Home Synthesis of (±)-3,4-dimethoxybenzyl-4-methyloctanoate as a novel internal standard for capsinoid determination by HPLC-ESI-MS/MS(QTOF)
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Synthesis of (±)-3,4-dimethoxybenzyl-4-methyloctanoate as a novel internal standard for capsinoid determination by HPLC-ESI-MS/MS(QTOF)

  • O Fayos , GF Barbero , M Savirón , J Orduna , AG Durán , M Palma , JMG Molinillo , FA Macías , CG Barroso , C Mallor and A Garcés-Claver EMAIL logo
Published/Copyright: February 21, 2018
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Open Chemistry
From the journal Open Chemistry Volume 16 Issue 1

Abstract

Capsinoids exhibit health-promoting properties and are therefore compounds of interest for medical and food sciences. They are minor compounds present in relatively high concentrations in only a few number of pepper cultivars. It is desirable to quantify capsinoids to provide selected cultivars with high capsinoid contents, which can then be employed as health food product. Quantifying low concentrations of capsinoids from pepper fruit requires a precise and selective analytical technique such as HPLC coupled to electrospray ionization - mass spectrometry, with development of an internal standard essential. In this work, the synthesis method of a novel compound analogue of capsinoids, the (±)-3,4-dimethoxybenzyl-4-methyloctanoate, which could be a suitable internal standard for capsinoid determination by electrospray ionization - mass spectrometry is described.

(±)-3,4-dimethoxybenzyl-4-methyloctanoate was stable under the analysis conditions and exerted chemical and physical properties similar to those of capsinoids. This internal standard will provide an accurate capsinoid determination by electrospray ionization - mass spectrometry, thus facilitating the pepper breeding programs, screening pepper cultivars and a better understanding of capsinoid biosynthetic pathway.

Graphical Abstract

Keywords: Capsiate; dihydrocapsiate; DMBO; fragmentation pattern; HPLC-MS/MS; internal standard; synthesis method

1 Introduction

Capsinoids are analogues to capsaicinoids, these are the main compounds responsible for pungency in pepper fruits (Capsicum spp.), and both are exclusively produced by fruits of this genus [1,2,3,4,5,6,7]. Although capsinoids also contribute to this effect, they are approximately 1,000 times less pungent than capsaicinoids [7]. Capsinoids are similar in structure to capsaicinoids, with the exception of an ester bond in the place of an amide bond found in capsaicinoids [8]. Until now, three capsinoids have been identified in nature: capsiate, dihydrocapsiate, and nordihydrocapsiate, with the first two the most common [8,9]. Both, capsaicinoids and capsinoids are powerful biocompounds with health-promoting properties, such as anti-oxidant, antiinflammatory, anti-obesity, and analgesic activities [10,11,12,13]. They are also used in arthritis treatments, digestive disorders or in some diseases like cancer, among others [14,15,16,17]. The advantage of capsinoids over capsaicinoids is that these do not present side effects like irritancy or a burning feeling [18,19]. Therefore, capsinoids could have a greater application range both in medical field and in food sciences, in the development of new drugs for long-term treatments or functional foods. In this regard, identifying pepper cultivars with high capsinoid content becomes really attractive for human consumption, pharmaceutical purposes and pepper breeding programs.

The analytical techniques used, routinely in laboratories, for capsinoid determination are high performance liquid chromatography (HPLC) coupled to UV or PDA/DAD detectors [2,3,4,20]. Since capsinoids and capsaicinoids are measured at the same wavelength (280 nm), their concentration could be overestimated by these techniques, which are based only on retention time and UV spectra, and could assign erroneously a peak to a given capsinoid. A promising high-resolution detection technique such as electrospray ionization (ESI)-mass spectrometry (MS) in combination with HPLC, would enable a more accurate, precise, and sensitive analysis of these compounds. This technique allows an unequivocal identification of compounds by exact mass-to-charge ratio (m/z), molecular formula and fragmentation pattern, all of them distinctive features for each compound [21,22,23,24]. Nevertheless, the addition of an internal standard (IS) to the sample is of crucial importance in order to improve the analytical parameters, avoid ionization fluctuations of analytes, and correct errors in detection [21,22,23,24,25,26,27]. Currently, there are not any commercially available internal standards for capsinoid analysis by HPLC-ESI-MS. Isotope-labeled analogues could be the internal standards. However, they have disadvantages, such as their scarce availability and high price. Thus, chemical synthesis is an interesting alternative to isotopic labelling for obtaining new synthetic analogues to capsinoids [22,28].

