No full-text available
To read the full-text of this research,
you can request a copy directly from the authors.
Flavonol glycosides from Cephalocereus senilis
Abstract
A new flavonol tetraglycoside, together with two known flavonol glycosides, kaempferol 7-rhamnoside and kaempferol 3-rhamnosyl(1-->6) galactoside-7-rhamnoside, were isolated from fresh plant material of Cephalocereus senilis. The structure of the new compound was established as kaempferol 3-O-beta-D-glucopyranosyl(1-->2)-O-[alpha-L-rhamnopyranosyl (1-->6)]-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside based on spectroscopic data. The whole plant flavonoid chemistry was strikingly different from that found previously in chitin-treated cell suspension cultures of the same plant.
... The phytochemical investigation of the seeds of L. culinaris lead to the isolation of compounds 1-3. Their structures were identified as kaempferol- [17], and robinin [17], via analysis of their spectroscopic data, as well as comparisons, of their data with published values, as shown in Table S1 and Figure 1. ...
... The phytochemical investigation of the seeds of L. culinaris lead to the isolation of compounds 1-3. Their structures were identified as kaempferol- [17], and robinin [17], via analysis of their spectroscopic data, as well as comparisons, of their data with published values, as shown in Table S1 and Figure 1. ...
Dipeptidyl peptidase IV (DPP-IV), a new target for the treatment of type 2 diabetes mellitus, degrades incretins such as glucagon-like peptide 1 (GLP-1) and glucose-dependent insulinotropic polypeptide. DPP-IV inhibitors shorten the inactivation of GLP-1, permitting the incretin to stimulate insulin release, thereby combating hyperglycemia. In our ongoing search for new DPP-IV inhibitors from medicinal plants and foods, three flavonol glycosides (1–3) were isolated from the seeds of Lens culinaris Medikus (Fabaceae) and tested for their DPP-IV–inhibitory activity. We demonstrated for the first time, that compounds 1–3 inhibited DPP-IV activity in a concentration-dependent manner in our in vitro bioassay system. In addition, molecular docking experiments of compounds 1–3 within the binding pocket of DPP-IV were conducted. All investigated compounds readily fit within the active sites of DPP-IV, in low-energy conformations characterized by the flavone core structure having optimal electrostatic attractive interactions with the catalytic triad residues of DPP-IV.
... The n-butanolic extract obtained from the plant was fractionated by a repeatedly chromatographic procedures with normal-phase and reversed-phase silica gel, layer chromatography (TLC) to isolate and characterize for the first time five compounds in L. lanuginosus: lotaustralin (1), [23] kaempferol-7-O-α-L-rhamnopyranoside (2), [24] kaempferol-3-O-apiofuranosyl-7-O-rhamnopyranosyl (3), [13] isorhamnetin 3-O-rutinoside (4), [25] ...
Abstract:
Background: Lotus taxa (Fabaceae) were well known as an important source of polyphenols and flavonoids. Lotus lanuginosus Vent. is a widespread plant in the northern region of Saudi Arabia. Phytochemical and biological activities screening focusing of the species are rare. Objective: The objectives of this study were to isolate secondary metabolites from the flowers of L. lanuginosus Vent., elucidate their structures, and evaluate their biological activities. Materials and Methods: Chromatography methods of the n-butanolic extract of fresh flowers of L. lanuginosus led five products (1–5). Their structures were characterized based on spectroscopic evidence (ultraviolet, infrared, high-resolution mass spectrometry, and nuclear magnetic resonance) and compared to the spectral data signaled in the literature. Cytotoxic activities of the isolated compounds were evaluated against HCT-116 and MCF-7 cancer cell lines. α-glucosidase and antioxidant activities were also performed. Results: Five compounds were isolated and characterized for the first time in L. lanuginosus Vent.: Lotaustralin (1), kaempferol-7-O-α-L-rhamnopyranoside (2), kaempferol-3-O-apiofuranosyl-7-O-rhamnopyranosyl (3), isorhamnetin-3-O-rutinoside (4), and kaempferol-3-O-(2''-β-D-xylopyranosyl)-α-L-rhamnopyranoside-7-O-α-L-rhamnopyranoside (5). The results of cytotoxic activities against HCT-116 and MCF-7 cancer cell lines of the isolated compounds were presented. Among them, compounds 2 and 3 showed a moderate activity on HCT-116 cancer cells with half maximal inhibitory concentration values ranging between 8 and 31.5 μM. Moreover, compounds (2–5) displayed significant antioxidant and moderate α-glucosidase activities. Discussion and Conclusions: All the isolated products (1–5) are signaled for the first time in L. lanuginosus Vent. Among flavonoids glycosides, compound 2 showed the best cytotoxic activity. By the end of the present study, L. lanuginosus have been characterized as a highly cyanogenic plant and as an important source of polyphenols and flavonoids.
