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Abstract

Objectives: Daniellia oliveri Rolfe is a well-known plant of Fabaceae family whose previous phytochemical and pharmacological studies led to the identification of triterpenoid, phenol, anthraquinone oxalate with antioxidant, antibacterial and antifungal activities. This study aimed to investigate chemical constituents and evaluate the antimicrobial potency of the root of D. oliveri. Methods: The methanol extract of the root barks of D. oliveri was subjected to silica gel chromatographic separation. The structures of the isolated compounds (1-9) were determined by analyzing their spectrometric and spectroscopic spectra. Single-crystal-Xray analysis was used to establish the absolute skeletal structure of compound 1. Crude extract, fractions and compounds were investigated against four bacteria vis Pseudomonas aeruginosa 27853, Escherichia coli 5, Staphylococcus aureus 25923 and Streptococcus sp. 9619 and, two yeast vis Candida albicans14053 and Candida tropicalis 018 using broth microdilution method. Results: The phytochemical prospection of the methanol extract of D. oliveri allowed the isolation of a naturally crystallized diterpenoid type furolabdane: polyalthic acid 1, as well as eight amorphous compounds (2-9). Among the tested samples, the crude extract, fractions and compounds selectively showed inhibitory effects against the tested microorganisms with MIC values ranging from 4 to 1024 μg/mL. Fraction D1 and compounds 1, 4, 7, 8 and 9 exhibited the broadest antimicrobial effects among fractions and compounds while D5 and compound 1 showed the best activity with MIC values of 16 and 4 μg/mL respectively against E. coli which appeared to be the most sensitive strain. Conclusion: Polyaltic acid (1) showed the best activity with significant MIC value of 4 μg/mL identical to that of ceftazidine against E. coli. The MIC values of the active compounds 1, 4 and 7 are comparable to those of ceftazidime. Then, these compounds from natural origin, could serve as markers in the standardization of Daniellia plant as phytomedicine.

Graphical abstract

This is a visual representation of the abstract.

Keywords

Fabaceae antimicrobial activity diterpene labdane single-crystal X-ray analysis

Introduction

Infectious illnesses are among the most common diseases and largest motive of mortality.¹ In recent years, the use of medicinal plants in alleviating various diseases, including infectious diseases have considerably increased.² Among these plants is Daniellia oliveri Rolfe a well-known plant of the Fabaceae family. In Africa, D. oliveri is very important in wooded savannas. It has a conical crown whose shape is generally tapered. It has up to 18.29 m-24.38 m tall with about 3.66 m in circumference, and the bark is pale gray and thick.^3,4 This African tree, is extensively found in Benin, Nigeria and Gambia.⁵

The stem, bark and leaves of D. oliveri are commonly used in the treatment of dysentery, syphilis, ring worms, wounds, typhoid fever, heart diseases, high blood, pains, asthma, skin infection and malaria.^5,6 In Nigeria the root is considered diuretic and a decoction is taken to treat veneral diseases, absence of menses, anxiety, jaundice, food poisoning, and skin diseases.^5,6 In northern Nigeria, leaves of D. oliveri are used to treat diabetes, gastrointestinal problems, diarrhea, as a diuretic and an aphrodisiac, the bark and the resin are used as a mosquito repellent.⁷ In the Adamawa region of Cameroon, D. oliveri is used in the treatment of skin infections, menstrual problems, wounds, diabetes and yellow fever. Previous phytochemical and pharmacological studies performed on D. oliveri led to the identification of triterpenoid, phenol, anthraquinone oxalate with antioxidant, antibacterial and antifungal compounds,^5,6 alkaloids with anti-inflammatory and antiparasitic potential,^5,6 tannin, phylate, diterpenoid, quinine, polyphenols, anthraquinone oxalate, saponins and steroid with antirheumatic, antidiabetic, antiseptic, diuretic, antiglycation and hypotensive properties.^8,9 In our permanent search for secondary metabolites with antimicrobial value from Cameroonian medicinal plants,^10–13 the investigation of the methanol extract of the root bark of D. oliveri was undertaken. Moreover, the extract, fractions and isolated compounds were investigated for their antimicrobial activity against Pseudomonas aeruginosa, Escherichia coli, Staphylococcus aureus, Streptococcus sp., Candida albicans and Candida tropicalis.

