Startseite Presence of short and cyclic peptides in Acacia and Ziziphus honeys may potentiate their medicinal values
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Presence of short and cyclic peptides in Acacia and Ziziphus honeys may potentiate their medicinal values

  • Wed Mohammed Ali ALaerjani , Saraa Abdullah Abu-Melha , Khalid Ali Khan , Hamed A. Ghramh , Ali Yahya A. Alalmie , Rahaf Mohammed Hussein Alshareef , Badria M. AL-Shehri und Mohammed Elimam Ahamed Mohammed EMAIL logo
Veröffentlicht/Copyright: 7. Dezember 2021
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Open Chemistry
Aus der Zeitschrift Open Chemistry Band 19 Heft 1

Abstract

Acacia honey is characterized by high nutritional, antioxidant, antibacterial and immuno-modulatory values. This work investigated the presence of short and cyclic peptides in Acacia and Ziziphus honey samples. Acacia honey samples (Acacia tortilis and Acacia hamulosa) and three Ziziphus honeys (Ziziphus spina-christi) were screened for their short and cyclic peptide contents using the LC-MS and the chemical structure databases. Moreover, the total protein content was determined using the Bradford method. The A. tortilis honey contained three short peptides; HWCC, DSST, and ECH, and the A. hamulosa honey sample contained five short peptides and one cyclic peptide. The short peptides of the A. hamulosa honey were Ac-GMGHG-OH (Ac-MGGHG-OH), Boc-R(Aloc)2-C(Pal)-OH, H-C (1)-NEt2·H-C (1)-NEt2, APAP (AAPP), and GAFQ (deamino-2-pyrid-4-yl-glycyl-dl-alanyl-dl-norvalyl-dl-asparagine). The cyclic peptide of the A. hamulosa honey was cyclo[Aad-RGD-d-F] (cyclo[Aad-Arg-Gly-Asp-d-Phe]). The Ziziphus honey was characterized by the presence of either Almiramide B or Auristatin-6-AQ. A. tortilis, A. hamulosa, and Ziziphus honeys are characterized by the presence of short and cyclic peptides which may contribute to their medicinal values.

Keywords: bioactive peptides; LC-MS; PubChem; ChemSpider; Molbase

1 Introduction

Nutritionally, honey is considered as energy food since it is majorly composed of carbohydrates and it is used in infants and children feeding to boost their growth. Moreover, honey contains some amounts of vitamins, minerals, amino acids, enzymes, and phenolic compounds which qualify it to act as antioxidant and to boost the athletic performance, immune system, and digestion and absorption. Medicinally, honey is used for wound healing due to its high sugar content, low moisture percentage, hydrogen peroxide, gluconic acid, and dicarbonyl molecules including the methylglyoxal. Furthermore, honey is used to treat disorders of hematology and immunity, metabolism and cardiovascular system, oral health, ophthalmology, and gastrointestinal tract beside its usage as anticancer (chemotherapy) and antimicrobial [1,2].

Honey is characterized by proteins such as the enzymes which originate from the honeybees or the plants’ nectars and secretions. The protein content of honey is associated with its medical and pharmaceutical value [3,4].

Short or bioactive peptides are composed of small number of amino acids in foods. The bioactive peptides are mostly produced by enzymatic hydrolysis of large proteins from animal and plant origins. Milk and its products, eggs, meat, marine organisms, spinach, soybeans, and cereal grains are the best examples of bioactive peptides containing foods. Some bioactive peptides are chemically synthesized and added to foods for the purpose of increasing their medicinal value. Short peptides affect different body systems including the cardiovascular, endocrine, immune, nervous, and digestive systems. The presence of short peptides in foods prevents their oxidation and degradation by microbes [5,6,7,8].

Cyclic peptides are short peptides with ring structure due to the binding of its amino terminal to its carboxyl terminal by amide bond or other chemical bonds such as the ether, disulfide, and lactone bonds. Cyclic peptides are reported to be found in roasted coffee, cocoa, and malt beside their presence in milk, beverages, chicken, and fermented foods. Biological activities of cyclic peptides include antibacterial, antitumor, immunosuppressive and antioxidant activities. Known functions of cyclic peptides are the cyclo (–Phe–Phe) of chicken essence which inhibits the serotonin transporter and the acetylcholinesterase and the cyclo (–His–Pro) which inhibits rat’s food intake and reduces their body weight [5,9].

