBC experiment to be at positions 4, 10, 11 and 17. Also, the oxygenated protons were assigned at carbons 3 and C8 through J 2 and J 3 HMBC cross-peak bond correlations from H3 4.64 to C1, C4 and C5 at 45.1, 152.2 and 51.1 ppm, respectively, and from H8 5.00 ppm to C6, C7 and C16 at δ c 78.6, 47.4 and 166.4. respectively. The last correlation (from H8 to C16) together with the correlation from olefinic methyl at δ c 1.92 to ester carbonyl at δ c 166.4 and from exomethylene protons at 5.62, 6.12 ppm (C19) to C16 and methyl 18 proved esterification position by acrylate moiety is at position 8. The aforementioned data confirmed that compound 1 identified as erguin previously isolated from Centaurea deflexa [21].

3.1 Compounds’ cytotoxic effects

Sesquiterpene lactones have long been suspected as potential anticancer agents and more compounds in this class may provide information on the chemical substituents that are important for the anticancer activity [21]. In particular, the reported antileukemic effects of these compounds supported the idea that these classes could be useful in the treatment of leukemia [22]. Hence, the antiproliferative activity of isolated compounds was tested against the THP-1 leukemic cell lines. Our results indicated that only compound 1 decreased the cell viability in a dose-dependent manner (Figure 3), while compounds 2 and 3 did not display any activity. The reported IC50 of compound 1 on the THP-1 cell line at 24 h was 7.5 μM (Table 2).

Figure 3 Effects of different concentrations of compound 1 on cell viability during a 24 h incubation period. MTT assay was employed to determine the cell viability after treatment. The experiment was carried out in triplicate and the results are reported as mean ± standard deviation (SD).
Figure 3

Effects of different concentrations of compound 1 on cell viability during a 24 h incubation period. MTT assay was employed to determine the cell viability after treatment. The experiment was carried out in triplicate and the results are reported as mean ± standard deviation (SD).

Table 2

IC50 values of compounds isolated from C. maximus against THP-1 cells

Compound IC50 (µM)
1 7.5 ± 0.1
2 —
3 —
Doxorubicin 0.73 ± 0.02

3.1.1 Compound 1 caused G2/M cell cycle arrest in THP-1 cells

A cell cycle assay was carried out to assess whether compound 1 treatment led to changes in the cell cycle progression. THP-1 cells treated with 7.5 or 15 µM of compound 1 showed a higher G2/M population (22.6 ± 1.1 and 33.9 ± 1.4%, respectively) compared with 18.7 ± 0.9% in the control (Figure 4). In addition, compound 1 treatment caused a concomitant decrease in the proportion of cells in the G1 phase of the cell cycle from control (54.0 ± 1.5%) to (50 ± 1.2% and 41.8 ± 1.2%). Hence, our data suggested that compound 1 induced cell cycle arrest at the G2/M phase (Figure 4). The results described here are also in line with the findings of Ahmed et al., who reported that the janerin compound isolated from the same species demonstrated the same effect against the same cells [19]. Since uncontrolled cell division is a hallmark feature of cancer cells, novel compounds that inhibit cell cycle progression have been sought in hopes of expanding available cancer-directed therapies [23]. In fact, several standard anticancer drugs that are isolated from plants, such as etoposide and Taxol, exerted their effects through cell cycle arrest at the G2/M phase [24].

Figure 4 Induction of the G2/M cell cycle arrest by compound 1 in THP-1 cells. (a) Cells were treated with compound at 2.5 and 5 µg/mL concentration for 24 h while untreated cells were served as control. (b) Bar graphs represent the cell phases. The data are presented as the mean ± SD, *p < 0.05 and **p < 0.01 vs group.
Figure 4

Induction of the G2/M cell cycle arrest by compound 1 in THP-1 cells. (a) Cells were treated with compound at 2.5 and 5 µg/mL concentration for 24 h while untreated cells were served as control. (b) Bar graphs represent the cell phases. The data are presented as the mean ± SD, *p < 0.05 and **p < 0.01 vs group.

