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Rare norisodinosterol derivatives from Xenia umbellata: Isolation and anti-proliferative activity

  • Nahed Obaid Bawakid , Walied Mohamed Alarif EMAIL logo and Ahmed Abdel-Lateff
Published/Copyright: March 23, 2021
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Open Chemistry
From the journal Open Chemistry Volume 19 Issue 1

Abstract

Two new rare 30-norisodinosterol derivatives, 23,24-dimethylcholest-16-ene-3β,5α,6β,11α,20(R)-pentol 3-monoacetate (1) and 23,24-dimethylcholest-16-ene-3β,5α,6β,20(R)-tertrol 3-monoacetate (2), along with a known steroid, 3β,5α,6β,11α,20β-pentahydroxygorgosterol (3), were identified from Xenia umbellata. The structures of the isolated compounds were determined by analyses of the measured spectra (1D and 2D nuclear magnetic resonance, mass spectrometry, and infrared). The biosynthetic pathway of the new norisodinosterols was proposed. Compound 1 exhibited potent cytotoxicity against HepG2, PC-3, and HT-29 with IC50 values of 4.70 ± 0.2, 5.60 ± 0.6, and 4.00 ± 0.4 μg/mL, respectively. On the contrary, compound 3 showed less potent cytotoxicity against HepG2 with IC50 value of 22.20 ± 1.0 μg/mL. Two DNA-binding dyes have been used for the morphological detection of viable, apoptotic, and necrotic cells. The early apoptotic cell death was observed in all types of treated tumour cells. The late apoptotic cells are highly present in HepG2 cells with compound 3 compared with other cancer cells except for compound 1. The anti-proliferative activity of compounds 1 and 3 warranted further investigation.

Graphical abstract

Keywords: Red Sea; Alcyonacea ; steroids; cytotoxicity; apoptosis

1 Introduction

Alcyonacea (Phylum: Cnidaria; Class: Anthozoa) survives worldwide in tropical and subtropical seawaters and does not have the hard calcium carbonate skeleton. Members of Alcyonacea inhabit the inner reefs below the stony corals [1]. They are known for their productivity of secondary metabolites such as terpenoids and steroids. The soft corals are important member of marine fauna which have cells in the form of toxic stinging nematocysts with the absence of the rigid protective skeleton of scleractinians. They also have the ability to produce toxic substances [2,3,4].

Family Xeniidae (Alcyonacea) consists of 20 genera and 162 species. They live in tropical waters as the Red Sea. They present as yellow cylindrical clavate colonies [3]. They have many varieties of long feather-like tentacles and their polyps pump water into the colony, creating a rhythmic pulsing motion. They are named as pulsing Xenia and pom-pom Xenia. This genus is known for its productivity of terpenoids and steroids [5,6].

In 2018, the Saudi Cancer Registry reported a total of 24,485 diagnosed cancer cases [7]. As a part of our interest is this study, which aimed at discovering the anti-cancer metabolites from marine sources [8,9]. Thus, the present study was designed to isolate bioactive secondary compounds from Xenia umbellata. The anti-proliferative activity of 23,24-dimethylcholest-16-ene-3β,5α,6β,11α,20(R)-pentol 3-monoacetate (1) and 3β,5α,6β,11α,20β-pentahydroxygorgosterol (3) was evaluated against HepG2, PC-3, and HT-29. Additionally, two DNA-binding dyes, acridine orange (AO) and ethidium bromide (EtBr), have been used for the morphological detection of viable, apoptotic, and necrotic cells [10].

2 Experimental

2.1 Soft coral sample

Xenia umbellata was gathered by Scuba technique at a depth of 15–20 m in October 2018, off the Red Sea coast at Jeddah, Saudi Arabia (21°29′31″N 39°11′24″E). Prof. Mohsen El-Sherbiny (Faculty of Marine Sciences, King Abdulaziz University [KAU]) identified the sample. A voucher specimen (XC-2018-11/2) was deposited in the Faculty of Marine Sciences, KAU.

2.2 Extraction and isolation

The semi-dried soft coral (265 g) was exhausted by CH2Cl2/MeOH (3 × 1 L, 22°C), yielding (21.4 g) an oily residue. The extract was loaded on 60 G silica gel column (100 × 3.2 cm) and eluted by gradient elution from n-hexane easing to CH2Cl2 (50 mL each fraction). The fraction that eluted with n-hexane–CH2Cl2 (65:35) afforded 23,24-dimethylcholest-16-ene-3β,5α,6β,20(R)-tetrol 3-monoacetate (2), whereas the fraction that eluted with n-hexane-CH2Cl2 (45:55) afforded compound 1. Finally, the fraction that eluted with n-hexane–CH2Cl2 (40:60) gave compound 3. The purification of compounds 1–3 has been done by preparative thin-layer chromatography (PTLC; normal phase silica gel).

2.3 Spectral data

2.3.1 Compound 1

Gummy material (1.6 mg, 0.00062%); [α]D 22 – 49.6 (c 0.01, CHCl3); infrared (IR) ʋ max (film)/cm: 3,403, 2,925, 2,853, 1,730, 1,713, 1,655, 1,461, 1,377, 1,264, 1,153; 1H nuclear magnetic resonance (NMR) (CDCl3, 850 MHz) and 13C NMR (CDCl3, 213 MHz) (Table 1); HRESIMS m/z = 520.3758 [M]+ (calculated m/z = 520.3764 for C31H52O6).

Table 1

1H and 13C NMR (850 and 213 MHz) spectral data of compound 1 in CDCl3 a

Carbon no. b δ C δ H (J in Hz) Carbon no. δ C δ H (J in Hz)
1 34.0 (CH2) 1.87, m 16 124.0 (CH) 5.48, dd (3.4, 1.7)
2.01, m
2 26.9 (CH2) 1.67, m 17 160.1 (C)
1.85, m
3 70.9 (CH) 5.13, dddd (11.1, 11.1, 5.1, 5.1) 18 19.4 (CH3) 0.98, s
4 37.4 (CH2) 1.58, m 19 16.9 (CH3) 1.35, s
2.19, m
5 76.4 (C) — 20 75.9 (C)
6 76.2 (CH) 3.55 dd (3.4, 1.7) 21 30.8 (CH) 1.37, s
7 34.6 (CH2) 1.86, m 22 49.3 (CH2) 1.42, m
2.01, m 1.59, m
8 28.1 (CH) 2.05, m 23 31.0 (CH) 1.40, m
9 53.2 (CH) 1.45, m 24 29.8 (CH) 1.60, m
10 40.2 (C) 25 45.5 (CH) 1.04, m
11 68.7 (CH) 3.99, dt (9.4, 5.1) 26 11.7 (CH3) 0.75, d (6.8)
12 48.1 (CH2) 1.49, dd (11.9, 5.1) 27 20.9 (CH3) 0.88 d (6.8)
2.52, dd (11.9, 6.0)
13 48.0 (C) 28 14.2 (CH3) 0.86, d (6.8)
14 56.2 (CH) 1.60, m 29 15.8 (CH3) 0.78, d (6.8)
15 31.0 (CH2) 1.83, m COCH3 170.0 (C)
2.08, ddd (15.3, 6.8, 3.4)
COCH 3 21.5 (CH3) 2.03, s
  1. a

    All data were obtained from 1D and 2D NMR measurements.

