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Three compounds isolated from the methanol (MeOH) leaf extract of Vallaris glabra (Apocynaceae) were those of caffeoylquinic acids (CQAs). This prompted a quantitative analysis of their contents in leaves of V. glabra in comparison with those of five other Apocynaceae species (Alstonia angustiloba, Dyera costulata, Kopsia fruticosa, Nerium oleander...
Citations
... These chemicals are well-known for their antioxidant activity, which is ascribed to their capacity to scavenge free radicals and protect cells from oxidative damage (Kiliç and Yeşiloğlu, 2013;Mateos et al., 2018). Both of these compounds have also been demonstrated to be anti-inflammatory (Jang et al., 2021) and anti-cancer (Wong et al., 2014). Cis-5-caffeoylquinic acid was discovered to suppress the development of human breast cancer cells and induce apoptosis in a study, while 4-p-coumaroylquinic acid found to inhibit the production of pro-inflammatory cytokines, indicating that it possesses anti-inflammatory effect (Alam et al., 2022). ...
... The MeOH extract of N. peltata roots was subjected to phytochemical investigation through liquid-liquid partitioning, column chromatography, and HPLC, leading to the isolation of one steroid derivative, one terpenoid saponin, six phenolic acid derivatives, and seven caffeoylquinic acid derivatives. The isolated compounds (1-15) were structurally identified as follows: α-spinasterol (1) ( Figure S1) [32] Figure S7) [33], protocatechuic acid (4) ( Figure S8) [34], vanillic acid (5) ( Figure S9) [34], p-coumaric acid (6) ( Figure S10) [35], caffeic acid (7) ( Figure S11) [36], ferulic acid (8) ( Figure S12) [37], neochlorogenic acid (neo-CQA) (9) ( Figure S13) [38], chlorogenic acid (CQA) (10) ( Figure S14) [38], cryptochlorogenic acid (crypto-CQA) (11) ( Figure S15) [38], isochlorogenic acid B (3,4-DCQA) (12) ( Figure S16) [39], isochlorogenic acid A (3,5-DCQA) (13) ( Figure S17) [39], isochlorogenic acid C (4,5-DCQA) (14) ( Figure S18) [39], and 3,4,5-tri-Ocaffeoylquinic acid (TCQA) ( Figure S19) (15) [40] (Figure 1). These identifications were based on their LC/MS data and comparison of their NMR spectroscopic data with those previously reported. ...
... The MeOH extract of N. peltata roots was subjected to phytochemical investigation through liquid-liquid partitioning, column chromatography, and HPLC, leading to the isolation of one steroid derivative, one terpenoid saponin, six phenolic acid derivatives, and seven caffeoylquinic acid derivatives. The isolated compounds (1-15) were structurally identified as follows: α-spinasterol (1) ( Figure S1) [32] Figure S7) [33], protocatechuic acid (4) ( Figure S8) [34], vanillic acid (5) ( Figure S9) [34], p-coumaric acid (6) ( Figure S10) [35], caffeic acid (7) ( Figure S11) [36], ferulic acid (8) ( Figure S12) [37], neochlorogenic acid (neo-CQA) (9) ( Figure S13) [38], chlorogenic acid (CQA) (10) ( Figure S14) [38], cryptochlorogenic acid (crypto-CQA) (11) ( Figure S15) [38], isochlorogenic acid B (3,4-DCQA) (12) ( Figure S16) [39], isochlorogenic acid A (3,5-DCQA) (13) ( Figure S17) [39], isochlorogenic acid C (4,5-DCQA) (14) ( Figure S18) [39], and 3,4,5-tri-Ocaffeoylquinic acid (TCQA) ( Figure S19) (15) [40] (Figure 1). These identifications were based on their LC/MS data and comparison of their NMR spectroscopic data with those previously reported. ...