... Several secondary metabolites including β-carboline alkaloids [8], coumarins [4], anthraquinone glycosides [9], sterols [4], and flavonoids [10] have been reported for this species. In the present study to uncover skin-protective components through bioassay-guided fractionation, a serotonin derivative and six flavonoid glycosides were isolated from the leaves and twigs of E. umbellata and identified as N-[2-(5-hydroxyl-1H-indol-3-yl)ethyl]-butanamide (1), kaempferol-3-O-β-D-xylopyranosyl(1 → 2)-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside (2) [11], kaempferol-3-O-β-Dgalactopyranoside-7-O-α-L-rhamnopyranoside (3) [12], kaempferol-3-O-α-L-rhamnopyranosyl(1 → 6)-β-D-galactopyranoside-7-O-α-L-rhamnopyranoside (4) [13], kaempferol-3-O-β-D-xylopyranosyl(1 → 2)-β-D-galactopyranoside (5) [14], kaempferol-3-O-rutinoside (6) [15], and kaempferol-3-O-β-glucopyranosyl(1 → 2)-β-galactopyranoside-7-O-αrhamnopyranoside (7) [16] through spectroscopic data analysis involving 1D and 2D nuclear magnetic resonance (NMR) (Fig. 1) and by comparing their data with reported values. Various bioactivities have been reported for these isolated compounds, such as the melatonininducing activity of 1, antioxidant activities of 2 and 4, melanogenesis inhibitory activities of 3 and 6, and antimalarial activity of 5 [17][18][19][20][21]. ...
Bioassay-guided fractionation of an extract of leaves and twigs of Elaeagnus umbellata led to the isolation of a serotonin derivative, N-[2-(5-hydroxyl-1H-indol-3-yl)ethyl]-butanamide (1), along with six flavonoid glycosides, kaempferol-3-O-β-d-xylopyranosyl(1 → 2)-β-d-galactopyranoside-7-O-α-l-rhamnopyranoside (2), kaempferol-3-O-β-d-galactopyranoside-7-O-α-l-rhamnopyranoside (3), kaempferol-3-O-α-l-rhamnopyranosyl(1 → 6)-β-d-galactopyranoside-7-O-α-l-rhamnopyranoside (4), kaempferol-3-O-β-d-xylopyranosyl(1 → 2)-β-d-galactopyranoside (5), kaempferol-3-O-rutinoside (6), and kaempferol-3-O-β-d-glucopyranosyl(1 → 2)-β-d-galactopyranoside-7-O-α-l-rhamnopyranoside (7). Their structures were elucidated using 1D/2D nuclear magnetic resonance spectroscopy and mass spectrometry. Compounds 1-6 were evaluated for their proliferative effects on HaCaT keratinocytes; 1-5 promoted keratinocyte proliferation dose dependently. Compounds 3 and 4 showed potent activities. These results suggest that the leaves and twigs of E. umbellata have wound healing and skin cell regeneration potentials.
... [24,25] Table 2. Compared with the data given in Ref. [28], compound 3 was identified as kaempferol 3-O-β-d-galactopyranoside-7-O-α-l-rhamnopyranoside. Table 2. Compared with the data given in Ref. [29], compound 4 was identified as kaempferol 3-0-a-l-rhamnopyranosyl(1 → 6)-β-d-galactopyranoside-7-O-a-l-rhamnopyranoside. Table 2. Compared with the data given in Ref. [31], compound 6 was identified as kaempferol 3-O-β-d-glucopyranosyl-7-O-α-l-rhamnopyranoside. ...
A method of using high-speed counter-current chromatography (HSCCC) and semi-preparative reversed-phase liquid chromatography (semi-preparative RPLC) to preparatively separate flavone glucosides and lignan from the crude extracts of Caragana korshinskii has been established for the first time in this study. Five flavone glucosides, including 9 mg of kaempferol 3-O-{β-d-glucopyranosyl(1→2)-[α-l-rhamonopyranosyl(1 → 6)]-β-d-galactopyranoside}, 21 mg of kaempferol 3-O-α-l-rhamnopyranosyl(1→6)-β-d-galactopyranoside-7-O-α-l-rhamnopyranoside, 34 mg of kaempferol 3-O-β-d-galactopyranoside-7-O-α-l-rhamnopyranoside, 27 mg of kaempferol 3-O-β-d-glucopyranosyl-7-O-α-l-rhamnopyranoside, and 14 mg of calycosin 7-O-β-d-glucopyranoside, and one lignan, 16 mg of alangilignoside B, were successfully isolated from 1.8 g of the crude sample through the combination of HSCCC with a two-phase solvent system composed of ethyl acetate–n-butanol–0.5 % formic acid (4:1:5, v/v/v) and semi-preparative RPLC with a mobile phase of methanol–water (20:80, v/v). The purities of the six compounds are all over 95 % as determined by HPLC and the structures are confirmed by the analysis of UV, 1H-NMR, and 13C-NMR and compared with published data.
... Acid hydrolysis of both compounds gave kaernpferol and isorhamnetin, respectively. Thus, compounds 3 and 5 were identified as kaempferol-7-0-glucoside and isorhamnetin-7-0-glucoside, respectively (Kaouadji, 1990;Liu et al., 1994;Ross, 1984;Singh and Pandey, 1986). ...
