Startseite Naturwissenschaften Anti-parasitic activity and computational studies on a novel labdane diterpene from the roots of Vachellia nilotica
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Anti-parasitic activity and computational studies on a novel labdane diterpene from the roots of Vachellia nilotica

  • Naser F. Al-Tannak EMAIL logo , John V. Anyam , Eman Y. Santali , Alexander I. Gray , Collins U. Ibeji und John O. Igoli
Veröffentlicht/Copyright: 23. März 2024
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Aus der Zeitschrift Open Chemistry Band 22 Heft 1

Abstract

A new labdane diterpene characterized as 18α-O-trans-p-feruloyl-15-methyl-8(17)-labdanoate has been isolated from the roots of Vachellia nilotica. Also isolated were p-coumaric acid, ferulic acid, stearic acid, lupeol, and a mixture of β-sitosterol and stigmasterol. The compounds were obtained after a series of column chromatography on silica gel, and their structures were elucidated using NMR and LC-MS analyses. The new diterpene showed good anti-parasitic activity with an IC50 of 0.0177 µM against Trypanosoma brucei and 0.0154 µM against Leishmania major using an Alamar Blue assay. The compound also displayed very good inhibitory activity against Leishmania major compared to Trypanosoma brucei rhodesiense with a binding energy of −10.5 and −7.8 kcal/mol, respectively. Density functional theory analysis showed that the studied compound has low LUMO–HOMO energy, signifying a high chemical reactivity with the ability to donate electrons to electron-accepting species.

Graphical abstract

Keywords: labdane diterpenes; phenylpropanoids; ferulic acid; anti-parasitic activity; Vachellia nilotica

1 Introduction

Ethnopharmacological practices have been a basis for drugs, and there is presently a rekindled interest in drug discovery from natural products [1,2]. A present drug discovery strategy is the in silico or computer-aided drug design (CADD) screening of compounds or libraries for active moieties and identifying pharmacophores pertinent for drug action [3,4] or any toxic properties [5,6]. Natural product libraries or boxes are also being created and interrogated for compounds with diverse chemical space and activities that they could provide. Thus, the isolation of novel natural compounds to add to the growing natural compound libraries and introduce more chemical space or diversity via CADD and in vitro screening is a new approach to drug discovery from natural compounds. Vachellia nilotica (L.) P.J.H.Hurter & Mabb. (Syn: Acacia nilotica Linn.) (Fabaceae), commonly known as Egyptian mimosa or thorn, grows freely in Nigeria, Egypt, and South Africa. It is also found or introduced in several other countries, regions, and continents [7]. The plant is a small to medium tree, 7–13 m tall, with a girth of 20–30 cm [8]. The plant attracts ants and other pests [9]. There are several ethnobotanical reports on the plant, including treatment of abdominal pains, diarrhoea, dysentery, genital and urinary tract infections, and as an expectorant [10]. In a previous report, extracts and fractions of the plant were reported to possess anti-trypanosomal activity [11], but some of the active compounds were not isolated. However, other studies have reported the isolation of niloticane, a cassane diterpene [12], umbelliferone, a coumarin [13], sandynone, niloticane B, and three seco-oxacassanes [14] from the plant as well as some flavonoids and phenolic compounds [15]. Docking simulations are based on the optimization of ligand–protein conformations and determine the interactions and mechanism of action of compounds at a binding site [16,17,18]. Other Acacia species have yielded some seco-oxacassanes and unusual diterpenoids such as schaffnerine from Acacia schaffneri (S.Watson) F.J.Herm. (Syn. of Vachellia schaffneri [S.Watson] Seigler & Ebinger) [19,20]. In our continued search for natural compounds that could serve as leads for anti-parasitic drug discovery [21], especially against Human African Trypanosomiasis and African Animal Trypanosomiasis which are neglected tropical diseases still plaguing Africa [1], and chagas disease, a further phytochemical study on the root bark of V. nilotica has been carried out in the present study and the isolation and docking study of a novel labdane diterpene is hereby reported. American trypanosomiasis is often referred to as Chagas disease. It is a type of trypanosomiasis that affects Latin Americans. The disease’s causal agent Trypanosoma cruzi belongs to a separate subgenus of Trypanosoma. The parasite is transmitted by kissing bugs and the disease characteristics are different from African trypanosomiasis transmitted by tse–tse fly.

