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Flavonoid constituents of Ephedra alata

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Abstract

Two new flavonol glucosides have been identified in Ephedra alata, namely, herbacetin 8-methyl ether 3-O- glucoside-7-O-rutinoside and herbacetin 7-O-(6″-quinylglucoside). The known flavonoids vicenin II, lucenin III, kaempferol 3-rhamnoside, quercetin 3-rhamnoside and herbacetin 7-glucoside were also found. The structure of the isolated compounds was determined mostly by FABMS and 1H NMR spectroscopy. The final structure of the new compounds and of herbacetin 7-glucoside was confirmed by 13C NMR spectroscopy.

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... The dried residue of 70% EtOH extract of Gleditsia triacanthos leaves was fractionated on a diion column followed by successive separation on Sephadex LH-20 columns with different eluting solvents (Fig. 1), and yielded eight flavonoids including six flavonoid glycosides viz Vicenin-II (1), Lucenin-I (2), Isoorientin (3), Orientin (4), Vitexin (5), Isovitexin (6) along with two aglycones viz; Luteolin (7) and apigenin (8) (Fig. 2). The isolated pure compounds were identified by different chromatographic and spectral techniques UV, 1 H, 13 C NMR, Negative ESI-MS , by comparison with previously published data [30,[45][46][47][48][49][50][51][52][53][54][55][56][57], as well as comparing with authentic samples (CoPC). ...
... The presence of free hydroxyl groups OH-4′ and OH-5 were deduced from the bathochromic shift in NaOMe and AlCl 3 spectra, where the bathochromic shift remained on addition of HCl. On account of the given above data and chromatographic properties, compound 1 was expected to be 5,7, 4′-trihydroxyglycosyl flavones [30,45]. Negative ESI/MS spectrum exhibited the molecular ion peak at m/z 593 [M -H]corresponding to the Mwt of 594 and molecular formula C 27 H 30 O 15 to support evidence of apigenin-di-hexoside structure in comparison with ESI-MS data of compounds 5 and 6. ...
... The bathochromic shift of band I in AlCl 3 together with hypsochromic shift observed after addition of HCl confirmed the presence of orthodihydroxyl groups at C-3′ and C-4′ in ring B, however the bathochromic shift in band II relative to MeOH remained after addition of HCl indicated the presence of a free 5-OH group. On account of the given above data and the chromatographic properties, compound 2 was expected to be 5,7,3′,4′-tetrahydroxy glycosyl flavones [30,45]. Negative ESI/MS spectrum exhibited the molecular ion peak at m/z 609 [M -H]ˉ, corresponding to molecular weight of 610 and molecular formula C 27 H 30 O 16 , to support evidence of luteolin-di--hexoside structure in comparison with the ESI/MS data of compounds 3 and 4. In 1 H NMR spectrum a flavone compound was confirmed by the appearance of a singlet at δ 6.54 for H-3. ...
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This study explored the constitutive polyphenols and certain bioactivities of Gleditsia triacanthos leaves including analgesic, anti-inflammatory, hepatoprotective and antimicrobial activities. The chromatographic separation of 70% EtOH leaf extract resulted in isolation of eight flavonoids including six flavonoid glycosides viz Vicenin-II (1), Lucenin-I (2), Isoorientin (3), Orientin (4), Vitexin (5), Isovitexin (6) along with two aglycones viz; Luteolin (7) and apigenin (8). Their structures were established by different chromatographic and spectral techniques UV, MS, 1 H and 13 C NMR. Bioactivity studies were carried out on 70% EtOH extract of G. triacanthos leaves (sample A) and three fractions; II (sample B), III (sample C) and V (sample D) obtained from fractionation of 70% EtOH leaf extract on di-ion column. All the samples (A, B, C, D) showed significant analgesic, anti-inflammatory and antimicrobial activities. Additionally, all the investigated samples showed hepatoprotective activities except for sample D.
... Besides, the World Health Organization (WHO) (Eriksen et al. 2002) estimates that nearly 80% of African populations depend on traditional medicine for primary health care. In Tunisia, for example, more than 25% of species of the local flora are recognized as medicinal and aromatic (Nabli 1991); according to Palici et al. (2015), a large part of the population still applies on traditional medicine to treat diseases in Sahara. Several medicinal plants with potential antidiabetic or hypoglycemic agents are reported in literature such as Allium sativum (Garlic), Vinca rosea (Nayantara), Trigonella foenum (Fenugrec), and Momordica charantia (Bitter gourd) (Aldouri 2000; Ahmed et al. 2010). ...