  2. b

    Implied multiplicities were determined by DEPT (C = s, CH = d, CH2 = t).

2.3.2 Compound 2

Gummy material (0.5 mg, 0.0002%); [α]D 22 – 81.1 (c 0.01, CHCl3); IR ʋ max (film)/cm: 3,387, 2,958, 2,853, 1,730, 1,674, 1,632, 1,377, 1,146; 1H NMR (CDCl3, 850 MHz); 13C NMR (CDCl3, 213 MHz) (Table 2); HRESIMS m/z = 504.3809 [M]+ (calculated m/z = 504.3815 for C31H52O5).

Table 2

1H and 13C NMR (850 and 213 MHz) spectral data of compound 2 in CDCl3 a

Carbon no. b δ C δ H (J in Hz) Carbon no. δ C δ H (J in Hz)
1 31.9 (CH2) 1.40, m 16 123.7 (CH) 5.48, dd (3.4, 1.7)
1.65, m
2 26.6 (CH2) 1.62, m 17 160.8 (C)
1.88, m
3 71.0 (CH) 5.17, dddd (11.1, 11.1, 5.1, 5.1) 18 18.4 (CH3) 0.99, s
4 37.0 (CH2) 1.68, m 19 16.6 (CH3) 1.23, s
2.18, dd (11.9, 11.1)
5 76.0 (C) — 20 75.9 (C)
6 76.2 (CH) 3.55, dd (3.4, 1.7) 21 29.6 (CH3) 1.37, s
7 34.4 (CH2) 1.60, m 22 49.0 (CH2) 1.49, m
1.76, m 1.56, m
8 28.2 (CH) 1.97, m 23 30.8 (CH) 1.41, m
9 45.7 (CH) 1.38, m 24 29.6 (CH) 1.80, m
10 38.6 (C) 25 45.5 (CH) 1.13, m
11 21.1 (CH2) 1.42, m 26 11.7 (CH3) 0.76, d (6.8)
1.48, m
12 36.1 (CH2) 2.08, m 27 21.6 (CH3) 0.88, d (6.8)
2.08, m
13 47.7 (C) 28 21.0 (CH3) 0.86, d (6.8)
14 57.1 (CH) 1.50, m 29 15.7 (CH3) 0.78, d (6.8)
15 30.9 (CH2) 1.84, dd (17.0, 12.8) COCH3 170.0
2.06, ddd (10.2, 6.8, 3.4)
COCH 3 21.5 2.03, s
  1. a

    All data were obtained from 1D and 2D NMR measurements.

  2. b

    Implied multiplicities were determined by DEPT (C = s, CH = d, CH2 = t).

2.4 Determination of anti-proliferative effect of compounds 1 and 3

The cytotoxicity of the isolated compounds was evaluated against (HepG2, PC-3, and HT-29) human cancer cells using sulphorhodamine B assay (SRB), according to the previously published [8,9].

2.5 AO/EtBr staining for detection of apoptosis

The DNA-binding dyes AO and EtBr have been used for the morphological detection of viable, apoptotic, and necrotic cells. The procedures have been done as previously reported [11,12].

2.6 Statistical analysis

Data are presented as mean and SD. Statistical significance was acceptable to a level of p < 0.05. All statistical analyses were performed using GraphPad Prism software, version 6.00 (GraphPad Software, La Jolla, CA, USA).

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

3 Results and discussion

A Red Sea soft coral specimen, identified as X. umbellata, was extracted with a mixture of organic solvents at room temperature, yielding a viscous oily material (21.4 g). The total extract was evaluated for its cytotoxic effect against HepG2 and displayed cytotoxicity with IC50 (19.74 ± 1.98 μg/mL). The aforementioned promising anti-proliferative results directed the further chemical investigation of the X. umbellata extract. It was subjected to normal-phase silica gel column chromatography and PTLC to give two new steroidal derivatives, compounds 1 and 2 together with a previously identified steroid compound 3 (Figure 1).

Figure 1 Chemical structures of compounds 1–6.
Figure 1

Chemical structures of compounds 1–6.

3.1 Structure elucidation

Compound 1, [α]D 23 = −49.6 (c 0.01, CHCl3), was obtained as a gummy material and had the molecular formula C31H52O6, as determined by high resolution electrospray ionization mass spectrometry (HRESIMS), requiring six degrees of unsaturation. The IR spectrum of 1 showed absorptions due to hydroxyl and acetyl groups (λ max 3,403 and 1,730/cm, respectively). The 13C NMR and distortionless enhancement by polarization transfer (DEPT) spectral data of 1 (Table 1) revealed the presence of 31 carbon atoms (Figure S1g–k), including six non-protonated carbons, nine sp3 methines, one sp2 methine, seven methylenes, and eight methyls. The quaternary carbons were assigned to one carbonyl (δ C 170.0 ppm), two oxygenated (76.4 and 75.9 ppm), and one olefinic (160.1 ppm) along with two in the upfield region (48.0 and 40.2 ppm). The methine carbon included three oxygenated (76.2, 70.9, and 68.7 ppm) and one olefinic (124.0). The total number of methine carbon counts ten after assigning eight methyls (δ H 30.8, 21.5, 20.9, 19.4, 16.9, 15.8, 14.2, and 11.7 ppm) from 1H NMR and heteronuclear single quantum correlation (HSQC) experiments (Figure S1p–r).