In this report, we describe for first time a simple synthesis approach of the (±)-3,4-dimethoxybenzyl-4-methyloctanoate ((±)-DMBO), a novel synthetic analogue to capsinoids, and their potential use as IS for capsiate and dihydrocapsiate determination by HPLC-ESI-MS(QTOF).

2 Materials and methods

2.1 Chemicals and reagents

For (±)-DMBO synthesis: 3,4-dimethoxybenzaldehyde (99%) (1), and (±)-4-methyloctanoic acid (98%) (3), and di-isobutyl aluminium hydride (1 mol L-1 in toluene) (DIBAL) were purchased from Sigma-Aldrich Chemical Co. (St. Louis, MO, USA). Sodium sulphate anhydrous (99%), dehydrated pyridine (99%), and tetrahydrofuran (THF) (99.5%) were purchased from Panreac Química S.L.U. (Barcelona, Spain). Ethyl acetate, methanol, and hexane, all of them HPLC grade, were procured from Scharlab S.L. (Barcelona, Spain). Thionyl chloride (SOCl2) (99%) was purchased from Merck Schuchardt OHG (Hohenbrunn, Germany). Capsiate and dihydrocapsiate standards were supplied by the Department of Organic Chemistry at the University of Cádiz, Spain. All standard solutions were prepared with analytical grade type I water (Milli-Q Synthesis, Millipore, Bedford, MA).

2.2 General experimental procedures

The synthesis of (±)-DMBO (5) was accomplished in three stages: reduction of the 3,4-dimethoxybenzaldehyde (1) carbonyl group, chloride formation from (±)-4-methyloctanoic acid (3) and esterification of 3,4-dimethoxybenzyl alcohol (2) with (±)-4-methyloctanoyl chloride (4).

The (±)-DMBO purity was determined by 1H NMR and 13C NMR analysis. 1H and 13C spectra were recorded using deuterated chloroform (CDCl3) (99.8%, Sigma-Aldrich Chemical Co. St. Louis, MO, USA) as the solvent, on an Agilent INOVA spectrometer (Agilent Technologies, Santa Clara, CA, USA) at 499.719 and 125.654 MHz, respectively. The resonances of residual chloroform for 1H and 13C were set to δH 7.25 ppm and δC 77.00 ppm, respectively, and used as internal reference. UV-Vis spectra were obtained by using a Varian Cary 50 BIO spectrophotometer (Agilent Technologies) with chloroform as the solvent. General IR spectra (KBr) were recorded on a Perkin-Elmer FT-IR Spectrum 2 spectrophotometer (PerkinElmer, Waltham, MA, USA). The reactions were monitored by thin-layer chromatography (TLC) on silica gel (F245 Merck plates).