This article measured the concentration of total proteins and investigated the presence of short and cyclic peptides in Acacia and Ziziphus honey samples after they were authenticated with regard to their floral origin and some quality parameters.

2 Materials and methods

2.1 Study design

This study is an observational descriptive study. The disadvantages of descriptive studies include the small number of samples and the difficulty in deriving a general conclusion. However, descriptive studies are useful since they highlight research areas for survey studies [10].

2.2 Honey samples and their authentication

Two Acacia and three Ziziphus honey samples were collected directly from the bee farms and their hives. The samples were involved in this study after confirming their floral origin and their conformance to some of the international standards for honey. The two Acacia honeys were collected during the flowering seasons of A. tortilis and A. hamulosa, while the dominant Ziziphus tree in the study area was Z. spina-christi. All the honey samples were collected from Asir region at the southwestern part of Saudi Arabia.

The Ziziphus 3 honey samples were collected from bee farms at sea level altitude, while the A. hamulosa, Ziziphus 1, and Ziziphus 2 samples were harvested from bee farms at 900 m above sea level. A. tortilis was harvested at 2,000 m above sea level. The flowering season of the Z. spina-christi and A. hamulosa ranges from September to November, while the flowering season of A. tortilis is from March to July [11,12].

The floral origin of the honey samples was determined following the method published by Louveaux et al. [13]. The moisture, pH and acidity, conductivity, and diastase activity were determined according to the methods of International honey commission, (2009) [14], while the glucose, fructose, sucrose, and HMF were measured following the methods of Agilent company.

2.3 Determination of total protein concentration

The total protein concentration was determined in the studied samples using the spectrophotometric method of Bradford (1976) [3]. The protein in the samples (50% W/V; 100 µL) was reacted with coomassie brilliant blue (5 mL) and the absorbance was measured at a wavelength of 595 nm. Albumin was used in preparation of standard curve (0–500 µg/mL).

2.4 Liquid chromatography-mass spectrometry (LC-MS)

The chemical constituents and the presence of short peptides in honey samples were investigated using the LC-MS. Reverse phase elution was used (Waters Symmetry LC18 column 250 × 4.6 mm, 5 µm) on Agilent 6500 Series Accurate-Mass Quadrupole Time-of Flight (Q-TOF; Agilent CA, USA); Chemical structure databases search was carried out to identify the molecular formula and structure of the spectra obtained. LC-MS system with Agilent 1200 Series Diode Array Detector (module G1315B; detection type: 1,024-element photodiode array; light source: deuterium and tungsten lamps; wavelength range 190–950 nm). The mobile phase was composed of (A) formic acid (0.1%, v/v); (B) acetonitrile + 0.1% formic acid; gradient (in solvent B): (i) 20%, from 0 to 20 min, (ii) 95%, from 20 to 27 min, and (iii) 35%, at 27–30 min of total run time; flow rate was 0.2 mL/min; and injection volume was 3 L. The ESI parameters were both negative and positive ion modes, mass range 100–1,200 m/z, spray voltage 4 kV, gas temperature 325°C, gas flow 10 L/min, and Nebulizer was 40 psi. The Agilent technologies Mass Hunter software was used to analyze the mass. Tuning and optimization are carried out before any run and on each single day as recommended by the manufacturer.

2.5 Chemical structure databases search

The molecular formulas obtained from the LC-MS were searched in the PubChem, ChemSpider, and Molbase databases to investigate the possible isomers. However, one short peptide is published by the University of Dortmund-Germany.

2.6 Statistical analysis

The agglomerative hierarchical Cluster analysis of the Statistical Package for Social Sciences (SPSS) was used to group the honey samples according to the values of the physicochemical parameters and the total proteins.

3 Results

The honey microscopic pollen analysis showed that all the honey samples were mono-floral with dominance of one pollen type by more than 60% (Figure 1).

Figure 1 Representative pollens of the studied honey samples.
Figure 1

Representative pollens of the studied honey samples.