The 1H NMR spectra (Figure S1a–f) displayed four tertiary methyls resonating at δ H (0.98, 1.35, 1.37, and 2.03 ppm) and four secondary methyls resonating at δ H [0.75 (d, J = 6.6 Hz), 0.86 (d, J = 6.8 Hz), 0.78 (d, J = 6.8 Hz), and 0.78 (d, J = 6.8 Hz)]. Two unsaturation degrees were accounted as one trisubstituted carbon–carbon double bond (δ H 5.48 and δ C 124.0 and 160.1 ppm) and an acetyl function (δ H 2.03 and δ C 21.5 and 170.0 ppm). Therefore, the remaining four unsaturation degrees suggest a tetracyclic structure for compound 1. The aforementioned information, together with the methylation pattern and several other features appearing in the 1D and 2D NMR spectra, suggested the steroidal nature of 1. The nature of the side chain was determined by the interpretation of the 1H–1H correlated spectroscopy (COSY) spectrum (Figure S1l–o). A sequence of correlations started from the isopropyl proton resonating at δ H 1.04 (H-25) with the signal at 1.60 (H-24), which in turn is correlated with a methyl at 0.86 (H-28) and a methine at 1.40 (H-23) protons, and the later methine is correlated with a methyl at 0.78 (H-29) and a methylene proton of H-22 was observed. The heteronuclear multiple bond correlation (HMBC) correlations from H-21 (1.37, s) to C-20 (75.9), C-22 (49.3), and C-17 (160.1) established the nature of the side chain as 4,5,6-trimethyl-2-heptyl-2-ol moiety (Figure S1s–v). The later deduction furnished the gross structure of 1 as 23,24-dimethylcholest-16-en-pentahydroxy monoacetate. The position of the five hydroxyl groups was deduced from 13C NMR, DEPT, and HSQC spectra. The methine proton resonating at δ H 5.13 (dddd, J = 11.1, 11.1, 5.1, and 5.1 Hz) implies acetylated hydroxyl located at C-3, since this is the sole available location flanked by two methylene groups. 1H–1H COSY and HMBC spectra recognized the positions of the other hydroxyl groups; H-3 and H-19 are both correlated with the quaternary carbon at δ C 76.4 (C-5) ppm as well as this carbon is also correlated with the proton resonating at δ H 3.55 (dd, J = 3.4 and 1.7 Hz, H-6), which implies that positions 5 and 6 are both hydroxylated. The fourth hydroxyl group was decided by observing the signal at δ H 3.99, which appeared as dt with J values 9.4 and 5.1 Hz. This proton could be positioned on several locations within the carboskeleton of 1; however, the HMBC correlations were observed between this proton and the two quaternary carbons at C-10 and C-13. The OH group is positioned on C-11. The fifth hydroxyl group was deduced from the HMBC to be depicted at C-20, based on the correlations between the methyl group resonated at (δ H 1.37, s) and the olefinic proton resonated at δ H 5.48 (dd, J = 3.4 and 1.7 Hz) with the C-20 resonated at δ C 75.9. The relative stereochemistry of 1 was elucidated on the basis of nuclear overhauser effect spectroscopy (NOESY) correlations (Figure S1w–y) and analyses of J values. The multiplicity of the methine assignment at 5.13 ppm had the normal complexity for the 3α-carbinol proton of an A/B trans-steroid. This unusually downshifted signal is typical of 3β-hydroxysterols bearing a 5α-hydroxyl group, which esterified by acetyl moiety [13]. The downshift of the Me-19 signal at 1.35 was indicative of the β-orientation of the C-6 hydroxyl group. The large J-value of H-11 implies its axial orientation and hence α-OH. The strong NOESY correlations between H-3 and H-6 and between Me-19 and H-11 supported the proposed orientations. Since the spectral data of 1 coincided with the reported data and the R configuration was recognized at C-20 [14]. From these data, compound 1 was concluded to be 23,24-dimethylcholest-16-ene-3β,5α,6β,11α,20(R)-pentol 3-monoacetate.

Compound 2, [α]D 22 – 81.1 (c 0.01, CHCl3), was obtained as a gummy substance and had the molecular formula C31H52O5, as determined by HRESIMS, requiring six degrees of unsaturation. The IR spectrum of 1 showed absorptions due to hydroxyl and acetyl groups (λ max 3,387 and 1,730/cm, respectively). The 13C NMR spectroscopical data of 2 (Table 2) revealed the presence of 31 carbon signals, which were identified by assistance of the DEPT spectrum. They were categorized into six quaternary carbons, eight sp3 methines, one sp2 methine, eight methylenes, and eight methyls. Analysis of the spectral data of 2 and comparison with those of 1 revealed the great similarity between both structures. However, the lack of 16 mass unit in mass spectrum and the absence of signals due to CH-11 in the NMR spectra (1H and 13C NMR, DEPT, HSQC, COSY, HMBC, and NOESY) in case of compound 2 allowed the determination of its structure as 23,24-dimethylcholest-16-ene-3β,5α,6β,20(R)-tetrol 3-monoacetate. 3β,5α,6β,11α,20β-Pentahydroxygorgosterol (3) was identified by comparing the measured spectral data with the reported [15].

3.2 Biological activities

In vitro cytotoxicity of compounds 1 and 3 was determined using SRB assay. These activities were assessed against HepG2, PC-3, and HT-29 tumour cell lines over concentration range of 0.01–1,000 μg/mL. Compound 1 showed potent cytotoxic profile against tumour cell lines HepG2, PC-3, and HT-29 with IC50 values of 4.70 ± 0.2, 5.60 ± 0.6, and 4.00 ± 0.4 μg/mL, respectively. On the other hand, compound 3 showed significant cytotoxicity effect against HepG2, PC-3, and HT-29 with IC50 values 22.20 ± 1.0, ≥100, and 99.30 ± 0.9 μg/mL, respectively. Doxorubicin (positive control) displayed cytotoxicity against HepG2, PC-3, and HT-29 with IC50 values of 0.79 ± 0.06, 1.16 ± 0.56, and 1.70 ± 0.16 μg/mL, respectively (Figure 2). After staining the cells with AO/EtBr, the cells appeared in the form of four colours as follows; living cells (green nuclei), early apoptotic (bright green nuclei), late apoptotic (orange-stained nuclei), and necrotic cells (uniformly orange-stained cell nuclei). In AO/EtBr dual staining, the cells were uniformly stained green with normal, round, intact nuclei, and cytoplasm which indicate the viability of the cell control. On the contrary, the highly early apoptotic cell death was observed in all types of treated tumour cells. The late apoptotic cells are highly present in HepG2 cells with compound 3 compared with other cancer cells except for 1, while no necrotic and late apoptotic appeared with HT-29 cells after treatment with compounds 1 and 3. These results were compared with the control without manifestations of cell death (Figure 3).

Figure 2 The dose–response curves of the compounds 1 and 3 cytotoxicity against HepG2, PC-3, and HT-29 human cell lines.
Figure 2

The dose–response curves of the compounds 1 and 3 cytotoxicity against HepG2, PC-3, and HT-29 human cell lines.

Figure 3 Cell apoptosis observed using fluorescence microscope (200×). Cells were treated with IC50S of compounds 1(B) and 3(C) for 48 h. The control (A) was similarly processed. They (A–C) were stained with acridine orange–ethidium bromide.
Figure 3

Cell apoptosis observed using fluorescence microscope (200×). Cells were treated with IC50S of compounds 1(B) and 3(C) for 48 h. The control (A) was similarly processed. They (A–C) were stained with acridine orange–ethidium bromide.