Nevertheless, animals including dogs, cats, pigs, goats, lagomorphs, rodents, primates, or humans are T. cruzi’s primary reported hosts. Trypanosomiasis has become more prevalent in urban areas due to immigration and a rise in blood transfusions. Chagas disease affects approximately 16–18 million people and puts over 100 million more at risk and is considered the fourth most common endemic illness in America [22].

2 Rationale and design

Drug discovery encompasses all aspects of chemistry and biological evaluations. Drug or lead compounds are presently being synthesized using rational chemistry or isolated from plants and other natural sources. Using ethnobotanical and phytochemical methods, several drugs have been discovered and are in use today. This study also follows the path of phytochemical screening of a well-known and useful medicinal plant to isolate compounds responsible for its ethnobotanical activity and assay it against a prevalent neglected disease in Africa and other parts of the world.

3 Research design

3

3.1 Materials and methods

3.1.1 General experimental procedure

Column chromatography was carried out using silica gel 60 (0.040–0.063 mm) (230–400 mesh ASTM). Thin-layer chromatography (TLC) was performed on pre-coated aluminium sheets with silica gel F250 (Merck, Germany). Nuclear magnetic resonance (1H, 13C [Dept-q], COSY, HSQC, HMBC, and NOESY) spectra were acquired on a Bruker AVIII (400 MHz) spectrophotometer using CDCl3 as solvent, and spectra were referenced against the residual solvent peak. High-resolution mass spectra were acquired on an Agilent 6130B Single Quadrupole LC/MS System.

3.1.2 Plant material

Roots of V. nilotica were collected from trees growing at the Joseph Sarwuan Tarka University Makurdi. The plant was identified by Mr. Titus Yeke of the College of Forestry and Fisheries of the University. A voucher specimen (UAM/FH/0439) was deposited at the herbarium of the college.

3.1.3 Isolation of compounds

The roots were dried under ambient conditions and powdered using a mortar and pestle. The plant powder (500 g) was macerated in 2 L of n-hexane for 48 h with intermittent stirring and thereafter filtered to obtain the hexane extract. Then, 2 L of ethyl acetate were added to the marc and left to stand with stirring for another 48 h and filtered to obtain the ethyl acetate extract. The solvents were removed from the extracts to yield the hexane (1.80 g) and ethyl acetate (2.60 g) extracts. The whole extracts were each subjected to silica gel column chromatography, wet packed in hexane, and eluted with hexane (250 mL) and then 200 mL of gradient amounts (10% increase each time) of ethyl acetate in hexane. The fractions were examined by TLC using a solvent mixture of 3:7 ethyl acetate in hexane. Similar fractions were combined and allowed to dry in a fume hood. The compounds obtained from the hexane extract were stearic acid waxy crystals ([62.8 mg] [fractions 12–14] [compound 4]), and lupeol ([30.0 mg] [fractions 9–10] [compound 5]), while from the ethyl acetate extract, compound 1 (208.0 mg [fractions 64–70]), compound 2 ([24.0 mg] [fractions 76–77]), compound 3 ([41.0 mg] [fractions 71–75]), and a mixture of compounds 6 and 7 in ratio 1 : 2 ([98.0 mg] [fractions 54–60]) as white crystalline solids were isolated (Figure 1). Their structures were determined or elucidated by NMR spectra (1D and 2D) and where necessary confirmed by HR-ESI.

Figure 1 Other compounds isolated.
Figure 1

Other compounds isolated.