The results of the measured quality parameters were within their ranges in the Codex Alimentarius standards of honey [15] (Table 1). However, some honeys were with marginal diastase activity compared to the standards which may be due to the geographical and climatic conditions.

Table 1

The results of the quality parameters of the honey samples

SN Quality parameter A. tortilis A. hamulosa Ziziphus 1 Ziziphus 2 Ziziphus 3 Range in CODEX standards
1 Moisture % 14.7 ± 0.51 16.2 ± 0.2 14.8 ± 0.35 16.9 ± 0.49 17 ± 0.5 Less than 20%
2 pH 4.5 ± 0.2 4.2 ± 0.31 5.7 ± 0.21 4.7 ± 0.07 5 ± 0.2 3.4–6.1
3 Acidity (meq acid/100 g) 39 ± 1.7 40 ± 2.1 25 ± 7.1 27.5 ± 3.5 30 ± 0.25 Not more than 50 meq acid/100 g
4 Fructose % 51.4 ± 0.32 43 ± 0.5 54 ± 0.7 41.2 ± 2.1 37.1 ± 0.1.6 NA
Glucose % 33.5 ± 0.47 30 ± 0.1 35.6 ± 0.1 35.7 ± 3.4 29 ± 0.5
Fructose + glucose % 84.9 73 89.6 76.9 66.1 Not less than 60 g/100 g
5 Sucrose % 0.08 ± 0.02 0.04 ± 0.01 0.03 ± 0.01 1.01 ± 0.21 0.83 ± 0.8 Not more than 5 g/100 g
6 HMF (mg/kg) 0.0 ± 0.0 0.0 ± 0.0 10 ± 1.5 1.3 ± 0.4 15 ± 0.5 Not more than 40 mg/kg
7 Diastase (diastase number – DN) 12 ± 2.6 15 ± 1.8 20 ± 2.5 7.5 ± 0.7 7.9 ± 0.8 Not less than 8 DN (Schade)
8 Total protein (µg/g) 222.54 ± 23.0 560.56 ± 28.1 307.04 ± 21.5 560.56 ± 32.7 518.30 ± 49.8 NA

All the quality parameters were within the CODEX ranges except the diastase which was with marginal activities in the Ziziphus 2 and 3 samples.

3.1 Total protein concentration

The R 2 was 0.976, while the equation of the standard curve line was Y = 0.00142X + 0.042. The A. hamulosa and the Ziziphus 2 honey samples had the highest concentration of proteins (Table 1).

3.2 The agglomerative hierarchical clustering

The honey samples were divided into three groups (levels). Level one was composed of A. hamulosa, Ziziphus 2, and Ziziphus 3 honey samples and level 2 contained the honey samples of A. tortilis and Ziziphus 1. Level 3 involved all the honey samples except Ziziphus 1 honey (Figure 2). The clustering analysis grouped the honey samples according to their flowering time in the case of group one (A. hamulosa, Ziziphus 2, and Ziziphus 3). Moreover, the clustering analysis grouped the honey samples according to their altitude (level 3); all the honey samples were from farm at 900–2,000  m above sea level except the Ziziphus 3 sample which was from farms at the sea level.

Figure 2 The agglomerative hierarchical clustering of the studied honey samples. The honey samples were clustered according to the values of their quality parameters and protein concentration.
Figure 2

The agglomerative hierarchical clustering of the studied honey samples. The honey samples were clustered according to the values of their quality parameters and protein concentration.

3.3 LC-MS and the search in chemical structure databases

The LC-MS showed that the Ziziphus honey samples had one short peptide. Three short peptides were found in the A. tortilis honey, while five short peptides and one cyclic peptide were reported for the A. hamulosa honey.

3.4 The short peptides of the A. tortilis honey

The three short peptides of the A. tortilis honey were:

  1. HWCC (His-Trp-Cys-Cys) with the molecular formula of C23H29N7O5S2 which is retrieved from the ChemSpider database (Table 2 and Figure 3) [16].

  2. DSST (Asp-Ser-Ser-Thr) which was obtained from the Molbase database and it had the molecular formula of C14H24N4O10 (Table 2 and Figure 3) [17].

  3. The search in the PubChem for the molecular formula of C14H22N6O5S showed two short peptide isomers containing three amino acids with different sequences; Gln-Cys-His (ECH) and Cys-His-Gln (CHE) (Table 2 and Figure 3) [18,19].

