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Isolation and Structure Elucidation of Phenolic Compounds of Carob Leaves Grown in Egypt
Abstract
Carob leaves (Ceratonia siliqua L.), grown in Egypt have not fully identified in Egypt. Therefore, eight major phenolic compounds were isolated from the aqueous ethanolic extract using different methods of chromatography; gallic acid, quercetin 3-O-4C1-B-D-glucoside (Isoquercetin), Kaempferol 3-O-1C4-α-Lrhamnoside (Afzelin), Quercetin 3-O-1C4-α-L-rhamnoside (Quercitrin), 1,2,6 tri-O-galloyl-B-D-4C1- glucopyranose, (-)-Epigallocatechin-3-O-gallate, kaempferol and quercetin. Their structures established by conventional methods of analysis. This is the first phytochemical study of polyphenolic content of carob leaves grown in Egypt.
... The majority are flowering plants, distributed mainly within tropical and neo-tropical regions of South America, southern Asia, and Africa (Castillo and Rossini 2010;Mahmoud et al. 2019;Samy et al. 2021). Extensive research interests have been focused on Bignoniaceous plants, owing to the great diversity of the bioactive secondary metabolites such as phenylpropanoids, iridoids, lignans, coumarins, flavonoids, quinones, and triterpenes (Chu et al. 2011;Mahmoud et al. 2019) The largest genus of the family Bignoniaceae is Tabebuia Gomes ex DC., which is currently composed of 99 species, mainly flowering trees distributed from the southwestern U.S. to northern Argentina and rich in various classes of secondary metabolites, including saponins, tannins, flavonoids, alkaloids, glycosides, iridoids, terpenes, and coumarins, with the exhibition of different pharmacological actions (Gentry 1992;Choudhury et al. 2011;Eldahshan 2011;Sianturi et al. 2016). Therefore, it is considered a good resource for discovering valuable compounds. ...
... Tabebuia species are traditionally applied as a diuretic and an astringent remedy, besides treating diabetes and ulcers (Samy et al. 2015;Luo et al. 2016). Additionally, there are many reports that revealed the diverse biological activities of Tabebuia, such as anti-inflammatory, cytotoxic, immunomodulatory, and antimicrobial activities (Morota et al. 1989;Eldahshan 2011;Samy et al. 2015;Sianturi et al. 2016;Luo et al. 2016). Tabebuia aurea (Silva Manso) Benth. ...
... T. aurea is famed as 'Craibeira', 'Paratudo' and 'Ip^e-amarelo' in Northeastern Brazil and is used to treat snake bites in the form of an infusion or maceration with alcohol or by chewing the stem bark during the day. In addition, it is used as an anti-inflammatory agent and a remedy for influenza (Morota et al. 1989;Beninger and Hosfield 1999;Eldahshan 2011;Samy et al. 2015;Sianturi et al. 2016;Luo et al. 2016). Our previous study revealed various compounds in ethyl acetate soluble fraction by LC-MS analysis, including triterpenoids and flavonoids (Mahmoud et al. 2021), and reported five triterpenes with cytotoxicity and antileishmanial activities recently (Mahmoud et al. 2022). ...
One new iridoid named aureanin (1) was isolated from the leaves of Tabebuia aurea (Silva Manso) Benth. & Hook.f. ex S.Moore, together with eight known compounds, isoquercetin (2), astragalin (3), callicoside B (4), amphipaniculoside E (5), rehmaglutin D (6), quercetin-3-sambubioside (7), rutin (8), kaempferol-3-O-rutinoside (9). The structures of the isolated compounds were elucidated and confirmed by spectroscopic methods, including 1 D and 2 D NMR experiments, as well as HR-ESI-MS. Compounds 1-9 were evaluated for their in vitro cytotoxic activity against three human cancer cell lines (A549, HepG2, and MCF-7) and Leishmania major. Compound 4 showed activity against A549 (IC 50 : 36.8 ± 1.5 lg/mL, etoposide (positive control): 28.1 ± 4.2 lg/mL), however, none of the compounds were active against L. major.
... Though this ferulic ester has previously been synthesized [35], this is the first report of its isolation from the plant kingdom. [36], FEQ-5, corresponding to C7H6O5, was therefore identified as trihydroxybenzoic acid, also known as gallic acid. It is being reported herein for the first time from the entire Entada genus. ...
... Additionally, isolated aglycone flavonoids were also characterized using FT-IR, melting point, 1D-NMR (Tables 5 and 6) [36], FEQ-5, corresponding to C 7 H 6 O 5 , was therefore identified as trihydroxybenzoic acid, also known as gallic acid. It is being reported herein for the first time from the entire Entada genus. ...
... The methanol-insoluble part was filtered off while the filtrate (33 mg) was purified on a preparative TLC plate using CHCl 3 : MeOH (60:40) as developing solvent to afford FEQ-7 (6.3 mg). Fraction F 2 G (118.2 mg) was subjected to silica gel column chromatography eluting with CHCl 3 : EA 90:10→0: 100 to afford combined fractions F2G 19-24 (44 mg), F2G 7-18 (38.5 mg) and F2G [28][29][30][31][32][33][34][35][36] (8.5 mg). Fraction F2G [19][20][21][22][23][24] was repeatedly purified on preparative TLC plates with EA: FA (90:10) to yield FEQ-8 (5.0 mg). ...
Digestive enzymes and free radical inhibitors are used to prevent complications resulting from diabetes. Entada spiralis (family Leguminosae), which is a well-known medicinal plant in herbal medicine due to its various traditional and medicinal applications, was studied. Crude extracts were successively obtained from the stem bark using petroleum ether, chloroform and methanol as extracting solvents. The antioxidant activity of all the extracts, fractions and isolated compounds were estimated using 2,2-diphenyl-1-picrylhydrazyl (DPPH), β-carotene and 2,2′-azinobis(-3-ethylbenzothiazine-6-sulfonic acid) (ABTS) assays, while digestive enzymes inhibitory activity was assessed using α-amylase and α-glucosidase inhibitory methods. Structure elucidation of pure compounds was achieved through different spectroscopic analysis methods. Fractionation and purification of the most active methanol extract resulted in the isolation of a ferulic ester namely; (e)-hexyl 3-(4-hydroxy-3-methoxyphenyl) acrylate (FEQ-2) together with five known phenolic constituents, identified as kaempferol (FEQ-3), 5,4′-dihydroxy-3,7,3′-trimethoxyflavone (FEQ-2), gallic acid (FEQ-5), (+)-catechin (FEQ-7) and (−)-epicatechin (FEQ-8). FEQ-5 exhibited the strongest antioxidant and enzyme inhibitory activities followed by FEQ-3 and FEQ-4. FEQ-2 also displayed potent free radical scavenging activity with IC50 values of 13.79 ± 2.13 (DPPH) and 4.69 ± 1.25 (ABTS) µg/mL, respectively. All other compounds were found active either against free radicals or digestive enzymes.
... 13 C NMR data showed five signals in aromatic region identical to that of gallic acid, δ 168.2 (C=O), 145.7 (C-3, 5), 138.5 (C-4), 121.8 (C-1) and 109.6 (C-2, 6). Gallic acid is widely distributed in tannin containing plants [33]. H NMR showed one singlet signal in aromatic region at δ 7.6 (2H, s, aromatic-H). ...
... According to mixed m.p. and color reaction on PC comparable with authentic sample; compound 5 identified as ellagic acid [34]. Table 1) which suggested that compound 6 was EGCG [33]. (Table 1) agree with the previous data and suggested that compound 7 identified as kaempferol-3-O-α-L-rhamnoside which previously isolated from other plants [33,35]. ...
... Table 1) which suggested that compound 6 was EGCG [33]. (Table 1) agree with the previous data and suggested that compound 7 identified as kaempferol-3-O-α-L-rhamnoside which previously isolated from other plants [33,35]. (Table 1), showed 13 signals, two oxymethylene at δ 70.5 (OCH 2 -7) and δ 60.3 (CH 2 OH, glu), five oxymethines (CHOH, glu), five methane (aromatic CH) and one quaternary carbon (aromatic C), it suggest presence of mono-substituted aromatic ring and hexose sugar. ...
Objectives: The present study on the methanol extract of Abutilon hirtum (Lam.) [Malvaceae] afforded ten compounds. Findings from this assessment indicated that A. hirtum leaves possessed vast potential as medicinal product especially in liver cancer treatment. Methods: Dried-powdered leaves were boiled under reflux in 10 L of petroleum ether for 8 hrs. After filtration, the solvent was evaporated; afforded 15 g of petroleum ether extract followed by boiling with reflux for 8 hrs with chloroform, then filtration and the residue was evaporated to give 34 g chloroform extract. Ethyl acetate was added and refluxed for 8 hrs, then filtration and evaporation to give 31 g ethyl acetate extract. Finally the leaves were refluxed with 10 L of 85 % aqueous MeOH, after cooling, the solution was filtered and evaporated and the residue was 210 g methanol extract then the residue was dissolved in de-ionized water (250 ml), then the salt was removed by adding excess methanol solution (2.5 L), and finally filtered. The cytotoxicity of the isolated compounds was evaluated towards HepG2 liver-carcinoma cell line using MTT assay, the antimicrobial activity was tested using the Disc agar plate method and the total antioxidant capacity was determined according to phosphomolybdenum method. Results: The isolated compounds identified as methyl gallate, cuneataside E, bergapten, gallic acid, ellagic acid, epigallocatechin-3-O-gallate, kaempferol-3-O-α-L-rhamnoside, benzyl-1-O-β-D-glucopyranoside, 2(4-hydroxyphenyl)ethyl-O-β-D-glucopyranoside and β-sitosterol. All the isolated compounds are known; but they were isolated from Abutilon hirtum for the first time. Conclusion: This report may serve as a footprint concerning the biological and pharmacological activities of A. hirtum leaves.
... Three new compounds were identified by their NMR ( 1 H, 13 C, HSQC, HMBC), UV and mass spectra, optical rotations, and by comparison with previously reported spectroscopic data. The five known galloylated and non-galloylated flavonol rhamnosides were quercetin-3-O-(3 00 -Ogalloyl)-a-L-rhamnopyranoside (4) (Moharram et al., 2006), quercetin-3-O-a-L-rhamnopyranoside (5) (Eldahshan, 2011), kaempferol-3-O-(2 00 ,3 00 -di-O-galloyl)-a-L-rhamnopyranoside (6) (Lee et al., 2009), kaempferol-3-O-(3 00 -O-galloyl)-a-L-rhamnopyranoside (7) (Mahmoud et al., 2001) and kaempferol-3-O-a-Lrhamnopyranoside (8) (Eldahshan, 2011); respectively. ...
... Three new compounds were identified by their NMR ( 1 H, 13 C, HSQC, HMBC), UV and mass spectra, optical rotations, and by comparison with previously reported spectroscopic data. The five known galloylated and non-galloylated flavonol rhamnosides were quercetin-3-O-(3 00 -Ogalloyl)-a-L-rhamnopyranoside (4) (Moharram et al., 2006), quercetin-3-O-a-L-rhamnopyranoside (5) (Eldahshan, 2011), kaempferol-3-O-(2 00 ,3 00 -di-O-galloyl)-a-L-rhamnopyranoside (6) (Lee et al., 2009), kaempferol-3-O-(3 00 -O-galloyl)-a-L-rhamnopyranoside (7) (Mahmoud et al., 2001) and kaempferol-3-O-a-Lrhamnopyranoside (8) (Eldahshan, 2011); respectively. ...
... These data suggested that compound 1 was a kaempferol rhamnoside derivative. The 1 H NMR spectrum of 1 was also similar to that of kaempferol-3-O-a-Lrhamnopyranoside (8) and kaempferol-3-O-(2 00 ,3 00 -di-O-galloyl)a-L-rhamnopyranoside (6), (Lee et al., 2009;Eldahshan, 2011), except for one additional galloyl moiety. The rhamnose H-1 00 proton of 1 showed a weak correlation to a carbon at 133.7 ppm (C-3) in a similar fashion to that shown in the HMBC spectrum for compound 8. ...