... The MeOH extract of N. peltata roots was subjected to phytochemical investigation through liquid-liquid partitioning, column chromatography, and HPLC, leading to the isolation of one steroid derivative, one terpenoid saponin, six phenolic acid derivatives, and seven caffeoylquinic acid derivatives. The isolated compounds (1-15) were structurally identified as follows: α-spinasterol (1) ( Figure S1) [32] Figure S7) [33], protocatechuic acid (4) ( Figure S8) [34], vanillic acid (5) ( Figure S9) [34], p-coumaric acid (6) ( Figure S10) [35], caffeic acid (7) ( Figure S11) [36], ferulic acid (8) ( Figure S12) [37], neochlorogenic acid (neo-CQA) (9) ( Figure S13) [38], chlorogenic acid (CQA) (10) ( Figure S14) [38], cryptochlorogenic acid (crypto-CQA) (11) ( Figure S15) [38], isochlorogenic acid B (3,4-DCQA) (12) ( Figure S16) [39], isochlorogenic acid A (3,5-DCQA) (13) ( Figure S17) [39], isochlorogenic acid C (4,5-DCQA) (14) ( Figure S18) [39], and 3,4,5-tri-Ocaffeoylquinic acid (TCQA) ( Figure S19) (15) [40] (Figure 1). These identifications were based on their LC/MS data and comparison of their NMR spectroscopic data with those previously reported. ...
Nymphoides peltata has been widely used pharmacologically in traditional Chinese medicine to treat heat strangury and polyuria. The aim of this study was to isolate the bioactive components from N. peltata and evaluate their potential use as antioxidant and anti-wrinkle agents. Phytochemical investigation of the methanolic extract of N. peltata roots led to the isolation of 15 compounds (1–15), which were structurally determined as α-spinasterol (1), 3-O-β-D-glucopyranosyl-oleanolic acid 28-O-β-D-glucuronopyranoside (2), 4-hydroxybenzoic acid (3), protocatechuic acid (4), vanillic acid (5), p-coumaric acid (6), caffeic acid (7), ferulic acid (8), neochlorogenic acid (neo-CQA) (9), chlorogenic acid (CQA) (10), cryptochlorogenic acid (crypto-CQA) (11), isochlorogenic acid B (3,4-DCQA) (12), isochlorogenic acid A (3,5-DCQA) (13), isochlorogenic acid C (4,5-DCQA) (14), and 3,4,5-tri-O-caffeoylquinic acid (TCQA) (15). Of these 15 compounds, compound 2 was a new oleanane saponin, the chemical structure of which was characterized by 1D and 2D nuclear magnetic resonance (NMR) spectroscopic data and high-resolution electrospray ionization mass spectrometry (HRESIMS), as well as chemical reaction. Biological evaluation of the isolated compounds revealed that 3,4,5-tri-O-caffeoylquinic acid (TCQA) significantly improved Nrf2 levels in an Nrf2–ARE reporter HaCaT cell screening assay. TCQA was found to potently inhibit the Nrf2/HO-1 pathway and to possess strong anti-wrinkle activity by modulating the MAPK/NF-κB/AP-1 signaling pathway and thus inhibiting MMP-1 synthesis in HaCaT cells exposed to UVB. Our results suggest that TCQA isolated from N. peltata might be useful for developing effective antioxidant and anti-wrinkle agents.
... Although it is a poisonous plant, it has lots of pharmacologically active substances and gut microbiota is important factor for pharmaco-toxicological properties of N. oleander [6]. Glycosides (kaneroside, neriumoside, odoroside-H, neridiginoside, nerizoside and neritaloside), triterpenes (betulinic acid, ursolic acid, oleanderol, oleandric acid, oleanerolide, epoxydammarane 3β, 25-diol, cis and trans karenin and oleanolic acid) and phenolics (3-O-Caffeoylquinic acid (3-CQA) and 5-O-Caffeoylquinic acid (5-CQA)) have been previously reported as bioactive compounds [7][8][9][10][11][12]. Antimicrobial activity, cardioprotective, antioxidant, hepatoprotective, anticancer, anti-HIV and antidiabetic effects of N.oleander have been reported [13][14][15][16][17][18]. ...
Background
Nerium oleander L. is ethnopharmacologically used for diabetes. Our aim was to investigate the ameliorative effects of ethanolic Nerium flower extract (NFE) in STZ-induced diabetic rats.