Results

General Information of the Isolated Compounds

Compounds 1-9 were obtained from the root bark of D. oliveri (Figure 1) by the means of chromatographic techniques. Among these compounds only polyaltic acid 1 was obtained in the form of crystal while other compounds 2-9 were isolated as amorphous white powders. This is the first time that such a natural crystal is reported from D. oliveri as well as its X-Ray data. The NMR data of compound 1 did not allow us to determine the absolute configuration of all its chiral centers, reason why crystallographic data were used.

Figure 1.

Structures of the isolated compound 1-9 from Daniellia oliveri.

The UV spectrum denoted a maximum absorption at 235 nm, while IR spectrum revealed absorption bands, indicating the existence of a γ-substitute furan ring (ether C-O at 1070 cm⁻¹ and aromatic C = C at 1470 cm⁻¹), unsaturated vinyldiene (-C = CH₂ at 1664 cm⁻¹) and carboxylic acid (C-O, C = O and O-H vibrating respectively at 1270, 1720 and 2960 cm⁻¹) functional groups. The ¹H and ¹³C NMR spectrometric properties were globally superimposable onto those of polyalthic acid (1) and that of its stereo-isomer daniellic acid.^14,15

The ¹HNMR (CDCl₃, 500 MHz)δ(ppm): 1.56/1.31 (2H, m, H-1a, H-1b), 1.53/1.43 (2H, m, H-2a, H-2b), 1.90/1.65 (2H, m, H-3a, H-3b),1.31 (1H, m, H-5), 1.96/1.89 (2H, m, H-6a, H-6b), 2.14/2.12 (2H, m, H-7a, H-7b),1.72(1H, m, H-9),1.61 (2H, m, H-11),2.55 (2H, m, H-12),6.24 (1H, s, H-14),7.33 (1H, m, H-15),7.18 (2H, s, H-16), 4.88/4.56 (2H, s, H-17a, H-17b),1.22 (3H, s, H-19),0.59 (3H, s, H-20) (Fig. S1); ¹³C NMR (CDCl₃, 125 MHz)δ(ppm): 40.4 (CH₂, C-1),19.8 (CH₂, C-2),37.2 (CH₂, C-3),44.2 (C, C-4),56.2 (CH, C-5),24.3 (CH₂, C-6),38.7(CH₂, C-7),147.8 (C, C-8),55.2 (CH, C-9),39.0 (C, C-10),28.9 (CH₂, C-11),26.0 (CH₂, C-12),125.4 (CH, C-13),111.0 (CH₂, C-14),142.6(CH₂, C-15),138.7 (CH₂, C-16),106.5 (CH, C-17),184.5 (C, C-18),28.9 (CH₃, C-19),12.7(CH₃, C-20) (Fig. S2).

The above mentioned information referred to diterpene type labdane derivative.^9,15 The molecular weight was 316.2 corresponding to the molecular formula C₂₀H₂₈O₃ corresponding to polyalthic acid and its stereo-isomer daniellic acid.¹⁵

Finally, the absolute stereochemistry of compound 1 was established based on single-crystal X-ray (Figure 2) which is its first X-ray analysis report. From the X-ray analysis, the final structure of compound 1 was found to be polyalthic acid instead of daniellic acid.

Figure 2.

Molecular structure of the crystals of compound 1in single-crystal-X ray.