Three galloylated flavonol glycosides 1 – 3, together with five known flavonol glycosides 4 – 8 were isolated from the active leaves extract of Calliandra tergemina. Their structures and molecular formula were established using spectroscopic analysis and their anti-MRSA (methicillin-resistant Staphylococcus aureus) activities were evaluated by broth microdilution. The isolation of compounds 1 – 8, together with the structural-activity relationship of these flavonol glycosides, based on their anti-MRSA activities, will be presented.
... This compound was reported from Pranus cerasus [10]. 13 C-NMR spectrum of 2 showed fifteen carbons including one carbon carbonyl at δ C 183.7 (C-4) and the others from δ C 95.0 to 166.2. Thus, the structure of 2 was identified as luteolin by comparing these data with those previously reported [10]. ...
... The signal of the chelated proton at δ H 12.63 indicated that C-5 was linked to a hydroxyl group and 4 could be kaempferol 3,7,4′-trimethyl ether. The obtained results for compound 4 were in agreement with the spectral data of kaempferol 3,7,4′trimethyl ether previously reported in the literature [13]. Thus, compound 4 was identified as kaempferol 3,7,4′-trimethyl ether, which was isolated from T. catappa for the first time. ...
Terminalia catappa L. (cây Bàng) belongs to the family Bàng (Combretaceae), is a large tree species living mainly in the tropics. The phytochemical studies of this plant have only focused on the volatile fraction and tannins. The main components in the plant include terpenes, flavonoids, tannins, saponins and phytosterols. T. catappa species has been recognized as an important medicinal plant. In traditional medicine, T. catappa leaf, bark and fruit are used in treating dysentery, rheumatism, cough and asthma. The fruit is also helpful in the treatment of leprosy and headaches and the leaves are specifically used in getting rid of intestinal parasites, treatment of eye problems, wounds, and liver problems. Due to its rich medicinal ingredients, the leaves and bark are used in various herbal medicines for different purposes. This study aims to characterize the phyto-chemical constituents present in the leaf extracts of Terminalia catappa using chromatographic and spectroscopicmethods. Four flavonoids, tectochrysin (1), luteolin (2), kaempferol 3,7,4′-trimethyl ether (4), and kaempferol (5), one phenolic, gallic acid (3), were isolated from the ethylacetate fraction of the leaves of Terminalia catappa L.. Their structures were elucidated on the basis of spectroscopic analysis and comparisons with known related compounds. Compounds 1 and 4 were reported for the first time from the leaves of Terminalia catappa.
... Four known phenolic compounds, a flavanone (naringenin), two flavonols (kaempferol and quercetin), and a phenolic acid, (gallic acid) (Figure 1), were isolated from the ethyl acetate fraction of the ethanol extract of W. robusta (EWR) through successive solvent extraction followed by repeated column fractionation and purification. The isolated secondary metabolites were characterized via physicochemical examination, spectral analysis (UV, 1 H NMR, and 13 C NMR), and by correlation to former reports [27][28][29][30][31]. Despite being widely distributed in nature, this is the earliest information concerning the isolation of these compounds from the leaves of W. robusta. ...
... of the ethanol extract of W. robusta (EWR) through successive solvent extraction followed by repeated column fractionation and purification. The isolated secondary metabolites were characterized via physicochemical examination, spectral analysis (UV, 1 H NMR, and 13 C NMR), and by correlation to former reports [27][28][29][30][31]. Despite being widely distributed in nature, this is the earliest information concerning the isolation of these compounds from the leaves of W. robusta. ...
Exposure to ionizing radiation usually results in cellular oxidative damage and may induce liver toxicity. The efficiency of the ethanol extracts of Washingtonia filifera (EWF) and Washingtonia robusta (EWR) leaves in alleviating γ-radiation-induced oxidative hepatotoxicity was herein explored. Proximate and macronutrient composition of the leaves was determined to establish reliable quality control criteria. Colorimetric estimation of total phenolic (TPC) and flavonoid (TFC) contents revealed their occurrence in larger amounts in EWR. In vitro evaluation of the antioxidant capacity by 2,2-azinobis (3-ethylbenzothiazoline-6-sulfonic acid (ABTS) and ferric reducing antioxidant power (FRAP) assays confirmed higher efficiency of EWR designating a close correlation with phenolic composition. Four phenolics, viz., naringenin, kaempferol, quercetin, and gallic acid, were isolated from EWR. In vivo assessment of the extracts' antioxidant potential was performed on γ-irradiated (7.5 Gy) female rats. EWR was found more efficient in restoring the elevated liver index, ALT, albumin, cholesterol, and reactive oxygen species (ROS) levels. Both extracts ameliorated the increase in the stimulator of interferon gene (STING) expression. Bioactivity was confirmed by immuno-histochemical examination of inflammatory and apoptotic biomarkers (TNF-α, IL-6 and caspase-3) and histopathological architecture. In addition, the interactions of the isolated compounds with STING were assessed in silico by molecular docking. Therefore, Washingtonia robusta leaves might be suggested as a valuable nutritional supplement to alleviate radiotherapy-induced hepatotoxicity.
... For example, the carob tree and its different parts have long been used in traditional medicine as a source of natural products for maintaining human health [39,40] and curing several diseases [16,18,41]. Several studies have revealed the presence in carob of valuable compounds with interesting biological activities, including kaempferol, catechin [42], apigenin, rutin [17], acid tannic and catechin hydrate [16]. Based on the good results obtained in humans, the effects of aqueous and ethanolic carob leaf extracts were tested as an alternative to chemotherapeutic agents in gilthead seabream to stimulate immune activities as well as to control, prevent or/and to treat fish diseases caused by microbial infection or chronic illness. ...
... What isimportant here is the confirmation of previous studies that Gram negative bacteria are more resistant to plant extracts than Gram-positive bacteria [45,[54][55][56]. In short, the interesting toxic effects of the ethanolic extract on the PLHC-1 cell line and V. harveyi, V. anguillarum and P. damselae might be explained mainly by the high amounts of quercetin, kaempferol, apigenin and rutin in carob leaf extracts [17,42], which are considered to be effective antitumoral and antibacterial compounds [39,[57][58][59][60]. ...
Carob leaves, the main residues of the carob tree, were investigated as a renewable and abundant source of bioactive compounds for fish aquaculture. Aqueous and ethanolic extracts obtained from carob leaves were characterized in terms of biochemical composition, antiradical and cytotoxic effects and immunostimulant and antibacterial activities. The ethanolic extract showed higher levels of total phenolics, flavonoids and condensed tannins and higher antioxidant activity than the aqueous extract. No significant immunostimulant effects were observed on gilthead seabream (Sparus aurata) head kidney leucocytes (viability, phagocytosis and respiratory burst activities and peroxidase content) after incubation for 24 h with different extracts. Furthermore, the ethanolic extracts used at 0.5, 0.75 and 1 mg mL-1 and aqueous extracts at 1 gmL-1 had a cytotoxic effect on PLHC-1 cells. When the bactericidal activity was tested against three fish pathogenic bacteria (Vibrio harveyi, Vibrio anguillarum and Photobacterium damselae) notable activity of the different extracts was detected against P. damselae at all three concentrations. A similar effect was demonstrated against V. haryeri when ethanolic extracts were used in the same range of concentrations. This work demonstrates interesting in vitro effects of carob leaf extracts and suggests it could be used as an alternative to chemical compounds with farmed fish. The concentration and nature of the extracts were very important in terms of any positive results.
... The results are documented in Table 1 and fragmentation pattern, and via comparison of MS spectra with the reported data [34][35][36][37][38][39][40][41][42][43][44]. * The structural elucidation of the isolated phenolic compounds (1-4) was based on spectral and chemical analyses as well as literature [45][46][47][48]. * Bold items referred to the main aglycones fragments. ...
... a Compounds isolated and identified via HPLC-DAD-ESI-MS/MS during this study. b The structural elucidation of the isolated phenolic compounds(1)(2)(3)(4) was based on spectral and chemical analyses as well as literature[45][46][47][48]. c Bold items referred to the main aglycones fragments. ...
Cyclophosphamide (CP) is a potent anti-neoplastic and immunosuppressive agent; however, it causes multi-organ toxicity. We elucidated the protective activities of Eucalyptus globulus (EG) leaf extract against CP-induced hepato–renal toxicity. Mice were treated with EG for 15 days plus CP on day 12 and 13 of the experiment. Using HPLC-DAD-ESI-MS/MS, 26 secondary metabolites were identified in EG leaf extract. Out of them, 4 polyphenolic compounds were isolated: (1) 4-(O-β-d-xylopyranosyloxy)-3,5-di-hydroxy-benzoic acid, (2) 4-(O-α-l-rhamnopyranosyloxy)-3,5-di-hydroxy-benzoic acid, (3) gallic acid, and (4) methyl gallate. Effects of EG extract on biochemical parameters, gene expression, and immune-histopathological changes were assessed in comparison to mesna positive control. Results showed that EG improved CP-increased serum ALT, AST, creatinine, and blood urea nitrogen levels. The hepatic and renal tissue levels of MDA, nitric oxide, protein carbonyl, TNF-α, IL-6, and immunohistochemical expression of nuclear factor kappa-B (NF-kB) and caspase-3 were reduced. Also, hepatic and renal GSH contents, and nuclear factor E2-related factor 2 (NRf2)/ hemoxygenase-1 (HO-1) signaling levels were increased. Histopathological findings supported our findings where hepatic and renal architecture were almost restored. Results revealed the protective effects of EG against CP-induced hepato–renal toxicity. These effects may be related to EG antioxidant, anti-inflammatory, and anti-apoptotic properties coupled with activation of Nrf2/HO-1 signaling.
... This sugar was identified as β-D-glucopyranose by comparison of the 13 C-NMR data of 3 with those in the literature. [4,5] The HMBC spectrum of 3 confirmed the position of the attachment of the glucopyranose unit. The anomeric proton H-1 at δH 5.46 showed a long-range correlation with signal at δC 133.3 (C-3) of the quercetin aglycon, indicating that the β-Dglucopyranosyl moiety connected to C-3 of the aglycon. ...
... The anomeric proton H-1 at δH 5.46 showed a long-range correlation with signal at δC 133.3 (C-3) of the quercetin aglycon, indicating that the β-Dglucopyranosyl moiety connected to C-3 of the aglycon. The above data and comparison with those in the literature [4,5,6] allowed to identify 3 as quercetin 3-O-β-D-glucopyranoside (or isoquercetin). ...
Chemical investigation of the ethyl acetate extract of Ficus consociata leaves, collected at Bien Hoa city, Dong Nai province, led to the isolation and structural elucidation of seven compounds, including luteolin (1), cirsiliol (2), isoquercetin (3), quercetin 3-O-α-L-arabinopyranoside (4), nikotoflorin (5), hesperidin (6) and (2E,4E,1'S,2'R,4'S,6'R)-dihydrophaseic acid (7). Their chemical structures were elucidated by a combination of electronic circular dichroism (ECD) experiments and spectroscopic data (HR-MS, 1D, 2D NMR) analysis, and comparison with those reported in the literature. Although, these compounds were already known in other species, but this is the first report on chemical constituents of F. consociata.
... A typical methyl 1 H-NMR signal of rhamnose appeared at δ H 0.85 (3H, d, J= 6.2 Hz). According to the literature [15], the methyl signal should be at δ H 0.95 if the -OH on the rhamnose was not esterified, and the methyl signal was high-shifted in position 4 confirmining the esterfication. Two A 2 X 2 coupling system (δ H 7.50 (2H, d, J= 8.6 Hz, H-5 , -9 ), 6.82 (2H, d, J= 8.6 Hz, H-6 , -8 ) and 7.50 (2H, d, J= 8.6 Hz, H-5 , -9 ), 6.85 (2H, d, J= 8.6, H-6 , -8 )] and two olefinic protons δ H 6.27, 7.55 (each 1H, d, J= 16.0 Hz, H-2 , -3 ) and δ H 6.42, 7.68 (each 1H, d, J= 16.0 Hz, H-2 , -3 ) in the 1 H-NMR spectrum indicated the occurrence of two (E)-p-coumaroyl group. ...