Table 2

The short and cyclic peptides of the Acacia and Ziziphus honey samples

Peak Analyte peak name RT min Precursor m/z Formula MS/MS fragment Proposed peptide fragment Score Honey sample Database
1 47 548.1764/4.31 4.33 548.1764 C23H29N7O5S2 548.1745 His-Trp-Cys-Cys 98.557 A. tortilis ChemSpider
549.1732 HWCC
2 375 409.1556/9.98 10.01 409.1556 C14H24N4O10 408.1879 l-Aspartic acid, l-seryl-l-seryl-l-threonyl-DSST 99.686 A. tortilis Molbase
409.1110
409.1565
410.0937
410.1186
410.1349
410.1595
411.1980
411.1254
412.1389
3 393 387.1454/10.33 10.32 387.1453 C14H22N6O5S 386.2884 Gln-Cys-His (ECH) 98.413 A. tortilis PubChem
387.1087 Cys-His-Gln (CHE)
387.1445
387.1984
388.1460
388.1819
388.3217
389.1444
390.1211
4 135 500.1933/5.16 5.15 500.1933 C19H29N7O7S 499.1383 Ac-Gly-Met-Gly-His-Gly-OH 99.811 A. hamulosa PubChem
499.1976 Ac-Met-Gly-Gly-His-Gly-OH
500.1411 Ac-GMGHG-OH
500.1340 Ac-MGGHG-OH
500.1922
501.1951
502.2071
502.3851
503.0817
503.3925
5 274 784.4526/9.58 9.58 784.4526 C38H65N5O10S 784.3932 Boc-Arg(Aloc)2-Cys(Pal)-OH 97.161 A. hamulosa University of Dortmund
784.4528 Boc-R(Aloc)2-C(Pal)-OH
784.7388 Nα-tert-Butyloxycarbonyl-(Nδ,ω-diallyloxycarbonyl)-l-arginyl-(S-palmitoyl)-l-cysteine [21].
785.4589
785.5045
786.4598
787.4499
6 709 351.2083/14.54 14.42 351.2083 C14H30N4O2S2 349.8780 l-Cysteine diethylamide (1 → 1′)-disulfide compound with l-cysteine diethylamide 98.603 A. hamulosa PubChem
350.1882 H–C (1)-NEt2·H–C (1)-NEt2
350.9728
351.1882
351.2357
352.1916
352.2651
353.1786
353.1982
353.2395
353.3566
354.2020
7 939 372.2242/15.32M+NH4+ 15.32 372.2242 C16H26N4O5 371.2996 Ala-Pro-Ala-Pro 96.085 A. hamulosa ChemSpider
372.0578 Ala-Ala-Pro-Pro PubChem
372.2239 APAP
372.2960 AAPP
373.2275
373.3502
374.2260
375.2158
8 979 444.1856/15.37M+Na+ 15.39 444.1856 C19H27N5O6 443.2626 Alfuzosin hydroxy acid 98.318 A. hamulosa PubChem
443.2857
444.1584 Deamino-2-pyrid-4-yl-glycyl-dl-alanyl-dl-norvalyl-dl-asparagine PubChem
444.2676
445.1865
445.2777 (Deamino-Gly(4-pyridyl)-dl-Ala-dl-Nva-dl-Asn-OH)
446.2936
446.9739 Deamino-G(4-pyridyl)dl-A-dl-NV-dl-N
447.3131
Gly-Ala-Phe-Gln ChemSpider
GAFQ
9 1057 619.2838/15.62 15.63 619.2838 C27H38N8O9 619.2836 Cyclo[Aad-Arg-Gly-Asp-d-Phe] 98.108 A. hamulosa PubChem
620.2860 Cyclo[Aad-RGD-d-F]
621.2891 Cyclo[l-alpha-homoglutamyl-l-arginyl-glycyl-l-alpha-aspartyl-d-phenylalanyl]
622.5138
10 1345 725.4955/18.51 18.48 725.496 C40H64N6O6 725.4441 725.4960 Auristatin-6-AQ or 99.94 Ziziphus-2 PubChem
725.6715 726.5013 Almiramide B ChemSpider
726.5954 727.5192
727.4981 727.5192
728.5191
Figure 3 The LC-MS spectra of the short peptides in the Acacia tortilis honey sample. The three short peptides were HWCC, DSST, and ECH (CHE). The molecular structure of the HWCC were retrieved from the ChemSpider, Molbase, and PubChem databases [16,17,18,19].
Figure 3

The LC-MS spectra of the short peptides in the Acacia tortilis honey sample. The three short peptides were HWCC, DSST, and ECH (CHE). The molecular structure of the HWCC were retrieved from the ChemSpider, Molbase, and PubChem databases [16,17,18,19].