3.1.4 In vitro anti-trypanosomal and anti-leishmanial activity of compound 1

Compound 1 was tested against BSF T. b. brucei S427 WT and L. major WT promastigotes to assess its anti-parasitic activity using a resazurin-based assay as previously described [23,24,25,26,27]. A stock solution of 20 mg/mL of the compound was prepared in DMSO. In a 96-well plate (Greiner Bio-one GmbH, Germany), the compound was made in 11 double dilutions, starting at 200 μg/mL and decreasing to 0.19 μg/mL in the 1st–11th well, with the 12th well having no drug. The drugs pentamidine and diminazene are most usually used in cattle, sheep, and goat infections since Trypanosoma brucei affects animals, and both Trypanosoma brucei gambiense and Trypanosoma brucei rhodesiense are subspecies that affect humans. Their solutions and respective dilutions were made in parallel to serve as positive controls. The cells were then placed in the proper medium, adjusted to twice the needed density, and introduced into the wells containing drug dilutions. This was followed by incubation for 48 or 72 h, after which 20 μL of 125 μg/mL of phosphate-buffered saline (PBS; Sigma Aldrich, UK) and Resazurin sodium salt was added. The plates were incubated for 24 or 48 h under the same conditions after which the plates were read using a FLUOstar Optima plate reader (BMGLabtech, United States), λ exc = 544 nm, λ em = 590 nm. The outcomes were presented as half maximal effective concentration (EC50) values, which were calculated by non-linear regression using an equation for a sigmoidal dose–response curve with variable slope (GraphPad Prism 5.0).

3.1.5 Docking studies

Compound 1 was subjected to docking studies on cysteine proteases (CPs) which are found in protozoan parasites to which trypanosomes are grouped. Their roles in pathogenesis, which include cell or tissue penetration, hydrolysis of host or parasite proteins, autophagy, and evasion or modulation of the host immune response, are well recognized, hence making them attractive chemotherapeutic and vaccine targets [28]. The docking was to ascertain the binding capacity of the compound against Leishmania major and CP T. b. rhodesiense. The crystal structure with proteins was retrieved from a protein data bank (PDB) with codes: 2P7U and 4G5D [29,30] (vinyl sulphones as antiparasitic agents and a structural basis for drug design) (structures of prostaglandin F synthase from the protozoa Leishmania major and T. cruzi with NADP). To create the size of the grid box, AutoDock tools 1.5.4 [8] was applied, and the compound was optimized to obtain a minimum structure using Gaussian 09 [31]. The dimensions of X = 22, Y = 24, Z = 26 with 1.00 Å as the grid spacing were used. The Lamarckian genetic algorithm technique was used to obtain an optimum binding site for the ligand (binding of chrysoidine to catalase: spectroscopy, isothermal titration calorimetry, and molecular docking studies) [32]. The Gasteiger charges were computed using the AutoDockTools graphical user interface built in MGL Tools [8] (AutoDock4 and AutoDockTools4: automated docking with selective receptor flexibility). The compound in the ground state was optimized using density functional theory (DFT). B3LYP functional [33,34] with 6-31+G(d,p) basis set, which is appropriate for a few heteroatoms [35,36,37]. The highest occupied molecular orbital (HOMO) and the lowest unoccupied molecular orbital (LUMO) calculations were carried out to determine the reactivity character [38,39,40].