... The 25 known compounds, including two monoterpenes, (E)-6-hydroxy-2,6-dimethylocta-2,7dienoic acid (7) [20] and trans-sobrerol (8) [21], seventeen sesquiterpenes: teucladiol (9) [22], globulol (10) [23], β-dictyopterol (11) [24], 4β,10α-aromadendranediol-10-methyl ether (12) [25], 4α,10β-alloaromadendranediol-10-methyl ether (13) [25], 4β,10α-aromadendranediol (14) [26], 4α,10β-alloaromadendranediol (15) [25], clovandiol (16) [17], caryophyllenol-II (17) [18], humulene diepoxide A (18) [18], isocaryolanediol (19) [18], β-caryophyllene-8,9-oxide (20) [18], kobusone (21) [18], 7,8-epoxy-1(12)-caryophyllene-9α-ol (22) [18], 8β-hydroxy-1(12)-caryophyllene (23) [27], 2β-methoxyclovan-9α-ol (24) [28] and 8,9-dihydroxy-1(12)caryophyllene (25) [29] and six steroids, β-sitosterol (26) [30], 5-stigmasten-3β,7β-diol (27) [31], 5-stigmasten-3β,7α-diol (28) [31], 5α,8αepidioxy-24-methylcholesta-6,9,22-trien-3β-ol (29) [32], 5α,8α-epidioxy-24-methylcholesta-6,22dien-3β-ol (30) [33], and 3β-hydroxystigmast-5-en-7-one (31) [34] were identified by comparison of their physical and reported spectroscopic data. ...
Inflammation is related to many diseases. Lindera akoensis Hayata was often used in folktherapy in Taiwan for inflammation. In this study, three new flavonol acyl glycosides, namelykaempferol-3-O--D-4”,6”-di-(E)-p-coumaroylglucoside (1), 3”-(E)-p-coumaroylafzelin (2) and 40-Omethyl-2”,4”-di-(E)-p-coumaroylquercitrin (3), and three components, 3-dodecyl-4-hydroxy-5-methyldihydrofuran-2-one (4), 2-acetoxyclovan-9-ol (5), (1,4,6)-trihydroxyeudesmane(6) that were isolated from the natural product for the first time were obtained along with 25 knowncompounds from L. akoensis. Their structures were determined by comprehensive spectroscopicanalyses (1D and 2D NMR, EI-, ESI- and HRESI-MS). The ability of 1 to decrease the LPS-stimulatedproduction of nitrite in RAW264.7 cell was evaluated, showing an IC50 value of 36.3 ± 3.2 μM.This result supports the value of L. akoensis as a traditional medicine resource.
... Statistically 60 % of premenopausal and of all these 7 compounds in EF of P. persica whole fruit. Of course, these seven compounds are already reported in literature, but from some other plant extracts [30][31][32][33][34] . ...
... The MS (ESI) showed ion at m/z 169.3 [M-H] -, corresponding to the molecular formula of C 7 H 6 O 5 . Based on these data, compound 4 was identified as gallic acid consistent with the data reported [32] . Ferulic acid was obtained as a white powder with an MP of 170-172°. ...
Prunus persica has been used as a source of traditional medicine in many countries for the treatment of different diseases in females. In the present study, cytotoxicity and reactive oxygen species scavenging effects of Prunus persica extract on human breast cancer and placenta choriocarcinoma cell lines were evaluated. Besides this, regulations of oestrogen synthesis and antiaromatase activity were observed on human placenta choriocarcinoma cells. Ethyl acetate and butanol fractions had the maximum cytotoxic activity among all the fractions. In comparison to butanol fraction, ethyl acetate fraction was found to scavenge maximum intracellular reactive oxygen species, which was correlated with its total phenolic and flavonoid contents. Ethyl acetate was found to reduce the aromatase activity by 50 % at the concentration of 200 µg/ml. This inhibitory effect on aromatase was accompanied by reduced 17β-estradiol levels in JEG-3 cells. It seemed that the ethyl acetate and n-butanol fractions of Prunus persica or its active compound appears to be acting through dual mechanisms, i.e. improvement of antioxidant system and by suppressing aromatase; it may potentially be used as therapeutic agent for the treatment of breast cancer. These findings suggested that Prunus persica extract could be an aromatase inhibitor for the treatment of oestrogen-sensitive breast cancer.
... Statistically 60 % of premenopausal and of all these 7 compounds in EF of P. persica whole fruit. Of course, these seven compounds are already reported in literature, but from some other plant extracts [30][31][32][33][34] . ...
... The MS (ESI) showed ion at m/z 169.3 [M-H] -, corresponding to the molecular formula of C 7 H 6 O 5 . Based on these data, compound 4 was identified as gallic acid consistent with the data reported [32] . Ferulic acid was obtained as a white powder with an MP of 170-172°. ...
... Fraction EE5 was further separated on a silica gel column, eluted with CHCl 3 :MeOH (from 50:1 to 1:1, v/v) to yield fourteen subfractions (EE5. [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. Subfraction EE5.11 was further chromatographed on silica gel CC, eluted with CHCl 3 :MeOH (10:1 to 1:1, v/v) to obtain seven subfractions (EE5.11.1-7). ...
... (5 mg). Based on their spectral data together with comparison with literature data, these isolated compounds were identified asquercitrin (1)[7], luteolin (2)[8], quercetin (3)[9] and caffeic acid (4) [10](Figure 1). ...
Euphorbia hirta L., a kind of herbs belonging to family Euphorbiaceae, has been found a lot in the Mekong Delta. From the ethyl acetat and methanol fractions of this plant, four pure compounds were isolated and identified their chemical structure by spectroscopic techniques including quercitrin (1), luteolin (2), quercetin (3) and caffeic acid (4). The effect of crude ethanolic extract and some fractioned extracts as well as four isolated compounds from E hirta L., collected in the Mekong Delta, on endoplasmic reticulum stress-induced cell death in mouse β-cell lines was investigated. The results showed that methanol fraction and a isolated compound, quercitrin gave strong cell-protective effect with the cell viability of 69% and 78% at the dose of 100 µg/mL and 10 µg/mL, respectively. This proves that E hirta L. might have anti-diabetic effects and worth conducting further pharmacological investigations related to type 2 diabetes mellitus.
... NMR data, see Table 1. (4). Yellow powder. ...
... It corresponded to an aromatic proton signal at δH 6.91 (2H, s) in the 1 H NMR spectrum. Therefore, compound (8) was identified as gallic acid through the comparison of its NMR data with the published ones in the literature [4]. ...
From L. racemosa leaves eight compounds were isolated: myricetin (1), quercetin (2), myricetin 3-O-α-L-rhamnopyranoside (3), myricetin 3-O-(2"-O-galloyl-α-L-rhamnopyranoside) (4), myricetin 3-O-(3"-Ogalloyl-α-L-rhamnopyranoside) (5), 3-Omethylellagic acid (6), (3S,5R,6S,7E)-3,5,6- trihydroxy-7-megastigmen-9-one (7) and gallic acid (8). Their chemical structures were unambiguously elucidated by analysis of 1D and 2D NMR and high resolution ESI mass spectroscopic data, as well as by comparison with those reported in the literature. The α- glucosidase inhibition was evaluated on isolated compounds. Among them, 1, 4, 5, 6 and 8 exhibited good activities with the IC50 values in the range of 1.3-19.3 µM.
... The chemical investigation on the L. racemosa leaves collected at Kien Giang province, Viet Nam led to the isolation of ten compounds including the new one (1) by the use of efficient separation techniques (Figure 1). The known compounds were identified as myricetin (2) [6], quercetin (3) [7], myricetin 3-O-α-Lrhamnopyranoside (4) [8], (7) [10], gallic acid (8) [11], kaempferol (9) [12] and (3S,5R,6S,7E)-3,5,6trihydroxy-7-megastigmen-9-one (10) [13] via spectroscopic data analysis and comparison with those reported in the literature. The 13 C NMR spectrum of 1 showed two galloyl units including two carboxyl carbons at δ C 165.8 and 165.5, eight carbon signals of two symmetrical aromatic rings comprising four oxygenated carbons at δ C 145.5 (C-3, C-5), 145.4 (C-3, C-5), 138.5 (C-4) and 138.2 (C-4), two aromatic methines at δ C 108.9 (C-2, C-6) and 108.8 (C-2, C-6), and two aromatic quaternary carbons at δ C 120.2 (C-1) and 119.6 (C-1). ...
... Fraction C2 (1.7 g) was rechromatographed over silica gel eluting with CHCl 3 -MeOH (stepwise, 1:0 to 9:1) and then with Sephadex LH20 eluted with methanol to afford compound 9 (10 mg). Fraction C3 (2.27 g) was applied to silica gel Galloyl glycoside from Lumnitzera racemosa Natural Product Communications Vol. 12 (11) 2017 1753 rechromatography eluted with CHCl 3 -MeOH (1:0 to 9:1) and then with Sephadex LH20 eluted with methanol to afford two compounds 2 (30 mg) and 3 (15 mg). Fraction C4 (14 g) was applied on the silica gel column and eluted by CHCl 3 -MeOH (stepwise, 1:0, 0:1) to give nine subfractions (C4.1-C4.9). ...
From Lumnitzera racemosa Willd., a new glycoside, 2-O-galloyl-α-L-rhamnopyranosyl-(3→4′)-3′-O-galloyl-α-L-rhamnopyranose (1), as well as nine known compounds were isolated. Their chemical structures were elucidated by spectroscopic data analysis as well as comparison with the ones in the literature. The evaluation of α-glucosidase inhibitory activity of the extracts and some isolated compounds was measured.
... Finally this new structure was identified as 17β-dammara-1-one -20 ene-3β-3', 8'-dimethyloctanoate or [12,13 Fig. (2). Also, isolation of two known saturated fatty acids capric (2) [26] & palmitic (3) [26] , from the chloroform extract as well as three phenolic acids: Gallic (4) [27] , Caffeic (5) [28,29] , Chlorogenic (6) [27,30] , six flavonols: Kaempferol 3-O--D-arabinopyranoside (7) [31] , afzelin (8) [32,33] [34] , and Kaempferol (12) [35] . Also, two isoflavones: Biochanin A (13) [36] , Biochanin A-7-O--D-rutinoside (14) [37] , were isolated from methanol extract. ...
... Also, two isoflavones: Biochanin A (13) [36] , Biochanin A-7-O--D-rutinoside (14) [37] , were isolated from methanol extract. All these compounds were isolated for the first time from Ixora finlaysoniana leaves and were elucidated by different chromatographic and spectroscopic techniques; UV, extensive 1D and 2D NMR and MS in comparison with previous published data [26][27][28][29][30][31][32][33][34][35][36][37] . LD 50 of both leaves and aqueous extracts of the aerial parts were (8.4 gm/Kg b.wt.) and (7.8 gm/Kg b.wt.), respectively. ...
The air-dried leaves of Ixora finlaysoniana Wall. ex. Don (family Rubiaceae) afforded a new dammarane triterpenoid named: 17β-dammara-1-one-20 ene-3β-3', 8'-dimethyloctanoate (1) together with two known saturated fatty acids capric (2) and palmitic (3) from the chloroform extract as well as three phenolic acids: gallic (4), caffeic (5), chlorogenic (6), six flavonols: (14) were isolated from methanol extract. All these structures were isolated for the first time from Ixora finlaysoniana leaves and were elucidated by different chromatographic and UV, extensive 1D and 2D NMR spectroscopy and MS.
... The results also agreed with [38], who found gallic acid at a retention time of 2.763 in Italian carob leaves, and [15], also found gallic acid in the methanolic extract of Portuguese carob leaves. The results also showed the presence of P-Coumaric acid and Cinnamic acid, which is identical to what was found [39], in the aqueous extract of the fruits of the Egyptian carob. The results also show that Cinnamic acid is the most concentrated phenolic compound in the leaves of the Iraqi carob. ...
The current study aimed to estimate the chemical composition of the powder of both leaves and seeds of Ceratonia siliqua, which was purchased from the local market in Iraq/Baghdad. Where the test included (moisture-fat-protein-carbohydrate-ash-fiber), both leaves and seeds were extracted by Soxhlet continuous extraction machine using ethanol solvent. Several chemical tests were conducted on the extracts, which included the following: Detection of phenolic compounds and flavonoids by HPLC technology (high-performance liquid chromatography), where the results showed the appearance of several peaks at a wavelength of 280 nm for several phenolic compounds and at different time lengths. The inhibition activity was evaluated for two types of bacteria (positive/gram-negative), one type of yeast, two types of molds, and four concentrations of extracts (25-50-75-100 mg/ml). The results showed that the alcoholic extract of the leaves of the carob plant was superior to the seeds against all microorganisms. As for the antioxidant activity, it was approved by the DPPH test compared to vitamin C, as it is a natural antioxidant. The results showed that both leaf and seed extracts were superior to vitamin C, as the IC50% of seed extract was 7 ppm 11 and leaf extract was 184. As for vitamin C, the percentage of free radical inhibition was 50%, 373PPM, as it is known that the higher the IC50 value, the lower the antioxidant activity.
