Antibacterial and antioxidant activities of compounds isolated from the leaves of Symphonia globulifera (Clusiaceae) and their chemophenetic significance
“…The presence of the polyprenylated benzophenones ( 1 – 3 ) is not surprising since benzophenones (polycyclic polyprenylated acylphloroglucinols) are known to be widespread in the Clusiaceae family [ 27 ]. Moreover, gaboxanthone ( 6 ), symphonin ( 9 ), lupeol ( 15 ), β -sitosterol ( 11 ), stigmasterol ( 12 ), and β -sitosterol 3- O - β -D-glucopyranoside ( 13 ) have been reported from S. globulifera [ 29 , 43 , 44 ]. In addition, the new tocotrienol derivative ( 4 ) has been isolated for the first time from the genus Symphonia .…”
The chemical investigation of the n-hexane fraction from the methanol extract of the stem bark of Symphonia globulifera Linn f., which displayed good in vitro activity against Leishmania donovani NR-48822 promastigotes (IC50 43.11 µg/mL), led to the isolation of three previously unreported polyprenylated benzophenones, guttiferone U (1), V (2)/W (3), and a new tocotrienol derivative named globuliferanol (4), along with 11 known compounds (5–15). Their structures were elucidated based on their NMR and MS data. Some isolated compounds were assessed for both their antileishmanial and cytotoxic activities against L. donovani and Vero cells, respectively. Guttiferone K (5) exhibited the best potency (IC50 3.30 μg/mL), but with low selectivity to Vero cells. The n-hexane fraction and some compounds were also assessed in vitro for their antibacterial activity against seven bacterial strains. All the samples exhibited moderate to potent antibacterial activity (MICs ≤ 15.6 µg/mL) against at least one of the tested strains.
“…The presence of the polyprenylated benzophenones ( 1 – 3 ) is not surprising since benzophenones (polycyclic polyprenylated acylphloroglucinols) are known to be widespread in the Clusiaceae family [ 27 ]. Moreover, gaboxanthone ( 6 ), symphonin ( 9 ), lupeol ( 15 ), β -sitosterol ( 11 ), stigmasterol ( 12 ), and β -sitosterol 3- O - β -D-glucopyranoside ( 13 ) have been reported from S. globulifera [ 29 , 43 , 44 ]. In addition, the new tocotrienol derivative ( 4 ) has been isolated for the first time from the genus Symphonia .…”
The chemical investigation of the n-hexane fraction from the methanol extract of the stem bark of Symphonia globulifera Linn f., which displayed good in vitro activity against Leishmania donovani NR-48822 promastigotes (IC50 43.11 µg/mL), led to the isolation of three previously unreported polyprenylated benzophenones, guttiferone U (1), V (2)/W (3), and a new tocotrienol derivative named globuliferanol (4), along with 11 known compounds (5–15). Their structures were elucidated based on their NMR and MS data. Some isolated compounds were assessed for both their antileishmanial and cytotoxic activities against L. donovani and Vero cells, respectively. Guttiferone K (5) exhibited the best potency (IC50 3.30 μg/mL), but with low selectivity to Vero cells. The n-hexane fraction and some compounds were also assessed in vitro for their antibacterial activity against seven bacterial strains. All the samples exhibited moderate to potent antibacterial activity (MICs ≤ 15.6 µg/mL) against at least one of the tested strains.
“…Thereafter, other flavonoids (TED 13, and ZTF 1016) previously isolated and characterized from plant extracts (see Fig. 1 ) were considered [ 33 , 34 ]. Fig.…”
Section: Methodsmentioning
confidence: 99%
“…1 Structures of flavonoids used in this study include quercetin, TED 13, and ZTF 1016. TED 13 was isolated from plant extracts [ 33 , 34 ]. ZTF 1016 was recently isolated from Erythrina abyssinica and has not been published …”
Flavonoids are a class of secondary plant metabolites with low molecular weights. Most flavonoids are highly polar and unsuitable for gas chromatographic analyses. Derivatization is commonly used to make them amenable to gas chromatography by altering their physicochemical properties. Although highly effective, derivatization techniques introduce extra preparation steps and often use hazardous chemicals. The aim of this study was to automate derivatization (specifically, silylation) by developing 3D printed microfluidic devices in which derivatization of flavonoids can occur. A microfluidic device was designed and 3D printed using clear polypropylene. Quercetin and other flavonoids (TED 13 and ZTF 1016) isolated from plant extracts were silylated with N-tert-butyldimethylsilyl-N-methyltrifluoroacetamide (MTBSTFA) at room temperature both in batch and in continuous flow. All the samples were analyzed using Fourier transform infrared (FTIR) spectroscopy, gas chromatography combined with mass spectrometry (GC–MS), and high-resolution accurate mass spectrometry (HR-MS). Interestingly, the HR-MS results showed that the flow method was about 25 times more efficient than the batch method for quercetin samples. The TED 13 flavonoid was completely derivatized in the flow method compared to the batch method where the reaction was incomplete. Similar results were observed for ZTF 1016, where the flow method resulted in a four times derivatized compound, while the compound was only derivatized once in batch. In conclusion, 3D printed microfluidic devices have been developed and used to demonstrate a semi-automated, inexpensive, and more efficient natural product derivatization method based on continuous flow chemistry as an alternative to the traditional batch method.
“…Impact of Water on Triterpenoid and 3-Coumaroyl-4-Caffeoylquinic Acids A pentacyclic triterpenoid was identified as 3-beta-hydroxy-5-glutinen-28-oic acid. This compound is derived from a natural anticancer botulin, which has pharmacological properties, including cholesterol reduction [60]. Metabolites (20)(21) were detected by their parent ion at a m/z of 491 based on their fragmentation patterns, Rt, shown in Table 8.…”
Section: Impact Of Water On Methyl Chlorogenate Acidsmentioning
The influence of water regimes on plants is crucial for integrating bush tea (Athrixia phylicoides DC.) into strategies in Sub-Saharan Africa to tackle food and nutritional insecurity by considering physiological aspects, nutritional yield, nutritional water productivity, and metabolite composition. The objective of the study was to determine the physiological aspects, including leaf gas exchange and chlorophyll fluorescence, nutritional yield, nutritional water productivity, and metabolite composition of bush tea under varying water regimes. The tunnel experiment was laid out in a randomized complete block design (RCBD) with treatments consisting of three water regimes: 100% of crop water requirement (ETa), 30% of ETa, and a control (no irrigation), all replicated three times. The morphological aspects were recorded on a weekly basis. However, yield, nutrient content, nutritional water productivity (NWP), and phytochemical composition were determined at harvest. The phytochemical analysis by liquid chromatography mass spectrometry (LC-MS), coupled with visualization of the detected chemical spaces through molecular networking, indicated Athrixia phylicoides DC. to be rich in various bioactive compound derivatives, including methyl chlorogenate, flavonoids, tartaric acid, caffeoylquinic acid, and glutinane. The results showed that 30% ETa enhanced plant growth, nutrient content, and nutritional water productivity compared to other water treatments. Nevertheless, 100% ETa yielded more (95.62 kg ha−1) than 30% ETa (60.61 kg ha−1) and control (12.12 kg ha−1). The accumulation of chlorogenic acids was higher under 30% ETa compared to 100% ETa and control. Therefore, this study is the first to determine the accumulation of various bioactive compounds in bush tea leaf extracts under varying water regimes. This confirms that in areas with low water availability, bush tea is well adapted for production without limiting nutrients.
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