All the other isolated compounds 2-9 were identified as: oleanolic acid 2,² sesamine 3,¹⁶ pinitol 4,¹⁷ sucrose 5,¹¹ a mixture of 7-O-[α-rhamnopyranosyl-(1→6)-β-glucopyranosyl]-5-hydroxy-4′-methoxyflavanone or didymin 6a and 7-O-[α-rhamnopyranosyl-(1→6)-β-glucopyranosyl]-4′,5-dihydroxyflavanone or narirutin 6b,¹⁸ 7-hydroxy-2-(4′-hydroxyphenyl)chroma-4-one or liquiritigenin 7,¹⁹ spinasterol 8,² and stigmasterol 9.²

Antimicrobial Assay

The crude extract demonstrated selective antimicrobial activity against the tested micro-organisms. It showed interesting activity on the tested strains of E. coli with MIC value of 32 μg/mL. The evaluated fractions (D1–D5) showed various degrees of antimicrobial activity (8 ≤ MIC ≤ 1024 µg/mL) with the best MIC value observed for fraction D5 on E. coli (MIC = 16 µg/mL). On yeasts, D1 and D2 appeared to be the most active fractions with MIC value of 512 µg/mL on C. albicans which showed more sensitivity compared to C. tropicalis (Table 1). As far as compounds are concerned, they showed various antimicrobial activities. Polyaltic acid 1 showed the best activity with MIC value of 4 μg/mL identical to that of the reference drug Ceftazidine against E. coli. Polyaltic acid 1 was isolated from one (D1) of the most active fractions. On all the tested microorganisms, fraction D1 and pinitol (4) exhibited the broadest antimicrobial effects among fractions and compounds respectively while D5 and Polyaltic acid (1) showed the best activity with MIC values of 8 and 4 μg/ml respectively against E. coli which appeared to be the most sensitive strain among both yeasts and bacteria. Liquiritigenin (7) isolated from D5 (The most active fraction against E. coli) was the most active compound on all the tested strains with MIC values ranging from 8 to 16 μg/ml. Yeasts are less sensitive compared to bacteria. The ratio MBC/MIC is globally less than 4. The MIC values of the active compounds 1, 4 and 7 are comparable to those of ceftazidime, the standard compound.

Table 1.

Minimum Inhibitory Concentrations (MIC) and Minimum Fungicidal Concentrations (MFC) of Crude Extract, Fractions, and Isolated Compounds in μg/mL.

Samples	MIC/MFC (µg/mL)
Samples	C. albicans	C. tropicalis	P. aeruginosa	E. coli	S. aureus	Streptococcus sp.
Crude extract	1024/-	/	/	32/128	/	/
D1	512/-	512/-	128/1024	64/256	128/512	/
D2	512/-	1024/-	/	256/512	/	/
D3	1024/-	/	/	512/1024	/	/
D4	1024/-	/	128/512	512/1024	/	/
D5	/	/	/	16/64	/	/
1	32/128	64/128	32/128	4/16	32/128	/
2	/	/	32/128	32/128	128/1024	/
3	/	/	/	/	/	/
4	32/-	256/512	16/64	128/512	16/64	16/64
5	/	/	/	/	/	/
6	512/-	512/-	/	/	/	/
7	/	16/128	8/32	8/32	8/16	8/64
8	/	512/-	32/128	64/128	32/128	128/256
9	512/-	/	32/64	32/128	32/64	64/128
Ceftazidine*	nd	nd	2/8	4/16	4/16	64/256
Nystatine*	16/64	8/16	nd	nd	nd	nd

MIC: Minimum inhibitory concentration. MFC: Minimum fungicidal concentration. nd: not determine. * Positive control./: not active