... Several studies have identified the principal phenolic compounds present in carob extracts, but their levels vary. A previous study by Eldahshan (2010) [22] has reported the presence of gallic acid, quercetin 3-O-β-D-glucoside (isoquercetin), kaempferol 3-O-α-Lrhamnoside (afzelin), quercetin 3-O-α-L-rhamnoside (quercitrin), 1,2,6 tri-O-galloyl-β-Dglucopyranose, (-)-epigallocatechin-3-O-gallate, kaempferol, and quercetin in the ethanolic extract of carob leaves. Similar compounds have been previously reported in carob pods and derived products. ...
The botanical species Ceratonia siliqua L., commonly referred to as the Carob tree, and locally as “L’Kharrûb”, holds significance as an agro-sylvo-pastoral species, and is traditionally utilized in
Morocco for treating a variety of ailments. This current investigation aims to ascertain the antioxidant, antimicrobial, and cytotoxic properties of the ethanolic extract of C. siliqua leaves (CSEE). Initially, we analyzed the chemical composition of CSEE through high performance liquid chromatography with
Diode-Array Detection (HPLC-DAD). Subsequently, we conducted various assessments, including DPPH scavenging capacity, β-carotene bleaching assay, ABTS scavenging, and total antioxidant
capacity assays to evaluate the antioxidant activity of the extract. In this study, we investigated the antimicrobial properties of CSEE against five bacterial strains (two gram-positive, Staphylococcus aureus, and Enterococcus faecalis; and three gram-negative bacteria, Escherichia coli, Escherichia vekanda, and Pseudomonas aeruginosa) and two fungi (Candida albicans, and Geotrichum candidum). Additionally, we evaluated the cytotoxicity of CSEE on three human breast cancer cell lines (MCF-7, MDA-MB-231, and MDA-MB-436) and assessed the potential genotoxicity of the extract using the comet assay.
Through HPLC-DAD analysis, we determined that phenolic acids and flavonoids were the primary constituents of the CSEE extract. The results of the DPPH test indicated a potent scavenging capacity of the extract with an IC50 of 302.78 ± 7.55 µg/mL, which was comparable to that of ascorbic acid with an IC50 of 260.24 ± 6.45 µg/mL. Similarly, the β-carotene test demonstrated an IC50 of 352.06 ± 12.16 µg/mL, signifying the extract’s potential to inhibit oxidative damage. The ABTS assay revealed IC50 values of 48.13 ± 3.66 TE µmol/mL, indicating a strong ability of CSEE to scavenge ABTS radicals, and the TAC assay demonstrated an IC50 value of 165 ± 7.66 µg AAE/mg. The results suggest that the CSEE extract had potent antioxidant activity. Regarding its antimicrobial
activity, the CSEE extract was effective against all five tested bacterial strains, indicating its broad-
spectrum antibacterial properties. However, it only showed moderate activity against the two tested
fungal strains, suggesting it may not be as effective against fungi. The CSEE exhibited a noteworthy
dose-dependent inhibitory activity against all the tested tumor cell lines in vitro. The extract did
not induce DNA damage at the concentrations of 6.25, 12.5, 25, and 50 µg/mL, as assessed by the
comet assay. However, the 100 µg/mL concentration of CSEE resulted in a significant genotoxic
effect compared to the negative control. A computational analysis was conducted to determine the
physicochemical and pharmacokinetic characteristics of the constituent molecules present in the
extract. The Prediction of Activity Spectra of Substances (PASS) test was employed to forecast the
potential biological activities of these molecules. Additionally, the toxicity of the molecules was
evaluated using the Protox II webserver.
... Several studies have identified the principal phenolic compounds present in carob extracts, but their levels vary. A previous study by Eldahshan, (2010) [22], has reported the presence of gallic acid, quercetin 3-O-β-D-glucoside (isoquercetin), kaempferol 3-O-α-L-rhamnoside (afzelin), quercetin 3-O-α-L-rhamnoside (quercitrin), 1,2,6 tri-O-galloyl-β-D-glucopyranose, (-)-epigallocatechin-3-O-gallate, kaempferol, and quercetin in the ethanolic extract of carob leaves. Similar compounds have been previously reported in carob pods and derived products. ...
The botanical species Ceratonia siliqua L., commonly referred to as the Carob tree, and locally as "L'Kharrûb", holds significance as an agro-sylvo-pastoral species, and is traditionally utilized in Morocco for treating a variety of ailments. This current investigation aims to ascertain the antioxidant, antimicrobial, and cytotoxic properties of the ethanolic extract of C. siliqua leaves (CSEE). Initially, we analyzed the chemical composition of CSEE through high-performance liquid chromatography with Diode-Array Detection (HPLC-DAD). Subsequently, we conducted various assessments, including DPPH scavenging capacity, β-carotene bleaching assay, ABTS scavenging, and total antioxidant capacity assays, to evaluate the antioxidant activity of the extract. In this study, we investigated the antimicrobial properties of CSEE against five bacterial strains (two gram-positive , Staphylococcus aureus, and Enterococcus faecalis; and three gram-negative bacteria, Escherichia coli, Escherichia vekanda, and Pseudomonas aeruginosa) and two fungi (Candida albicans, and Geotrichum candidum). Additionally, we evaluated the cytotoxicity of CSEE on three human breast cancer cell lines (MCF-7, MDA-MB-231, and MDA-MB-436) and assessed the potential genotoxicity of the extract using the comet assay. Through HPLC-DAD analysis, we determined that phenolic acids and flavonoids were the primary constituents of the CSEE extract. The results of the DPPH test indicated a potent scavenging capacity of the extract with an IC50 of 302.78 ± 7.55 µg/mL, which was comparable to that of ascorbic acid with an IC50 of 260.24 ± 6.45 µg/mL. Similarly, the β-carotene test demonstrated an IC50 of 352.06 ± 12.16 µg/mL, signifying the extract's potential to inhibit oxidative damage. The ABTS assay revealed IC50 values of 48.13 ± 3.66 TE µmol/mL, indicating a strong ability of CSEE to scavenge ABTS radicals, and the TAC assay demonstrated an IC50 value of 165 ± 7.66 µg AAE/mg. The results suggest that the CSEE extract had potent antioxidant activity. Regarding its antimicrobial activity, the CSEE extract was effective against all five tested bacterial strains, indicating its broad-spectrum antibacterial properties. However, it only showed moderate activity against the two tested fungal strains, suggesting it may not be as effective against fungi. The CSEE exhibited a noteworthy dose-dependent inhibitory activity against all the tested tumor cell lines in vitro. The extract did not induce DNA damage at the concentrations of 6.25, 12.5, 25, and 50 µg/ml, as assessed by the comet assay. However, the 100 µg/ml concentration of CSEE resulted in a significant geno-toxic effect compared to the negative control. A computational analysis was conducted to determine the physicochemical and pharmacokinetic characteristics of the constituent molecules present in the extract. The Prediction of Activity Spectra of Substances (PASS) test was employed to forecast the potential biological activities of these molecules. Additionally, the toxicity of the molecules was evaluated using the Protox II webserver.
... (25S)− 5β-spirostan-3β-ol-3-O-β-D-glucopyranoside (1) (Huang et al., 2008), (25S)− 5β-spirostan-3β-ol-3-O-α-L-rhamnopyranosyl-(1→2)-β-Dglucopyranoside (2) (Shvets et al., 1994), (25S)− 5β-spirostan-3βol-3-O-β-D-glucopyranosyl-(1→2)-β-D-glucopyranoside (3) (Terada et al., 1995), asparenydiol (14) (Miyakoshi et al., 2000), 5-[5-(4-hydr oxyphenoxy)− 3-penten-1-ynyl]− 2-methoxyphenol (15), previously isolated from Asparagus gobicus under the name of 1-methoxy-2-hydroxy -4-[5-(4-hydroxyphenoxy)− 3-penten-1-ynyl]-phenol (Yang et al., 2005), nyasol (16) (Tsui and Brown, 1996;Oketch-Rabah et al., 1997), 3'-methoxynyasol (17), 3 ′ -hydroxy-4 ′ -methoxy-4 ′ -dehydroxynyasol (18) (Zhang et al., 2004), iso-agatharesinol (19) (Yang et al., 2004a), 1-O-p-coumaroylglycerol (20) (Luo et al., 2012), syringaresinol (21), syringaresinol-4-O-β-D-glucopyranoside (22) (Tong et al., 2005;Inui et al., 2010), hordénine (23) (Küçükosmanoǧlu et al., 2005), N-methyltyramine (24) (Nash et al., 1992), apigenin 6-C-β-D-glucopyranosyl -8-C-β-D-ribopyranoside (25), apigenin 6-C-α-L-arabinopyranosyl-8-C-β-D-glucopyranoside (26), vicenin 3 (27) (Chimichi et al., 1998;Chen et al., 2019) (29) (Adell et al., 1988;Eldahshan, 2011), benzyl-O-α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside (30) (De Tommasi et al., 1996), aurantiamide acetate (31) (Zhou et al., 2017), Table 1 NMR spectroscopic data for compounds 4-5 in DMSO-d 6 (δ in ppm). (Catalán et al., 2003) and sesamin (33) that was identified by comparison with spectral data available at our laboratory. ...
Phytochemical study of the roots and aerial parts of Asparagus africanus Lam. have led to the identification of thirty-three specialized metabolites (1–33) including two undescribed steroidal saponins: (25 S)− 5β-spirostan-3β-ol-3-O-β-d-xylopyranosyl-(1→2)-β-d-glucopyranoside (4) and (25 S)− 5β-spirostan-3β-ol-3-O-β-d-glucopyranosyl-(1→6)-[β-d-glucopyranosyl-(1→2)-]β-d-glucopyranoside (5) and eight undescribed norlignans Aspafricanol A-E (6–10), Aspafricanene (11) and Aspafricanone A-B (12–13). Their structures were characterized by using a combination of 1D, and ²D NMR spectroscopic and mass spectrometry (HR-ESI-MS) analyses, as well as by comparison with literature values. The antioxidant potential of the phenolic constituents was evaluated by the 2,2-diphenyl-1-picrylhydrazyl (DPPH), hydroxyl radical antioxidant capacity (HORAC) and cupric ion reducing antioxidant capacity (CUPRAC) methods. The results revealed higher antioxidant capacity for syringaresinol (21) in DPPH, HORAC and CUPRAC assays with IC50 values of 15.9 ± 0.3, 86.0 ± 6.9 and 18.0 ± 1.7 µg/mL, respectively, compared to the positive controls (ascorbic acid, quercetin and Trolox). Additionally, compounds 7, 9 and 28 showed similar or stronger activities than the positive controls in DPPH (IC50 = 33.3 ± 5.7, 40.3 ± 0.6 and 46.7 ± 2.9 µg/mL, respectively), HORAC (IC50 = 74.7 ± 4.6, 66.7 ± 5.8 and 99.3 ± 1.1 µg/mL, respectively), and CUPRAC assays (IC50 = 128.7 ± 9.6, 123.3 ± 3.0 and 59.0 ± 1.7 µg/mL, respectively).
... The 13 C-NMR spectrum (100 MHz, showed carbon resonances at δC ppm; 120.90 (C-1, quaternary aromatic carbon), 109.20 (C-2 and 6, two symmetric aromatic methine carbons), 146.13 (C-3 and 5, two symmetric oxygenated aromatic carbons), 139.02 (C-4, oxygenated carbon), and 166.82 (C-7, carbonyl group). As a result, metabolite 1 was identified as gallic acid (Eldahshan, 2011). ...
... and 13 C NMR and MS data and identified as afzelin (2) [40], catechin (4) [41], chlorogenic acid (6) [42], epicatechin (9) [41], and quercitrin (13) [42] (the NMR data are shown in S3-S12 Figs in S1 File) . Compounds 1, 3, 7, 8, 11, and 12 were putatively identified as neochlorogenic acid (1), laurolitsine (3), coclaurine (7), dihydrokaempferol (8), roemerine (11), and phenylalanine (12), respectively, based on a literature search and comparison of MS/MS patterns [43][44][45][46]. ...