3.1.2 Compound 1 caused apoptosis in THP-1 cells

Apoptosis is a vital biological process that permits the elimination of damaged or abnormal cells. As a result, inducing apoptosis appears to be an attractive goal for killing tumor cells as well as a useful strategy for cancer treatment [25]. Therefore, the ability of compound 1 to induce apoptosis initiation was further examined by staining the cells with Annexin V-FITC/PI for the quantification of apoptotic cells using flow cytometry. As shown in Figure 5, compound 1 exposure at (7.5 and 15 µM) concentrations resulted in dose-dependent increments of early apoptotic cells population (4.2.0 ± 0.8 and 16.7 ± 1%) compared to control (1.8 ± 0.4%). There was also a significant increase in the late apoptotic population (8.5 ± 0.7 and 51.0 ± 1.2%). Around 11% of the cell population displayed a necrotic death when treated with a high dose (5 µg/mL) of compound 1. A similar effect against human U-937 leukemia cells was reported for guaianolides compounds (chlorohyssopifolins and Linichlorin) isolated from Centaurea hyssopifolia and Centaurea linifolia, respectively. Both compounds demonstrated a potent apoptotic effect, which provided an important insight into the cell death pathway induced by guaianolides compounds [26].

Figure 5 Compound 1 induced apoptosis in THP-1 cells. The cells were treated at 2.5 and 5 µg/mL followed by FITC/PI staining. (a) Quadrant charts show A1 (necrotic cells), A2 (late apoptotic cells), A3 (live cells) and A4 (early apoptotic cells). (b) Apoptosis percentages of untreated and treated cells are represented as bars. Values are represented by mean ± SD, *p < 0.05, **p < 0.01 and ***p < 0.001 vs group.
Figure 5

Compound 1 induced apoptosis in THP-1 cells. The cells were treated at 2.5 and 5 µg/mL followed by FITC/PI staining. (a) Quadrant charts show A1 (necrotic cells), A2 (late apoptotic cells), A3 (live cells) and A4 (early apoptotic cells). (b) Apoptosis percentages of untreated and treated cells are represented as bars. Values are represented by mean ± SD, *p < 0.05, **p < 0.01 and ***p < 0.001 vs group.

4 Conclusions

In comparison to other types of sesquiterpene lactones, guaianolide-type sesquiterpene lactones have attracted more attention due to their more cytotoxic effect. Herein, deoxycynaropicrin was isolated from the C. maximus for the first time. We found that deoxycynaropicrin (compound 1) inhibited the proliferation of THP-1 leukemia cells via apoptosis induction and triggered cell cycle arrest at the G2/M phase. These in vitro findings suggested that deoxycynaropicrin had a therapeutic potential against human leukemia cells, which is needed to confirm it using the in vivo model.

Acknowledgments

The authors are thankful to the Researchers Supporting Project number (RSP-2021/132), King Saud University, Riyadh, Saudi Arabia, for funding this research work.

  1. Funding information: This research was funded by Researchers Supporting Project number (RSP-2021/132), King Saud University, Riyadh, Saudi Arabia.

  2. Author contributions: Conceptualization, A.S.A.; methodology, F.A.N., N.A.S., O.A.B. and S.M.M.; validation and data curation, A.G. and W.M.A.; writing – original draft preparation, F.A.N. and N.A.S.; writing – review and editing, N.A.S., F.A.N. and A.S.A.; resources: M.R.H.; funding acquisition, A.S.A. All authors have read and agreed to the published version of the manuscript.

  3. Conflict of interest: The authors declare no conflict of interest.

  4. Ethical approval: The conducted research is not related to either human or animal use.

  5. Data availability statement: All the data related to these findings are included in the MS.

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Received: 2022-02-25
Revised: 2022-04-22
Accepted: 2022-04-27
Published Online: 2022-05-19

© 2022 Fahd A. Nasr et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution 4.0 International License.