Crystal Structure Report for Compound 1

Compound 1, obtained in crystal form by atmospheric evaporation from the n-hexane/ethyl acetate (70:30) system, was applied to X-Ray (Figure 2). A specimen of C₈₀H₁₁₂O₁₂, approximate dimensions 0.110 mm × 0.120 mm × 0.190 mm, was used for the X-ray crystallographic analysis. The X-ray intensity data were measured (λ = 1.54178 Å). The integration of the data using a trigonal unit cell yielded a total of 77964 reflections to a maximum θ angle of 68.46 (0.83 Å resolution), of which 13437 were independent (average redundancy 5.802, completeness = 99.6%, R_int= 8.83%, R_sig= 5.28%) and 9750 (72.56%) were greater than 2σ(F²). The final cell constants of a = 13.0313 (3) Å, b = 13.0313 (3) Å, c = 37.5187 (9) Å, volume = 5517.6 (3) Å³, are based upon the refinement of the XYZ-centroids of reflections above 20 σ(I). The calculated minimum and maximum transmission coefficients (based on crystal size) are 0.8960 and 0.9380. The structure was solved and refined using the Bruker SHELXTL Software Package, using the space group P 32, with Z = 3 for the formula unit, C₈₀H₁₁₂O₁₂. The final anisotropic full-matrix least-squares refinement on F² with 827 variables converged at R1 = 7.49%, for the observed data and wR2 = 21.31% for all data. The goodness-of-fit was 1.046. The largest peak in the final difference electron density synthesis was 0.422 e⁻/Å³ and the largest hole was −0.245 e⁻/Å³ with an RMS deviation of 0.060 e⁻/Å³. Based on the final model, the computed density was 1.143 g/cm³ and F(000), 2064 e⁻.

Structure Feature

The crystal structure of title compound 1 was solved in trigonal system with P2 (3) space group having four independent molecules per asymmetric unit. One of the molecule in asymmetric unit shows disordered pyrrole ring and isotopically refined which further shows spliting on anisotopic refinement. The ORTEP view of compounds 1, shown in (Figure 3), demonstrated that the title compound 1 comprises of two six member ring A (C1-C6) and B (C5-C10) connected with each other via C5-C6 atoms and one planer five member pyrrole ring C(C13-C16/O3). Both the ring A and B acquirers chair conformation having carboxylic moiety at C1 position. In the crystal lattice molecules are connected with each other to form two six-member ring motif R²₂(8) via O1-H1…O4 (O1-H1…O4 = 155˚, H3A…O2 = 1.69 Å), O5-H5…O2 (O5-H5…O2 = 138˚, H12B…O2 = 1.93 Å) and O11-H8…O8 (O11-H8…O8 = 144˚, H8…O8 = 1.82 Å), O7-H7…O10 (O7-H7…O10 = 173˚, H7…O10 = 1.63) intermolecular interaction. Further C75-H75…O10 and C36-H36…O10 intermolecular interactions further contributed to stabilize the molecule in three-dimensional network (Figure 3, Table 2). Crystallographic data and experimental details for structural analysis of compound 1 is summarized in Table 3.

Figure 3.

The unit cell packing diagram of compound 1.

Table 2.

Crystallographic Data of Compound 1.

Identification code	Compound 1
Chemical formula	C₈₀H₁₁₂O₁₂
Formula weight	1265.69 g/mol
Temperature	273(2) K
Wavelength	1.54178 Å
Crystal system	Trigonal
Space group	P 3(2)
Unit cell dimensions	a = 13.0313(3)Å b = 13.0313(3)Å c = 37.5187(9)Å α = 90° β = 90° γ = 120°
Volume	5517.6(3)Å
Z	3
Calculated density	1.143 g/cm³
Absorption coefficient	0.593 mm⁻¹
F(000)	2064
Crystal size	0.110 mm × 0.120 mm × 0.190 mm
Theta range for data collection	3.53 to 68.46°
Limiting indices	−13<=h<=15 -15<=k<=15 -45<=l<=45
Reflections collected	77964
Refinement method	Full-matrix least-squares on F²
Independent reflections	3125 [R(int) = 0.0883]
Data / restraints/parameters	13437 / 3 / 827
Goodness-of-fit on F²	1.046
Final R indices I > 2σ(I)	R1 = 0.0749 wR2 = 0.1949
R indices (all data)	R1 = 0.1023 wR2 = 0.2131
Largest diff. peak and hole	0.422 and -0.245 eÅ⁻³

Table 3.