2.3 HPLC-ESI-MS and ESI-MS/MS(QTOF) analysis

Individual standard solutions in 60% methanol (20 μmol L-1 for (±)-DMBO and 10 μmol L-1 for capsiate and dihydrocapsiate) were introduced by direct injection with a syringe pump (Cole-Parmer Instrument Co., Vernon Hills, IL, USA) operating at 4 μL min-1, in a Quadrupole Time-of-Flight (QTOF) mass spectrometer equipped with an Electrospray Ionization Source (ESI) (MicrOTOF-Q, Bruker Daltonics, Bremen, Germany). ESI-MS(QTOF) and ESI-MS/MS(QTOF) analysis were carried out in positive-ion mode, with capillary and endplate offset voltages of 4500 and -500 V, respectively, and using N2 as the collision gas. The collision cell energy was set to 10 eV, with an isolation width for the precursor ion of 2 mass-to-charge ratio (m/z) units. The nebulizer gas (N2) pressure, the drying gas (N2) flow rate and the drying gas temperature were 1.6 bar, 8.0 L min-1 and 200 o̱C, respectively. Spectra were acquired in the m/z 50–800 range. The mass axis was calibrated by using Na-formate adducts [10 mmol L-1 NaOH, 2.5% (v/v) formic acid and 50% (v/v) 2-propanol] that were introduced through a divert valve at the beginning of each direct injection. For MS/MS spectra the [M+Na]+ ions with m/z values of 329 and 331 m/z for capsiate and dihydrocapsiate and (±)-DMBO, respectively, were chosen as precursors, with an isolation width of 4 m/z units and an amplitude voltage of 0.45 V. The structures of capsiate, (±)-DMBO, and dihydrocapsiate are shown in Table 1. Bruker Daltonik software packages micrOTOF Control v.2.3 and HyStar v.3.2 were used to control the system. Data Analysis v.4.0 was used to process data. Capsiate, (±)-DMBO, and dihydrocapsiate standards were detected by coupling the HPLC instrument to the QTOF mass spectrometer. Chromatographic separation was performed on an Agilent 1100 series HPLC system (Agilent Technologies, Waldbron, Germany) equipped with an isocratic pump, an autosampler, and a thermostated column compartment. The column used was an analytical HPLC C18 column (Symmetry® C18, 2.1 × 150 mm; 3.5 μm spherical particle size, Waters, Milford, MA, USA) protected by a guard column (Symmetry® C18, 2.1 mm i.d. × 10 mm length, 3.5 μm spherical particle size, Waters). The HPLC conditions were methanol (solvent A) and Milli-Q water acidified with 0.1% (v/v) acetic acid (solvent B) as eluents, 0.2 μL min-1 as flow rate, 25 o̱C as column temperature, and 5 μL as injection volume. The elution program was set according to the following gradient: 0-7 min, 60% B; 7-15 min, 60-70% B; 15-52 min, 70-100% B.

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

Table 1

Common name, chemical formula, molecular weight, and [M+Na]+ of capsiate, (±)-DMBO, and dihydrocapsiate.

Common NameChemical StructureChemica1 FormulaMolecular WeightMeasured [M+Na]+
Capsiate
C18H26O4306.3966329.1678
Dihydrocapsiate
C18H28O4308.4125331.1879
(±)-DMBO
C18H28O4308.4125331.1855

3 Results and discussion

3.1 (±)-DMBO Synthesis procedure (5)

3.1.1 Reduction of the 3,4-dimethoxybenzaldehyde (1) carbonyl group

The initial reaction stage involved the reduction of the carbonyl group of 3,4-dimethoxybenzaldehyde (1) to its corresponding alcohol (2) (Figure 1). The reduction of the carbonyl group was performed by using DIBAL (1 mol L-1 in toluene). The compound (1) (3.0042 g, 0.0181 mol) was dissolved in 40 mL of dry THF. subsequently, 2 equivalents of DIBAL (1 mol L-1 in toluene) were added slowly, with a syringe, in an ice bath, and the reaction mixture was stirred, under argon, at ambient temperature, for 2 h. The reaction was monitored by TLC (eluent: 20% ethyl acetate, 80% hexane; chromogenic reagent: anisaldehyde). Then, the reaction was stopped with water and after purification of the reaction mixture, by column chromatography (eluent: 20% ethyl acetate, 80% hexane; chromogenic reagent: anisaldehyde), and (2) was obtained with a yield of 77.16%.

Figure 1 Step 1 of the synthesis procedure of (±)-DMBO. Reduction of 3,4-dimethoxybenzaldehyde (1) to 3,4-dimethoxybenzyl alcohol (2).
Figure 1

Step 1 of the synthesis procedure of (±)-DMBO. Reduction of 3,4-dimethoxybenzaldehyde (1) to 3,4-dimethoxybenzyl alcohol (2).