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  35. Impact of a live bacterial-based direct-fed microbial (DFM) postpartum and weaning system on performance, mortality, and health of Najdi lambs
  36. Anti-tumor effect of liposomes containing extracted Murrayafoline A against liver cancer cells in 2D and 3D cultured models
  37. Physicochemical properties and some mineral concentration of milk samples from different animals and altitudes
  38. Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies
  39. Diagnostic and therapeutic radioisotopes in nuclear medicine: Determination of gamma-ray transmission factors and safety competencies of high-dense and transparent glassy shields
  40. Calculation of NaI(Tl) detector efficiency using 226Ra, 232Th, and 40K radioisotopes: Three-phase Monte Carlo simulation study
  41. Isolation and identification of unstable components from Caesalpinia sappan by high-speed counter-current chromatography combined with preparative high-performance liquid chromatography
  42. Quantification of biomarkers and evaluation of antioxidant, anti-inflammatory, and cytotoxicity properties of Dodonaea viscosa grown in Saudi Arabia using HPTLC technique
  43. Characterization of the elastic modulus of ceramic–metal composites with physical and mechanical properties by ultrasonic technique
  44. GC-MS analysis of Vespa velutina auraria Smith and its anti-inflammatory and antioxidant activities in vitro
  45. Texturing of nanocoatings for surface acoustic wave-based sensors for volatile organic compounds
  46. Insights into the molecular basis of some chalcone analogues as potential inhibitors of Leishmania donovani: An integrated in silico and in vitro study
  47. (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity
  48. On the relative extraction rates of colour compounds and caffeine during brewing, an investigation of tea over time and temperature
  49. Characterization of egg shell powder-doped ceramic–metal composites
  50. Rapeseed oil-based hippurate amide nanocomposite coating material for anticorrosive and antibacterial applications
  51. Chemically modified Teucrium polium (Lamiaceae) plant act as an effective adsorbent tool for potassium permanganate (KMnO4) in wastewater remediation
  52. Efficiency analysis of photovoltaic systems installed in different geographical locations
  53. Risk prioritization model driven by success factor in the light of multicriteria decision making
  54. Theoretical investigations on the excited-state intramolecular proton transfer in the solvated 2-hydroxy-1-naphthaldehyde carbohydrazone
  55. Mechanical and gamma-ray shielding examinations of Bi2O3–PbO–CdO–B2O3 glass system
  56. Machine learning-based forecasting of potability of drinking water through adaptive boosting model
  57. The potential effect of the Rumex vesicarius water seeds extract treatment on mice before and during pregnancy on the serum enzymes and the histology of kidney and liver
  58. Impact of benzimidazole functional groups on the n-doping properties of benzimidazole derivatives
  59. Extraction of red pigment from Chinese jujube peel and the antioxidant activity of the pigment extracts
  60. Flexural strength and thermal properties of carbon black nanoparticle reinforced epoxy composites obtained from waste tires
  61. A focusing study on radioprotective and antioxidant effects of Annona muricata leaf extract in the circulation and liver tissue: Clinical and experimental studies
  62. Clinical comprehensive and experimental assessment of the radioprotective effect of Annona muricata leaf extract to prevent cellular damage in the ileum tissue
  63. Effect of WC content on ultrasonic properties, thermal and electrical conductivity of WC–Co–Ni–Cr composites
  64. Influence of various class cleaning agents for prosthesis on Co–Cr alloy surface
  65. The synthesis of nanocellulose-based nanocomposites for the effective removal of hexavalent chromium ions from aqueous solution
  66. Study on the influence of physical interlayers on the remaining oil production under different development modes
  67. Optimized linear regression control of DC motor under various disturbances
  68. Influence of different sample preparation strategies on hypothesis-driven shotgun proteomic analysis of human saliva
  69. Determination of flow distance of the fluid metal due to fluidity in ductile iron casting by artificial neural networks approach
  70. Investigation of mechanical activation effect on high-volume natural pozzolanic cements
  71. In vitro: Anti-coccidia activity of Calotropis procera leaf extract on Eimeria papillata oocysts sporulation and sporozoite
  72. Determination of oil composition of cowpea (Vigna unguiculata L.) seeds under influence of organic fertilizer forms
  73. Activated partial thromboplastin time maybe associated with the prognosis of papillary thyroid carcinoma
  74. Treatment of rat brain ischemia model by NSCs-polymer scaffold transplantation
  75. Lead and cadmium removal with native yeast from coastal wetlands
  76. Characterization of electroless Ni-coated Fe–Co composite using powder metallurgy
  77. Ferrate synthesis using NaOCl and its application for dye removal