Five aromatic compounds, of which two are new glucosides, and six flavonols were isolated and identified for the first time from the flower heads and aerial shoots of Helichrysum conglobatum (Asteraceae). Their structures were established on the basis of chemical and spectroscopic methods including UV, MS, 1D- and 2D-NMR. Some fractions and isolates were screened for anti-microbial activities. This is the first report of the isolation of the chemical constituents of this species.
... The appearance of the anomeric protons at downfield shift as broad singlets proved the αnature of the rhamnopyranoses [14]. The 7-O-glycosylation was deduced from the UV data and confirmed by the presence of a signal C -7 at δ = 162.1 [15][16][17]. The (1→2) interglycosidic linkages were deduced from the downfield shift of carbon at position 2 (C-2'' at δ = 77.3 and C-2''' at δ = 77.2) and upfield shift of carbons at position 3 (C-3'' at δ = 71.1 and C-3''' at δ = 71.6) of the two non-terminal rhamnopyranoses [18]. ...
... In spite of the species of Cactaceae have been used all over the world in folk medicine for the treatment of several diseases (1)(2)(3)(4)(5)(6)(7) in Brazil this practice has usually been limited and the therapeutic potential of these cacti remains quite unexplored with few reports about their bioactivity and chemical constitution (8,9). Phytochemical studies of stems, roots, flowers and fruits of Cactaceae species, have led to the isolation and/or detection of triterpenoids (10,11), triterpenoid glycosides (12), steroids (13), flavonoids (14), flavonoid glycosides (15), alkaloids (16,17), betalain pigments (7,18) and others (19,20). Among these metabolites the alkaloids have assumed a prominent place since mescaline (3,4,5-trimethoxy-ß -phenylethylamine) was determined as the main psychoactive compound from the Mexican cactus peyote (Lophophora williamsii) (21). ...
Brazilian species of five genus of the family Cactaceae were screened for in vitro antitumor activity in a mechanism-based yeast bioassay using DNA repair-or recombination-deficient mutants of the yeast Saccharomyces cerevisiae, and in an assay using six different tumor cells. Whereas some species showed to be selectively active against some tumor cells, all of them were inactive in the S. cerevisiae assay, thus, demonstrating that the antitumor activity is not related either to the DNA damaging and/or to the topoisomerase I and II inhibition mechanisms. An evaluation for trypanocidal activity in trypomastigote forms of Trypanosoma cruzi showed that three species were especially active. The determination of the alkaloid profile of four species through TLC, HT-HRGC, HT-HRGC-MS and HPLC-PAD revealed, in all the species, low concentrations of alkaloids in complex mixtures with no major compounds.
... Phytochemical analysis of the aerial parts of G. psilostemon led to the isolation of nine compounds, identified as gallic acid (1) [11], methyl gallate (2) [6], pusilagin (3) [12], 1,3,6-tri-O-galloyl-βglucopyranoside (4) [13], 1,2,3,4,6-penta-O-galloyl-βglucopyranoside (5) [14], kaempferol (6) [15], quercetin (7) [15], kaempferol 7-O-α-rhamnopyranoside (8) [16], and quercetin 7-O-α-rhamnopyranoside (9) [17] by comparing their spectroscopic data with those reported in the literature. H 2 O 2 -induced lipid peroxidation inhibitory activity of different extracts of G. psilostemon in human red blood cells was tested at 50 µg/mL ( Figure 1). ...
An investigation was made of the effects on endogenous antioxidant enzyme activities and H2O2-induced lipid peroxidation inhibition in human red blood cells of the crude MeOH extract and its EtOAc, n-BuOH, and H2O sub-extracts obtained from aerial parts of Geranium psilostemon Ledeb., as well as compounds isolated from the most active EtOAc extract. Gallic acid (1), methyl gallate (2), pusilagin (3), 1,3,6-tri-O-galloyl-beta-glucopyranoside (4), 1,2,3,4,6-penta-O-galloyl-beta-glucopyranoside (5), kaempferol (6), quercetin (7), kaempferol 7-O-alpha-rhamnopyranoside (8), and quercetin 7-O-alpha-rhamnopyranoside (9) were isolated from the aerial parts of the title plant, and their structures identified from spectroscopic (UV, 1D- and 2D- NMR) and spectrometric (TOF-MS) data. All extracts and isolated compounds inhibited H2O2-induced lipid peroxidation and also enhanced the activity of superoxide dismutase (SOD) and catalase (CAT).
... Three sugar moieties were identified as two glucoses and one galactose from the 13 C NMR spectral data. From the 13 C NMR spectrum, the presence of a (1 f 2) linked glucosyl-galactosyl unit was suggested because of a downfield shift of C-2 00 (from 71.4 to 80.0 ppm) and an upfield shift of C-1 00 of galactosyl moiety (from 102.5 to 98.5 ppm) in this structure (28,30,31). The anomeric carbon at δ 98.5 ppm and proton shifts (5.67 ppm, 1H, d, J = 7.7 Hz) of the galactosyl moiety indicated the direct connection of the galactosyl moiety at C-3 of the kaempferol moiety. ...