Methods
Seven random groups including control group, NFE group (50 mg/kg), diabetic group, glibenclamide group and NFE treated groups (25 mg/kg, 75 mg/kg, and 225 mg/kg) were composed of forty-nine rats. Blood glucose level, glycated hemoglobin (HbA1c), insulin level, liver damage parameters and lipid profile parameters were investigated. Antioxidant defense system enzyme activities and reduced glutathione (GSH) and malondialdehyde (MDA) contents and immunotoxic and neurotoxic parameters were determined in liver tissue. Additionally, the ameliorative effects of NFE were histopathologically examined in liver. mRNA levels of SLC2A2 gene encoding glucose transporter 2 protein were measured by quantitative real time PCR.
Results
NFE caused decrease in glucose level and HbA1c and increase in insulin and C-peptide levels. Additionally, NFE improved liver damage biomarkers and lipid profile parameters in serum. Moreover, lipid peroxidation was prevented and antioxidant enzyme activities in liver were regulated by NFE treatment. Furthermore, anti-immunotoxic and anti-neurotoxic effects of NFE were determined in liver tissue of diabetic rats. Histopathogically, significant liver damages were observed in the diabetic rats. Histopathological changes were decreased partially in the 225 mg/kg NFE treated group. SLC2A2 gene expression in liver of diabetic rats significantly reduced compared to healthy rats and NFE treatment (25 mg/kg) caused increase in gene expression.
Conclusion
Flower extract of Nerium plant may have an antidiabetic potential due to its high phytochemical content.
Graphical Abstract
... [13] Anti-inflammatory activity of tangeretin and ethyl caffeate from different plants and its mechanism of action has been investigated. [14] The presence of tangeretin and ethyl caffeate, including as phenolics and flavonoids group compounds, in P. tectorius fruits has also been reported by Andriani et al. [15] Besides tangeretin and ethyl cafeate, the fruits contain caffeoylquinic acids (flavonoid compound) Wong et al. [16] Besides antioxidant properties, this compound displays various bioactivities including anti-inflammatory. [16] Hence, we assume that these three compounds which were reported exist in P. tectorius fruits may have contributed to the its anti-inflammatory potency of P. tectorius fruits extract or fraction. ...
... [14] The presence of tangeretin and ethyl caffeate, including as phenolics and flavonoids group compounds, in P. tectorius fruits has also been reported by Andriani et al. [15] Besides tangeretin and ethyl cafeate, the fruits contain caffeoylquinic acids (flavonoid compound) Wong et al. [16] Besides antioxidant properties, this compound displays various bioactivities including anti-inflammatory. [16] Hence, we assume that these three compounds which were reported exist in P. tectorius fruits may have contributed to the its anti-inflammatory potency of P. tectorius fruits extract or fraction. Although several studies on anti-inflammatory potential of P. tectorius have previously been conducted, most of them involved the plant leaves extracts. ...
... Ten microliters of the obtained solution was sampled using an HPLC autosampler (SIL-10 AF, Shimadzu Corporation, Kyoto, Japan) and injected into the HPLC apparatus. The flow rate was 1.0 mL/min, and the wavelength was set to 280 nm for PB2 [45,46], 5CQA [47,48], and epicatechin [49,50]. ...
The Maypole apple is a new, promising species of small apples with a prominent flavor and deep red flesh and peel. This study divided Maypole apples into outer flesh, inner flesh, and peel, and used subcritical water at 100–175 °C for 10–30 min to extract various phytochemicals (procyanidin B2 (PB2), 5-caffeoylquinic acid (5CQA), and epicatechin). The obtained Maypole apple extracts and extraction residues in this work were analyzed using a SEM, HPLC, FT-IR, and UV-Vis spectrophotometer. Under different subcritical water extraction conditions, this work found the highest extraction rate: to be PB2 from the peel (4.167 mg/mL), 5CQA (2.296 mg/mL) and epicatechin (1.044 mg/mL) from the inner flesh. In addition, this work regressed the quadratic equations of the specific yield through ANOVA and found that temperature is a more significant affecting factor than extraction time. This aspect of the study suggests that phytochemicals could be obtained from the Maypole apple using the new extraction method of subcritical water.