  78. Antioxidant, antidiabetic, and anticholinesterase potential of Chenopodium murale L. extracts using in vitro and in vivo approaches
  79. Study on essential oil, antioxidant activity, anti-human prostate cancer effects, and induction of apoptosis by Equisetum arvense
  80. Experimental study on turning machine with permanent magnetic cutting tool
  81. Numerical simulation and mathematical modeling of the casting process for pearlitic spheroidal graphite cast iron
  82. Design, synthesis, and cytotoxicity evaluation of novel thiophene, pyrimidine, pyridazine, and pyridine: Griseofulvin heterocyclic extension derivatives
  83. Isolation and identification of promising antibiotic-producing bacteria
  84. Ultrasonic-induced reversible blood–brain barrier opening: Safety evaluation into the cellular level
  85. Evaluation of phytochemical and antioxidant potential of various extracts from traditionally used medicinal plants of Pakistan
  86. Effect of calcium lactate in standard diet on selected markers of oxidative stress and inflammation in ovariectomized rats
  87. Identification of crucial salivary proteins/genes and pathways involved in pathogenesis of temporomandibular disorders
  88. Zirconium-modified attapulgite was used for removing of Cr(vi) in aqueous solution
  89. The stress distribution of different types of restorative materials in primary molar
  90. Reducing surface heat loss in steam boilers
  91. Deformation behavior and formability of friction stir processed DP600 steel
  92. Synthesis and characterization of bismuth oxide/commercial activated carbon composite for battery anode
  93. Phytochemical analysis of Ziziphus jujube leaf at different foliar ages based on widely targeted metabolomics
  94. Effects of in ovo injection of black cumin (Nigella sativa) extract on hatching performance of broiler eggs
  95. Separation and evaluation of potential antioxidant, analgesic, and anti-inflammatory activities of limonene-rich essential oils from Citrus sinensis (L.)
  96. Bioactivity of a polyhydroxy gorgostane steroid from Xenia umbellata
  97. BiCAM-based automated scoring system for digital logic circuit diagrams
  98. Analysis of standard systems with solar monitoring systems
  99. Structural and spectroscopic properties of voriconazole and fluconazole – Experimental and theoretical studies
  100. New plant resistance inducers based on polyamines
  101. Experimental investigation of single-lap bolted and bolted/bonded (hybrid) joints of polymeric plates
  102. Investigation of inlet air pressure and evaporative cooling of four different cogeneration cycles
  103. Review Articles
  104. Comprehensive review on synthesis, physicochemical properties, and application of activated carbon from the Arecaceae plants for enhanced wastewater treatment
  105. Research progress on speciation analysis of arsenic in traditional Chinese medicine
  106. Recent modified air-assisted liquid–liquid microextraction applications for medicines and organic compounds in various samples: A review
  107. An insight on Vietnamese bio-waste materials as activated carbon precursors for multiple applications in environmental protection
  108. Antimicrobial activities of the extracts and secondary metabolites from Clausena genus – A review
  109. Bioremediation of organic/heavy metal contaminants by mixed cultures of microorganisms: A review
  110. Sonodynamic therapy for breast cancer: A literature review
  111. Recent progress of amino acid transporters as a novel antitumor target
  112. Aconitum coreanum Rapaics: Botany, traditional uses, phytochemistry, pharmacology, and toxicology
  113. Corrigendum
  114. Corrigendum to “Petrology and geochemistry of multiphase post-granitic dikes: A case study from the Gabal Serbal area, Southwestern Sinai, Egypt”
  115. Corrigendum to “Design of a Robust sliding mode controller for bioreactor cultures in overflow metabolism via an interdisciplinary approach”
  116. Corrigendum to “Statistical analysis on the radiological assessment and geochemical studies of granite rocks in the north of Um Taghir area, Eastern Desert, Egypt”
  117. Corrigendum to “Aroma components of tobacco powder from different producing areas based on gas chromatography ion mobility spectrometry”
  118. Corrigendum to “Mechanical properties, elastic moduli, transmission factors, and gamma-ray-shielding performances of Bi2O3–P2O5–B2O3–V2O5 quaternary glass system”
  119. Erratum
  120. Erratum to “Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies”
  121. Special Issue on Applied Biochemistry and Biotechnology (ABB 2021)
  122. Study of solidification and stabilization of heavy metals by passivators in heavy metal-contaminated soil
  123. Human health risk assessment and distribution of VOCs in a chemical site, Weinan, China
  124. Preparation and characterization of Sparassis latifolia β-glucan microcapsules
  125. Special Issue on the Conference of Energy, Fuels, Environment 2020
  126. Improving the thermal performance of existing buildings in light of the requirements of the EU directive 2010/31/EU in Poland
  127. Special Issue on Ethnobotanical, Phytochemical and Biological Investigation of Medicinal Plants