3.3 Biosynthesis of 30-norisodinosterols carbon skeleton

Dinosterol (4), a C-30 sterol isolated from free swimming dinoflagellates, is the biosynthetic precursor to the cyclopropyl-containing sterol gorgosterol (5) (Figure 1) [16]. Despite the reported information, gorgosterol was originally isolated from several gorgonian species and, moreover, was proved to be a symbiont product and was not isolated from the free swimming dinoflagellates [16].

The unsaturation (∆24) was common among the initial tetracyclic precursor, lanosterol and cycloartenol, in all sterol-building organisms. The presence of such unsaturation site renders the molecules prone to decorations by reduction (e.g. formation of cholesterol) and methylation, which started from simple methylation at C-24, may extend to multiple alkylations. This situation was common among marine organisms [17]. A hypothetical biosynthetic pathway of the current isolated norisodinosterol derivatives (1 and 2) could be started with brassicasterol (6) which undergoes methylation by a methyalting agent (mainly S-adenosylmethionine). Then reduction of ∆5 and formation of ∆16 could be performed. A more evidenced route to the biosynthesis of these C-29 sterols (Scheme 1) started from compound 4, which lead to the construction of 30-norisodinosterol skeleton through the reduction of ∆22, demethylation at C-4 and then formation of ∆16. It is worthy to mention that the isolation of 23,24-dimethylchlesta-5,22-dien-3β-ol from the soft coral Sarcophyton elegans supports the speculation that dinosterol is the precursor of compounds 1 and 2 along with the symbiont production nature of these compounds [18].

Scheme 1 Proposed biosynthesis of 30-norisodinosterol.
Scheme 1

Proposed biosynthesis of 30-norisodinosterol.

The compounds isolated in the current manuscript are steroidal derivatives. They are characterized by the presence of four rings arranged in a unambiguous molecular configuration. Multi-functionality gave them unique molecular structures. Consequently, the steroids have potential diversity of bioactivity. Generally, steroids have two common biological functions: as vital components of cell membranes that alter membrane fluidity and as signalling molecules. The isolated steroids showed different chemical functionality and potent anti-proliferative activities. After further pharmacological investigation and mechanistically studies, they may be a lead of anti-cancer drug.

4 Conclusion

Xenia umbellata, a soft coral, was collected from the Red Sea and found to produce two new steroidal derivatives, compounds 1 and 2, together with a known steroid, compound 3. The chemical structures of the isolated compounds were determined by analyses of the measured spectroscopic data. The anti-proliferative activities of compounds 1 and 3 have been evaluated against hepatocellular carcinoma (HepG2), prostate adenocarcinoma (PC-3), and colorectal adenocarcinoma (HT-29) human cell lines. Compound 1 exhibited potent cytotoxic effect against tumour cell lines, HepG2, PC-3, and HT-29. Compounds 1 and 3 displayed late apoptotic effect in HepG2 cells. The anti-proliferative activity of compounds 1–3 warranted further investigation. Extra work should be carried out to establish the chemoecological functions of nordinosterols (1 and 2) and to assess their impact on the host soft coral organism.

Acknowledgements

The authors thank the Deanship of Scientific Research for the technical and financial support.

  1. Funding information: This project was funded by the Deanship of Scientific Research at King Abdulaziz University, Jeddah (grant no J: 14-247-1440).

  2. Author contributions: N. O. B., A. A., and W. M. A. was in charge of the study design, supervised the experimental work, carried out collection and interpretation of the data, literature search and wrote the manuscript; and performed the cytotoxicity and apoptosis experiments. W. M. A. and A. A. equally edited the manuscript.

  3. Supplementary materials: The following are available online. The NMR data (1H, 13C, 1H–1H COSY, HMQC, and HMBC) of compounds 1 and 2.

  4. Conflict of interest: The authors state they have no competing interest.

  5. Data availability statement: All data generated or analysed during this study are included in this published article (and its supplementary information files).

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Received: 2020-08-19
Revised: 2021-01-09
Accepted: 2021-03-01
Published Online: 2021-03-23