Hydrogen Bonding Table for Compound 1.

D	H	A	D-H	H…A	D…A	D-H…A
O1	H1	O4	1.00	1.69	2.638(8)	155(12)
O5	H5	O2	0.91	1.93	2.6775(7)	138(15)
O7	H7	O10	1.00	1.63	2.624(8)	173
O11	H8	O8	1.01	1.82	2.701 (8)	144
C75	H75	O10	0.93	2.47	3.31(2)	150
C36	H36	O10	0.93	2.66	3.431(11)	150.7

Symmetry Codes: x-1,y,z^#1, x + 1, y, z^#2.

Discussion

The crude extract showed selective antimicrobial activity against the tested micro-organisms. According to Kuete,¹ the activity of extracts is classified as significant when MIC < 100 µg/mL, as moderate when 100 < MIC <625 µg/mL and as weak when (MIC > 625 µg/mL). Based on this classification, the crude extract showed significant activity on the tested strains of E. coli. Previous studies revealed the antimicrobial activities of Daniellia oliveri. In fact, it was shown that the leaf essential oils of D. oliveri showed marginal antibacterial activity against Bacillus cereus, Cutibacterium acnes, Staphylococcus aureus, Staphylococcus epidermidis, Streptococcus pyogenes, Pseudomonas aeruginosa, and Serratiamarcescens, and antifungal activity against Aspergillus fumigatus, Aspergillus niger, Cryptococcus neoformans, Microsporum canis, Microsporum gypseum, Trichophyton mentagrophytes, Trichophyton rubrum, and Candida albicans while D. oliveri bark essential oil showed notable antifungal activity against Aspergillus niger and Trichophyton rubrum with a minimum inhibitory concentration (MIC) of 78.1 µg/mL for each.⁷ These findings are different from the obtained results and could be justified by the difference in the extract type.²⁰

The tested fractions (D1–D5) showed various degrees of antimicrobial activity (8 ≤ MIC ≤ 1024 µg/mL) with the significant MIC value observed for fraction D5 on E. coli. These results are different from previous findings which revealed that four chromatographic fractions of the aqueous ethanolic extract of the leaves of Daniellia oliveri showed activity against Staphylococcus aureus while one chromatographic fraction showed significant activity against the fungus Tricophyton rubrum with an inhibition diameter of 10.5 mm.²¹ Moreover, to the contrary of our findings, they showed no activity against Staphylococcus aureus, Escherichia coli, Pseudomonas aeruginosa. This difference in activity could be astribed to the difference in the testing methods because they used disk dilution methods against broth microdillution method used in this study. It could also be due to the difference in the type of extraction solvent which can modify the composition of the extract hence the biological activity.²⁰ On Bacteria strains, D5 showed a significant MIC value on E. coli. Compounds showed various antimicrobial activities. According to Kuete,¹ the activity of pure compounds was classified as significant when (MIC < 10 µg/mL), as moderate when (10 < MIC <100 µg/mL) and as weak when (MIC > 100 µg/mL). Polyaltic acid 1 showed the best activity with significant MIC value against E. coli. Polyaltic acid 1 was isolated from one (D1) of the most active fractions and the observed antimicrobial efficacy is in agreement with previously reported data for diterpene.⁹ In the literature, several authors have demonstrated the antimicrobial potential of natural diterpernoid which corroborates the present findings.^2,6 While polyaltic acid (1) was evaluated against P. aeruginosa, S. aureus, C. albicans and C. tropicalis,^5,6 this is the first report against E. coli and Streptococcus spp. On all the tested microorganisms, D5 and Polyaltic acid (1) showed the significant activity with MIC values of 8 and 4 μg/ml respectively against E. coli which appeared to be the most sensitive strain among both yeasts and bacteria. Liquiritigenin (7) showed significant activity against almost all the tested strains. Yeasts are less sensitive compared to bacteria. This could be astribed to the difference in their genetic materials since they belong to two different kingdoms.²² The non-active compounds 3 and 5 respectively isolated from fractions 1 and 3 which were among the most active fractions against yeasts and bacteria showed that their constituents may be acting by synergy.²⁰ Pinitol (4) globally displayed moderate activities against bacteria but low anti-yeast activities. The same observation is made with spinasterol (8) and β-sistosterol (9). This is in line with previous findings.²² The ratio MBC/MIC is globally less than 4 showing that the extract has bactericidal activity against all the tested strains.²³ The MIC values of the active compounds 1, 4 and 7 are comparable to those of ceftazidime, the standard compound. Then, it is particularly interesting to notice that these compounds, which are from natural origin, could serve as markers in the standardization of Daniellia plant as phytomedicine.