3.1.2 Chloride formation from (±)-4-methyloctanoic acid (3)

The (±)-4-methyloctanoic acid (3) was transformed into (±)-4-methyloctanoyl chloride (4), in order to subsequently perform the acylation of this compound (2) (Figure 2). To do so, 2 equivalents of (3) (4.4307 g, 0.028 mol) were placed in a 50-mL round-bottom flask into which argon was introduced. An amount of SOCl2, sufficient to dissolve the acid, was added very slowly, dropwise from a syringe, and stirred magnetically. After the addition of SOCl2, the reaction mixture was heated at 60 °C for 1 h. subsequently, the excess of SOCl2 excess was eliminated in vacuo, and the transparent oil of (4) was obtained. This compound (4) was dissolved in dry THF for the subsequent acylation with compound (2).

Figure 2 Step 2 of the synthesis procedure of (±)-DMBO. Preparation of (±)-4-methyloctanoyl chloride (4) from (±)-4-methyloctanoic acid (3).
Figure 2

Step 2 of the synthesis procedure of (±)-DMBO. Preparation of (±)-4-methyloctanoyl chloride (4) from (±)-4-methyloctanoic acid (3).

3.1.3 Esterification of 3,4-dimethoxybenzyl alcohol (2) with (±)-4-methyloctanoyl chloride (4)

The (±)-3,4-dimethoxybenzyl-4-methyloctanoate ((±)-DMBO) (5) was prepared by the acylation of the 3,4-dimethoxybenzyl alcohol ring (2) using a (±)-4-methyloctanoyl chloride chain (4) (Figure 3). The final product (±)-DMBO (5) is a racemic mixture since the synthesis has been started from the racemic product (±)-4-methylocatanoic acid (3) and the proposed synthesis is not stereoselective. Compound (2) (2.3321 g, 0.0140 mol) was dissolved in 20-25 mL of dry pyridine in a 50-mL round-bottom flask under a protective atmosphere with argon. Then, 2 equivalents of (4) were added slowly to this solution and agitated for 18 h. The reaction was monitored by TLC (eluent: 20% ethyl acetate, 80% hexane; chromogenic reagent: anisaldehyde) up to the reaction’s completion.

Figure 3 Step 3 of the synthesis procedure of (±)-DMBO. Procedure for the preparation of (±)-DMBO (5) from the acylation of 3,4-dimethoxybenzyl alcohol (2) with (±)-4-methyloctanoyl chloride (4).
Figure 3

Step 3 of the synthesis procedure of (±)-DMBO. Procedure for the preparation of (±)-DMBO (5) from the acylation of 3,4-dimethoxybenzyl alcohol (2) with (±)-4-methyloctanoyl chloride (4).

The (±)-DMBO esterification step was simpler than that reported for capsinoid and capsaicinoids standards synthesis [29]. Through this synthesis procedure, (±)-DMBO (5) was obtained, after purification of the reaction mixture, with a yield of 95% and a purity ≥ 98%. The overall yield obtained for the synthesis of (±)-DBMO starting from the initial material has therefore been 73.15%. This yield was higher than those obtained by other synthesis procedures previously reported for capsinoid and capsaicinoid standards [12,29,30,31,32,33]. Thus, this procedure would be an efficient alternative to other synthesis methodologies for capsinoid derivatives, such as enzymatic catalysis or labeled compound synthesis, due to its lower cost and higher yield.