3.5 The short and cyclic peptides of the A. hamulosa honey

The A. hamulosa honey was characterized by five short peptides and one cyclic peptide.

  1. The five short peptides and their databases were:

    1. The PubChem search showed that the molecular formula C19H29N7O7S is similar to the molecular formula of two short peptides Ac-GMGHG-OH (Ac-Gly-Met-Gly-His-Gly-OH) and Ac-MGGHG-OH (Ac-Met-Gly-Gly-His-Gly-OH) (Table 2 and Figure 4) [20].

    2. Eisele (2000) [21] did his diploma degree at the university of Dortmund and synthesized a short peptide with the molecular formula of C38H65N5O10S similar to the molecular formula reported in the A. hamulosa honey. The short peptide was Boc-R(Aloc)2-C(Pal)-OH (Boc-Arg(Aloc)2-Cys(Pal)-OH) or Nα-tert-Butyloxycarbonyl-(Nδ,ω-diallyloxycarbonyl)-l-arginyl-(S-palmitoyl)-l-cysteine (Table 2 and Figure 4) [21].

    3. The third molecular formula was C14H30N4O2S2 which is corresponding to H–C (1)-NEt2·H–C (1)-NEt2 (l-cysteine diethylamide (1 → 1′)-disulfide compound with l-cysteine diethylamide) in the PubChem database (Table 2 and Figure 4) [22].

    4. APAP (Ala-Pro-Ala-Pro) in the ChemSpider database and AAPP (Ala-Ala-Pro-Pro) in the PubChem. The molecular formula was C16H26N4O5 (Table 2 and Figure 4) [23,24].

    5. The fifth short peptide of the A. hamulosa honey was with the molecular formula of C19H27N5O6 which corresponds the sequence of deamino-G(4-pyridyl)dl-A-dl-NV-dl-N (deamino-Gly(4-pyridyl)-dl-Ala-dl-Nva-dl-Asn-OH) in the PubChem and the sequence of GAFQ (Gly-Ala-Phe-Gln) in the ChemSpider database (Table 2 and Figure 4) [25,26]. Moreover, the C19H27N5O6 is the molecular formula of Alfuzosin hydroxy acid. However, the Alfuzosin and its metabolites are routine drugs for Benign Prostatic Hyperplasia (BPH) [27].

  2. The cyclic peptide found in the A. hamulosa honey is the cyclo[l-alpha-homoglutamyl-l-arginyl-glycyl-l-alpha-aspartyl-d-phenylalanyl] (cyclo[Aad-RGD-d-F]) with the molecular weight of C27H38N8O9. The LC-MS molecular formula was searched in the PubChem database (Table 2 and Figure 4) [28].

Figure 4 The LC-MS spectra of the short and cyclic peptides in the Acacia hamulosa honey sample. Five short peptides were found; Ac-GMGHG-OH or Ac-MGGHG-OH, Boc-R(Aloc)2-C(Pal)-OH, H–C (1)-NEt2·H–C (1)-NEt2, APAP or AAPP, and deamino-G(4-pyridyl)dl-A-dl-NV-dl-N or GAFQ. The cyclic peptide: cyclo[l-alpha-homoglutamyl-l-arginyl-glycyl-l-alpha-aspartyl-d-phenylalanyl] (cyclo[Aad-Arg-Gly-Asp-d-Phe]). The molecular structures of the studied compounds were cited from [20,21,22,23,24,25,26,27,28].
Figure 4

The LC-MS spectra of the short and cyclic peptides in the Acacia hamulosa honey sample. Five short peptides were found; Ac-GMGHG-OH or Ac-MGGHG-OH, Boc-R(Aloc)2-C(Pal)-OH, H–C (1)-NEt2·H–C (1)-NEt2, APAP or AAPP, and deamino-G(4-pyridyl)dl-A-dl-NV-dl-N or GAFQ. The cyclic peptide: cyclo[l-alpha-homoglutamyl-l-arginyl-glycyl-l-alpha-aspartyl-d-phenylalanyl] (cyclo[Aad-Arg-Gly-Asp-d-Phe]). The molecular structures of the studied compounds were cited from [20,21,22,23,24,25,26,27,28].