... The 1 H-and 13 C-NMR spectroscopic data of 1 were very similar to those of sargentodoside E (2) isolated from Sargentodoxa cuneata (Lardizabalaceae) [19] except for the presence of an additional α-L-rhamnose unit at Glc-6′′ in 1. Therefore, the chemical structure of compound 1 was determined to be 1-(3,4-dihydroxyphenyl)-2-hydroxyethanone-2-O-rutinoside and named oddioside A. The structures of the known compounds were identified as sargentodoside E (2) [19], protocatechuic acid (3) [20], p-hydroxybenzoic acid (4) [21], benzyl-O-β-D-glucopyranoside (5) [22], eugenyl glucoside (6) [23], 2-O-β-D-glucopyranosyl-4,6-dihydroxybenzaldehyde (7) [24], catechol (8) [25], chlorogenic acid (9) [26], cryptochlorogenic acid (10) [27], (7S,8R)erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (11) [27], pinoresinol-4-O-β-D-glucopyranoside (12) [28], quercetin (13) [29], isoquercitrin (14) [30], rutin (15) [31], quercimeritrin (quercetin-7-O-β-D-glucopyranoside) (16) [32], morkotin A (17), nicotiflorin (18) [33], taxifolin (19) [34], taxifolin-7-O-β-D-glucopyranoside (20) [35], pinellic acid (21) [18] and 5-hydroxymethylfurfural (22) [36] by comparison of their NMR spectroscopic data with those previously reported data. The structures of the known compounds were identified as sargentodoside E (2) [19], protocatechuic acid (3) [20], p-hydroxybenzoic acid (4) [21], benzyl-O-β-D-glucopyranoside (5) [22], eugenyl glucoside (6) [23], 2-O-β-D-glucopyranosyl-4,6-dihydroxybenzaldehyde (7) [24], catechol (8) [25], chlorogenic acid (9) [26], cryptochlorogenic acid (10) [27], (7S,8R)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (11) [27], pinoresinol-4-O-β-D-glucopyranoside (12) [28], quercetin (13) [29], isoquercitrin (14) [30], rutin (15) [31], quercimeritrin (quercetin-7-O-β-D-glucopyranoside) (16) [32], morkotin A (17), nicotiflorin (18) [33], taxifolin (19) [34], taxifolin-7-O-β-D-glucopyranoside (20) [35], pinellic acid (21) [18] and 5-hydroxymethylfurfural (22) [36] by comparison of their NMR spectroscopic data with those previously reported data. ...
... Therefore, the chemical structure of compound 1 was determined to be 1-(3,4-dihydroxyphenyl)-2-hydroxyethanone-2-O-rutinoside and named oddioside A. The structures of the known compounds were identified as sargentodoside E (2) [19], protocatechuic acid (3) [20], p-hydroxybenzoic acid (4) [21], benzyl-O-β-D-glucopyranoside (5) [22], eugenyl glucoside (6) [23], 2-O-β-D-glucopyranosyl-4,6-dihydroxybenzaldehyde (7) [24], catechol (8) [25], chlorogenic acid (9) [26], cryptochlorogenic acid (10) [27], (7S,8R)erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (11) [27], pinoresinol-4-O-β-D-glucopyranoside (12) [28], quercetin (13) [29], isoquercitrin (14) [30], rutin (15) [31], quercimeritrin (quercetin-7-O-β-D-glucopyranoside) (16) [32], morkotin A (17), nicotiflorin (18) [33], taxifolin (19) [34], taxifolin-7-O-β-D-glucopyranoside (20) [35], pinellic acid (21) [18] and 5-hydroxymethylfurfural (22) [36] by comparison of their NMR spectroscopic data with those previously reported data. The structures of the known compounds were identified as sargentodoside E (2) [19], protocatechuic acid (3) [20], p-hydroxybenzoic acid (4) [21], benzyl-O-β-D-glucopyranoside (5) [22], eugenyl glucoside (6) [23], 2-O-β-D-glucopyranosyl-4,6-dihydroxybenzaldehyde (7) [24], catechol (8) [25], chlorogenic acid (9) [26], cryptochlorogenic acid (10) [27], (7S,8R)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (11) [27], pinoresinol-4-O-β-D-glucopyranoside (12) [28], quercetin (13) [29], isoquercitrin (14) [30], rutin (15) [31], quercimeritrin (quercetin-7-O-β-D-glucopyranoside) (16) [32], morkotin A (17), nicotiflorin (18) [33], taxifolin (19) [34], taxifolin-7-O-β-D-glucopyranoside (20) [35], pinellic acid (21) [18] and 5-hydroxymethylfurfural (22) [36] by comparison of their NMR spectroscopic data with those previously reported data. The structures of the known compounds were identified as sargentodoside E (2) [19], protocatechuic acid (3) [20], p-hydroxybenzoic acid (4) [21], benzyl-O-β-D-glucopyranoside (5) [22], eugenyl glucoside (6) [24], catechol (8) [25], chlorogenic acid (9) [26], cryptochlorogenic acid (10) [27], (7S,8R)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (11) [27], pinoresinol-4-O-β-D-glucopyranoside (12) [28], quercetin (13) [29], isoquercitrin (14) [30], rutin (15) [31], quercimeritrin (quercetin-7-O-β-D-glucopyranoside) (16) [32], morkotin A (17), nicotiflorin (18) [33], taxifolin (19) [34], taxifolin-7-O-β-D-glucopyranoside (20) [35], pinellic acid (21) [18] and 5-hydroxymethylfurfural (22) [36] by comparison of their NMR spectroscopic data with those previously reported data. ...
... The structures of the known compounds were identified as sargentodoside E (2) [19], protocatechuic acid (3) [20], p-hydroxybenzoic acid (4) [21], benzyl-O-β-D-glucopyranoside (5) [22], eugenyl glucoside (6) [23], 2-O-β-D-glucopyranosyl-4,6-dihydroxybenzaldehyde (7) [24], catechol (8) [25], chlorogenic acid (9) [26], cryptochlorogenic acid (10) [27], (7S,8R)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (11) [27], pinoresinol-4-O-β-D-glucopyranoside (12) [28], quercetin (13) [29], isoquercitrin (14) [30], rutin (15) [31], quercimeritrin (quercetin-7-O-β-D-glucopyranoside) (16) [32], morkotin A (17), nicotiflorin (18) [33], taxifolin (19) [34], taxifolin-7-O-β-D-glucopyranoside (20) [35], pinellic acid (21) [18] and 5-hydroxymethylfurfural (22) [36] by comparison of their NMR spectroscopic data with those previously reported data. The structures of the known compounds were identified as sargentodoside E (2) [19], protocatechuic acid (3) [20], p-hydroxybenzoic acid (4) [21], benzyl-O-β-D-glucopyranoside (5) [22], eugenyl glucoside (6) [24], catechol (8) [25], chlorogenic acid (9) [26], cryptochlorogenic acid (10) [27], (7S,8R)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (11) [27], pinoresinol-4-O-β-D-glucopyranoside (12) [28], quercetin (13) [29], isoquercitrin (14) [30], rutin (15) [31], quercimeritrin (quercetin-7-O-β-D-glucopyranoside) (16) [32], morkotin A (17), nicotiflorin (18) [33], taxifolin (19) [34], taxifolin-7-O-β-D-glucopyranoside (20) [35], pinellic acid (21) [18] and 5-hydroxymethylfurfural (22) [36] by comparison of their NMR spectroscopic data with those previously reported data. The structures of the known compounds were identified as sargentodoside E (2) [19], protocatechuic acid (3) [20], p-hydroxybenzoic acid (4) [21], benzyl-O-β-D-glucopyranoside (5) [22], eugenyl glucoside (6) [23], 2-O-β-D-glucopyranosyl-4,6-dihydroxybenzaldehyde (7) [24], catechol (8) [25], chlorogenic acid (9) [26], cryptochlorogenic acid (10) [27], (7S,8R)-erythro-7,9,9'-trihydroxy-3,3'-dimethoxy-8-O-4'-neolignan-4-O-β-D-glucopyranoside (11) [27], pinoresinol-4-O-β-D-glucopyranoside (12) [28], quercetin (13) [29], isoquercitrin (14) [30], rutin (15) [31], quercimeritrin (quercetin-7-O-β-D-glucopyranoside) (16) [32], morkotin A (17), nicotiflorin (18) [33], taxifolin (19) [34], taxifolin-7-O-β-D-glucopyranoside (20) [35], pinellic acid (21) [18] and 5-hydroxymethylfurfural (22) [36] by comparison of their NMR spectroscopic data with those previously reported data. ...