© 2021 Nahed Obaid Bawakid et al., published by De Gruyter

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

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  7. Investigating a human pesticide intoxication incident: The importance of robust analytical approaches
  8. Induction of apoptosis and cell cycle arrest by chloroform fraction of Juniperus phoenicea and chemical constituents analysis
  9. Recovery of γ-Fe2O3 from copper ore tailings by magnetization roasting and magnetic separation
  10. Effects of different extraction methods on antioxidant properties of blueberry anthocyanins
  11. Modeling the removal of methylene blue dye using a graphene oxide/TiO2/SiO2 nanocomposite under sunlight irradiation by intelligent system
  12. Antimicrobial and antioxidant activities of Cinnamomum cassia essential oil and its application in food preservation
  13. Full spectrum and genetic algorithm-selected spectrum-based chemometric methods for simultaneous determination of azilsartan medoxomil, chlorthalidone, and azilsartan: Development, validation, and application on commercial dosage form
  14. Evaluation of the performance of immunoblot and immunodot techniques used to identify autoantibodies in patients with autoimmune diseases
  15. Computational studies by molecular docking of some antiviral drugs with COVID-19 receptors are an approach to medication for COVID-19
  16. Synthesis of amides and esters containing furan rings under microwave-assisted conditions
  17. Simultaneous removal efficiency of H2S and CO2 by high-gravity rotating packed bed: Experiments and simulation
  18. Design, synthesis, and biological activities of novel thiophene, pyrimidine, pyrazole, pyridine, coumarin and isoxazole: Dydrogesterone derivatives as antitumor agents
  19. Content and composition analysis of polysaccharides from Blaps rynchopetera and its macrophage phagocytic activity
  20. A new series of 2,4-thiazolidinediones endowed with potent aldose reductase inhibitory activity
  21. Assessing encapsulation of curcumin in cocoliposome: In vitro study
  22. Rare norisodinosterol derivatives from Xenia umbellata: Isolation and anti-proliferative activity
  23. Comparative study of antioxidant and anticancer activities and HPTLC quantification of rutin in white radish (Raphanus sativus L.) leaves and root extracts grown in Saudi Arabia
  24. Comparison of adsorption properties of commercial silica and rice husk ash (RHA) silica: A study by NIR spectroscopy
  25. Sodium borohydride (NaBH4) as a high-capacity material for next-generation sodium-ion capacitors
  26. Aroma components of tobacco powder from different producing areas based on gas chromatography ion mobility spectrometry
  27. The effects of salinity on changes in characteristics of soils collected in a saline region of the Mekong Delta, Vietnam
  28. Synthesis, properties, and activity of MoVTeNbO catalysts modified by zirconia-pillared clays in oxidative dehydrogenation of ethane
  29. Synthesis and crystal structure of N,N′-bis(4-chlorophenyl)thiourea N,N-dimethylformamide
  30. Quantitative analysis of volatile compounds of four Chinese traditional liquors by SPME-GC-MS and determination of total phenolic contents and antioxidant activities
  31. A novel separation method of the valuable components for activated clay production wastewater
  32. On ve-degree- and ev-degree-based topological properties of crystallographic structure of cuprite Cu2O
  33. Antihyperglycemic effect and phytochemical investigation of Rubia cordifolia (Indian Madder) leaves extract
  34. Microsphere molecularly imprinted solid-phase extraction for diazepam analysis using itaconic acid as a monomer in propanol
  35. A nitric oxide-releasing prodrug promotes apoptosis in human renal carcinoma cells: Involvement of reactive oxygen species
  36. Machine vision-based driving and feedback scheme for digital microfluidics system
  37. Study on the application of a steam-foam drive profile modification technology for heavy oil reservoir development
  38. Ni–Ru-containing mixed oxide-based composites as precursors for ethanol steam reforming catalysts: Effect of the synthesis methods on the structural and catalytic properties
  39. Preparation of composite soybean straw-based materials by LDHs modifying as a solid sorbent for removal of Pb(ii) from water samples
  40. Synthesis and spectral characterizations of vanadyl(ii) and chromium(iii) mixed ligand complexes containing metformin drug and glycine amino acid
  41. In vitro evaluation of lactic acid bacteria with probiotic activity isolated from local pickled leaf mustard from Wuwei in Anhui as substitutes for chemical synthetic additives
  42. Utilization and simulation of innovative new binuclear Co(ii), Ni(ii), Cu(ii), and Zn(ii) diimine Schiff base complexes in sterilization and coronavirus resistance (Covid-19)
  43. Phosphorylation of Pit-1 by cyclin-dependent kinase 5 at serine 126 is associated with cell proliferation and poor prognosis in prolactinomas
  44. Molecularly imprinted membrane for transport of urea, creatinine, and vitamin B12 as a hemodialysis candidate membrane
  45. Optimization of Murrayafoline A ethanol extraction process from the roots of Glycosmis stenocarpa, and evaluation of its Tumorigenesis inhibition activity on Hep-G2 cells
  46. Highly sensitive determination of α-lipoic acid in pharmaceuticals on a boron-doped diamond electrode
  47. Synthesis, chemo-informatics, and anticancer evaluation of fluorophenyl-isoxazole derivatives
  48. In vitro and in vivo investigation of polypharmacology of propolis extract as anticancer, antibacterial, anti-inflammatory, and chemical properties
  49. Topological indices of bipolar fuzzy incidence graph
  50. Preparation of Fe3O4@SiO2–ZnO catalyst and its catalytic synthesis of rosin glycol ester
  51. Construction of a new luminescent Cd(ii) compound for the detection of Fe3+ and treatment of Hepatitis B
  52. Investigation of bovine serum albumin aggregation upon exposure to silver(i) and copper(ii) metal ions using Zetasizer
  53. Discoloration of methylene blue at neutral pH by heterogeneous photo-Fenton-like reactions using crystalline and amorphous iron oxides
  54. Optimized extraction of polyphenols from leaves of Rosemary (Rosmarinus officinalis L.) grown in Lam Dong province, Vietnam, and evaluation of their antioxidant capacity
  55. Synthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents
  56. Potency and selectivity indices of Myristica fragrans Houtt. mace chloroform extract against non-clinical and clinical human pathogens
  57. Simple modifications of nicotinic, isonicotinic, and 2,6-dichloroisonicotinic acids toward new weapons against plant diseases
  58. Synthesis, optical and structural characterisation of ZnS nanoparticles derived from Zn(ii) dithiocarbamate complexes
  59. Presence of short and cyclic peptides in Acacia and Ziziphus honeys may potentiate their medicinal values
  60. The role of vitamin D deficiency and elevated inflammatory biomarkers as risk factors for the progression of diabetic nephropathy in patients with type 2 diabetes mellitus
  61. Quantitative structure–activity relationship study on prolonged anticonvulsant activity of terpene derivatives in pentylenetetrazole test
  62. GADD45B induced the enhancing of cell viability and proliferation in radiotherapy and increased the radioresistance of HONE1 cells
  63. Cannabis sativa L. chemical compositions as potential plasmodium falciparum dihydrofolate reductase-thymidinesynthase enzyme inhibitors: An in silico study for drug development
  64. Dynamics of λ-cyhalothrin disappearance and expression of selected P450 genes in bees depending on the ambient temperature