  128. Study of plant resources with ethnomedicinal relevance from district Bagh, Azad Jammu and Kashmir, Pakistan
  129. Studies on the chemical composition of plants used in traditional medicine in Congo
  130. Special Issue on Applied Chemistry in Agriculture and Food Science
  131. Strip spraying technology for precise herbicide application in carrot fields
  132. Special Issue on Pharmacology and Metabolomics of Ethnobotanical and Herbal Medicine
  133. Phytochemical profiling, antibacterial and antioxidant properties of Crocus sativus flower: A comparison between tepals and stigmas
  134. Antioxidant and antimicrobial properties of polyphenolics from Withania adpressa (Coss.) Batt. against selected drug-resistant bacterial strains
  135. Integrating network pharmacology and molecular docking to explore the potential mechanism of Xinguan No. 3 in the treatment of COVID-19
  136. Chemical composition and in vitro and in vivo biological assortment of fixed oil extracted from Ficus benghalensis L.
  137. A review of the pharmacological activities and protective effects of Inonotus obliquus triterpenoids in kidney diseases
  138. Ethnopharmacological study of medicinal plants in Kastamonu province (Türkiye)
  139. Protective effects of asperuloside against cyclophosphamide-induced urotoxicity and hematotoxicity in rats
  140. Special Issue on Essential Oil, Extraction, Phytochemistry, Advances, and Application
  141. Identification of volatile compounds and antioxidant, antibacterial, and antifungal properties against drug-resistant microbes of essential oils from the leaves of Mentha rotundifolia var. apodysa Briq. (Lamiaceae)
  142. Phenolic contents, anticancer, antioxidant, and antimicrobial capacities of MeOH extract from the aerial parts of Trema orientalis plant
  143. Chemical composition and antimicrobial activity of essential oils from Mentha pulegium and Rosmarinus officinalis against multidrug-resistant microbes and their acute toxicity study
  144. Special Issue on Marine Environmental Sciences and Significance of the Multidisciplinary Approaches
  145. An insightful overview of the distribution pattern of polycyclic aromatic hydrocarbon in the marine sediments of the Red Sea
  146. Antifungal–antiproliferative norcycloartane-type triterpenes from the Red Sea green alga Tydemania expeditionis
  147. Solvent effect, dipole moment, and DFT studies of multi donor–acceptor type pyridine derivative
  148. An extensive assessment on the distribution pattern of organic contaminants in the aerosols samples in the Middle East
  149. Special Issue on 4th IC3PE
  150. Energetics of carboxylic acid–pyridine heterosynthon revisited: A computational study of intermolecular hydrogen bond domination on phenylacetic acid–nicotinamide cocrystals
  151. A review: Silver–zinc oxide nanoparticles – organoclay-reinforced chitosan bionanocomposites for food packaging
  152. Green synthesis of magnetic activated carbon from peanut shells functionalized with TiO2 photocatalyst for Batik liquid waste treatment
  153. Coagulation activity of liquid extraction of Leucaena leucocephala and Sesbania grandiflora on the removal of turbidity
  154. Hydrocracking optimization of palm oil over NiMoO4/activated carbon catalyst to produce biogasoline and kerosine
  155. Special Issue on Pharmacology and metabolomics of ethnobotanical and herbal medicine
  156. Cynarin inhibits PDGF-BB-induced proliferation and activation in hepatic stellate cells through PPARγ
  157. Special Issue on The 1st Malaysia International Conference on Nanotechnology & Catalysis (MICNC2021)
  158. Surfactant evaluation for enhanced oil recovery: Phase behavior and interfacial tension
  159. Topical Issue on phytochemicals, biological and toxicological analysis of aromatic medicinal plants
  160. Phytochemical analysis of leaves and stems of Physalis alkekengi L. (Solanaceae)
  161. Phytochemical and pharmacological profiling of Trewia nudiflora Linn. leaf extract deciphers therapeutic potentials against thrombosis, arthritis, helminths, and insects
  162. Pergularia tomentosa coupled with selenium nanoparticles salvaged lead acetate-induced redox imbalance, inflammation, apoptosis, and disruption of neurotransmission in rats’ brain
  163. Protective effect of Allium atroviolaceum-synthesized SeNPs on aluminum-induced brain damage in mice
  164. Mechanism study of Cordyceps sinensis alleviates renal ischemia–reperfusion injury
  165. Plant-derived bisbenzylisoquinoline alkaloid tetrandrine prevents human podocyte injury by regulating the miR-150-5p/NPHS1 axis
  166. Network pharmacology combined with molecular docking to explore the anti-osteoporosis mechanisms of β-ecdysone derived from medicinal plants
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  168. Special Issue on Advanced Nanomaterials for Energy, Environmental and Biological Applications - Part I
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  170. Special Issue on Applied Biochemistry and Biotechnology (ABB 2022)
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https://doi.org/10.1515/chem-2022-0163
Keywords for this article
Centaurothamnus maximus; guaianolide; leukemia; THP-1 cells
Creative Commons
BY 4.0