In our preliminary study, a hot water extract from the fruits of Morus alba (mulberry) inhibited the secretion of metalloproteinase-1 (MMP-1) against tumor necrosis factor-α (TNF-α)-stimulated human dermal fibroblasts (HDFs), and therefore we researched its active compounds. In the present study, a new phenolic glycoside (oddioside A, 1) and 21 known compounds (2−22) were isolated from the hot water extract from the fruits of M. alba by repeated chromatography. The chemical structure of the new compound 1 was elucidated by its spectroscopic data (1D− and 2D−NMR and HRMS) measurement and by acidic hydrolysis. The presence of sargentodoside E (2), eugenyl glucoside (6), 2-O-β-d-glucopyranosyl-4,6-dihydroxybenzaldehyde (7), 7S,8R-erythro-7,9,9’-trihydroxy-3,3’-dimethoxy-8-O-4’-neolignan-4-O-β-d-glucopyranoside (11), pinoresinol-4-O-β-d-glucopyranoside (12), taxifolin-7-O-β-d-glucopyranoside (20), and pinellic acid (21) were reported from M. alba for the first time in this study. The new compound oddioside A (1) suppressed the secretion of MMP-1 and increased collagen in TNF-α-stimulated HDFs. In addition, the phosphorylation of mitogen-activated protein kinases (MAPKs) was inhibited by oddioside A. In conclusion, the extract from fruits of M. alba and its constituent oddioside A may be a potential agent to prevent inflammation-related skin aging and other skin disorders.
... These findings greatly enrich the compound diversity of H. citrina. Their structures were identified by the comparison of their spectroscopic data with literature values and were assigned as (E)-p-coumaric acid (1) [25], (Z)-p-coumaric acid (2) [26], 3-O-(E)-p-coumaroylquinic acid (3) [27], 3-O-(Z)-p-coumaroylquinic acid (4) [28], 3-O-(E)-p-coumaroylquinic acid methyl ester (5) [29], 3-O-(Z)-p-coumaroylquinic acid methyl ester (6) [30], 3-O-(E)-p-coumaroylquinide (7) [31], 4-O-(E)-p-coumaroylquinic acid (9) [32], 4-O-(Z)-p-coumaroylquinic acid (10), 5-O-(E)-p-coumaroylquinic acid (11) [33], neochloro-genic acid (12) [34], crypto-chlorogenic acid (13) [35], chlorogenic acid (14) [36], 3-O-(E)feruloylquinic acid (15) [37], quercetin (16) [38], quercetin-3-O-α-L-arabinopyranoside (17) [39], quercetin-3-O-β-D-galactpyranoside (18) [40], quercetin-3-O-β-D-glucopyranoside (19) [41], quercetin-3-O-rutinoside (20) [41], quercetin-3-O-α-L-rhamnopyranosyl-(1→6)-β-D-galactpyranoside (21) [42], quercetin-3-O-α-L-rhamnopyranosyl-(1→2)-[α-L-rhamnopyranosyl-(1→6)-β-D-glucopyranoside] (22) [43], quercetin-3-O-α-L-rhamnopyranosyl-(1→2)-[α-Lrhamnopyranosyl-(1→6)-β-D-galactpyranoside] (23) [44], isorhamnetin (24) [45], isorhamnetin-3-O-β-D-galactopyranoside (25) [46], isorhamnetin-3-O-β-D-glucopyranoside (26) [47,48] (29) [42], kaempferol (30) [49], kaempferol-3-O-α-L-arabinoside (31) [53]. As far as we know, the nuclear magnetic data of compound 10 was reported for the first time. ...