Limitations

The tested compounds were not in sufficient quantity to allow the study of their activities on more strains of microorganisms.

Conclusion

The results obtained in this research revealed the presence of antimicrobial phytochemical components from the root bark of D. oliveri. Single-crystal-X Ray was used to determine the absolute stereochemistry of compound 1. The presence of the active phytochemical constituents in D. oliveri could justify its traditional use in the treatment of infectious diseases of microbial origin.

Experimental

Plant Material

The root barks of Daniellia oliveri Rolfe were collected in October 2021 from Adamawa region of Cameroon. The plant was identified by Mr Eric Ngansop, a botanist at the Cameroon National Herbarium in Yaoundé by comparison with an existing voucher specimen HNC10672/SFR/CAM.

Chemicals and Instruments

TLC was performed on silica gel 60 F₂₅₄ (Merck) plates, after what they were sprayed with H₂SO₄ (10%) reagent, heating and spots visualized on 254-364 nm UV. Silica gel mesh 60- 120 (Merck) was used for Column chromatography while a JASCO 7300 FTIR spectrometer helped in recording IR spectra as KBr pellets. The NMR (1D &2D) hetero- and homonuclear spectra were obtained on a Bruker spectrometer (AMX-500) with TMS (δ(ppm)) as the reference at 500 and 600 MHz; while Hertz (Hz) is the unit of coupling constants (J). HRESIMS (high resolution electrospray ionization mass spectrometry) spectrograms were recorded on a Varian MAT 311A spectrometer X-ray analysis was performed on Bruker D8 Quest Photon 100 diffractometer equipped with an Incoatec IμS high brilliance Cu Kα (1.54178 Å) X-ray.

Extraction and Chromatographic Separation

The powder obtained from air-dried D. oliveri root barks (1.0 kg) was extracted with 4L MeOH at room temperature for 3 days. After filtration, the extract was concentrated using a rotary evaporator to yield 80.5 g of a viscous dark yellow methanolic crude extract (ME). 60.0 g of ME was subjected to a silica gel column (70-230 mesh) and eluted with n-hexane then n-hexane-EtOAc (100:0→0:100) and EtOAc-MeOH (100:0→0:100) in increasing polarity to yield 110 subfractions (150 mL each) combined into five main fractions (D1–D5) based on their TLC profiles. Fraction D1 (19.7 g) was applied to column (70-230 mesh) and eluted with n-hexane then n-hexane-EtOAc (90:10-50:50) to give 03 sub fractions(D1A1 – D1A3). D1A1 (12.1 g) was assessed on silica gel column (70-230 mesh) eluted with n-hexane-EtOAc (60:40) isocratic to afford a crystalline polyalthic acid (1, 2.1 g) and an amorphous white powder of oleanolic acid (2, 5.0 mg). From D1A2 (3.2 g) and D1A3 (2.1 g), sesamine (3, 4.2 mg), was obtained in the form of white powder and was subsequently purified. By comparing their TLC profiles, the fraction D2 (11.3 g)was applied to column (70-230 mesh) and eluted with n-hexane-EtOAc (100:0-80:20) to give 01 sub fractions(D2A1), spinasterol (8, 6.0 mg) and β-sistosterol (9, 4.4 mg) were isolated from D2A1. The fraction D3 (12.3 g) was subjected to silica gel column (70-230 mesh) using a gradient elution system of n-hexane-EtOAc (100:0-60:40) to have two subfractions (D3A4 and D3A5), Pinitol (4, 5.0 mg) was isolated from D3A4 and sucrose (5, 7.2 mg) was isolated from D3A5. While7-O-[α-rhamnopyranosyl-(1→6)-β-glucopyranosyl]-5-dihydroxy-4′-methoxyflavanone (6, 5.1 mg) and 6-dihydroxy-2-(4.hydroxyphenyl) chroma-4-one (7, 5.2 mg) were isolated from Fraction D4 (8.3 g) and D5 (11.3 g) respectively.