3.2 Chemical characterization of (±)-DMBO (5)

The formation of (±)-DMBO was confirmed by 1H NMR and 13C NMR analysis. Since (±)-DMBO (5) (Figure 4) has never been previously described in the bibliography, its chemical characterization is presented below:

Yellow oil. 1H NMR (500 MHz, CDCl3, δ, ppm) (Assignments with identical superscripts are interchangeable) (S1 _Figure): 6.91 (dd, 1H, J = 2.0 Hz, J = 8.1 Hz, 6), 6.87 (bd, 1H, J = 1.9 Hz, 2), 6.83 (bd, 1H, J = 8.1 Hz, 5), 5.03 (s, 2H, 8), 3.87 (sa, 3H, 7), 3.86 (sa, 3H, 7’), 2.38-2.26 (m, 2H, 2”), 1.69-1.63 (m, 1H, 3a”), 1.47-1.41 (m, 1H, 3b”), 1.41-1.35 (m, 1H, 4”), 1.30-1.17 (m, 1H, 5a”), 1.30-1.17 (m, 2H, 7”), 1.30-1.17 (m, 2H, 6”), 1.12-1.07 (m, 1H, 5b”), 0.86 (t, 3H, J = 6.4 Hz, 8”), 0.84 (d, 3H, J = 6.5 Hz, 9”); 13C NMR (125 MHz, CDCl3, δ, ppm): 173.98 (1”), 148.99b (4), 148.91b (3), 128.59 (1), 121.17 (6), 111.70 (2), 110.94 (5), 66.14 (8), 55.85c (7), 55.81c (7’), 36.27 (5”), 32.31 (4”), 32.12 (2”), 31.85 (3”), 29.09 (6”), 22.87 (7”), 19.24 (9”), 14.05 (8”); IR (cm-1): 2956, 1735, 1519, 1162; λmax (nm) 279.9; ε (L/mol⋅cm-1) 338; HRMS (ESI) calculated for C18H28O4 [M+Na]+: 331.1879, found: 331.1884.

Figure 4 Chemical structure of (±)-DMBO (5). Chemical characterization of (±)-DMBO by 1H NMR and 13C NMR analysis.
Figure 4

Chemical structure of (±)-DMBO (5). Chemical characterization of (±)-DMBO by 1H NMR and 13C NMR analysis.

3.3 HPLC-ESI-MS(QTOF) and HPLC-ESI-MS/ MS(QTOF) analysis of capsiate, (±)-DMBO, and dihydrocapsiate standards

In order to evaluate the suitability of (±)-DMBO as an IS for capsinoid determination by ESI-mass spectrometry, its retention time and ionization behaviour were determined by HPLC-ESI-MS(QTOF) and HPLC-ESI-MS/MS(QTOF) and compared to those of capsiate and dihydrocapsiate standards.

The MS spectra of capsiate, (±)-DMBO, and dihydrocapsiate were acquired, in positive ion mode, by direct injection of the standard solutions on the QTOF mass analyser. The major peaks observed in the MS spectra corresponding with the [M+Na]+ ions were at the m/z 329.1678 for capsiate, 331.1879 for dihydrocapsiate and 331.1855 for (±)-DMBO (Table 1). These molecular ions were in agreement with the calculated m/z 329.1723 for capsiate and 331.1880 for (±)-DMBO and dihydrocapsiate; therefore, they were selected as precursors for ESI-MS/ MS experiments. Figure 5 shows the MS/MS spectra obtained for capsiate, (±)-DMBO, and dihydrocapsiate. For both capsinoid standards, the most intense peak was observed at m/z 159.0375 for capsiate and 159.0418 for dihydrocapsiate, in accordance with the calculated m/z 159.0417, corresponding to sodiated vanillyl ring. Other minor product ions detected at m/z 137.0570 and 137.0605, in conformity with the calculated m/z 137.0597, corresponding to the protonated vanillyl ring of capsiate and dihydrocapsiate, respectively, and generated by the cleavage of the C7-O8 bond of these molecules (Figure 5, A and B). On (±)-DMBO MS/MS spectrum, the most intense peak was observed at m/z 151.0750 (Figure 5C), in agreement with the calculated m/z 151.0754 for the expected vanillyl-type ring resulting from fragmentation at the ester bond. The ionization behaviour and break site of (±)-DMBO molecules were similar to those shared by capsinoid standards. MS/MS spectra obtained for (±)-DMBO, capsiate, and dihydrocapsiate matched well with the typical fragmentation pattern for capsinoids [34] and capsaicinoids [35].