... comparison of their spectroscopic data with literature values and were assigned as (E)-pcoumaric acid (1) [25], (Z)-p-coumaric acid (2) [26], 3-O-(E)-p-coumaroylquinic acid (3) [27], 3-O-(Z)-p-coumaroylquinic acid (4) [28], 3-O-(E)-p-coumaroylquinic acid methyl ester (5) [29], 3-O-(Z)-p-coumaroylquinic acid methyl ester (6) [30], 3-O-(E)-p-coumaroylquinide (7) [31], 4-O-(E)-p-coumaroylquinic acid (9) [32], 4-O-(Z)-p-coumaroylquinic acid (10), 5-O-(E)-p-coumaroylquinic acid (11) [33], neochlorogenic acid (12) [34], cryptochlorogenic acid (13) [35], chlorogenic acid (14) [36], 3-O-(E)-feruloylquinic acid (15) [37], quercetin (16) [38], quercetin-3-O-α-L-arabinopyranoside (17) [39], quercetin-3-O-β-Dgalactpyranoside (18) [40], quercetin-3-O-β-D-glucopyranoside (19) [41], quercetin-3-Orutinoside (20) [53]. As far as we know, the nuclear magnetic data of compound 10 was reported for the first time. ...
The World Health Organization predicts that over the next several years, depression will become the most important mental health issue globally. Growing evidence shows that the flower buds of Hemerocallis citrina Baroni (H. citrina) possess antidepressant properties. In the search for new anti-depression drugs, a total of 15 phenylpropanoids and 22 flavonoids were isolated and identified based on spectral data (1D and 2D NMR, HR-ESI-MS, UV) from H. citrina. Among them, compound 8 was a novel compound, while compounds 1–4, 6, 9, 10, 15, 17, 24–26, 28, and 37 were isolated for the first time from Hemerocallis genus. To study the antidepressant activity of phenylpropanoids and flavonoids fractions from H. citrina, macroporous resin was used to enrich them under the guidance of UV characteristics. UHPLC-MS/MS was applied to identify the constituents of the enriched fractions. According to behavioral tests and biochemical analyses, it showed that phenylpropanoid and flavonoid fractions from H. citrina can improve the depressive-like mental state of chronic unpredictable mild stress (CUMS) rats. This might be accomplished by controlling the amounts of the inflammatory proteins IL-6, IL-1β, and TNF-α in the hippocampus as well as corticosterone in the serum. Thus, the monomer compounds were tested for their anti-neuroinflammatory activity and their structure–activity relationship was discussed in further detail.
... Their flower is bisexual, with a histellous calyx and a glabrous corolla on the outer portion. At the same time, numerous and fine secondary veins are observed on the elliptical, subacuminate or obtuse leaves (Figure 1), which have stout petioles in whorls of eight to sixteen centimetres long [15]. ...
... Additionally, betulinic acid was successfully purified from Alstonia boonei, which hinders folate biosynthesis in malarial Plasmodium and promotes mitochondrial pore opening and F1F0 ATPase activity in mice [43]. Wong et al. (2014) reported the presence of 3-O-caffeoylquinic acid, 4-Ocaffeoylquinic acid and 5-O-caffeoylquinic acid in the leaves extract of A. angustiloba [15]. In contrast, our study has detected cis-5-caffeoylquinic acid in the aqueous extract of A. angustiloba leaves and 1-O-caffeoylquinic acid in the 60% methanolic extract. ...
... Additionally, betulinic acid was successfully purified from Alstonia boonei, which hinders folate biosynthesis in malarial Plasmodium and promotes mitochondrial pore opening and F1F0 ATPase activity in mice [43]. Wong et al. (2014) reported the presence of 3-O-caffeoylquinic acid, 4-Ocaffeoylquinic acid and 5-O-caffeoylquinic acid in the leaves extract of A. angustiloba [15]. In contrast, our study has detected cis-5-caffeoylquinic acid in the aqueous extract of A. angustiloba leaves and 1-O-caffeoylquinic acid in the 60% methanolic extract. ...