Impact of radiation processing on the lipid profile of fenugreek and turmeric was investigated. Oleic and linoleic acid were the dominant fatty acids with an appreciable amount of linolenic acid in both cases. Gamma-irradiation did not bring about any significant changes in the fatty acid profile of these spices despite a high content of unsaturation. The ability of aqueous methanolic extract of both spices with high phenolic content to prevent lipid peroxidation suggests a possible role of phenolic constituents in preventing lipid radiolysis. Among the phenolics identified, kaempferol-3-O-alpha-L-rhamnoside, kaempferol 3,7-O-alpha-L-dirhamnoside, quercetin 3,7-O-alpha-L-dirhamnoside, and 3-O-alpha-L-rhamnosyl quercetin are reported here to occur in fenugreek for the first time. The role of phenolic antioxidants in preventing lipid oxidation in the above spices is discussed.
... The fourth major component presents a correlation to log D = −9.88 for an anomeric proton at 5.23 ppm (broad s) and a methyl proton at 0.82 ppm (d, J = 6.2 Hz), suggesting a rhamnopyranose unit. [59,64,65] The diffusion coefficients were measured over the correlation peaks related to the anomeric protons. Figure 5 matches the proposed structures for the major components of the mixture with the diffusion data. ...
2D DOSY 1H NMR has proved to be a useful technique in the identification of the molecular skeleton of the four major compounds of ethyl acetate extract of aerial parts of Bidens sulphurea (Asteraceae). The combination of this technique with HPLC, mass spectrometry and other NMR techniques enabled the identification of four flavonoid glycosides: quercetin-3-O-beta-D-galactopyranoside, quercetin-3-O-beta-D-glycopyranoside, quercetin-3-O-alpha-L-arabinofuranoside and quercetin-3-O-beta-D-rhamnopyranoside.
Five undescribed fatty acid esters of flavonol glycosides, nephelosides A−E, along with eight known compounds, were isolated from the seeds of Nephelium lappaceum L. The structures were elucidated by extensive analysis of spectroscopic data in combination with GC-MS analysis. Potency of compounds toward nitric oxide suppression was assessed by monitoring the inhibition of lipopolysaccharide-stimulated nitric oxide production in J744.A1 macrophage cells. Nepheloside D, kaempferol and kaempferol 7-O-α-L-rhamnopyranoside showed significant activity with IC50 values of 26.5, 11.6 and 12.0 μM, respectively.
A variable number of phenolics have been detected in pollen of the following species of Cactaceae: Stenocactus multicostatus subsp. zacatecasensis, Echinocereus enneacanthus, Echinocereus pectinatus, Echinocereus triglochidiatus var. coccineus and Mammillaria heyderi sensu lato. The phenolics were characterized by means of chromatographic (HPLC) and spectrometric (UV) properties. The most abundant flavonols were 3-O-glycoside derivatives of kaempferol and 3-Oglycoside derivatives of quercetin. 3-Oglycoside derivatives of herbacetin were found in lower abundance. Each species had a particular pollen phenolic profile. Intrapopulation variability in phenolic profiles was detected in all cases. The phenolic composition of these species is reported for the first time.
Recently, researchers have focused on dietary products due to the many health benefits and remedial potential of pharmacologically active compounds such as flavonoids. Kaempferol (3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one) is a flavonoid linked to diverse glycoside moieties and is extremely plentiful in most edible plants such as tea, fruits and vegetables including Allium cepa (onion), Camellia sinensis (tea), Citrus paradisi (grapefruit), Fragaria vesca (strawberry), Lactuca sativa (lettuce), and Morinda citrifolia (Indian mulberry) as well as in medicinal plants such as Acacia nilotica (L), Aloe vera (L.), Crocus sativus (L.), Euphorbia pekinensis Rupr., Ginkgo biloba (L.), Hypericum perforatum (L.), Phyllanthus acidus (L.), Ribes nigrum (L.), Rosmarinus officinalis (L.), Cerbera manghas, and Persicaria chinensis (L.). Numerous epidemiological investigations determined that kaempferol rich foods ameliorate several disorders including cancer and cardiovascular disease. Molecular mechanistic studies report that kaempferol modulates a number of key elements in the cellular signal transduction pathway linked to apoptosis, angiogenesis, inflammation, and metastasis. These studies show that kaempferol has lower toxicity in comparison to standard chemotherapy drugs. Kaempferol demonstrates poor oral bioavailability and is commonly metabolized into different forms such as methyl, sulfate or glucuronide, however its combination with other anticancer agents enhances its anticancer properties. This chapter provides several natural sources of kaempferol with its pharmacokinetics (oral availability) and safety. This review shows the dietary wealth of kaempferol with its bioavailability and may contribute to the further use of this flavonoid as a prospective novel candidate for future drug development.