4 Results and discussion

4.1 Structure elucidation

Compound 1 (Figure 2) was obtained as a white crystalline solid. The molecular formula (C31H44O6) was established based on its sodium adduct ion mass observed under high-resolution ESI at m/z = 535.3035 [M + Na]+ (calc 535.3030) corresponding to [C31H44NaO6]+. The 1H NMR (400 MHz, CDCl3) showed two trans-coupled doublets characteristic of the olefinic protons of a cinnamic acid type compound at δ H (J in Hz) 6.27 (1H, d, J = 15.9, H-8ʹ) and 7.58 ppm (1H, d, J = 15.9, H-7ʹ). The phenyl ring showed three ABX coupled protons at 7.07 (1H, dd, J = 8.2, 2.0, H-6ʹ), 7.03 (1H, d, J = 2.0, H-2ʹ), and 6.91 (1H, d, J = 8.2, H-5ʹ). It also showed one aromatic ring methoxy group at 3.94 (3H, s, 3ʹ-OCH3) and an ester methoxy at 3.66 (3H, s, 15-OCH3). The compound showed an aliphatic diterpene component with two ethylenic protons of an exocyclic double bond at 4.50 (1H, d, J = 1.7, H-17a) and 4.82 (1H, d, J = 1.7, H-17b), two methyl singlets at 0.72 (3H, s, H-20) and 1.03 (3H, s, H-19), a methyl doublet at 0.94 (3H, d, J = 6.6, H-16), and three methines at 1.31 (1H, m, H-5), 1.61 (3H, m, H-9), and 1.93 (1H, m, H-13). Two oxymethylene protons were also observed at 4.37 (1H, d, J = 11.4, H-18a) and 3.98 (1H, d, J = 11.4, H-18b), while the rest of the methylene protons were observed between 1.12 and 2.50 ppm. The 13C NMR (Dept-q) spectrum showed 31 signals including two carbonyl carbons at δ C 173.9 and 167.7 ppm for two ester carbonyl groups (C-9ʹ and C-15); two olefinic CH at 116.8 and 144.4; three aromatic CH at 112.9, 119.9, and 125.2; two oxygenated aromatic carbons at 143.3 and 153.0; a quaternary carbon at 126.7; and a methoxy carbon at 56.2 ppm. This part of the structure was identified as a ferulic acid moiety, and its NMR spectral data agreed with literature reports for a feruloyl ester moiety [41] as the carboxylic acid carbon was not that of acid but an ester observed at ẟ C 167.7 ppm; hence, it must be esterified. The second part of the spectrum was typical of a diterpene of the 8, (17)-labdene type, and it was represented by 21 carbon signals, including the ester carbonyl at 173.9; an olefinic CH2 at 106.7 (C-17); a quaternary olefinic carbon at 148.1 (C-8); three methyl carbons at 15.5 (C-20), 19.8 (C-16), 28.1 (C-19); an ester methoxy at 51.8 (C-15–COOCH3); and an ester oxymethylene (C-18–COOCH2–) at 67.0 ppm. The rest of the carbons comprised two quaternary carbons at 37.6 (C-4) and 39.6 (C-10); three methines at 56.5 (C-5), 57.1 (C-9), and 30.9 (C-13); and eight methylene carbons between 19.0 and 50.0 ppm. The structure was confirmed by examining the HSQC, COSY, and NOESY correlations and the long-range (2 J and 3 J) correlations in its HMBC spectrum. The COSY spectrum identified all the germinal and vicinal protons, especially the methyl doublet at 0.97 ppm (H-16), the trans-coupled olefinic protons, and the aromatic protons of the ABX spin system. In the HMBC spectrum, a long-range correlation from H-18 to the C-9ʹ carbonyl confirmed the ester linkage of the ferulic acid to the labdane moiety at C-18, while the correlation from C-15-OCH3 to C-15 also confirmed the methyl ester at C-15. The trans olefinic protons (H-7ʹ and H-8ʹ) identified C-9ʹ, C-1ʹ, C-2ʹ, and C-6ʹ while the olefinic protons, H-17 identified C-7 and C-9. The phenolic methoxy confirmed its attachment via a 3 J correlation with C-3ʹ. The rest of the correlations (1b) were typical of a labdene diterpene, and the compound was identified as 18α-O-trans-p-feruloyl-8(17)-labden-15-methanoate (1a). Its relative stereochemistry was determined using correlations in its NOESY spectrum (1b) and its chemical shifts (Table 1) compared favourably with a similar ent-18-(E)-caffeoyloxy-8(17)-labden-15-oic acid isolated from Nuxia sphaerocephala (clerodane and labdane diterpenoids from N. sphaerocephala) [42]. The compound is not an artefact as the labdane diterpene moiety has not been previously isolated from the plant, and methanol was not used at any point of the isolation and characterization of assay process and procedures; hence, the possibility of methylation by methanol does not exist. Other compounds isolated were the phenolic acids; p-coumaric acid 2 (phenolic extractives from the root bark of Picea abies) [41], ferulic acid 3 (metabolism of ferulic acid by Paecilomyces variotii and Pestalotia palmarum) [41], the fatty acid stearic acid 4 (determination of the fatty acid profile by 1H NMR spectroscopy) [43], and the triterpenes, lupeol 5 [44] (assignment of 1H and 13C spectra and investigation of hindered side-chain rotation in lupeol derivatives), and a mixture of sitosterol and stigmasterol 6 and 7 (isolation of stigmasterol and sitosterol from the dichloromethane extract of Rubus suavissimus) [45]. Their identities were determined and confirmed by comparison to the literature reports and data cited against the compounds. The 1H NMR, 13C NMR, and other spectra for compound 1 are presented in supplementary information (Figures S1–S7).