Plants have a wide range of active compounds crucial in treating various diseases. Most people consume plants and herbals as an alternative medicine to improve their health and abilities. A. angustiloba extract showed antinematodal activity against Bursaphelenchus xylophilus, antitrypanosomal action against Trypanosoma brucei and anti-plasmodial activity against the chloroquine-resistant Plasmodium falciparum K1 strain. Moreover, it has demonstrated growth inhibitory properties towards several human cancer cell lines, such as MDA-MB-231, SKOV-3, HeLa, KB cells and A431. DPPH and ABTS assays were carried out to determine the antioxidant activity of the aqueous and 60% methanolic extract of A. angustiloba leaves. Moreover, total phenolic and flavonoid contents were quantified. The presence of potential active compounds was then screened using liquid chromatography coupled with a Q-TOF mass spectrometer (LC–MS) equipped with a dual electrospray ionisation (ESI) source. The EC50 values measured by DPPH for the 60% methanolic and aqueous extracts of A. angustiloba leaves were 80.38 and 94.11 µg/mL, respectively, and for the ABTS assays were 85.80 and 115.43 µg/mL, respectively. The 60% methanolic extract exhibited the highest value of total phenolic and total flavonoid (382.53 ± 15.00 mg GAE/g and 23.45 ± 1.04 mg QE/g), while the aqueous extract had the least value (301.17 ± 3.49 mg GAE/g and 9.73 ± 1.76 mg QE/g). The LC–MS analysis revealed the presence of 103 and 140 compounds in the aqueous and 60% methanolic extract, respectively. It consists of phenolic acids, flavonoids, alkaloids, amino acids, glycosides, alkaloids, etc. It can be concluded that the therapeutic action of this plant is derived from the presence of various active compounds; however, further research is necessary to determine its efficacy in treating diseases.
... Their flower is bisexual, with a histellous calyx and a glabrous corolla on the outer portion. At the same time, numerous and fine secondary veins are observed on the elliptical, subacuminate or obtuse leaves (Figure 1), which have stout petioles in whorls of eight to sixteen centimetres long [15]. ...
... Additionally, betulinic acid was successfully purified from Alstonia boonei, which hinders folate biosynthesis in malarial Plasmodium and promotes mitochondrial pore opening and F1F0 ATPase activity in mice [43]. Wong et al. (2014) reported the presence of 3-O-caffeoylquinic acid, 4-Ocaffeoylquinic acid and 5-O-caffeoylquinic acid in the leaves extract of A. angustiloba [15]. In contrast, our study has detected cis-5-caffeoylquinic acid in the aqueous extract of A. angustiloba leaves and 1-O-caffeoylquinic acid in the 60% methanolic extract. ...
... Additionally, betulinic acid was successfully purified from Alstonia boonei, which hinders folate biosynthesis in malarial Plasmodium and promotes mitochondrial pore opening and F1F0 ATPase activity in mice [43]. Wong et al. (2014) reported the presence of 3-O-caffeoylquinic acid, 4-Ocaffeoylquinic acid and 5-O-caffeoylquinic acid in the leaves extract of A. angustiloba [15]. In contrast, our study has detected cis-5-caffeoylquinic acid in the aqueous extract of A. angustiloba leaves and 1-O-caffeoylquinic acid in the 60% methanolic extract. ...
... Alstonia angustiloba is locally known as pulai or jelutong in Malaysia; it is native to Thailand, Peninsular Malaysia, Singapore, Sumatra, and Java, and is commonly found in a variety of habitats from sea level to 200 meters (700 ft) altitude [3]. Phytochemical studies of this genus have resulted in the isolation of indole alkaloids [4], triterpenes [5], flavonoids [6], caffeoylquinic acids [7] and found to possess various biological properties such as antioxidant, antidiabetic [8], antiplasmodial [9], antimalarial [10], antibacterial, antibiofilm [11], and antiproliferative [12] activities. Essential oils are one of the promising candidates amongst natural compounds for the development of safe therapeutic agents. ...
This study was aimed to investigate the chemica l compositions and lipoxygenase inhibitory activity of the essential oil from Alstonia angustiloba growing in Malaysia. The essential oils were obtained by hydrodistillation and fully characterized by gas chromatography and gas chromatography-mass spectrometry. Analysis of the A. angustiloba essential oil resulted in the identification of twenty-five chemical components, attributed 90.8% of the total oil. The most abundant components of A. angustiloba oil were linalool (21.2%), 1,8-cineole (16.8%), α-terpineol (9.5%), terpinene-4-ol (8.5%), β-caryophyllene (6.2%), and caryophyllene oxide (5.2%). The essential oil displayed moderate activity towards lipoxygenase activity with IC50 value of 45.8 μg/mL.