Articles in the same Issue

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  9. Design of a Robust sliding mode controller for bioreactor cultures in overflow metabolism via an interdisciplinary approach
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  11. Bridging chiral de-tert-butylcalix[4]arenes: Optical resolution based on column chromatography and structural characterization
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  19. Statistical analysis on the radiological assessment and geochemical studies of granite rocks in the north of Um Taghir area, Eastern Desert, Egypt
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  31. Cytotoxic activity of guaiane-type sesquiterpene lactone (deoxycynaropicrin) isolated from the leaves of Centaurothamnus maximus
  32. Effects of welding parameters on the angular distortion of welded steel plates
  33. Simulation of a reactor considering the Stamicarbon, Snamprogetti, and Toyo patents for obtaining urea
  34. Effect of different ramie (Boehmeria nivea L. Gaud) cultivars on the adsorption of heavy metal ions cadmium and lead in the remediation of contaminated farmland soils
  35. Impact of a live bacterial-based direct-fed microbial (DFM) postpartum and weaning system on performance, mortality, and health of Najdi lambs
  36. Anti-tumor effect of liposomes containing extracted Murrayafoline A against liver cancer cells in 2D and 3D cultured models
  37. Physicochemical properties and some mineral concentration of milk samples from different animals and altitudes
  38. Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies
  39. Diagnostic and therapeutic radioisotopes in nuclear medicine: Determination of gamma-ray transmission factors and safety competencies of high-dense and transparent glassy shields
  40. Calculation of NaI(Tl) detector efficiency using 226Ra, 232Th, and 40K radioisotopes: Three-phase Monte Carlo simulation study
  41. Isolation and identification of unstable components from Caesalpinia sappan by high-speed counter-current chromatography combined with preparative high-performance liquid chromatography
  42. Quantification of biomarkers and evaluation of antioxidant, anti-inflammatory, and cytotoxicity properties of Dodonaea viscosa grown in Saudi Arabia using HPTLC technique
  43. Characterization of the elastic modulus of ceramic–metal composites with physical and mechanical properties by ultrasonic technique
  44. GC-MS analysis of Vespa velutina auraria Smith and its anti-inflammatory and antioxidant activities in vitro
  45. Texturing of nanocoatings for surface acoustic wave-based sensors for volatile organic compounds
  46. Insights into the molecular basis of some chalcone analogues as potential inhibitors of Leishmania donovani: An integrated in silico and in vitro study
  47. (1R,2S,5R)-5-Methyl-2-(propan-2-yl)cyclohexyl 4-amino-3-phenylbutanoate hydrochloride: Synthesis and anticonvulsant activity
  48. On the relative extraction rates of colour compounds and caffeine during brewing, an investigation of tea over time and temperature
  49. Characterization of egg shell powder-doped ceramic–metal composites
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  52. Efficiency analysis of photovoltaic systems installed in different geographical locations
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  54. Theoretical investigations on the excited-state intramolecular proton transfer in the solvated 2-hydroxy-1-naphthaldehyde carbohydrazone
  55. Mechanical and gamma-ray shielding examinations of Bi2O3–PbO–CdO–B2O3 glass system
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  58. Impact of benzimidazole functional groups on the n-doping properties of benzimidazole derivatives
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  61. A focusing study on radioprotective and antioxidant effects of Annona muricata leaf extract in the circulation and liver tissue: Clinical and experimental studies
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  68. Influence of different sample preparation strategies on hypothesis-driven shotgun proteomic analysis of human saliva
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  78. Antioxidant, antidiabetic, and anticholinesterase potential of Chenopodium murale L. extracts using in vitro and in vivo approaches
  79. Study on essential oil, antioxidant activity, anti-human prostate cancer effects, and induction of apoptosis by Equisetum arvense