3.6 The short peptide of the Ziziphus honey samples

The Ziziphus 2 honey sample contained a short peptide with the molecular formula of C40H64N6O6. In the PubChem, the short peptide is registered as Auristatin-6-AQ, a dipeptide containing two methylated valine residues [29]. The ChemSpider and PubChem search showed that the molecular formula is for Almiramide B, a short peptide with phenylalaninamide, three methylated valine residues and one methyl alanine (Table 2 and Figure 5) [30,31].

Figure 5 The short peptide of the Z. spina-christi honey. The short peptide was defined as Auristatin-6-AQ or Almiramide B [29,30,31].
Figure 5

The short peptide of the Z. spina-christi honey. The short peptide was defined as Auristatin-6-AQ or Almiramide B [29,30,31].

4 Discussion

All the studied quality parameters of the honey samples were within the ranges of the Codex Alimentarius standards except the diastase activity of two Ziziphus honey samples which was in the lower margin. The marginal activity of the diastase enzyme may be due to the climatic conditions of Tehama (Geographical region). The Ziziphus honey had no short peptides, while the two Acacia honeys contained short and cyclic peptides.

The first short peptide of the A. tortilis honey is the (His-Trp-Cys-Cys) which is available in the ChemSpider database [16]. It proposed that presence of cross links between His-Cys and Trp-Cys play a regulatory role of host enzymes [32]. Dipeptides that possess tryptophan, tyrosine, cysteine, or methionine have antioxidant activities [33].

The l-aspartic acid-l-seryl-l-seryl-l-threonyl (DSST) (CAS No.: 748808-93-7) of the A. tortilis honey sample has the molecular formula of C14H24N and is registered in the Molbase database [17]. Proteins and short peptides containing Asp, Ser, and threonine are reported to act as binders and transporters of cations and their related substrates [34,35]. Thus, the presence of the DSST short peptide in the A. tortilis honey may be an indication for its mineral content.

The A. tortilis honey contained a third short peptide identified as Gln-Cys-His (ECH) [18] or Cys-His-Gln (CHE) [19]. No published article containing the three amino acids was retrieved. However, Cys-His are known to be responsible for acetyl transfer reactions in enzyme mimics [36].

Concerning the short peptides of the A. hamulosa, the N-acetyl-l-methionyl-glycyl-glycyl-l-histidyl-glycine is the first identified short peptide in the PubChem of the national center for biotechnology information [20]. Peptides that contain the sequence of Gly-Gly-His are known to act as copper binding proteins [37,38,39]. Moreover, it is reported that presence of tyrosine, tryptophan, methionine, lysine, cysteine, and histidine in a short peptide increases its antioxidant activity [40].

Nα-tert-Butyloxycarbonyl-(Nδ,ω-diallyloxycarbonyl)-l-arginyl-(S-palmitoyl)-l-cysteine (Boc-Arg(Aloc)2-Cys(Pal)-OH) was the second short peptide of the A. hamulosa honey. A search of the literature showed that this short peptide is synthesized for the purpose of identifying the function of viral proteins and their modified forms [21]. Cysteine residues of short peptides and their position are well-known to possess an antioxidant activity because of the direct interaction between the SH and the radicals [41]. Some Arginine containing short peptides in royal jelly samples have been proved to possess antioxidant activities [42]. Since this short peptide contains both arginine and cysteine, it may qualify the A. hamulosa honey to act as antioxidant diet.