Polyaltic acid (1). White crystal; UV (MeOH) λ_max: 235 nm; IR (KBr) ν_max: 1070, 1470, 1664, 1270,1720, 2960cm⁻¹; ¹HNMR (CDCl₃, 500 MHz) and ¹³C NMR (CDCl₃, 125 MHz) data (Tables 1); LR-EI-MS m/z: 316.2.

Evaluation of in Vitro Antimicrobial Activity

Bacteriological assay. The antimicrobial activity of the tested stuffs was carried out on six microbial strains including four bacterial strains (P. aeruginosa 27853, E. coli 5, S. aureus 25923 and Streptococcus sp. 9619) and two strains of yeast (C. albicans14053 and C. tropicalis 018). These strains were obtained from the Research Unit of Microbiology and Antimicrobial Substances of the University of Dschang-Cameroon. The choice of these micro-organisms was motivated by their impact in human health. In fact, Pseudomonas aeruginosa, can cause infections in the blood, lungs (pneumonia), or other parts of the body after surgery,²⁴ E. coli is a group of bacteria that can cause infections in gut, urinary tract and other parts of the body.²⁵ Staphylococcus aureus acts as a commensal of the human microbiota, but can also become an opportunistic pathogen, being a common cause of skin infections including abscesses, respiratory infections such as sinusitis, and food poisoning.²⁶ Streptococcus species are responsible for many cases of pink eye, meningitis, bacterial pneumonia, endocarditis, erysipelas, and necrotizing fasciitis.²⁷ Candida albicans and C. tropicalis are usually commensal organisms, but can become pathogenic to immunocompromised individuals under a variety of conditions. Species of the genus Candida cause the human infection candidiasis, which results from an overgrowth of the fungus.^28,29

Microorganisms were activated for one or two days respectively for bacteria and yeasts growth before being used in the experiment. Bacteria and yeasts inocula were separately prepared from 24 h Muller Hinton agar and 48 h Sabouraud Dextrose Agar cultures respectively for bacteria and yeasts. Colonies from each microorganism were diluted in 0.9% NaCl to have a turbidity matching the 0.5 of Mc Farland standard turbidity scale equivalent to about 1.5 × 10⁸ CFU/mL. The microorganism suspensions were diluted to match the absorbance of 0.1 for bacteria and 0.09 for yeast at 600 nm (Jenway 6105 UV/Vis spectrophotometer, 50 Hz/60 Hz) equivalent to about 2.5 × 10⁵ spores/mL for yeast and 10⁶ CFU/mL for bacteria.³⁰ The broth microdilution method,^31,32 was employed to evaluate the MIC as well as the fungicidal concentration (MFC) of the tested stuffs utilizing 96 well microplates.