Figure 5 ESI-MS/MS spectra in positive ion mode of capsiate, dihydrocapsiate and (±)-DMBO. The individual standard solutions in 60% methanol of 10 μmol L-1 capsiate (A) and dihydrocapsiate (B), and 20 μmol L-1 (±)-DMBO (C) were acquired by direct injection on the QTOF mass analyser.
Figure 5

ESI-MS/MS spectra in positive ion mode of capsiate, dihydrocapsiate and (±)-DMBO. The individual standard solutions in 60% methanol of 10 μmol L-1 capsiate (A) and dihydrocapsiate (B), and 20 μmol L-1 (±)-DMBO (C) were acquired by direct injection on the QTOF mass analyser.

Ion chromatograms were extracted for the exact m/z values corresponding to the [M+Na]+ species of capsiate, (±)-DMBO, and dihydrocapsiate (Figure 6). The peaks of the capsiate, (±)-DMBO, and dihydrocapsiate standards showed their elution times at 31.0, 34.0, and 35.3 min, respectively. Since the chromatogram traces corresponding to m/z 331 were extracted for (±)-DMBO and dihydrocapsiate, the resolution (Rs) of these two compounds was calculated in order to confirm the correct separation of both compounds. The Rs of dihydrocapsiate and (±)-DMBO (defined as 2 times the separation between peaks divided by the sum of the peak base widths) was 1.2, a value that can be considered as adequate.

Figure 6 HPLC-ESI-MS(QTOF) chromatograms of capsiate, (±)-DMBO and dihydrocapsiate standards. Ion chromatograms were extracted for the exact m/z values corresponding to the [M+Na]+ species of capsiate, (±)-DMBO and dihydrocapsiate.
Figure 6

HPLC-ESI-MS(QTOF) chromatograms of capsiate, (±)-DMBO and dihydrocapsiate standards. Ion chromatograms were extracted for the exact m/z values corresponding to the [M+Na]+ species of capsiate, (±)-DMBO and dihydrocapsiate.

The potentiality of using (±)-DMBO as IS in capsinoid determination by ESI-mass spectrometry was supported by the following facts i) it is a capsinoid analogue not occurring naturally in Capsicum species, ii) the ionization behaviour of (±)-DMBO in ESI mass is similar to that of capsiate and dihydrocapsiate, and iii) its retention time is similar to that of capsiate and dihydrocapsiate, (±)-DMBO eluting between the two analytes but being able to be separated from dihydrocapsiate.

4 Conclusion

In this study, a (±)-DMBO synthesis procedure has been described. The synthesis procedure developed is simple, economical, and achievable in any basic chemistry laboratory, and it also allows the obtaining of yields greater than 95%.

(±)-DMBO could be a potential IS for capsinoid determination because: (i) it is not present in pepper fruits; (ii) it is stable under analysis conditions; (iii) it elutes between capsiate and dihydrocapsiate; (iv) its chemical structure is closely related to that of capsinoids; (v) and its ionization behaviour and fragmentation pattern is shared by capsiate and dihydrocapsiate.

As far as we know, there is not any other IS available for capsinoid determination by HPLC-ESI-MS/ MS(QTOF) analysis. Synthetic analogues have already been successfully used as IS for another compound determination by ESI-MS techniques [36-37]. We have described for first time a simple synthesis approach of a capsinoid analogue suitable for IS. The development of a new IS will allow an accurate quantification of capsinoid by HPLC-ESI-MS, a useful tool for screening and selecting of cultivars containing capsinoids in pepper breeding programs and for gaining understanding of the metabolism of capsinoids.

Acknowledgments

This study was supported by the National Institute for Agriculture and Food Research and Technology (INIA) and has been co-financed by the European Fund for Regional Development (FEDER) (grant number RTA2011-00118-C02 and RTA2015-00042-C02-00). Also, it was supported for Aragon Government-A16. Author O. Fayos has received research grants from INIA (RTA2011-00118-C02-01).