The diversity of secondary metabolites of individual plants results from multiple enzymatic processes in planta and various environmental factors, such as temperature, moisture, and soil conditions. Chemical composition analysis of plants can lead to a new method to understand relationship among comparable plants along with biological classification such as genetic and anatomical method. In this study, the chemical diversity of nine different Lauraceae species was investigated, and the plant samples were chemically analyzed and classified. Multivariate analysis methods, such as PLS-DA, were used to select important metabolites distinguishing the nine Lauraceae species. The selected metabolites were identified through preparative LC-MS or MS/MS fragment pattern analysis. In addition, the chemical dendrogram for the nine Lauraceae species was interpreted through molecular network analysis and compared with the genetic dendrogram. This approach enabled us to compare the complete chemical compositions of multiple plant samples to identify relationships among plants.
... Carob leaves contain different classes of bioactive compounds, such as simple phenols, polyphenols, free flavonoids, glycosylated flavonoids, and tannins [27]. The characteristics of the extracts are closely linked to the structural diversity of the extractable phenolic compounds and strictly depend on the solvent and extraction techniques, while the temperature, pressure, and time represent important parameters to be considered [28]. ...
This work is focused on the preparation of an innovative gluten-free (GF) bread with remarkable softness and antioxidant features over time. To overcome the technological inconveniences related to the removal of gluten from bread, the kefir beverage fortified with antioxidant vegetable extracts is employed as a functional ingredient in the bread-making process. In this context, carob (Ceratonia siliqua L.) leaves represent an outstanding source of active molecules and are proposed to enrich milk-based beverages. Different extraction strategies were evaluated, and the process was improved to select a solvent (water, ethanol, or hydroalcoholic solution) and methodology (Soxhlet or ultrasound-assisted extraction) able to guarantee the best performances in terms of yield and antioxidant capacity. For kefir addition, two varieties of carob leaves (Selvatica and Amele) are employed. Functional GF bread, obtained by partially replacing the water with the enriched kefir, is prepared, and the final product is characterized in terms of its antioxidant and rheological properties. The final product shows improved compositional and technological parameters over time.
... The butanol extract from Paronychia capitata (L.) Lam. was fractionated using vacuum liquid chromatography (VLC) on silica gel reversed phase C-18. The obtained fractions were subjected to a multistep chromatographic separation to yield two new oleanane-type triterpene glycosides named capitatoside A (1) and capitatoside B (2) (Fig. 1), together with seven known secondary metabolites identified as ageratoside B1 (3) (Sakai et al., 1999), isoorientin (4) (Chulia and Maiuoite, 1985), isoquercetrin (5) (Eldahshan, 2011), citrioside A (6) (Xiaopeng et al., 2014), narcissin (7) (Beck and Häberlein, 1999), (Wang et al., 2008), (Allaoua et al., 2016). A pair of olefinic carbon atoms was observed on 13 C NMR spectrum with typical resonances at δ C 145.0 and 123.6, suggesting a Δ 12 pentacyclic triterpene derivatives (Mahato and Kundu, 1994). ...
Two new oleanane-type triterpene glycosides, 3˗O˗β˗D˗glucopyranosyl˗28˗O˗[β˗D˗glucopyranosyl˗(1→2)˗β˗D˗xylopyranosyl˗(1→6)˗β˗D˗glucopyranosyl]medicagenic acid (1) and 3˗O˗β˗D˗glucopyranosyl˗28˗O˗[β˗D˗glucopyranosyl˗(1→6)˗β˗D˗glucopyranosyl˗(1→2)˗ β˗D˗xylopyranosyl]oleanolic acid (2), named capitatosides A and B respectively, were isolated from the butanol extract of Paronychia capitata (L.) Lam., along with seven known compounds. The structures of the isolated compounds were established by spectroscopic methods, mainly HRMS, 1D and 2D NMR (¹H, ¹³C, COSY, HSQC, HMBC and NOESY) techniques, whereas those of the known compounds were identified by spectral comparison with reported literature data.
... Carob is a rich source of flavonols glycosides viz. isorhamnetin, kaempferol, myricetin, and quercetin [11] [12]. Apigenin, chrysoeriol, luteolin, naringenin, and genistein were detected at lower levels [4] [13]. ...
... The high fiber content of carob suggests that it could reduce blood cholesterol levels [42]. The carob pods have a high concentration of condensed tannins (16-20%), which are composed of flavan-3-ol groups and their galloyl esters [43,44], gallic acid [45,46], (+)-catechin, (-)-epicatechingallate, (-)-epigallocatechingallate, and quercetin glycosides [47]. ...
The effect of C. siliqua pulp corrosion inhibition on carbon steel has been studied by gravimetric testing and electrochemical methods. In this study, two raw extracts were prepared from the pod pulp of C. siliqua: the first is methanolic and the second is aqueous. The UHPLC/DAD analysis indicated gallic acid's presence in the extracts (methanolic and aqueous) of C. siliqua as a major compound. The inhibition results achieved revealed that the aqueous extract with gallic acid had a good anticorrosion activity with an inhibition rate of 91.32% at 3 g/l for a temperature of 323 K. Potentiodynamic polarization was performed in 1 M HCl without and with different concentrations of C. siliqua extracts clearly proves that inhibitor extracts behave as mixed type. Adsorption of this inhibitor for different extracts studied on the surface of the carbon steel obeys Langmuir adsorption with negative values of \({\Delta G}_{\mathrm{ads}}^{^\circ }\), suggesting a stable and spontaneous inhibition process.
... Methyl 3,4,5-trihydroxybenzoate has been investigated for its anticancer properties [213] , as an antimicrobial [211] and antibacterial [214] , an antidepressant [215] and for its potential inhibitory effects against herpes [212] , the growth of intestinal bacteria [216] and oral bacteria [217] . The identification of 1,2,6-tri(3,4,5-trihydroxybenzoate)--D-glucopyranose from the spectral properties described is consistent with those detailed in previous studies by Owen et al. [218] , Bag et al. [219] , Eldahshan [220] , Nawaar et al. [198] . There was no comparison available for the optical rotary value obtained. ...
Pheromones, semiochemicals that trigger a natural response in a second member of the same species, have been extensively investigated across a variety of vertebrates and invertebrates to manipulate their behaviour. In aquatic species, these pheromones play important roles in larval settlement and metamorphosis, courtship and mating, and foraging. Pheromones responsible for the initiation of mating behaviour in carp and goldfish have been investigated extensively in sexually mature carp but there has been limited investigation on the role the environment plays on behaviour. The introduction of environmental stimuli was investigated to test the hypothesis that environmental cues can be used, like pheromones, to manipulate carp behaviour. Ceratophyllum demersum and Myriophyllum spicatum, a native and invasive aquatic macrophyte, were placed in bioassay tanks with sexually mature carp and spawning incidences recorded across a 15 min monitoring period. A clear preference for the invasive M. spicatum over the native C. demersum was observed even in the presence of yarn used as control. Crude extracts of each plant were tested using yarn as the spawning substrate with similar observations made removing the impact of the physical characteristics to the observed preference. Crude extracts of seven aquatic macrophytes collected from wetlands around Victoria where carp aggregations have been observed (Myriophyllum aquaticum, Egeria densa, Potamogeton crispus. Vallisneria australis, Cabomba caroliniana, Potamogeton sulcatus, and Chara australis) were used in behavioural bioassays mimicking those used for spawning activity to determine if juvenile carp exhibit a behavioural modification in the presence of one of these species. M. aquaticum exhibited the most significant and consistent change to preference and was selected for isolation and purification of potential attractants. In total twelve compounds were isolated and structurally identified using 1D and 2D NMR, mass spectrometry and optical rotation data. Each compound was assessed to determine the preference of juvenile carp. Eight of the twelve compounds tested resulted in a positive behavioural change and provides strong evidence that compounds derived from aquatic flora can potentially be used to manipulate carp behaviour. A final study looking at water collected from known carp aggregation hot spots at Lake Sorell in Tasmania and the Banrock Station wetlands in South Australia was conducted to see if leachates, from the surrounding environment or plants in the water, can result in similar observations. Water collected from the Silver Plains marsh at lake Sorell and the wetland outlet at Banrock station resulted in the most substantial change in carp behaviour. This observation was supported by tracking data of radio-tagged carp obtained during the periods of water collection. While no compounds were able to be successfully isolated from these samples there is potential for future work using water from the wetlands to manipulate carp behaviour. The potential to use environmental attractants to manipulate carp preferences to controlled aggregation sites, or for juvenile aggregation prior to reaching sexual maturity will contribute as part of a broad pest management program assisting in the eradication of carp in our waterways.
... Trên phổ HSQC cho biết tương tác của H-2 và H-6 tại δ H 7,11 (1H, s) với C-2 và C-6 tại δ C 110,3 ppm. Trên phổ HMBC cho biết tương tác xa của proton H-2 và H-6 với các cacbon vòng thơm và cacbon nhóm cacboxyl.Phân tích dữ liệu phổ NMR của 4 kết hợp so sánh với dữ liệu phổ của hợp chất với REFERENCES[12,13], chúng tôi kết luận hợp chất 4 là gallic acid. ...
Từ cặn chiết n-hexane lá cây Thầu dầu (Ricinus communis L.), 4 hợp chất được phân lập và xác định cấu trúc, bao gồm 1 hợp chất steroid: β-sitosterol (1) và daucosterol (2), 1 hợp chất alkaloid: 3-carboxy-4-methoxy-N-methyl-2-pyridone (3) và 1 hợp chất dẫn xuất phenolic: gallic acid (4) đã được phân lập. Cấu trúc hóa học của chúng được xác định bằng các phương pháp phổ MS và 1D-, 2D-NMR kết hợp so sánh dữ liệu với REFERENCES.
... Compounds 1-7 were identified as quercetin (1), myricitrin (2), biapigenin (3), myricetin (4), hyperoside (5), myricetin-3-O-β-D-galactopyranoside (6) and myricetin-3'-O-β-D-glucopyranoside (7) [7][8][9][10][11][12][13]. Compound 7 was isolated from the genus hypericum for the first time. ...
The in vitro activity of L. donovani (promastigotes, axenic amastigotes and intracellular amastigotes in THP1 cells) and T. brucei, from the fractions obtained from the hydroalcoholic extract of the aerial part of Hypericum afrum and the isolated compounds, has been evaluated. The chloro-form, ethyl acetate and n-butanol extracts showed significant antitrypanosomal activity towards T. brucei, with IC50 values of 12.35, 13.53 and 12.93 µg/mL and with IC90 values of 14.94, 19.31 and 18.67 µg/mL, respectively. The phytochemical investigation of the fractions led to the isolation and identification of quercetin (1), myricitrin (2), biapigenin (3), myricetin (4), hyperoside (5), myricetin-3-O-β-D-galactopyranoside (6) and myricetin-3'-O-β-D-glucopyranoside (7). Myricetin-3'-O-β-D-glu-copyranoside (7) has been isolated for the first time from this genus. The chemical structures were elucidated by using comprehensive one-and two-dimensional nuclear magnetic resonance (1D and 2D NMR) spectroscopic data, as well as high-resolution electrospray ionization mass spectrometry (HR-ESI-MS). These compounds have also been evaluated for their antiprotozoal activity. Querce-tin (1) and myricetin (4) showed noteworthy activity against T. brucei, with IC50 and IC90 values of 7.52 and 5.71 µM, and 9.76 and 7.97 µM, respectively. The T. brucei hexokinase (TbHK1) enzyme was further explored as a potential target of quercetin and myricetin, using molecular modeling studies. This proposed mechanism assists in the exploration of new candidates for novel antitrypa-nosomal drugs.
... Compounds 1-7 were identified as quercetin (1), myricitrin (2), biapigenin (3), myricetin (4), hyperoside (5), myricetin-3-O-β-D-galactopyranoside (6) and myricetin-3'-O-β-D-glucopyranoside (7) [7][8][9][10][11][12][13]. Compound 7 was isolated from the genus hypericum for the first time. ...