The third short peptide in the A. hamulosa was the l-cysteine diethylamide (1 → 1′)-disulfide compound with l-cysteine diethylamide (H-C (1)-NEt2·H-C (1)-NEt2) [22], with score percentage of 98.6%. This dipeptide was produced and tested as inhibitor of l-cystine crystallization and a possible treatment for cystinuria and prevention of cystine renal stones [22]. The A. hamulosa honey may be a possible inhibitor of the formation of cystine renal stones.

The fourth supposed short peptide in the A. hamulosa honey have sequence of Ala-Ala-Pro-Pro in the PubChem [23] and the sequence of Ala-Pro-Ala-Pro in the ChemSpider database [24]. Short peptides rich in proline are known to possess an antioxidant activity [43,44]. Strong capacity of hydroxyl radical scavenging was reported for the Alanine containing dipeptides [45].

The A. hamulosa fifth short peptide was reported as deamino-2-pyrid-4-yl-glycyl-dl-alanyl-dl-norvalyl-dl-asparagine (deamino-G(4-pyridyl)dl-A-dl-NV-dl-N) in the PubChem [25] and gly-ala-phe-gln in the ChemSpider [26]. Presence of hydrophobic amino acids such as alanine, glycine, and valine in the sequence of short peptides facilitates the binding of these short peptides to fatty acids leading to the inhibition of lipid oxidation [39]. Presence of phenylalanine in a short peptide indicates its radical scavenging capability [40], while short peptides containing Asparagine or glutamine in the mid exhibited antihypertensive activity [46,47].

The cyclic peptide of the A. hamulosa honey was the cyclo[l-alpha-homoglutamyl-l-arginyl-glycyl-l-alpha-aspartyl-d-phenylalanyl] (cyclo[Aad-RGD-d-F]) which is found in the PubChem database [28]. The cyclic peptide is used in bioassay for integrin receptor [28]. According to its cyclic nature and amino acid content, this peptide could be used as antioxidant, antimicrobial, antitumor and can also be used as weight loss inducing peptide [5,9].

The Z. spina-christi honey contained Almiramide B short peptide which acts as anti-Leishmania donovani and anti-Trypanosoma brucei brucei [48,49]. Auristatin-6-AQ is potently active against human cancer cell lines [50].

This study is limited due to the small number of honey samples. Future studies should be designed to involve more Acacia honey samples and the short peptides should be extracted or synthesized so as to investigate their biological and medicinal activities.

5 Conclusion

The A. tortilis honey contained three short peptides, while five short peptides and one cyclic peptide were found in the A. hamulosa honey. The Ziziphus spina-christi honey can be used as anticancer, anti-Leishmania donovani, and anti-Trypanosoma brucei brucei. The presence of the short and cyclic peptides in the Acacia honey qualifies it to act as a natural medicine such as the Manuka honey.

Acknowledgements

The authors extend their appreciation for the Poison Control and Medical Forensic Chemistry Centre, Ministry of Health, Asir region, Saudi Arabia for permitting them to perform the LC-MS analysis.

  1. Funding information: This research is funded by the Scientific Research Deanship at King Khalid University and the Ministry of Education in KSA through the project number (IFP-KKU-2020/5).

  2. Authors contributions: A.W. – conceptualization and formal analysis; A.S. and G.H. – conceptualization; KK – formal analysis and revision of manuscript; A.A., A.R., and A.B. – formal analysis; MM – conceptualization, management, formal analysis, statistical analysis, manuscript writing, and revision.

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

  4. Informed consent (if applicable): The bee keepers did not agree to publish the latitude and longitude of their bee farms, because they believe that if their location is published, many beekeepers will bring their bee farms to the location. The geographical location of the samples is mentioned as wide areas such as Bisha and Tehama.

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

  6. Data availability statement: The research data are available upon request.

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Received: 2021-06-04
Revised: 2021-11-01
Accepted: 2021-11-15
Published Online: 2021-12-07

© 2021 Wed Mohammed Ali ALaerjani et al., published by De Gruyter

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

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https://doi.org/10.1515/chem-2021-0106
Schlagwörter für diesen Artikel
bioactive peptides; LC-MS; PubChem; ChemSpider; Molbase
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Artikel in diesem Heft

  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
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  17. Simultaneous removal efficiency of H2S and CO2 by high-gravity rotating packed bed: Experiments and simulation
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  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
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  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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Heruntergeladen am 1.10.2025 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2021-0106/html
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