  1. Conflict of interest: Authors state no conflict of interest.

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Received: 2017-10-19
Accepted: 2017-12-15
Published Online: 2018-02-21

© 2018 O Fayos et al., published by De Gruyter

This work is licensed under the Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 License.

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https://doi.org/10.1515/chem-2018-0007
Keywords for this article
Capsiate; dihydrocapsiate; DMBO; fragmentation pattern; HPLC-MS/MS; internal standard; synthesis method
Creative Commons
BY-NC-ND 4.0

Articles in the same Issue

  1. Regular Articles
  2. The effect of CuO modification for a TiO2 nanotube confined CeO2 catalyst on the catalytic combustion of butane
  3. The preparation and antibacterial activity of cellulose/ZnO composite: a review
  4. Linde Type A and nano magnetite/NaA zeolites: cytotoxicity and doxorubicin loading efficiency
  5. Performance and thermal decomposition analysis of foaming agent NPL-10 for use in heavy oil recovery by steam injection
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  8. M-Polynomials And Topological Indices Of Zigzag And Rhombic Benzenoid Systems
  9. Photochemical Transformation of some 3-benzyloxy-2-(benzo[b]thiophen-2-yl)-4Hchromen-4-ones: A Remote Substituent Effect
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  89. A numerical analysis of heat transfer in a cross-current heat exchanger with controlled and newly designed air flows
  90. Freshwater green macroalgae as a biosorbent of Cr(III) ions
  91. The main influencing factors of soil mechanical characteristics of the gravity erosion environment in the dry-hot valley of Jinsha river
  92. Free amino acids in Viola tricolor in relation to different habitat conditions
  93. The influence of filler amount on selected properties of new experimental resin dental composite
  94. Effect of poultry wastewater irrigation on nitrogen, phosphorus and carbon contents in farmland soil
  95. Response of spring wheat to NPK and S fertilization. The content and uptake of macronutrients and the value of ionic ratios
  96. The Effect of Macroalgal Extracts and Near Infrared Radiation on Germination of Soybean Seedlings: Preliminary Research Results
  97. Content of Zn, Cd and Pb in purple moor-grass in soils heavily contaminated with heavy metals around a zinc and lead ore tailing landfill
  98. Topical Issue on Research for Natural Bioactive Products
  99. Synthesis of (±)-3,4-dimethoxybenzyl-4-methyloctanoate as a novel internal standard for capsinoid determination by HPLC-ESI-MS/MS(QTOF)
  100. Repellent activity of monoterpenoid esters with neurotransmitter amino acids against yellow fever mosquito, Aedes aegypti
  101. Effect of Flammulina velutipes (golden needle mushroom, eno-kitake) polysaccharides on constipation
  102. Bioassay-directed fractionation of a blood coagulation factor Xa inhibitor, betulinic acid from Lycopus lucidus
  103. Antifungal and repellent activities of the essential oils from three aromatic herbs from western Himalaya
  104. Chemical composition and microbiological evaluation of essential oil from Hyssopus officinalis L. with white and pink flowers
  105. Bioassay-guided isolation and identification of Aedes aegypti larvicidal and biting deterrent compounds from Veratrum lobelianum
  106. α-Terpineol, a natural monoterpene: A review of its biological properties
  107. Utility of essential oils for development of host-based lures for Xyleborus glabratus (Coleoptera: Curculionidae: Scolytinae), vector of laurel wilt
  108. Phenolic composition and antioxidant potential of different organs of Kazakh Crataegus almaatensis Pojark: A comparison with the European Crataegus oxyacantha L. flowers
  109. Isolation of eudesmane type sesquiterpene ketone from Prangos heyniae H.Duman & M.F.Watson essential oil and mosquitocidal activity of the essential oils
  110. Comparative analysis of the polyphenols profiles and the antioxidant and cytotoxicity properties of various blue honeysuckle varieties
  111. Special Issue on ICCESEN 2017