The in vitro activity of L. donovani (promastigotes, axenic amastigotes and intracellular amastigotes in THP1 cells) and T. brucei, from the fractions obtained from the hydroalcoholic extract of the aerial part of Hypericum afrum and the isolated compounds, has been evaluated. The chloroform, ethyl acetate and n-butanol extracts showed significant antitrypanosomal activity towards T. brucei, with IC50 values of 12.35, 13.53 and 12.93 µg/mL and with IC90 values of 14.94, 19.31 and 18.67 µg/mL, respectively. The phytochemical investigation of the fractions led to the isolation and identification of quercetin (1), myricitrin (2), biapigenin (3), myricetin (4), hyperoside (5), myricetin-3-O-β-d-galactopyranoside (6) and myricetin-3’-O-β-d-glucopyranoside (7). Myricetin-3’-O-β-d-glucopyranoside (7) has been isolated for the first time from this genus. The chemical structures were elucidated by using comprehensive one- and two-dimensional nuclear magnetic resonance (1D and 2D NMR) spectroscopic data, as well as high-resolution electrospray ionization mass spectrometry (HR-ESI–MS). These compounds have also been evaluated for their antiprotozoal activity. Quercetin (1) and myricetin (4) showed noteworthy activity against T. brucei, with IC50 and IC90 values of 7.52 and 5.71 µM, and 9.76 and 7.97 µM, respectively. The T. brucei hexokinase (TbHK1) enzyme was further explored as a potential target of quercetin and myricetin, using molecular modeling studies. This proposed mechanism assists in the exploration of new candidates for novel antitrypanosomal drugs.
... C. siliqua seed is a great source of bioactive compounds such as fiber, polyphenols, cyclitols, and low levels of fresh fat (16), and its fruit contains flavonoids, like quercetin, luteolin, and kaempferol (17). Beside, gallic acid has been isolated from the leaves and pods of the C. siliqua (18), and lupeol, genistein, and liquiritigenin have also been found in the C. siliqua extract (19). Also, its seed stem cells contain fatty acids including myristic acid, palmitic acid, oleic acid, linoleic acid, and arachidonic acid (20). ...
Background: Spermatogenesis is a complex process that takes place under the influence of many different genes.
Objective: The aim of this study was to investigate the possible effects of Ceratonia siliqua hydroalcoholic extract (CSHAE) on protamine gene expression, testicular function, and testicular histology in doxorubicin-treated rats.
Materials and Methods: 56 adult male rats with a age range of 2.5 to 3 months (210
±
10 gr) were divided into seven groups (n = 8/each). A) Control group was left untreated; B) Sham group received 0.3 ml distilled water intraperitoneally, C) Negative control group received 3 mg/kg doxorubicin, intraperitoneally once a week for 28 days; and D) Positive control group received 600 mg/kg of CSHAE orally for 48 days; E, F, G) the experimental groups 1, 2, and 3 received 150, 300, and 600 mg/kg of CSHAE respectively orally, for 48 days, as well as 3 mg/kg doxorubicin once a week for 28 days. Hematoxylin-eosin staining was used in the histological study of testes, and enzyme-linked immunosorbent assay method was used in measuring serum levels of testosterone. Protamine gene expression was determined by real-Time PCR method.
Results: The mean body weight, testicular weight, testicular volume, testosterone level (p = 0.022), the count of Leydig, spermatogonia, spermatocyte, and spermatid cells, as well as protamine gene expression (p = 0.008) were significantly increased in the experimental group 2 compared to the negative control group. The regeneration of testicular tissue was observed in the experimental group 2.
Conclusion: CSHAE has protective effect on doxorubicin-induced testicular injuries.
... In a survey of Othmen et al. [60], the condensed tannins content from C. siliqua leaf extracts reached 18.52 ± 0.03 g catechin equivalents (CE) 100/g DW. Highly polymerized condensed tannins containing a flavan nucleus were previously isolated from C. siliqua pods [67]. ...
Ceratonia siliqua L. is a Mediterranean medicinal plant traditionally cultivated for its ethnopharmacological benefits, such as antidiarrheal, antidiabetic, enhance acetylcholine, antioxidant, antiatherosclerotic, and for its possible anti-neurodegenerative potential. The aim of the present study was to evaluate the chemical composition, as well as the cognitive-enhancing, anxiolytic, and antioxidant activities of the aqueous extract from C. siliqua (CsAE) leaves against 6-hydroxydopamine (6-OHDA) zebrafish Parkinson’s disease (PD) model. CsAE (0.1, 0.3, and 1 mg/L) was administered by immersion to zebrafish (Danio rerio) for eight consecutive days and one hour before each behavioral test of each day, while 6-OHDA (250 µM) treatment was supplied one day before the novel tank diving test (NTT). Qualitative and quantitative analyses were performed by the ultra-high-performance liquid chromatography (UHPLC) analysis. The memory performance was evaluated through the NTT and Y-maze tests. Additionally, the in vitro and in vivo antioxidant status and acetylcholinesterase (AChE) activity was also assessed. Our finds demonstrated that CsAE presented positive antioxidant and anti-AChE activities, which contributed to the improvement of cognitive function in the 6-OHDA zebrafish PD model.
... and its derivatives as methyl gallate comprised the major fraction of phenolic acids likely attributed for gallic acid release from tannins during the extraction procedures (Torun et al. 2013) ranging from 24-165 mg/100 g dry weight, other less abundant phenolic acids include gentisic, ellagic, vanillic, syringic acids and pyrogallol Fig. 36.2(2-6) (Loullis and Pinakoulaki 2018;Eldahshan 2011;Owen et al. 2003). The phenolic acids of cinnamates origin viz. ...
Ceratonia siliqua (Carob); is a Mediterranean legume globally recognized for its commercial value, being used as a cold beverage, in bakery and confectionary products. It is widely used as a Cocoa substitute not only due to its richness in sugar but rather the absence of caffeine and theobromine stimulant action. Both fruit pulp and seeds are of potential nutritive and medicinal values. The pulp comprises a high sugar content dominantly sucrose as well as polyphenols viz. phenolic acids, flavonoids and tannins. Seeds potential usage is attributed to its locust bean gum (LBG), commercially and pharmaceutically used as gelling and stiffening agent. Carob syrup is a traditional product native to the Mediterranean region, enriched in D-pinitol sugar of anti-diabetic effect. Considering the diversity of carob active constituents’ classes, a myriad of biological effects is recorded to include antioxidant, anticancer, antimicrobial and anti-hyperlipidemic effects. This book chapter presents up to date information on carob usage and chemistry while providing insight on research questions or applications yet to be addressed.
... The 1 H-NMR spectrum (CDCl3) showed only one peak at δ 6.46, which showed HMBC correlations with all of the quaternary carbons. NMR, IR, MS and melting point data were consistent with literature data for gallic acid(Eldahshan 2011, Sarria-Villa 2017. ...
... The molecular formula, C 7 H 6 O 5 , was deduced from the combination of 1 H-, 13 C-NMR and DEPT spectroscopic data. Compound 1 was identified as gallic acid when the data was compared with those in the literature [11,12]. Compound 2, an off-white powder, showed a quasi-molecular ion peak at m/z 198 [M] − in the negative ESI-MS. ...
This study was designed to explore the in vitro anticancer effects of the bioactive compounds isolated from Ricinodendron heudelotii on selected cancer cell lines. The leaves of the plant were extracted with ethanol and partitioned in sequence with petroleum ether, ethyl acetate, and n-butanol. The ethyl acetate fraction was phytochemically studied using thin layer chromatography (TLC) and column chromatography (CC). Structural elucidation of pure compounds obtained from the ethyl acetate fraction was done using mass spectra, 1H-NMR, and 13C-NMR analysis. The isolated compounds were subsequently screened using five different cancer cell lines: HL-60, SMMC-7721, A-549, MCF-7, SW-480, and normal lung epithelial cell line, BEAS-2B, to assess their cytotoxic effects. Nine compounds were isolated and structurally elucidated as gallic acid, gallic acid ethyl ester, corilagin, quercetin-3-O-rhamnoside, myricetin-3-O-rhamnoside, 1,4,6-tri-O-galloyl glucose, 3,4,6-tri-O-galloyl glucose, 1,2,6-tri-O-galloyl glucose, and 4,6-di-O-galloyl glucose. Corilagin exhibited the most cytotoxic activity with an IC50 value of 33.18 μg/mL against MCF-7 cells, which were comparable to cisplatin with an IC50 value of 27.43 µg/mL. The result suggests that corilagin isolated from R. heudelotii has the potential to be developed as an effective therapeutic agent against the growth of breast cancer cells.
... Sub-fractions C4 (0.333417 g) and C5 (1.0736 g) were treated separately on silica gel CC using a gradient of CHCl 3 /MeOH. Sub-fraction C4.4 and C5.5 yielded 69 mg and 58 mg, respectively of crystals of compound 4, identified as gallic acid (Eldahshan, 2011). Fraction D (24.8 mg) was passed through silica gel CC with a gradient of CHCl 3 /MeOH. ...
Ethnopharmacological relevance: In Mexico, plants are an important element of traditional medicine, and many are considered part of Mexican cultural heritage from prehispanic and colonial times. Nevertheless, relatively few systematic scientific studies have been conducted to fully characterize the chemical composition and pharmacological activities of Mexican medicinal plants. Acacia farnesiana is used in Mexican traditional medicine to treat dysentery and tuberculosis and therefore could have bioactive compounds that may explain its traditional use. Aims of the study: i) To isolate and characterize the compounds from the hexanic, chloroformic and methanolic extracts; ii) to identify the volatile compounds from methylated hexanic and chloroformic extracts using GC-FID and GC-MS methods; iii) to identify the compounds from methanolic and aqueous extracts using HPLC-Q-TOF-MS; iv) to test the activity of extracts and isolated compounds against Mycobacterium tuberculosis and dysentery bacteria. Material and methods: A. farnesiana fruits were collected in Acatlán de Osorio, Puebla, Mexico. Hexanic, chloroformic, methanolic and aqueous extracts were prepared and analyzed by different chromatographic techniques including column chromatography, flash chromatography, GC-FID, GC-MS and HPLC-Q-TOF-MS. Structural elucidation was carried out by NMR spectroscopic analysis. The activity of extracts, phytochemicals and semi-synthetic derivatives against Mycobacterium tuberculosis H37Rv and G122 as well as dysentery bacteria (Campylobacter jejuni, Shigella flexneri, Salmonella enteritidis, Yersinia enterocolitica and enterohemorrhagic Escherichia coli) was determined by the broth microdilution method and reported as minimal inhibitory concentration (MIC µg/mL). Results: From both hexane and chloroform extracts, tetracosanoic acid (2S)-2,3-dihydroxypropyl ester (1) and (3β,22E)-estigmasta-5,22-dien-3-yl β-D-glucopyranoside (2) were isolated and characterized. From the methanolic extract, methyl gallate (3), gallic acid (4), (3β,22E)-estigmasta-5,22-dien-3-yl β-D-glucopyranoside (2), (2S) naringenin 7-O-β-glucopyranoside (prunin, 5), pinitol (6) and sucrose (7) were isolated and characterized. Furthermore, hexanic and chloroformic extracts were analyzed by GC-FID and GC-MS and 18 methylated fatty acids were identified for each extract in addition to three sterols. The methanolic and aqueous extracts were analyzed separately by HPLC-Q-TOF-MS, and 15 compounds were identified in each extract. The compounds 1, 2, and 7, in addition to 13 fatty acids and eight phenolic compounds, were identified for the first time in A. farnesiana. The extracts showed antitubercular (MIC 100–200 µg/mL) and antidysentery activity (MIC 100–200 µg/mL). Methyl gallate and its acetylated derivative showed activity against the sensible strain M. tuberculosis H37Rv with MIC values of 50–25 µg/mL, respectively. The flavanone prunin showed activity against multidrug resistant M. tuberculosis G122 (MIC 50 μg/mL). Methyl gallate, gallic acid and prunin showed activity against C. jejuni (MIC 50 μg/mL). Conclusions: The activity of tested extracts and isolated compounds against M. tuberculosis and dysentery bacteria justifies the ethnomedical use of A. farnesiana fruits for the treatment of tuberculosis and dysentery.
... The ) within the cubic box centered on the co-crystallized ligand. After receptor grid generation, the prepared ligands were docked using the Glide 5.8 module (Glide, version 5.8, 2012, Schr€ odinger, New York, NY, USA) in extra-precision mode (18). ...