Figure 2 Structure of compound 1 and selected COSY HMBC and NOESY correlations.
Figure 2

Structure of compound 1 and selected COSY HMBC and NOESY correlations.

Table 1

NMR data for compound 1 (400 MHz in CDCl3, δ in ppm, J in Hz)

Position Experimental Literature (CDCl3)* [42]
1H δ ppm. (mult, J in Hz) 13C (mult) Selected HMBC 1H δ ppm (mult, J in Hz) 13C (mult)
1 1.84–1.86 (m), 1.10–1.12 (m) 38.7 (CH2) 1.09, m, 1.83, m 39.8
2 1.53–1.55 (m) 19.2 (CH2) 1.59, m, 1.70, m 19.7
3 1.81–1.83 (m), 1.12–1.14 (m) 36.5 (CH2) 1.47, m 37.2
4 — 37.8 (C) — 38.3
5 1.30–1.33 (m) 56.5 (CH) 1.51, m 50.8
6 1.42–1.44 (m) 24.7 (CH2) 1.40, m, 1.69, m 25.6
7 2.42–2.44(m), 1.96–1.98 (m) 39.0 (CH2) 1.99, m, 2.38, m 39.2
8 — 148.1 (C) — 149.6
9 1.60–1.62 (m) 57.1 (CH) 1.65, m 58.4
10 — 39.7 (C) — 40.6
11 1.28 1.30(m) 22.8 (CH2) 1.42, m, 1.52, m 22.0
12 1.82–1.84 (m), 1.08–1.10 (m) 35.9 (CH2) 1.16, m, 1.37, m 36.9
13 1.93–1.95 (m) 31.0 (CH) 1.89, m 32.1
14 2.13 (dd, 14.7, 8.0), 2.29 (dd, 14.7, 6.1) 42.1 (CH2) C-15, C-16, C-13, C-12 2.08, dd (7.7; 14.6), 2.24, dd (6.6, 14.6) 43.3
15 — 174.0 (C) — 177.6
16 0.94 (d, 6.6) 19.7 (CH3) 0.96, d (6.6) 20.0
17 4.82 (d, 1.7), 4.50 (s) 106.9 (CH2) C-7, C-9 4.53, s, 4.83, s 107.2
18 4.37 (d, 11.0), 3.98 (d, 11.1) 66.9 (CH2) C-3, C-19, C-9ʹ 3.75, d (10.8), 3.99, d (10.8) 73.7
19 0.88 (s) 27.9 (CH3) 0.89, s 18.0
20 0.72 (s) 15.4 (CH3) 0.77, s 15.4
1ʹ — 127.2 (C) — — 127.7
2ʹ 7.03 (d, 2.0) 115.9 (CH) C-4, C-6, C-7 7.06, d (2.0) 115.2
3ʹ — 146.9 (C) — — 147.0
4ʹ — 148.1 (C) — — 149.5
5ʹ 6.91 (d, 8.2) 114.8 (CH) C-1, C-3 6.78, d (8.2) 116.5
6ʹ 7.07 (dd, 8.2, 2.0) 123.2 (CH) C-2, C-4, C-7 6.97, dd (2.0, 8.2) 123.0
7ʹ 7.58 (d, 15.9) 144.7 (CH) C-2, C-6, C-9 7.55, d (15.9) 146.9
8ʹ 6.27 (d, 15.9) 115.9 (CH) C-1, C-9 6.29, d (15.9) 115.0
9ʹ — 167.7 (C) — — 169.3
3ʹ-OCH3 3.94 (s) 56.1 (CH3) C-3ʹ —
15-OCH3 3.66 (s) 51.5 (CH3) C-15

*1H (400 MHz), 13C (100 MHz), and HMBC data for compound 1 in CDCl3 compared to literature report for ent-18-E-caffeoyloxy-8(17)-labden-15-oic acid in CD3OD [42] (clerodane and labdane diterpenoids from N. sphaerocephala) (the potential of anti-malarial compounds derived from African medicinal plants. Part I: A pharmacological evaluation of alkaloids and terpenoids).