  112. Modelling world energy security data from multinomial distribution by generalized linear model under different cumulative link functions
  113. Pine Cone and Boron Compounds Effect as Reinforcement on Mechanical and Flammability Properties of Polyester Composites
  114. Artificial Neural Network Modelling for Prediction of SNR Effected by Probe Properties on Ultrasonic Inspection of Austenitic Stainless Steel Weldments
  115. Calculation and 3D analyses of ERR in the band crack front contained in a rectangular plate made of multilayered material
  116. Improvement of fuel properties of biodiesel with bioadditive ethyl levulinate
  117. Properties of AlSi9Cu3 metal matrix micro and nano composites produced via stir casting
  118. Investigation of Antibacterial Properties of Ag Doped TiO2 Nanofibers Prepared by Electrospinning Process
  119. Modeling of Total Phenolic contents in Various Tea samples by Experimental Design Methods
  120. Nickel doping effect on the structural and optical properties of indium sulfide thin films by SILAR
  121. The effect mechanism of Ginnalin A as a homeopathic agent on various cancer cell lines
  122. Excitation functions of proton induced reactions of some radioisotopes used in medicine
  123. Oxide ionic conductivity and microstructures of Pr and Sm co-doped CeO2-based systems
  124. Rapid Synthesis of Metallic Reinforced in Situ Intermetallic Composites in Ti-Al-Nb System via Resistive Sintering
  125. Oxidation Behavior of NiCr/YSZ Thermal Barrier Coatings (TBCs)
  126. Clustering Analysis of Normal Strength Concretes Produced with Different Aggregate Types
  127. Magnetic Nano-Sized Solid Acid Catalyst Bearing Sulfonic Acid Groups for Biodiesel Synthesis
  128. The biological activities of Arabis alpina L. subsp. brevifolia (DC.) Cullen against food pathogens
  129. Humidity properties of Schiff base polymers
  130. Free Vibration Analysis of Fiber Metal Laminated Straight Beam
  131. Comparative study of in vitro antioxidant, acetylcholinesterase and butyrylcholinesterase activity of alfalfa (Medicago sativa L.) collected during different growth stages
  132. Isothermal Oxidation Behavior of Gadolinium Zirconate (Gd2Zr2O7) Thermal Barrier Coatings (TBCs) produced by Electron Beam Physical Vapor Deposition (EB-PVD) technique
  133. Optimization of Adsorption Parameters for Ultra-Fine Calcite Using a Box-Behnken Experimental Design
  134. The Microstructural Investigation of Vermiculite-Infiltrated Electron Beam Physical Vapor Deposition Thermal Barrier Coatings
  135. Modelling Porosity Permeability of Ceramic Tiles using Fuzzy Taguchi Method
  136. Experimental and theoretical study of a novel naphthoquinone Schiff base
  137. Physicochemical properties of heat treated sille stone for ceramic industry
  138. Sand Dune Characterization for Preparing Metallurgical Grade Silicon
  139. Catalytic Applications of Large Pore Sulfonic Acid-Functionalized SBA-15 Mesoporous Silica for Esterification
  140. One-photon Absorption Characterizations, Dipole Polarizabilities and Second Hyperpolarizabilities of Chlorophyll a and Crocin
  141. The Optical and Crystallite Characterization of Bilayer TiO2 Films Coated on Different ITO layers
  142. Topical Issue on Bond Activation
  143. Metal-mediated reactions towards the synthesis of a novel deaminolysed bisurea, dicarbamolyamine
  144. The structure of ortho-(trifluoromethyl)phenol in comparison to its homologues – A combined experimental and theoretical study
  145. Heterogeneous catalysis with encapsulated haem and other synthetic porphyrins: Harnessing the power of porphyrins for oxidation reactions
  146. Recent Advances on Mechanistic Studies on C–H Activation Catalyzed by Base Metals
  147. Reactions of the organoplatinum complex [Pt(cod) (neoSi)Cl] (neoSi = trimethylsilylmethyl) with the non-coordinating anions SbF6– and BPh4–
  148. Erratum
  149. Investigation on Two Compounds of O, O’-dithiophosphate Derivatives as Corrosion Inhibitors for Q235 Steel in Hydrochloric Acid Solution
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