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  81. Numerical simulation and mathematical modeling of the casting process for pearlitic spheroidal graphite cast iron
  82. Design, synthesis, and cytotoxicity evaluation of novel thiophene, pyrimidine, pyridazine, and pyridine: Griseofulvin heterocyclic extension derivatives
  83. Isolation and identification of promising antibiotic-producing bacteria
  84. Ultrasonic-induced reversible blood–brain barrier opening: Safety evaluation into the cellular level
  85. Evaluation of phytochemical and antioxidant potential of various extracts from traditionally used medicinal plants of Pakistan
  86. Effect of calcium lactate in standard diet on selected markers of oxidative stress and inflammation in ovariectomized rats
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  88. Zirconium-modified attapulgite was used for removing of Cr(vi) in aqueous solution
  89. The stress distribution of different types of restorative materials in primary molar
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  93. Phytochemical analysis of Ziziphus jujube leaf at different foliar ages based on widely targeted metabolomics
  94. Effects of in ovo injection of black cumin (Nigella sativa) extract on hatching performance of broiler eggs
  95. Separation and evaluation of potential antioxidant, analgesic, and anti-inflammatory activities of limonene-rich essential oils from Citrus sinensis (L.)
  96. Bioactivity of a polyhydroxy gorgostane steroid from Xenia umbellata
  97. BiCAM-based automated scoring system for digital logic circuit diagrams
  98. Analysis of standard systems with solar monitoring systems
  99. Structural and spectroscopic properties of voriconazole and fluconazole – Experimental and theoretical studies
  100. New plant resistance inducers based on polyamines
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  102. Investigation of inlet air pressure and evaporative cooling of four different cogeneration cycles
  103. Review Articles
  104. Comprehensive review on synthesis, physicochemical properties, and application of activated carbon from the Arecaceae plants for enhanced wastewater treatment
  105. Research progress on speciation analysis of arsenic in traditional Chinese medicine
  106. Recent modified air-assisted liquid–liquid microextraction applications for medicines and organic compounds in various samples: A review
  107. An insight on Vietnamese bio-waste materials as activated carbon precursors for multiple applications in environmental protection
  108. Antimicrobial activities of the extracts and secondary metabolites from Clausena genus – A review
  109. Bioremediation of organic/heavy metal contaminants by mixed cultures of microorganisms: A review
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  112. Aconitum coreanum Rapaics: Botany, traditional uses, phytochemistry, pharmacology, and toxicology
  113. Corrigendum
  114. Corrigendum to “Petrology and geochemistry of multiphase post-granitic dikes: A case study from the Gabal Serbal area, Southwestern Sinai, Egypt”
  115. Corrigendum to “Design of a Robust sliding mode controller for bioreactor cultures in overflow metabolism via an interdisciplinary approach”
  116. Corrigendum to “Statistical analysis on the radiological assessment and geochemical studies of granite rocks in the north of Um Taghir area, Eastern Desert, Egypt”
  117. Corrigendum to “Aroma components of tobacco powder from different producing areas based on gas chromatography ion mobility spectrometry”
  118. Corrigendum to “Mechanical properties, elastic moduli, transmission factors, and gamma-ray-shielding performances of Bi2O3–P2O5–B2O3–V2O5 quaternary glass system”
  119. Erratum
  120. Erratum to “Copper(ii) complexes supported by modified azo-based ligands: Nucleic acid binding and molecular docking studies”
  121. Special Issue on Applied Biochemistry and Biotechnology (ABB 2021)
  122. Study of solidification and stabilization of heavy metals by passivators in heavy metal-contaminated soil
  123. Human health risk assessment and distribution of VOCs in a chemical site, Weinan, China
  124. Preparation and characterization of Sparassis latifolia β-glucan microcapsules
  125. Special Issue on the Conference of Energy, Fuels, Environment 2020