4.2 Docking analysis

Docking simulation was performed for compound 1 using AutoDocTools. The protein–inhibitor complex containing the isolated compound and the individual interactions with the active site amino acids are presented in Figures 3 and 4. The docking results showed that the isolated compound interacted with the amino acids in the active site of CP T. b. rhodesiense and Leishmania major, with a binding energy of −7.8 and −10.5 kcal/mol, respectively. The isolated compound displayed the formation of hydrogen bonding, Pi alkyl, carbon–hydrogen bond, and Van der Waals interactions. As shown in Figures 3 and 4, the carbonyl group of the isolated compound formed hydrogen bonds with glutamine (GLN) 159 of the protease. Notably Van der Waals interaction has been formed with CYS 25, which is the core amino acid residue in the active site of CP T. b. rhodesiense. The compound also showed hydrogen bond interactions with SER198, one of the active site amino acid residues of Leishmania major. From Figure 4, the compound binds with a higher affinity with L. major compared to its binding with T. b. rhodesiense. These differences in the binding potentials may be due to the structural conformation of the proteins. The docking protocol was validated by docking the internal ligand with the prepared protein, and the docking is presented in Figures 4 and 5. The docking results show the alignment between the internal ligand and the isolated compound in the active site of CP T. b. rhodesiense and L. major. Docking simulations generate binding scores that show the affinity between drugs and targets, while in vitro studies investigate the biological responses [18]. The binding energies obtained in this study are similar and agree with the in vitro data obtained.

Figure 3 3D structure of (a) compound 2 in complex CP Trypanosoma brucei rhodesiense (b) representations, showing the hydrogen bonding interactions with amino acid residues around the binding pocket.
Figure 3

3D structure of (a) compound 2 in complex CP Trypanosoma brucei rhodesiense (b) representations, showing the hydrogen bonding interactions with amino acid residues around the binding pocket.

Figure 4 2D structure (a) of compound 1 aligned with (b) internal ligand (c) 3D representations showing the binding of the isolated compound and the internal ligand in the active binding pocket of CP Trypanosoma brucei rhodesiense.
Figure 4

2D structure (a) of compound 1 aligned with (b) internal ligand (c) 3D representations showing the binding of the isolated compound and the internal ligand in the active binding pocket of CP Trypanosoma brucei rhodesiense.

Figure 5 3D structure (a) of compound 1 in complex Leishmania major (b) representations, showing the hydrogen bonding interactions with amino acid residues around the binding pocket.
Figure 5

3D structure (a) of compound 1 in complex Leishmania major (b) representations, showing the hydrogen bonding interactions with amino acid residues around the binding pocket.

4.3 Anti-trypanosomal and anti-leishmanial activity of compound 1

The pIC50 of the compound shows an identical value of 4.8 against T. brucei and L. major (Table 2). The in silico and in vitro data, put together, suggest that the compound is promising but needs to be optimized. The binding of the compound with active site amino acid residues of selected proteins could provide insight into proposing the enzyme’s catalytic mechanism.

Table 2

Anti-parasitic activity of compound 1

S/No. Parasite species Test compound EC50 pIC50
1 Trypanosoma brucei Compound 1 9.085 ± 0.966 µg/mL 4.8
Diminazene 0.0012 ± 0.002 µM/mL 8.7
2 Leishmania major Compound 1 7.916 ± 0.390 µg/mL 4.8
Pentamidine 0.638 ± 0.179 µM/mL 6.8

4.4 DFT analysis

The optimized geometries of compound 1 using the DF method are shown in Figure 6.

Figure 6 Optimized 2D structure of compound 1 obtained at B3LYP/6-31+G(d,p).
Figure 6

Optimized 2D structure of compound 1 obtained at B3LYP/6-31+G(d,p).

HOMO–LUMO are described as frontier molecular orbitals [38,46]. The electron-donating ability of a compound is aligned with the E HOMO, and the higher the energy for E HOMO, the higher the ability of the compound to donate electrons [40,47]. The distribution of electrons of the HOMO (Figure 7) is conspicuous around the phenyl ring with high donating ability.

Figure 7 The distribution of electrons of the HOMO is conspicuous around the phenyl ring with high donating ability.
Figure 7

The distribution of electrons of the HOMO is conspicuous around the phenyl ring with high donating ability.