Triple negative breast cancer (TNBC) has high metastatic and mortality potential and lacks effective and selective therapeutic options. Aberrant dysregulation of the receptor tyrosine kinase c-Met promotes TNBC progression, motility and survival and therefore considered a valid therapeutic target. Plant polyphenols, including flavonoids, have been proven for their antitumor activity through modulating diverse macromolecular targets. This study reports the bioassay-guided identification of the common flavonol glycoside rutin as breast cancer cell proliferation, migration and invasion inhibitor. The cell free Z'-LYTE kinase assay, Western blot analysis and in silico docking assessments provided a snapshot that rutin attenuates TNBC, at least in-part, via targeting the c-Met kinase domain. Likewise, intraperitoneal treatment of rutin at 30 mg/kg, 3X/week, significantly reduced the primary tumor growth of the TNBC MDA-MB-231/GFP orthotopic xenograft in nude mouse model. This study results designate the functional dietary flavonoid rutin as a potential lead for the prevention and control of c-Met- dependent breast malignancies.
... 13 C-NMR (DMSO-d 6 ), d ppm: 121.04 (C-1), 109.314 (C-2 and C-6), 145.2 (C-3 and C-5), 137.99 (C-4), 167.54 (C-7) [Eldahshan, 2011]. ...
Preclinical Research
Nine known phenolic compounds were isolated from an aqueous methanolic extract of Acrocarpus fraxinifolius Weight and Arn leaves (AFL) family Fabaceae. This extract of AFL contained approximately 169 mg gallic acid/g as assessed by HPLC. The AFL extract had marginal antitumor activity (IC50 > 200 µL/mL) but showed a concentration‐dependent hepatoprotective effect against CCl4‐induced hepatotoxicity in vitro. Cell viability was increased, ALT and AST activity declined and reduced GSH concentration and SOD activity were restored as compared with silymarin. In vivo concurrent administration of AFL extract (500 mg/kg po) showed a hepatoprotective effect against gamma irradiation and CCl4 as evidenced by reduction of TNF‐α, interleukin‐6, malondialdehyde, nitric oxide, DNA fragmentation, caspase‐3 activity, and downregulation of its m‐RNA level and decreased proapoptotic protein Bax expression. AFL extract enhanced glutathione peroxidase, superoxide dismutase, and catalase activities, reduced glutathione concentrations and upregulated the expression of antiapoptotic Bcl‐2. The extract could ameliorate hepatic injuries induced by gamma irradiation and CCl4 in rats suggesting potent hepatoprotective activity. Drug Dev Res 78 : 210–226, 2017. © 2017 Wiley Periodicals, Inc.
... The signals of H-6 protons shifted downfield at δ 4.05, 4.28 indicating the probable esterification to pcoumaroyl that gave AA'BB' spin system at δ 6.86, 7.38 and the ethylenic H-7, H-8 at δ 6.12, 7.35 as a pair of doublets with trans coupling of 16 Hz. The probable glycosidation at C-3-OH was excluded on the bases of notable shifts of ring B signals [10,11]. Thus, 1 was identified as kaempferol 4'-O-(6"-O-E-pcoumaroyl)-β-D-glucopyranoside, rather than its isomer cephacoside, isolated previously from the same species [9].The proposed structure for 1 was confirmed by 1-and 2-D NMR analysis ( ...
The carob tree (Ceratonia siliqua L.) is currently considered one of the most valuable fruit and forest trees in various fields and sectors of activity. It is a versatile plant, belonging to the Fabaceae family. It is widely used in traditional medicine to treat many diseases such as diabetes, hypertension, and gastrointestinal disorders, given that all its parts (leaves, flowers, pods, seeds, wood, bark, and roots) are useful and hold value in many areas. Its importance has increased significantly in recent years. Originating from the Middle East, it is recognized for its ecological and industrial significance. Previous studies conducted on Ceratonia siliqua L. have revealed the presence of several compounds, including polyphenols, flavonoids, carbohydrates, minerals, and proteins. The carob tree demonstrates antihypertensive, antidepressant, anti-obesity, and antihyperglycemic activities. This plant is known for its medicinal and therapeutic virtues. Moreover, it is particularly interesting to consider the pharmacological activities of the major phytochemical compounds present in the different extracts of this plant, such as phenolic acids, for example, coumaric and gallic acids, as well as flavonoids such as kaempferol and quercetin. Therefore, this review aims to analyze some aspects of this plant, especially the taxonomy, cytogeography, traditional uses, phytochemical constituents, and pharmacological activities of Ceratonia siliqua L., in addition to its biological properties.
Breast cancer is one of the main global diseases with a high mortality rate that mainly affects the female population. Despite the important advances that have been made concerning the treatments for this disease, research on less invasive therapies that generate fewer side effects for patients continues to develop. Consequently, researchers have turned their attention to using natural compounds (such as flavonoids) involved in molecular processes implicated in this type of cancer and are studying how these processes can be exploited to develop possible chemotherapies. This review offers a general description of studies on the antiproliferative activity of flavonoids obtained from natural sources for breast cancer treatment and their mechanism of action related to their structural characteristics. Reports were retrieved from electronic databases, such as Web of Science and Scopus using the following keywords: breast cancer, antiproliferative, flavonoids, and structure-activity. Articles published between 2015-2022 related to the topics mentioned above were selected, focusing on the flavonoids apigenin, luteolin, quercetin, and naringenin, as they are the ones with the highest activity and relevance according to the literature found.
Ceratonia siliqua L. (carob tree) is an endemic plant to the eastern Mediterranean region. In the present study, anatomical and physiological traits of successively grown compound leaves (i.e., the first, third, fifth and seventh leaves) of C. siliqua were investigated in an attempt to evaluate their growth under urban and suburban environmental conditions. Chlorophyll and phenolic content, as well as the specific leaf area of the compound leaves were determined. Structural traits of leaflets (i.e., thickness of palisade and spongy parenchyma, abaxial and adaxial epidermis, as well as abaxial and adaxial periclinal wall) were also investigated in expanding and fully expanded leaflets. Fully expanded leaflets from urban sites exhibited increased thickness of the lamina and the palisade parenchyma, while the thickness of the spongy parenchyma was thicker in suburban specimens. The palisade tissue was less extended than the spongy tissue in expanding leaflets, while the opposite held true for the expanded leaflets. Moreover, the thickness of the adaxial and the abaxial epidermises, as well as the adaxial and abaxial periclinal wall were higher in suburban leaflets. The chlorophyll content increased concomitantly with the specific leaf area (SLA) of both expanding and expanded leaflets, and strong positive correlations were detected, while the phenolic content declined with the increased SLA of expanding and expanded leaflets. It is noteworthy that the SLA of expanding leaflets in the suburban site was comparable to the SLA of expanded leaflets experiencing air pollution in urban sites; the size and the mass of leaf blades of C. siliqua possess adaptive features to air pollution. These results, linked to the functional structure of expanding and expanded successive foliar tissues, provide valuable assessment information coordinated with an adaptive process and yield of carob trees exposed to the considered ambient conditions, which have not hitherto been published.
Background
Olive (Olea europaea L.) and carob (Ceratonia siliqua L.), which contain considerable amounts of phenolic compounds, are the most important nutritional and therapeutic plants in the Mediterranean basin.
Objectives
The goal of this work is to revalue carob and olive leaves as key sources of polyphenols, hence increasing the value of waste goods.
Objective
The goal of this work is to revalue carob and olive leaves as key sources of polyphenols, hence increasing the value of waste goods.
Methods
In this study, aqueous acetone or ethanol (80% v/v) extracts of olive (O. europaea L. cultivar aimel) and carob (C. siliqua L.) leaves from Algeria were evaluated for phenolic content, and the extracts were characterized by reverse-phase high-performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-ESI-MS).
Discussion/Results
The total phenolic content of olive and carob leaf extracts ranged from 5.6 to 23 mg GAE/g. The use of HPLC-ESI-MS to investigate phenolics revealed that the extracts included a variety of phenolic compounds, including 23 compounds in olive leaf extracts and 17 compounds in carob leaf extracts. In olive and carob, the major phenolic components are oleuropein and myricetin rhamnoside, respectively.
Conclusion
According to our findings, olea europaea and Ceratonia siliqua appear to be rich suppliers of natural chemicals. These plants have a lot of potential in terms of medications and functional foods.
Conclusion
Olea europaea and Ceratonia siliqua appear to be rich suppliers of natural chemicals, according to our findings. This plant has a lot of potential in terms of medications and functional foods.
The use of medicinal plants, which is one of the forms of traditional medicine treatments, has been considered as a model in the treatment of various diseases for thousands of years before the Industrial Revolution and the era of discoveries and inventions. With the beginning of a new era in modern medicine and the discovery of chemical drugs, the use of traditional medicine and herbs gradually became less and less. But over time, when man became acquainted with the harms of chemical medicine and its inability to prevent and treat some diseases, man again turned his attention to traditional medicine and medicinal plants. Our goal in this book is to change the common approach in some academic communities to the importance of medicinal plants. The approach that is sometimes presented with a scientific appearance and as an academic exposure to medicinal plants indicates that the treatment with medicinal plants is unscientific. In response to this type of exposure, we can refer to cases such as the presence of a large number of chemical drugs of plant origin, which indicates the presence of effective substances in the treatment of various diseases in a variety of plants.
Background: Kelussia odoratissima Mozaff. from Apiaceae family is a perennial herbaceous plant endemic to the west of Iran. The aromatic aerial parts of this species are traditionally used by indigenous people to flavor some local foods, as well as for various therapeutic purposes. Objective: The present study was designed to analyze phenolic compounds and essential oil constituents of K. odoratissima fruits. Methods: The n-butanol fraction obtained from hydroalcoholic extract of K. odoratissima fruits was investigated by chromatography on normal phase and Sephadex LH-20 columns. Chemical structures of the isolated compounds were clarified by ¹H-NMR and ¹³C-NMR spectral analyses. Essential oil constituents of the fruits were also analyzed using GC-MS. Results: Phytochemical investigation of the K. odoratissima fruits resulted in the isolation of five flavonol glycosides; isorhamnetin 3-O-glucoside (1), quercetin 3-O-glucoside (isoquercetin) (2), isorhamnetin 3-O-rutinoside (narcissin) (3), isorhamnetin 3-O-glucuronide (4) and quercetin 3-O-glucuronide (mequilianin) (5). GC-MS analysis of the fruits essential oil led to the identification of the thirty six compounds, of which (Z)-ligustilide (15.93 %), δ-cadinene (12.26 %) and germacrene D (12.18 %) were the main compounds. Conclusion: The results of this study introduce K. odoratissima fruits as a source of flavonoid glycosides and phthalate derivatives. The presence of these compounds with known biological properties and health beneficial effects provides more medicinal potentials for the fruits of K. odoratissima and suggest it an appropriate option for further studies.
Euphorbia hirta L. has been proved a medicinally important plant. This study aimed to investigate the antioxidant capacities of fractioned extracts and some isolated compounds from Euphorbia hirta L. on pancreatic β-cells MIN6 exposed to hydrogen peroxide-oxidative stress conditions. Four pure compounds were isolated from ethyl acetate and methanol extracts and identified as quercitrin (1), luteolin (2), quercetin (3) and caffeic acid (4). The results showed that the ethyl acetate extract as well as quercetin possess strong protective effects with the cell viability of 81% and 82% at the dose of 0.1 mg/mL. This proves that E hirta L. is a potentially natural antioxidative plant and worth testing for further pharmacological potential in the treatment of oxidative stress which may be related to neurodegenerative diseases.
A new dehydrodigallic acid derivative (1), along with 19 known compounds, including 6 phenolic derivatives, 2 steroids and 11 triterpenoids were isolated from the ethanol extract of the root of Geum urbanum. Herein, there is the first report of steroid and triterpene in Geum urbanum. The purified metabolites were characterised by NMR spectroscopic and mass spectrometric analyses. The identification of the known compounds (2–20) was based on the comparison of their NMR spectroscopic features with previously published data. The structural characteristics of compound 1 were elucidated by comprehensive 1D and 2D NMR spectroscopic methods and acid hydrolysis.