  65. Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques
  66. Study on the speciation of arsenic in the genuine medicinal material honeysuckle
  67. Two Cu(ii)-based coordination polymers: Crystal structures and treatment activity on periodontitis
  68. Conversion of furfuryl alcohol to ethyl levulinate in the presence of mesoporous aluminosilicate catalyst
  69. Review Articles
  70. Hsien Wu and his major contributions to the chemical era of immunology
  71. Overview of the major classes of new psychoactive substances, psychoactive effects, analytical determination and conformational analysis of selected illegal drugs
  72. An overview of persistent organic pollutants along the coastal environment of Kuwait
  73. Mechanism underlying sevoflurane-induced protection in cerebral ischemia–reperfusion injury
  74. COVID-19 and SARS-CoV-2: Everything we know so far – A comprehensive review
  75. Challenge of diabetes mellitus and researchers’ contributions to its control
  76. Advances in the design and application of transition metal oxide-based supercapacitors
  77. Color and composition of beauty products formulated with lemongrass essential oil: Cosmetics formulation with lemongrass essential oil
  78. The structural chemistry of zinc(ii) and nickel(ii) dithiocarbamate complexes
  79. Bioprospecting for antituberculosis natural products – A review
  80. Recent progress in direct urea fuel cell
  81. Rapid Communications
  82. A comparative morphological study of titanium dioxide surface layer dental implants
  83. Changes in the antioxidative properties of honeys during their fermentation
  84. Erratum
  85. Erratum to “Corrosion study of copper in aqueous sulfuric acid solution in the presence of (2E,5E)-2,5-dibenzylidenecyclopentanone and (2E,5E)-bis[(4-dimethylamino)benzylidene]cyclopentanone: Experimental and theoretical study”
  86. Erratum to “Modified TDAE petroleum plasticiser”
  87. Corrigendum
  88. Corrigendum to “A nitric oxide-releasing prodrug promotes apoptosis in human renal carcinoma cells: Involvement of reactive oxygen species”
  89. Special Issue on 3rd IC3PE 2020
  90. Visible light-responsive photocatalyst of SnO2/rGO prepared using Pometia pinnata leaf extract
  91. Antihyperglycemic activity of Centella asiatica (L.) Urb. leaf ethanol extract SNEDDS in zebrafish (Danio rerio)
  92. Selection of oil extraction process from Chlorella species of microalgae by using multi-criteria decision analysis technique for biodiesel production
  93. Special Issue on the 14th Joint Conference of Chemistry (14JCC)
  94. Synthesis and in vitro cytotoxicity evaluation of isatin-pyrrole derivatives against HepG2 cell line
  95. CO2 gas separation using mixed matrix membranes based on polyethersulfone/MIL-100(Al)
  96. Effect of synthesis and activation methods on the character of CoMo/ultrastable Y-zeolite catalysts
  97. Special Issue on Electrochemical Amplified Sensors
  98. Enhancement of graphene oxide through β-cyclodextrin composite to sensitive analysis of an antidepressant: Sulpiride
  99. Investigation of the spectroelectrochemical behavior of quercetin isolated from Zanthoxylum bungeanum
  100. An electrochemical sensor for high sensitive determination of lysozyme based on the aptamer competition approach
  101. An improved non-enzymatic electrochemical sensor amplified with CuO nanostructures for sensitive determination of uric acid
  102. Special Issue on Applied Biochemistry and Biotechnology 2020
  103. Fast discrimination of avocado oil for different extracted methods using headspace-gas chromatography-ion mobility spectroscopy with PCA based on volatile organic compounds
  104. Effect of alkali bases on the synthesis of ZnO quantum dots
  105. Quality evaluation of Cabernet Sauvignon wines in different vintages by 1H nuclear magnetic resonance-based metabolomics
  106. Special Issue on the Joint Science Congress of Materials and Polymers (ISCMP 2019)
  107. Diatomaceous Earth: Characterization, thermal modification, and application
  108. Electrochemical determination of atenolol and propranolol using a carbon paste sensor modified with natural ilmenite
  109. Special Issue on the Conference of Energy, Fuels, Environment 2020
  110. Assessment of the mercury contamination of landfilled and recovered foundry waste – a case study
  111. Primary energy consumption in selected EU Countries compared to global trends
  112. Modified TDAE petroleum plasticiser
  113. Use of glycerol waste in lactic acid bacteria metabolism for the production of lactic acid: State of the art in Poland
  114. Topical Issue on Applications of Mathematics in Chemistry
  115. Theoretical study of energy, inertia and nullity of phenylene and anthracene
  116. Banhatti, revan and hyper-indices of silicon carbide Si2C3-III[n,m]
  117. Topical Issue on Agriculture
  118. Occurrence of mycotoxins in selected agricultural and commercial products available in eastern Poland
  119. Special Issue on Ethnobotanical, Phytochemical and Biological Investigation of Medicinal Plants
  120. Acute and repeated dose 60-day oral toxicity assessment of chemically characterized Berberis hispanica Boiss. and Reut in Wistar rats
  121. Phytochemical profile, in vitro antioxidant, and anti-protein denaturation activities of Curcuma longa L. rhizome and leaves
  122. Antiplasmodial potential of Eucalyptus obliqua leaf methanolic extract against Plasmodium vivax: An in vitro study
  123. Prunus padus L. bark as a functional promoting component in functional herbal infusions – cyclooxygenase-2 inhibitory, antioxidant, and antimicrobial effects
  124. Molecular and docking studies of tetramethoxy hydroxyflavone compound from Artemisia absinthium against carcinogens found in cigarette smoke
  125. Special Issue on the Joint Science Congress of Materials and Polymers (ISCMP 2020)
  126. Preparation of cypress (Cupressus sempervirens L.) essential oil loaded poly(lactic acid) nanofibers
  127. Influence of mica mineral on flame retardancy and mechanical properties of intumescent flame retardant polypropylene composites
  128. Production and characterization of thermoplastic elastomer foams based on the styrene–ethylene–butylene–styrene (SEBS) rubber and thermoplastic material
  129. Special Issue on Applied Chemistry in Agriculture and Food Science
  130. Impact of essential oils on the development of pathogens of the Fusarium genus and germination parameters of selected crops
  131. Yield, volume, quality, and reduction of biotic stress influenced by titanium application in oilseed rape, winter wheat, and maize cultivations
  132. Influence of potato variety on polyphenol profile composition and glycoalcaloid contents of potato juice
  133. Carryover effect of direct-fed microbial supplementation and early weaning on the growth performance and carcass characteristics of growing Najdi lambs
  134. Special Issue on Applied Biochemistry and Biotechnology (ABB 2021)
  135. The electrochemical redox mechanism and antioxidant activity of polyphenolic compounds based on inlaid multi-walled carbon nanotubes-modified graphite electrode
  136. Study of an adsorption method for trace mercury based on Bacillus subtilis
  137. Special Issue on The 1st Malaysia International Conference on Nanotechnology & Catalysis (MICNC2021)
  138. Mitigating membrane biofouling in biofuel cell system – A review
  139. Mechanical properties of polymeric biomaterials: Modified ePTFE using gamma irradiation
https://doi.org/10.1515/chem-2021-0038
Keywords for this article
Red Sea; Alcyonacea; steroids; cytotoxicity; apoptosis
Creative Commons
BY 4.0