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  127. Special Issue on Ethnobotanical, Phytochemical and Biological Investigation of Medicinal Plants
  128. Study of plant resources with ethnomedicinal relevance from district Bagh, Azad Jammu and Kashmir, Pakistan
  129. Studies on the chemical composition of plants used in traditional medicine in Congo
  130. Special Issue on Applied Chemistry in Agriculture and Food Science
  131. Strip spraying technology for precise herbicide application in carrot fields
  132. Special Issue on Pharmacology and Metabolomics of Ethnobotanical and Herbal Medicine
  133. Phytochemical profiling, antibacterial and antioxidant properties of Crocus sativus flower: A comparison between tepals and stigmas
  134. Antioxidant and antimicrobial properties of polyphenolics from Withania adpressa (Coss.) Batt. against selected drug-resistant bacterial strains
  135. Integrating network pharmacology and molecular docking to explore the potential mechanism of Xinguan No. 3 in the treatment of COVID-19
  136. Chemical composition and in vitro and in vivo biological assortment of fixed oil extracted from Ficus benghalensis L.
  137. A review of the pharmacological activities and protective effects of Inonotus obliquus triterpenoids in kidney diseases
  138. Ethnopharmacological study of medicinal plants in Kastamonu province (Türkiye)
  139. Protective effects of asperuloside against cyclophosphamide-induced urotoxicity and hematotoxicity in rats
  140. Special Issue on Essential Oil, Extraction, Phytochemistry, Advances, and Application
  141. Identification of volatile compounds and antioxidant, antibacterial, and antifungal properties against drug-resistant microbes of essential oils from the leaves of Mentha rotundifolia var. apodysa Briq. (Lamiaceae)
  142. Phenolic contents, anticancer, antioxidant, and antimicrobial capacities of MeOH extract from the aerial parts of Trema orientalis plant
  143. Chemical composition and antimicrobial activity of essential oils from Mentha pulegium and Rosmarinus officinalis against multidrug-resistant microbes and their acute toxicity study
  144. Special Issue on Marine Environmental Sciences and Significance of the Multidisciplinary Approaches
  145. An insightful overview of the distribution pattern of polycyclic aromatic hydrocarbon in the marine sediments of the Red Sea
  146. Antifungal–antiproliferative norcycloartane-type triterpenes from the Red Sea green alga Tydemania expeditionis
  147. Solvent effect, dipole moment, and DFT studies of multi donor–acceptor type pyridine derivative
  148. An extensive assessment on the distribution pattern of organic contaminants in the aerosols samples in the Middle East
  149. Special Issue on 4th IC3PE
  150. Energetics of carboxylic acid–pyridine heterosynthon revisited: A computational study of intermolecular hydrogen bond domination on phenylacetic acid–nicotinamide cocrystals
  151. A review: Silver–zinc oxide nanoparticles – organoclay-reinforced chitosan bionanocomposites for food packaging
  152. Green synthesis of magnetic activated carbon from peanut shells functionalized with TiO2 photocatalyst for Batik liquid waste treatment
  153. Coagulation activity of liquid extraction of Leucaena leucocephala and Sesbania grandiflora on the removal of turbidity
  154. Hydrocracking optimization of palm oil over NiMoO4/activated carbon catalyst to produce biogasoline and kerosine
  155. Special Issue on Pharmacology and metabolomics of ethnobotanical and herbal medicine
  156. Cynarin inhibits PDGF-BB-induced proliferation and activation in hepatic stellate cells through PPARγ
  157. Special Issue on The 1st Malaysia International Conference on Nanotechnology & Catalysis (MICNC2021)
  158. Surfactant evaluation for enhanced oil recovery: Phase behavior and interfacial tension
  159. Topical Issue on phytochemicals, biological and toxicological analysis of aromatic medicinal plants
  160. Phytochemical analysis of leaves and stems of Physalis alkekengi L. (Solanaceae)
  161. Phytochemical and pharmacological profiling of Trewia nudiflora Linn. leaf extract deciphers therapeutic potentials against thrombosis, arthritis, helminths, and insects
  162. Pergularia tomentosa coupled with selenium nanoparticles salvaged lead acetate-induced redox imbalance, inflammation, apoptosis, and disruption of neurotransmission in rats’ brain
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