Book Description:
Kaempferol is a natural plant product known for its health promoting effects and its pharmacological and nutraceutical properties. It is common in vegetables, fruits, plants and herbal medicines. Studies have shown that it reduces cancer, arteriosclerosis, cardiovascular disorders, and serves as an antioxidant and anti-inflammatory. This book discusses the biosynthesis of kaempferol derivatives and the other flavonols identified in grapes, and the nutraceutical characteristics of these compounds with particular emphasis for kaempferol, by reporting its contents in grapes and wines. Also, the influence of different elicitors in flavonol composition (and more specifically in kaempferol) is presented. Moreover, the antitumor and the anti-inflammatory activities of kaempferol on diverse diseases are studied together with the importance of flavonoids in co-therapy. Also, molecular mechanistic studies report that kaempferol modulates a number of key elements in the cellular signal transduction pathway linked to apoptosis, angiogenesis, inflammation, and metastasis. Additionally, this book examines different natural sources of kaempferol with its pharmacokinetics (oral availability) and safety. Finally, saffron petals can be a readily exploitable good source of kaempferol for many applications. The occurrence of kaempferol and its glycosidic patterns in different crocus species is shown. This book presents an overview of the biosynthesis, food sources and therapeutic uses of this promising compound. (Imprint: Nova)
Three known flavonol glycosides, i.e., kaempferol 3,7-O-α-L-dirhamnopyranoside (1), kaempferol 3-O-β-D-glucopyranosyl-(1→2)-α-L-rhamnopyranoside-7-O-α-L- rhamnopyranoside (2) and kaempferol 3-O-α-L-rhamnopyranoside-7-O-β-D-glucopyranosyl-(1→2)-α-L- rhamnopyranoside (3), were isolated for the first time from the flowers of Consolida armeniaca, and the structures of flavonol glycosides were deduced by high field 1D and 2D NMR and FAB-MS spectroscopies. The acetyl derivatives of 1-3 were also prepared (1a, 2a, 3a) and identified by NMR and positive FAB mass spectra.
Aim: To study the chemical constituents of Artemisia scoparia Waldst. et kit. Method: The chemical constituents were isolated by using repeated silical gel column chromatography, and their structures were elucidated on the basis of spectral analysis. Result: 12 compounds have been isolated from this plant, and the structures of chem have been identified as Capillone(1), Capillin(2), Jaceosidin (3), Chrysoeriol (4), Arcapillin (5), Luteolin (6), Chrysoeriol-7-O-β-D-glucopyranoside (7), Cacticin (8), Isorhamnetin-3-O-β-D-glucopyranoside(9), Quercetin-7-O-α-L-rhamnopyranoside(10), Hyperin(11), n-butyl-β-D-fructopyranoside(12). Conclusion: Compounds1,3,4,6,7,9,10 and 12 have been isolated from this plant for the first time.
The anthocyanin pigments are contained in the flowers, fruits, leaves and roots of almost plant species. On the other hand, distribution of the betacyanins are limited in eight families of the order Caryophyllales, i.e. Aizoaceae, Amaranthaceae, Basellaceae, Cactaceae, Didiereaceae, Nyctaginaceae, Phytolaccaceae and Portulacaceae. However, other flavonoids, i.e. flavones, C-glycosylflavones, flavonols, flavanones, dihydroflavonols, chalcones, aurones, and flavan and proanthocyanidins, are synthesized in betalain-containing families. In this review, distribution and properties of the flavonoids in eight betalain-containing families are described.
4-O-Octanoylation of methyl α-L-rhamnopyranoside (2) was carried out via blocking-deblocking
technique. Methyl α-L-rhamnopyranoside (2) was first converted in to 2,3-O-isopropylidene derivative
(5) with 2,2-dimethoxypropane, which on octanoylation followed by deacetonation gave the 4-Ooctanoylrhamnopyranoside (7) in good yield. A number of 2,3-di-O-acyl substituted derivatives of 7 were also prepared for structure elucidation and to get newer rhamnopyranoside derivatives of biological importance.
4-O-Palmitoylation of methyl α-L-rhamnopyranoside (2) was carried out via blocking-deblocking technique. Methyl α-L-rhamnopyranoside (2) was first converted into 2,3-O-isopropylidene derivative (5) which on palmitoylation followed by deacetonation gave the desired 4-O-palmitoylrhamnopyranoside (7) in good yield. A number of 2,3-di-O-acyl derivatives of 7 were also prepared to get newer rhamnopyranosides (8-14) of biological importance. All the rhamnopyranosides (2, 5-14) were employed as test chemicals for in vitro antibacterial and antifungal functionality test against ten human pathogenic bacteria and four fungi, respectively. The study revealed that some of the tested rhamnopyranoside derivatives showed excellent antimicrobial functionalities as compared to the standard antibiotic.
Chenopodium ambrosioides (Chenopodiaceae) growing wildly in Egypt was subjected to antioxidant guided phytochemical investigation and the EtOAc fraction afforded the two new flavone glycosides; scutellarein-7-O-alpha-rhamnopyranosyl-(1 -> 2)-alpha-rhamnopyranosyl-(1 -> 2)-alpha-rhamnopyranoside (1) and scutellarein-7-O-alpha-rhamnopyranosyl-(1 -> 2)-alpha-rhamnopyranoside (2). In addition, the in vitro antioxidant activities of the plant alcohol extract, CHCl3 fraction, EtOAc fraction and isolates were studied.