Articles in the same Issue

  1. Regular Articles
  2. Qualitative and semi-quantitative assessment of anthocyanins in Tibetan hulless barley from different geographical locations by UPLC-QTOF-MS and their antioxidant capacities
  3. Effect of sodium chloride on the expression of genes involved in the salt tolerance of Bacillus sp. strain “SX4” isolated from salinized greenhouse soil
  4. GC-MS analysis of mango stem bark extracts (Mangifera indica L.), Haden variety. Possible contribution of volatile compounds to its health effects
  5. Influence of nanoscale-modified apatite-type calcium phosphates on the biofilm formation by pathogenic microorganisms
  6. Removal of paracetamol from aqueous solution by containment composites
  7. Investigating a human pesticide intoxication incident: The importance of robust analytical approaches
  8. Induction of apoptosis and cell cycle arrest by chloroform fraction of Juniperus phoenicea and chemical constituents analysis
  9. Recovery of γ-Fe2O3 from copper ore tailings by magnetization roasting and magnetic separation
  10. Effects of different extraction methods on antioxidant properties of blueberry anthocyanins
  11. Modeling the removal of methylene blue dye using a graphene oxide/TiO2/SiO2 nanocomposite under sunlight irradiation by intelligent system
  12. Antimicrobial and antioxidant activities of Cinnamomum cassia essential oil and its application in food preservation
  13. Full spectrum and genetic algorithm-selected spectrum-based chemometric methods for simultaneous determination of azilsartan medoxomil, chlorthalidone, and azilsartan: Development, validation, and application on commercial dosage form
  14. Evaluation of the performance of immunoblot and immunodot techniques used to identify autoantibodies in patients with autoimmune diseases
  15. Computational studies by molecular docking of some antiviral drugs with COVID-19 receptors are an approach to medication for COVID-19
  16. Synthesis of amides and esters containing furan rings under microwave-assisted conditions
  17. Simultaneous removal efficiency of H2S and CO2 by high-gravity rotating packed bed: Experiments and simulation
  18. Design, synthesis, and biological activities of novel thiophene, pyrimidine, pyrazole, pyridine, coumarin and isoxazole: Dydrogesterone derivatives as antitumor agents
  19. Content and composition analysis of polysaccharides from Blaps rynchopetera and its macrophage phagocytic activity
  20. A new series of 2,4-thiazolidinediones endowed with potent aldose reductase inhibitory activity
  21. Assessing encapsulation of curcumin in cocoliposome: In vitro study
  22. Rare norisodinosterol derivatives from Xenia umbellata: Isolation and anti-proliferative activity
  23. Comparative study of antioxidant and anticancer activities and HPTLC quantification of rutin in white radish (Raphanus sativus L.) leaves and root extracts grown in Saudi Arabia
  24. Comparison of adsorption properties of commercial silica and rice husk ash (RHA) silica: A study by NIR spectroscopy
  25. Sodium borohydride (NaBH4) as a high-capacity material for next-generation sodium-ion capacitors
  26. Aroma components of tobacco powder from different producing areas based on gas chromatography ion mobility spectrometry
  27. The effects of salinity on changes in characteristics of soils collected in a saline region of the Mekong Delta, Vietnam
  28. Synthesis, properties, and activity of MoVTeNbO catalysts modified by zirconia-pillared clays in oxidative dehydrogenation of ethane
  29. Synthesis and crystal structure of N,N′-bis(4-chlorophenyl)thiourea N,N-dimethylformamide
  30. Quantitative analysis of volatile compounds of four Chinese traditional liquors by SPME-GC-MS and determination of total phenolic contents and antioxidant activities
  31. A novel separation method of the valuable components for activated clay production wastewater
  32. On ve-degree- and ev-degree-based topological properties of crystallographic structure of cuprite Cu2O
  33. Antihyperglycemic effect and phytochemical investigation of Rubia cordifolia (Indian Madder) leaves extract
  34. Microsphere molecularly imprinted solid-phase extraction for diazepam analysis using itaconic acid as a monomer in propanol
  35. A nitric oxide-releasing prodrug promotes apoptosis in human renal carcinoma cells: Involvement of reactive oxygen species
  36. Machine vision-based driving and feedback scheme for digital microfluidics system
  37. Study on the application of a steam-foam drive profile modification technology for heavy oil reservoir development
  38. Ni–Ru-containing mixed oxide-based composites as precursors for ethanol steam reforming catalysts: Effect of the synthesis methods on the structural and catalytic properties
  39. Preparation of composite soybean straw-based materials by LDHs modifying as a solid sorbent for removal of Pb(ii) from water samples
  40. Synthesis and spectral characterizations of vanadyl(ii) and chromium(iii) mixed ligand complexes containing metformin drug and glycine amino acid
  41. In vitro evaluation of lactic acid bacteria with probiotic activity isolated from local pickled leaf mustard from Wuwei in Anhui as substitutes for chemical synthetic additives
  42. Utilization and simulation of innovative new binuclear Co(ii), Ni(ii), Cu(ii), and Zn(ii) diimine Schiff base complexes in sterilization and coronavirus resistance (Covid-19)
  43. Phosphorylation of Pit-1 by cyclin-dependent kinase 5 at serine 126 is associated with cell proliferation and poor prognosis in prolactinomas
  44. Molecularly imprinted membrane for transport of urea, creatinine, and vitamin B12 as a hemodialysis candidate membrane
  45. Optimization of Murrayafoline A ethanol extraction process from the roots of Glycosmis stenocarpa, and evaluation of its Tumorigenesis inhibition activity on Hep-G2 cells
  46. Highly sensitive determination of α-lipoic acid in pharmaceuticals on a boron-doped diamond electrode
  47. Synthesis, chemo-informatics, and anticancer evaluation of fluorophenyl-isoxazole derivatives
  48. In vitro and in vivo investigation of polypharmacology of propolis extract as anticancer, antibacterial, anti-inflammatory, and chemical properties
  49. Topological indices of bipolar fuzzy incidence graph
  50. Preparation of Fe3O4@SiO2–ZnO catalyst and its catalytic synthesis of rosin glycol ester
  51. Construction of a new luminescent Cd(ii) compound for the detection of Fe3+ and treatment of Hepatitis B
  52. Investigation of bovine serum albumin aggregation upon exposure to silver(i) and copper(ii) metal ions using Zetasizer
  53. Discoloration of methylene blue at neutral pH by heterogeneous photo-Fenton-like reactions using crystalline and amorphous iron oxides
  54. Optimized extraction of polyphenols from leaves of Rosemary (Rosmarinus officinalis L.) grown in Lam Dong province, Vietnam, and evaluation of their antioxidant capacity
  55. Synthesis of novel thiourea-/urea-benzimidazole derivatives as anticancer agents
  56. Potency and selectivity indices of Myristica fragrans Houtt. mace chloroform extract against non-clinical and clinical human pathogens
  57. Simple modifications of nicotinic, isonicotinic, and 2,6-dichloroisonicotinic acids toward new weapons against plant diseases
  58. Synthesis, optical and structural characterisation of ZnS nanoparticles derived from Zn(ii) dithiocarbamate complexes
  59. Presence of short and cyclic peptides in Acacia and Ziziphus honeys may potentiate their medicinal values
  60. The role of vitamin D deficiency and elevated inflammatory biomarkers as risk factors for the progression of diabetic nephropathy in patients with type 2 diabetes mellitus
  61. Quantitative structure–activity relationship study on prolonged anticonvulsant activity of terpene derivatives in pentylenetetrazole test
  62. GADD45B induced the enhancing of cell viability and proliferation in radiotherapy and increased the radioresistance of HONE1 cells