8(17)-Labden-15-oic acid has not been previously isolated or reported from the plant species, and its isolation as a ferulic acid ester is novel. The unesterified ferulic acid isolated confirms its presence as a metabolite, and its esterification to the labdane alcohol is part of compound 1 biosynthetic pathway. It is certainly not a product of esterification during the work up or isolation process of compound 1 as no acids or alkali was used or any esterifying conditions. The other compounds 2–7 were not tested for anti-parasitic activity as they are quite familiar compounds and have been tested previously [48]. The crude extracts and fractions were not tested as they will contain several mixtures and the identity of any active constituent cannot be determined easily.

5 Conclusion

In this study, further phytochemical and biological studies on the root bark of A. nilotica have led to the isolation of a novel labdane triterpene, 18α-O-trans-p-feruloyl-8(17)-labden-15-methanoate. The compound demonstrated promising anti-parasitic activity against T. brucei and L. major. The DFT studies of the compound revealed low ∆E, a strong indication of high reactivity. The silico study and DFT revealed critical energies that could provide information regarding the catalytic mechanism. Optimized synthetic iterations of the compound could provide essential leads in developing effective drugs against the parasites.

The structure of the novel labdane has been uploaded to PubChem with a release date set for 11 February, 2023, when it can be accessed by the following link: https://pubchem.ncbi.nlm.nih.gov/upload/#substance-118572.

Acknowledgements

The authors acknowledge Kuwait University for allowing using their facilities and space as well as CHPC (www.chpc.ac.za) and UKZN for operational and infrastructural support.

  1. Funding information: Authors state no funding involved.

  2. Author contributions: NFA, JVA, JOI, AIG and EYS carried out the isolation, purification, structure elucidation and bioassay of the compound and wrote the first draft. CUI performed the in silico studies and wrote the second draft. NFA and JOI supervised, edited, and revised the manuscript. All authors analysed, read, edited, and approved the final manuscript. Naser F. Al-Tannak and John V. Anyam are joint first authors.

  3. Conflict of interest: Authors declare no conflict of interest.

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

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

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Received: 2023-10-17
Revised: 2024-03-07
Accepted: 2024-03-08
Published Online: 2024-03-23

© 2024 the author(s), published by De Gruyter

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

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  142. Chemical composition and bioactivities of the methanol root extracts of Saussurea costus
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  152. Does Erodium trifolium (Cav.) Guitt exhibit medicinal properties? Response elements from phytochemical profiling, enzyme-inhibiting, and antioxidant and antimicrobial activities
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  154. 6-Methoxyflavone improves anxiety, depression, and memory by increasing monoamines in mice brain: HPLC analysis and in silico studies
  155. Simultaneous extraction and quantification of hydrophilic and lipophilic antioxidants in Solanum lycopersicum L. varieties marketed in Saudi Arabia
  156. Biological evaluation of CH3OH and C2H5OH of Berberis vulgaris for in vivo antileishmanial potential against Leishmania tropica in murine models
https://doi.org/10.1515/chem-2024-0005
Schlagwörter für diesen Artikel
labdane diterpenes; phenylpropanoids; ferulic acid; anti-parasitic activity; Vachellia nilotica
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  151. Phyto-fabrication and characterization of gold nanoparticles by using Timur (Zanthoxylum armatum DC) and their effect on wound healing
  152. Does Erodium trifolium (Cav.) Guitt exhibit medicinal properties? Response elements from phytochemical profiling, enzyme-inhibiting, and antioxidant and antimicrobial activities
  153. Integrative in silico evaluation of the antiviral potential of terpenoids and its metal complexes derived from Homalomena aromatica based on main protease of SARS-CoV-2
  154. 6-Methoxyflavone improves anxiety, depression, and memory by increasing monoamines in mice brain: HPLC analysis and in silico studies
  155. Simultaneous extraction and quantification of hydrophilic and lipophilic antioxidants in Solanum lycopersicum L. varieties marketed in Saudi Arabia
  156. Biological evaluation of CH3OH and C2H5OH of Berberis vulgaris for in vivo antileishmanial potential against Leishmania tropica in murine models
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Heruntergeladen am 6.12.2025 von https://www.degruyterbrill.com/document/doi/10.1515/chem-2024-0005/html
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