Sophora is a genus of the Fabaceae family, contains about 52 species, nineteen varieties, and seven forms that are widely distributed in Asia, Oceanica, and the Pacific islands, in the family Fabaceae of herbaceous (Sophora flavescens Aiton) to trees (Sophora japonica L.). More than fifteen species in this genus have a long history of use in traditional Chinese medicines. In the last decades the use of this genus in traditional Chinese drugs has led to rapid increase in the information available on active components and reported to posses various pharmacological/ therapeutic properties. The paper reviews the ethnopharmacology, the biological activities and the correlated chemical compounds of genus Sophora, Fabaceae. More than 300 compounds has been isolated, among them major are quinolizidine alkaloids particularly matrine and oxymatrine and flavonoids particularly prenylated and isoprenylated flavonoids. Modern pharmacological studies and clinical studies demonstrated that these chemical constituens possess wide reaching pharmacological actions like anti oxidant, anticancer, anti-asthamatic, anti-neoplastic, antimicrobial, antiviral, antidote, anti pyretic, cardiotonic, antinflammatory, diuretic and in the treatment of skin diseases like eczema, colitis and psoriasis.
A new flavonoid, kaempferol-3,4′-di-O-α-L-rhamnopyranoside (1), and three known flavonoids (2–4) were isolated from the aerial parts of T. communis L. The structure of the new compound was elucidated on the basis of spectroscopic data. Compounds 1 and 2 showed significant antioxidant activity (IC50 187.151 ± 0.821 μM, and 92.079±0.513 μM, respectively), whereas compounds 3 and 4 showed moderate activity in DPPH free radical scavenging assays.
Legumes and the polyphenolic compounds present in them have gained a lot of interest due to their beneficial health implications. Dietary polyphenolic compounds, especially flavonoids, exert antioxidant properties and are potent inhibitors of xanthine oxidase (XO) activity. XO is the main contributor of free radicals during exercise but it is also involved in pathogenesis of several diseases such as vascular disorders, cancer and gout. In order to discover new natural, dietary XO inhibitors, some polyphenolic fractions and pure compounds isolated from two legume plant extracts were tested for their effects on XO activity. The fractions isolated from both Vicia faba and Lotus edulis plant extracts were potent inhibitors of XO with IC(50) values range from 40-135 µg/mL and 55-260 µg/mL, respectively. All the pure polyphenolic compounds inhibited XO and their K(i) values ranged from 13-767 µM. Ten of the compounds followed the non competitive inhibitory model whereas one of them was a competitive inhibitor. These findings indicate that flavonoid isolates from legume plant extracts are novel, natural XO inhibitors. Their mode of action is under investigation in order to examine their potential in drug design for diseases related to overwhelming XO action.
Scrophularia nodosa (figwort), an indigenous medicinal plant grows in moist and cultivated waste ground. It contains saponins, cardioactive glycosides, flavonoids, resin, sugar and organic acids. It is traditionally used for anti-inflammatory purpose and in skin disorders. It has diuretic and cardiac stimulant properties. The present studies were carried out on crude extract of Scrophularia nodosa and its n-hexane, chloroform, ethyl acetate, n-butanol and aqueous fractions. During phytochemical studies seven known compounds of flavonoid nature were isolated from the chloroform fraction of crude extract of S. nodosa. The structures of these compounds were elucidated by spectroscopic (UV, IR, Mass (EIMS, HREIMS) and NMR ((1)H-NMR, (13)C-NMR, DEPT, and (1)H-(1)H, COSY, HMQC, HMBC and NOESY) techniques. Compound 1 was identified as 5, 4`-hydroxy-3, 6, 7-trimethoxyflavone, compound 2 as 5-hydroxy-3,6,7,4'-tetramethoxyflavone, compound 3 as Centaurein, compound 4 as 5-hydroxy-7,8,2',3',4'-pentamethoxyflavone (Serpyllin), compound 5 as Kaempferol 7-O-α-L-rhamnopyranoside, compound 6 as sakuranetin 4'-O (6''-O-α-L-rhamnopyranosyl)-β-D-glucopyranoside (Vitexoside) and compound 7 as Spinoside. Crude extract and its fractions were tested on isolated rabbit intestine (in vitro) for their effects. The results of crude extract and its fractions in different doses showed the decrease in normal movement of the smooth muscles of rabbit intestine (jejunum). The chloroform fraction showed maximum relaxant effect (77.37%) at 15mg/ml dose and aqueous fraction showed 38.56% spasmogenic response which was not present in the crude extract. Further study was carried out on different fractions to investigate the possible mechanism of action of S. nodosa extract. For this purpose spasmolytic effect of different fractions were compared with agonist and antagonist activities of standard drugs including adrenaline, atropine andacetylcholine (1x10(-2), 1x10(-4) and 10(-6) M conc.). It is concluded that the chemical constituents present in S. nodosa having spasmolytic action are possibly acting through muscarinic receptors.
Topoisomerases are essential enzymes involved in all processes of DNA metabolism, and their inhibitors have been identified as potential anticancer agents. The present study examined the effect of nine polyphenolic compounds derived from parts of two unique varieties of the Leguminosae, Vicia faba and Lotus edulis, on the activity of eukaryotic topoisomerases. We identified polyphenolic compounds that act as catalytic inhibitors of wheat germ topoisomerase I (IC50: 120-350 μM), human topoisomerase I (IC50: 110-260 μM), and human topoisomerase II (IC50: 240-600 μM) activities. Some compounds inhibited all enzymatic activities to a similar extent, while others exhibited specificity toward individual enzymes. The strongest catalytic inhibitor of all the examined enzymes was a kaempherol glycoside with an acetyl group linked to a sugar moiety. In addition, this compound inhibited the growth of human cancer cell lines MCF7, HeLa, and HepG2. The inhibition of topoisomerase I and II activities observed by the specific compounds possibly implies a role as potential agents in the prevention and therapy of cancer.