  63. Cannabis sativa L. chemical compositions as potential plasmodium falciparum dihydrofolate reductase-thymidinesynthase enzyme inhibitors: An in silico study for drug development
  64. Dynamics of λ-cyhalothrin disappearance and expression of selected P450 genes in bees depending on the ambient temperature
  65. Identification of synthetic cannabinoid methyl 2-{[1-(cyclohexylmethyl)-1H-indol-3-yl] formamido}-3-methylbutanoate using modern mass spectrometry and nuclear magnetic resonance techniques
  66. Study on the speciation of arsenic in the genuine medicinal material honeysuckle
  67. Two Cu(ii)-based coordination polymers: Crystal structures and treatment activity on periodontitis
  68. Conversion of furfuryl alcohol to ethyl levulinate in the presence of mesoporous aluminosilicate catalyst
  69. Review Articles
  70. Hsien Wu and his major contributions to the chemical era of immunology
  71. Overview of the major classes of new psychoactive substances, psychoactive effects, analytical determination and conformational analysis of selected illegal drugs
  72. An overview of persistent organic pollutants along the coastal environment of Kuwait
  73. Mechanism underlying sevoflurane-induced protection in cerebral ischemia–reperfusion injury
  74. COVID-19 and SARS-CoV-2: Everything we know so far – A comprehensive review
  75. Challenge of diabetes mellitus and researchers’ contributions to its control
  76. Advances in the design and application of transition metal oxide-based supercapacitors
  77. Color and composition of beauty products formulated with lemongrass essential oil: Cosmetics formulation with lemongrass essential oil
  78. The structural chemistry of zinc(ii) and nickel(ii) dithiocarbamate complexes
  79. Bioprospecting for antituberculosis natural products – A review
  80. Recent progress in direct urea fuel cell
  81. Rapid Communications
  82. A comparative morphological study of titanium dioxide surface layer dental implants
  83. Changes in the antioxidative properties of honeys during their fermentation
  84. Erratum
  85. Erratum to “Corrosion study of copper in aqueous sulfuric acid solution in the presence of (2E,5E)-2,5-dibenzylidenecyclopentanone and (2E,5E)-bis[(4-dimethylamino)benzylidene]cyclopentanone: Experimental and theoretical study”
  86. Erratum to “Modified TDAE petroleum plasticiser”
  87. Corrigendum
  88. Corrigendum to “A nitric oxide-releasing prodrug promotes apoptosis in human renal carcinoma cells: Involvement of reactive oxygen species”
  89. Special Issue on 3rd IC3PE 2020
  90. Visible light-responsive photocatalyst of SnO2/rGO prepared using Pometia pinnata leaf extract
  91. Antihyperglycemic activity of Centella asiatica (L.) Urb. leaf ethanol extract SNEDDS in zebrafish (Danio rerio)
  92. Selection of oil extraction process from Chlorella species of microalgae by using multi-criteria decision analysis technique for biodiesel production
  93. Special Issue on the 14th Joint Conference of Chemistry (14JCC)
  94. Synthesis and in vitro cytotoxicity evaluation of isatin-pyrrole derivatives against HepG2 cell line
  95. CO2 gas separation using mixed matrix membranes based on polyethersulfone/MIL-100(Al)
  96. Effect of synthesis and activation methods on the character of CoMo/ultrastable Y-zeolite catalysts
  97. Special Issue on Electrochemical Amplified Sensors
  98. Enhancement of graphene oxide through β-cyclodextrin composite to sensitive analysis of an antidepressant: Sulpiride
  99. Investigation of the spectroelectrochemical behavior of quercetin isolated from Zanthoxylum bungeanum
  100. An electrochemical sensor for high sensitive determination of lysozyme based on the aptamer competition approach
  101. An improved non-enzymatic electrochemical sensor amplified with CuO nanostructures for sensitive determination of uric acid
  102. Special Issue on Applied Biochemistry and Biotechnology 2020
  103. Fast discrimination of avocado oil for different extracted methods using headspace-gas chromatography-ion mobility spectroscopy with PCA based on volatile organic compounds
  104. Effect of alkali bases on the synthesis of ZnO quantum dots
  105. Quality evaluation of Cabernet Sauvignon wines in different vintages by 1H nuclear magnetic resonance-based metabolomics
  106. Special Issue on the Joint Science Congress of Materials and Polymers (ISCMP 2019)
  107. Diatomaceous Earth: Characterization, thermal modification, and application
  108. Electrochemical determination of atenolol and propranolol using a carbon paste sensor modified with natural ilmenite
  109. Special Issue on the Conference of Energy, Fuels, Environment 2020
  110. Assessment of the mercury contamination of landfilled and recovered foundry waste – a case study
  111. Primary energy consumption in selected EU Countries compared to global trends
  112. Modified TDAE petroleum plasticiser
  113. Use of glycerol waste in lactic acid bacteria metabolism for the production of lactic acid: State of the art in Poland
  114. Topical Issue on Applications of Mathematics in Chemistry
  115. Theoretical study of energy, inertia and nullity of phenylene and anthracene
  116. Banhatti, revan and hyper-indices of silicon carbide Si2C3-III[n,m]
  117. Topical Issue on Agriculture
  118. Occurrence of mycotoxins in selected agricultural and commercial products available in eastern Poland
  119. Special Issue on Ethnobotanical, Phytochemical and Biological Investigation of Medicinal Plants
  120. Acute and repeated dose 60-day oral toxicity assessment of chemically characterized Berberis hispanica Boiss. and Reut in Wistar rats
  121. Phytochemical profile, in vitro antioxidant, and anti-protein denaturation activities of Curcuma longa L. rhizome and leaves
  122. Antiplasmodial potential of Eucalyptus obliqua leaf methanolic extract against Plasmodium vivax: An in vitro study
  123. Prunus padus L. bark as a functional promoting component in functional herbal infusions – cyclooxygenase-2 inhibitory, antioxidant, and antimicrobial effects
  124. Molecular and docking studies of tetramethoxy hydroxyflavone compound from Artemisia absinthium against carcinogens found in cigarette smoke
  125. Special Issue on the Joint Science Congress of Materials and Polymers (ISCMP 2020)
  126. Preparation of cypress (Cupressus sempervirens L.) essential oil loaded poly(lactic acid) nanofibers
  127. Influence of mica mineral on flame retardancy and mechanical properties of intumescent flame retardant polypropylene composites
  128. Production and characterization of thermoplastic elastomer foams based on the styrene–ethylene–butylene–styrene (SEBS) rubber and thermoplastic material
  129. Special Issue on Applied Chemistry in Agriculture and Food Science
  130. Impact of essential oils on the development of pathogens of the Fusarium genus and germination parameters of selected crops
  131. Yield, volume, quality, and reduction of biotic stress influenced by titanium application in oilseed rape, winter wheat, and maize cultivations
  132. Influence of potato variety on polyphenol profile composition and glycoalcaloid contents of potato juice
  133. Carryover effect of direct-fed microbial supplementation and early weaning on the growth performance and carcass characteristics of growing Najdi lambs
  134. Special Issue on Applied Biochemistry and Biotechnology (ABB 2021)
  135. The electrochemical redox mechanism and antioxidant activity of polyphenolic compounds based on inlaid multi-walled carbon nanotubes-modified graphite electrode
  136. Study of an adsorption method for trace mercury based on Bacillus subtilis
  137. Special Issue on The 1st Malaysia International Conference on Nanotechnology & Catalysis (MICNC2021)
  138. Mitigating membrane biofouling in biofuel cell system – A review
  139. Mechanical properties of polymeric biomaterials: Modified ePTFE using gamma irradiation
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