Gallic acid, one of the naturally occurring antioxidants, has been characterized in terms of its structural and chemical properties using the density functional approach. The intramolecular interactions have been identified using natural bond orbital (NBO) analysis. The gallic acid anion and dianion have also been studied for determining the first two pKa values. Further, an investigation of the molecular orbitals reveals a dependence of the frontier molecular orbitals on external factors, viz. pH and dielectric of the medium. Consequently, the electronic spectra have been simulated in a range of solvents using steered molecular dynamics. Furthermore, the IR and NMR spectra of the neutral and the deprotonated state have been simulated. Additionally, the spectra have been experimentally recorded to validate the methodology followed. The present work also examines the variation in global and local reactivities of gallic acid under the influence of external factors. Each atom has been quantitatively assessed for its susceptibility towards nucleophilic, electrophilic, and radical attack.
Prangos ferulacea (L.) Lindl. (Apiaceae) is a medicinal plant distributed in Mediterranean regions, Caucasia and southwest of Asia. In the present study phytochemical constituents of the extract obtained from the aerial parts of P. ferulacea were investigated using various chromatographic and spectroscopic methods. Essential oil of the plant aerial parts was also analyzed using GC-MS. Five phenolic derivatives, isoimperatorin (1), ferudenol (2), caffeic acid glucosyl ester (3), isorhamnetin-3-O-β-D-glucopyranoside (4) and quercetin-3-O-β-D-glucopyranoside (5) were isolated from the aerial parts of P. ferulacea and their structures were elucidated using 1 H-NMR, 13 C-NMR, EI-MS and UV spectral analyses. Twenty-seven compounds were also identified in the essential oil of plant aerial parts, of which β-pinene (43.1%), α-pinene (22.1%) and δ-3-carene (16.9%) were characterized as main compounds. The results of this study introduce P. ferulacea as a source of potentially bioactive phenolic compounds and suggest it as an appropriate candidate for further studies.
Plants are endless reservoir for several phytochemicals including antioxidant and cytotoxic drugs. The objective of this study was the investigation of the antioxidant and the cytotoxic activities (against Vero and HEp-2 cell lines) of the aqueous ethanolic extract of carob leaves. The extract inhibited xanthine oxidase at IC 50 of 244 µg/ml. There is a marked cytotoxic activity of crude aqueous extract of carob on both mammalian cell lines (Vero and HEp-2) and the effect is more obvious on the human cell line (HEp-2). The results revealed that the crude aqueous extract of carob leaves could be a promising source for antioxidant as well as antitumor bioactive agents.
The cell adhesion molecule intercellular adhesion molecule-1 (ICAM-1) plays a pivotal role in inflammatory responses. Quercetin (3,3',4',5,7-pentahydroxyflavone), a naturally occurring dietary flavonol, has potent anti-inflammatory properties. The effect of quercetin on ICAM-1 expression induced by agonists phorbol 12-myristate 13-acetate (PMA) and tumor necrosis factor-alpha (TNF-alpha) in human endothelial cell line ECV304 (ECV) was investigated. Quercetin treatment downregulated both PMA- and TNF-alpha-induced surface expression, as well as the ICAM-1 mRNA levels, in ECV cells in a dose-dependent (10-50 microM) manner. Quercetin had no effect on PMA- or TNF-alpha-induced nuclear factor-kappaB (NF-kappaB) activation. However, under similar conditions a remarkable dose-dependent downregulation of activator protein-1 (AP-1) activation was observed. This decrease in AP-1 activation was observed to be associated with the inhibitory effects of quercetin on the c-Jun NH2-terminal kinase (JNK) pathway. These results suggest that quercetin downregulates both PMA- and TNF-alpha-induced ICAM-1 expression via inhibiting both AP-1 activation and the JNK pathway.
Estrogens used in hormone replacement therapy regimens may increase the risk of developing breast cancer. Paradoxically, high
consumption of plant-derived phytoestrogens, particularly soybean isoflavones, is associated with a low incidence of breast
cancer. To explore the molecular basis for these potential different clinical outcomes, we investigated whether soybean isoflavones
elicit distinct transcriptional actions from estrogens. Our results demonstrate that the estrogen 17β-estradiol effectively
triggers the transcriptional activation and repression pathways with both estrogen receptors (ERs) ERα and ERβ. In contrast,
soybean isoflavones (genistein, daidzein, and biochanin A) are ERβ-selective agonists of transcriptional repression and activation
at physiological levels. The molecular mechanism for ERβ selectivity by isoflavones involves their capacity to create an activation
function-2 surface of ERβ that has a greater affinity for coregulators than ERα. Phytoestrogens may act as natural selective
estrogen receptor modulators that elicit distinct clinical effects from estrogens used for hormone replacement by selectively
recruiting coregulatory proteins to ERβ that trigger transcriptional pathways.
Tannins isolated from ripe carob pods were subjected to thioglycolic acid degradation and mild and strong acid hydrolysis. Mild acid hydrolysis did not degrade the tannins, strong acid hydrolysis resulted in the production of delphinidin, cyanidin and pelargonidin. The ethyl acetate-soluble thioglycolic acid degradation products were identified by paper chromatography, UV and IR spectral analysis as (−) epigallocatechin, (−) epigallocatechin gallate and (−) epicatechin gallate. The minimum molecular weight of the polymers, 3200, was estimated on Sephadex columns. It is concluded that the polymeric condensed tannins from ripe carobs consist of subunits of flavan-3-ols and their gallate esters.
Depending on their structure, flavonoids display more or less potent inhibitory effects on the growth and proliferation of certain malignant cells in vitro, and these effects are thought to be due to inhibition of various enzymes. We investigated the inhibitory action of fourteen flavonoids of different chemical classes on phosphatidylinositol 3-kinase a (PI 3-kinase a) activity, an enzyme recently shown to play an important role in signal transduction and cell transformation. Of the fourteen flavonoids tested, myricetin was the most potent PI 3-kinase inhibitor (ic50 = 1.8 μM), while luteolin and apigenin were also effective inhibitors, with ic50 values of 8 and 12 μM, respectively. Fisetin and quercetin, as previously reported, were also found to significantly inhibit PI 3-kinase activity. The same flavonoids were also analyzed for inhibition of epidermal growth factor receptor (EGF-R), intrinsic tyrosine kinase and bovine brain protein kinase C (PKC). At elevated doses, some of these flavonoids were found to also cause significant inhibition of PKC and tyrosine kinase activity of EGF-R. A structure-activity study indicated that the position, number and substitution of the hydroxyl group of the B ring, and saturation of the C2C3 bond are important factors affecting flavonoid inhibition of PI 3-kinase. They may also play a significant role in specificity of inhibition and could help to provide a basis for the further design of specific inhibitors of this lipid kinase. Finally, possible relationships between the antitumoral properties of these flavonoids and their biological activities are discussed.
IN the United States, coronary heart disease — principally myocardial infarction — accounts for approximately 1 of every 3 deaths, or nearly 600,000 deaths each year.1 Almost 50 percent of the deaths attributed to myocardial infarction occur before the victims reach the hospital, and of the 500,000 people admitted each year for myocardial infarction, about 15 percent die during the hospitalization and another 7 to 10 percent die during the ensuing several years.2 , 3 A therapy for myocardial infarction that improved survival by even 20 percent would therefore affect tens of thousands of lives, and a similar benefit in the primary . . .
Dioxins invade the body mainly through the diet, and produce toxicity through the transformation of aryl hydrocarbon receptor (AhR). An inhibitor of the transformation should therefore protect against the toxicity and ideally be part of the diet. We examined flavonoids ubiquitously expressed in plant foods as one of the best candidates, and found that the subclasses flavones and flavonols suppressed antagonistically the transformation of AhR induced by 1 nM of 2,3,7,8-tetrachlorodibenzo-p-dioxin, without exhibiting agonistic effects that transform AhR. The antagonistic IC(50) values ranged from 0.14 to 10 microM, close to the physiological levels in human.
The presence of molecules with high affinity for central and peripheral benzodiazepine receptors was determined in the pod and leaves of Ceratonia siliqua (carob). The amount of the substances able to selectively bind the central benzodiazepine receptor recovered from carob pods and leaves was respectively 12.17 and 18.7 ng diazepam equivalent/g. The amount of compounds active on peripheral benzodiazepine receptor in both pods and leaves was higher in comparison with the central one, being 49.83 and 40.00 PK 11195 equivalent/g, respectively. In particular the compounds acting on peripheral benzodiazepine receptors were found to be extremely concentrated in the young leaves (2572.57 ng PK 11195 equivalent/g). The presence of substances with central benzodiazepine activity in carob extracts seems of great importance in view of the possibility to use carob extract as potential natural products with anxiolytic-sedative effects. Moreover, the prevalence in leaves of substances acting on peripheral benzodiazepine receptor suggests the possible utilisation of leave extracts as chemopreventive agents.
Extracts from pods and leaves of carob (Ceratonia siliqua L.) were tested for their ability to inhibit cell proliferation of mouse hepatocellular carcinoma cell line (T1). The two extracts showed a marked alteration of T1 cell proliferation in a dose-related fashion reaching the maximal effect at 1 mg/ml. Moreover, we demonstrated that leaf and pod extracts were able to induce apoptosis in T1 cell lines after 24-h treatment mediating a direct activation of the caspase 3 pathway. HPLC analysis revealed the presence of gallic acid, (-) epigallocatechin-3-gallate and (-) epicatechin-3-gallate in pod and leaf extracts, compounds well known to exert antiproliferative effects. Their concentration reached 6.28 mg/g in carob leaves and 1.36 mg/g in carob pods extract. The discovery that carob pod and leaf extracts contained antiproliferative agents could be of practical importance in the development of functional foods and/or chemopreventive drugs.
Polyphenols, which have beneficial effects on health and occur ubiquitously in plant foods, are extremely diverse. We developed a method for simultaneously determining all the polyphenols in foodstuffs, using HPLC and a photodiode array to construct a library comprising retention times, spectra of aglycons, and respective calibration curves for 100 standard chemicals. The food was homogenized in liquid nitrogen, lyophilized, extracted with 90% methanol, and subjected to HPLC without hydrolysis. The recovery was 68-92%, and the variation in reproducibility ranged between 1 and 9%. The HPLC eluted polyphenols with good resolution within 95 min in the following order: simple polyphenols, catechins, anthocyanins, glycosides of flavones, flavonols, isoflavones and flavanones, their aglycons, anthraquinones, chalcones, and theaflavins. All the polyphenols in 63 vegetables, fruits, and teas were then examined in terms of content and class. The present method offers accuracy by avoiding the decomposition of polyphenols during hydrolysis, the ability to determine aglycons separately from glycosides, and information on simple polyphenol levels simultaneously.
Phytochemical and biological studies on certain tradional medicinal plants having potential bioactivities Quercetin inhibits inducible ICAM- 1 expression in human endothelial cells through the JNK pathway
- O A Eldahshan
- H Kobuchi
- S Roy
- C K Sen
- H G Nguyen
- L Packer
Eldahshan, O.A., 2006. Phytochemical and biological studies on certain tradional medicinal plants having potential bioactivities. Ph.D. Thesis, Ain Shams University, Faculty of Pharmacy. Kobuchi, H., S. Roy, C.K. Sen, H.G. Nguyen and L. Packer, 1999. Quercetin inhibits inducible ICAM- 1 expression in human endothelial cells through the JNK pathway. Am. J. Physiol. Cell Physiol., 277: 403-411. Manson, J.E., H. Tosteson, P.M. Ridker, S. Satterfield, P.O. Hebert, G.T. Connor, J.E. Buring and C.H
Phytochemical and biological studies on certain tradional medicinal plants having potential bioactivities
- O A Eldahshan
Eldahshan, O.A., 2006. Phytochemical and biological
studies on certain tradional medicinal plants having
potential bioactivities. Ph.D. Thesis, Ain Shams
University, Faculty of Pharmacy.
Determination of phenolic composition of carob pods grown in different regions of Morocco
- E Rakib
- H Chicha
- S Abouricha
- M Alaoui
- A A Bouli
- M Hansali
- R W Owen
Rakib, E., H. Chicha, S. Abouricha, M. Alaoui,
A.A. Bouli, M. Hansali and R.W. Owen, 2010.
Determination of phenolic composition of carob pods
grown in different regions of Morocco. J. Nat. Prod.,
3: 134-140.