Epidemiological studies have revealed that a diet rich in plant-derived foods has a protective effect on human health. Identifying bioactive dietary constituents is an active area of scientific investigation that may lead to new drug discovery. Kaempferol (3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4H-1-benzopyran-4-one) is a flavonoid found in many edible plants (e.g. tea, broccoli, cabbage, kale, beans, endive, leek, tomato, strawberries and grapes) and in plants or botanical products commonly used in traditional medicine (e.g. Ginkgo biloba, Tilia spp, Equisetum spp, Moringa oleifera, Sophora japonica and propolis). Some epidemiological studies have found a positive association between the consumption of foods containing kaempferol and a reduced risk of developing several disorders such as cancer and cardiovascular diseases. Numerous preclinical studies have shown that kaempferol and some glycosides of kaempferol have a wide range of pharmacological activities, including antioxidant, anti-inflammatory, antimicrobial, anticancer, cardioprotective, neuroprotective, antidiabetic, anti-osteoporotic, estrogenic/antiestrogenic, anxiolytic, analgesic and antiallergic activities. In this article, the distribution of kaempferol in the plant kingdom and its pharmacological properties are reviewed. The pharmacokinetics (e.g. oral bioavailability, metabolism, plasma levels) and safety of kaempferol are also analyzed. This information may help understand the health benefits of kaempferol-containing plants and may contribute to develop this flavonoid as a possible agent for the prevention and treatment of some diseases.
A high-performance liquid chromatography method was developed to obtain fingerprints of secondary metabolites of 12 lentil cultivars grown under the same environmental condition. Extracts (100% methanol and methanol-water (1:1)) were analyzed by RP-HPLC. Full photodiode array (191-360 nm) data were collected and used for cluster analysis. Methanol and methanol-water extracts showed slightly different clustering patterns. In the dendogram of methanol extracts, CDC Richlea appeared as an isolated group, whereas Indianhead was the isolated group in methanol-water extracts. The cultivar CDC Milestone was selected for further evaluation because of the presence of three peaks (8.9, 16.7, and 32.7 min) that were absent in other cultivars or present in very small amounts. Chromatographic separations of the methanol extract afforded several compounds including the novel 4-chloro-1H-indole-3-N-methylacetamide (13) as well as itaconic acid (3), arbutin (5), gentisic acid 5-O-[beta-d-apiofuranosyl-(1-->2)-beta-d-xylopyranoside] (9), and (6S,7Z,9R)-9-hydroxymegastigma-4,7-dien-3-one-9-O-beta-d-apiofuranosyl-(1-->2)-beta-d-glucopyranoside (14), which are described for the first time from lentils. Structures were determined by high-resolution NMR experiments.
Not available Biological Sciences, School of
Two kaempferol glycosides [kaempferol 3-O-beta-D-glucosyl(1-->2)-beta-D-galactoside 7-O-beta-D-glucoside and kaempferol 3-O-beta-D-glucosyl(1-->2)-(6"-O-acetyl)-beta-D-galactoside 7-O-beta-D-glucoside] as well as the quercetin glycoside [quercetin 3-O-beta-D-glucosyl(1-->2)-beta-D-galactoside 7-O-beta-D-glucoside] were isolated from the stems of Trigonella foenum-graecum L. (Leguminosae) along with a known kaempferol glycoside, lilyn [kaempferol 3-O-beta-D-glucosyl(1-->2)-beta-D-galactoside]. Their structures were established by analysis of chemical and spectral evidence.
Six new flavonoid glycosides, quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (1), quercetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (2), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (3), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(3-O-trans-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (4), isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-cis-p-coumaroyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (5), and isorhamnetin 3-O-alpha-L-rhamnopyranosyl(1-->6)-[alpha-L-rhamnopyranosyl(1-->2)]-(4-O-trans-feruloyl)-beta-D-galactopyranoside-7-O-alpha-L-rhamnopyranoside (6), were isolated from the dried aerial parts of Rhazya orientalis. The structures of 1-6 were determined by spectroscopic and chemical means.
A flavonol tetraglycoside, kaempferol 3-O-alpha-L-rhamnopyranosyl(1-->6)-beta-D-glucopyranosyl(1-->2)- beta-D-glucopyranoside-7-O-alpha-L rhamnopyranoside, together with nine known compounds were isolated from the seeds of Sophora japonica L. Their structures were elucidated on the basis of spectral and chemical evidence.