Supplemental Material

sj-docx-1-npx-10.1177_1934578X241282853 - Supplemental material for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid

Supplemental material, sj-docx-1-npx-10.1177_1934578X241282853 for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid by Larissa M. Magnibou, Dabole Bernard, Peron B. Leutcha, Guy S.S. Njateng, Larissa Y. Chimi, Maurice F. Tagatsing, Sammer Yousuf, Atia-tul-Wahab, Muhammad I. Choudhary and Emmanuel Talla in Natural Product Communications

Supplemental Material

sj-docx-2-npx-10.1177_1934578X241282853 - Supplemental material for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid

Supplemental material, sj-docx-2-npx-10.1177_1934578X241282853 for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid by Larissa M. Magnibou, Dabole Bernard, Peron B. Leutcha, Guy S.S. Njateng, Larissa Y. Chimi, Maurice F. Tagatsing, Sammer Yousuf, Atia-tul-Wahab, Muhammad I. Choudhary and Emmanuel Talla in Natural Product Communications

Supplemental Material

sj-docx-3-npx-10.1177_1934578X241282853 - Supplemental material for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid

Supplemental material, sj-docx-3-npx-10.1177_1934578X241282853 for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid by Larissa M. Magnibou, Dabole Bernard, Peron B. Leutcha, Guy S.S. Njateng, Larissa Y. Chimi, Maurice F. Tagatsing, Sammer Yousuf, Atia-tul-Wahab, Muhammad I. Choudhary and Emmanuel Talla in Natural Product Communications

Supplemental Material

sj-docx-4-npx-10.1177_1934578X241282853 - Supplemental material for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid

Supplemental material, sj-docx-4-npx-10.1177_1934578X241282853 for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid by Larissa M. Magnibou, Dabole Bernard, Peron B. Leutcha, Guy S.S. Njateng, Larissa Y. Chimi, Maurice F. Tagatsing, Sammer Yousuf, Atia-tul-Wahab, Muhammad I. Choudhary and Emmanuel Talla in Natural Product Communications

Footnotes

Acknowledgments

Authors are grateful to TWAS- ICCBS for the fellowship award.

Declaration of Conflicting Interests

The authors declared no potential conflicts of interest with respect to the research, authorship, and/or publication of this article.

Ethical Approval

Ethical Approval is not applicable for this article since our study does involve neither animals nor humans.

Funding

The authors disclosed receipt of the following financial support for the research, authorship, and/or publication of this article: This work was financially supported by Third World Academy of Science (TWAS)- International Center for Chemical and Biological Sciences (ICCBS) fellowship (N⁰: 3240311212). The recipient was Dr Larissa M. Magnibou.

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Guy S.S. Njateng

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Supplementary Material

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Phytochemical Constituents,Antimicrobial Activity of Daniellia oliveri,and X-ray Crystal Structure of Polyalthic Acid

Abstract

Keywords

Introduction

Results

General Information of the Isolated Compounds

Antimicrobial Assay

Crystal Structure Report for Compound 1

Structure Feature

Discussion

Limitations

Conclusion

Experimental

Plant Material

Chemicals and Instruments

Extraction and Chromatographic Separation

Evaluation of in Vitro Antimicrobial Activity

Supplemental Material

sj-docx-1-npx-10.1177_1934578X241282853 - Supplemental material for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid

Supplemental Material

sj-docx-2-npx-10.1177_1934578X241282853 - Supplemental material for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid

Supplemental Material

sj-docx-3-npx-10.1177_1934578X241282853 - Supplemental material for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid

Supplemental Material

sj-docx-4-npx-10.1177_1934578X241282853 - Supplemental material for Phytochemical Constituents, Antimicrobial Activity of Daniellia oliveri, and X-ray Crystal Structure of Polyalthic Acid

Footnotes

Acknowledgments

Declaration of Conflicting Interests

Ethical Approval

Funding

ORCID iD

Statement of Human and Animal Rights

Statement of Informed Consent

Supplemental Material

References

Supplementary Material