Crude methanol extracts from four cultivated varieties of mature lentil seeds (Lens culinaris Medik.) were found to possess antifeedant and insecticidal properties in laboratory tests with the rice weevil (Sitophilus oryzae L.), an insect pest of stored products. Flash chromatography with silica gel on active Diaion HP-20 methanol extracts gave flavonol, lysolecithin, soyasaponin, and peptide fractions, as determined by HPLC and electrospray ionization LC/MS. The flavonol fraction was shown by high-resolution NMR experiments to contain a mixture of kaempferol 3-O-beta-glucopyranosyl(1-->2)-O-[alpha-rhamnopyranosyl(1-->6)]-beta-galactopyranoside-7-O-alpha-rhamnopyranoside and, tentatively, kaempferol 3-O-beta-glucopyranosyl(1-->2)-O-[alpha-rhamnopyranosyl(1-->6)]-beta-glucopyranoside-7-O-alpha-rhamnopyranoside. These inactive tetraglycosides, although inseparable under the reported HPLC conditions, were detected by NMR spectroscopy in nearly equal proportions. Three lysolecithins were identical to those previously identified in pea extracts. Soyasaponin I (soyasaponin Bb) and soyasaponin VI (soyasaponin betag) were found in Diaion HP-20 methanol extracts. An insecticidal lentil peptide with a mass of 3881 Da, isolated from an Eston variety in small quantities by anion exchange chromatography, was related to the cysteine-rich pea albumin 1b class of botanical insecticides. Binary mixtures of the insecticidal lentil peptide and soybean soyasaponin I were synergistic in tests with S. oryzae.
Five major flavonoids induced by chitin in Cephalocereus senilis cell suspension cultures have been reported previously. We describe here five minor induced flavonoids including two new and three known ones. The two new compounds are (2S)-5,6,7-trihydroxyflavanone 7-glucoside and baicalein 7-(6″-malonylglucoside).
Two new flavonoid glycosides, 6,7-dihydroxy-5-methoxyflavone 7-O-β-d-glucopyranoside and (2S)-6,7-dihydroxy-5-methoxyflavanone 7-O-β-d-glucopyranoside, together with two known compounds baicalein and baicalein 7-O-β-d-glucopyranoside, were isolated from chitin-elicited cell suspension cultures of Cephalocereus senilis. All structures, which were established by spectroscopic methods as well as chemical modifications, share the same unusual substitution pattern of the aurone previously described from the same culture. Each has an unsubstituted B-ring and 5,6,7-oxygenation in the A-ring, thus suggesting that a novel cinnamate:CoA ligase may be functional under these circumstances.
A new aurone, 4,5-methylenedioxy-6-hydoxyaurone, isolated from chitin-treated liquid suspension cultures of Cephalocereus senilis showed antibacterial activity. The structure of the aurone, cephalocerone, was elucidated by chemical and spectroscopic methods.
Treatment of old-man-cactus (Cephalocereus senilis) suspension cultures with chitin elicits synthesis of an aurone phytoalexin, cephalocerone. Elicitor-inducedde novo synthesis of cephalocerone was demonstrated by incubating elicited cactus cultures with [3H]phenylalanine; this resulted in the labelling of five induced phenolic compounds including cephalocerone. Increased extractable activities of the phenylpropanoid pathway enzymes phenylalanine ammonia-lyase (PAL), chalcone synthase (CHS) and chalcone isomerase (CHI) accompanied the synthesis of cephalocerone. CHS and PAL, which are both involved in the biosynthesis of cephalocerone, showed maximum activity at 12 and 24 hr post-elicitation, respectively. CHS and CHI activities catalysing the synthesis and subsequent isomerization of 2′,4′,6′-trihydroxychalcone were present in the cell cultures, consistent with the formation of cephalocerone via a chalcone with no B-ring substituents.
A new kaempferol triglycoside and three known kaempferol glycosides, among them two apiosides, have been isolated from the aerial parts ofMonnina sylvatica. The structures were established on the basis of acid and enzymatic hydrolysis and spectral data (UV,1H and13C NMR, NOE difference measurements, D/CI and FAB-MS) of the isolates and of some derivatives. The triglycoside kaempferol 3-O-β-d-glucosyl-(1→2)-O-[α-l-rhamnosyl(1→6)]-β-dgalactoside is a new natural product. The configuration of the apiosyl moiety in kaempferol 3-O-β-d-apiosyl(1→2)β-d-galactoside kaempferol 3-O-β-d-apiosyl(1→2)-O-[α-l-rhamnosyl(1→6)]-β-d-galactoside was established through NOE difference measurements on the peracetate.
Eight kinds of flavonoids were isolated by crystallization or paper-chromatography from the tepals of several cactaceous plants,
i.e.,Astrophytum ornatum Web.,Notocactus apricus A. Berg.,Echinopsis huotii Lab.,Aylostera pseudodeminuta Backbg. andNeochilenia napina Backbg. The structures of six flavonols were determined by UV spectral means and co-PC comparison as quercetin and its 7-O-galactoside (coptiside II), kaempferol and its 3-O-rhamnosylglucoside (nicotiflorin), and isorhamnetin and its 3-O-rhamnosylglucoside (narcissin). The remaining two flavonoids were partially characterized as kaempferol 3, 7-O-diglycoside and 5-hydroxy-3,4′-oxygenated flavonol derivative.
Phytochemistry Methods Frontiers
- Liu