... subsp. alenda (Stapf) Trab is a dioecious species that occurs naturally in the grand erg oriental (Nabli 1991). This chamaephyte, 5 m tall, is an endemic Saharian plant of the Ephedraceae family that is strictly related to coarse sands and grows in Rjim Mâatoug, Tunisia (Chaieb and Boukhris 1998). ...
... Flowering occurs during late winter and spring and seeds begin to ripen from mid-May to early August (Derbel and Chaieb 2012). In Tunisia, people use it for pasture, for fuel (Nabli 1991;Chaieb and Boukhris 1998), and as a sand-stabilizer as well as to inhibit desert advance (Derbel et al. 2010). In folk medicine, it was used as a decoction like a stimulant and a disinfectant to treat the kidneys, bronchi, circulatory system, disorders of the digestive system, and to relieve asthma crisis, thus to treat cancer (Gupta and Mandowara 2008;Al-Qarawi et al. 2012). ...
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Ephedra alata, known as a medicinal plant in China, was used in this study as aqueous extract from aerial parts, for diabetes mellitus treatment. This study was carried out on two parts, in vitro, we tested the effect of the studied extract on the inhibition of α-glucosidase and α-amylase activities, and in vivo on Wistar male rats receiving alloxan intraperitoneally at a rate of 125 mg/kg. Extract (100, 200, and 300 mg/kg of body weight) was administrated for 28 days by oral gavage. Blood glucose, amylase, lipase, and lipid profile level were determined. Oxidative stress was evaluated by enzymatic activities of superoxide dismutase (SOD), catalase (CAT) and glutathione peroxidase (GPx), and by estimation of lipid peroxidation and protein carbonyl (PC) level. Histopathological changes in pancreas were investigated under photonic microscopy using immunohistochemical procedure. Our findings showed that aqueous extract inhibited in vitro both α-glucosidase and α-amylase activities and its use in vivo at 300 mg/kg of body weight restored pancreas weight and weight gain, ameliorated significantly (p ˂ 0.05) biochemical parameters; it prevented the increase in lipid and protein oxidation and the decrease in enzymatic and non-enzymatic defense system. Histological study of treated animals showed a comparable healed regeneration of beta cells.
... From the plant entire, a wide range of E. alata natural products including alkaloids, tannins, saponins, proanthocyanidins, phenolic acids, flavonoids and essential oils have been mentioned and the plants-derived polyphenols are of great importance for their potential antioxidant activities (Hegazi and El-Lamey, 2011;Moussaoui et al., 2010;Nawwar et al., 1984). Isolation and identification of flavonoid constituents of this species have been early reported including c-glycosylflavones (Wallace et al., 1982), flavonol-3-O-glycosides (Nawwar et al., 1984;Wallace et al., 1982), proanthocyanidins, herbacetin, 8-methyl ether 3-0glucoside-7-0-rutinoside, herbacetin 7-O-(6″-quinylglucoside), vicenin II, lucenin III, kaempferol3-rhamnoside, quercetin-3-rhamnoside and herbacetin-7-glucoside (Nawwar et al., 1984). ...
... From the plant entire, a wide range of E. alata natural products including alkaloids, tannins, saponins, proanthocyanidins, phenolic acids, flavonoids and essential oils have been mentioned and the plants-derived polyphenols are of great importance for their potential antioxidant activities (Hegazi and El-Lamey, 2011;Moussaoui et al., 2010;Nawwar et al., 1984). Isolation and identification of flavonoid constituents of this species have been early reported including c-glycosylflavones (Wallace et al., 1982), flavonol-3-O-glycosides (Nawwar et al., 1984;Wallace et al., 1982), proanthocyanidins, herbacetin, 8-methyl ether 3-0glucoside-7-0-rutinoside, herbacetin 7-O-(6″-quinylglucoside), vicenin II, lucenin III, kaempferol3-rhamnoside, quercetin-3-rhamnoside and herbacetin-7-glucoside (Nawwar et al., 1984). Fatty acids like hexadecanoic acid, 2-Propenoic acid, benzoic acid,7,2-propenoic acid, benzene-acetic acid, α-hydroxy benzene-dicarboxylic acid and benzene-propanoic acid have been also, identified in the organic extract of this species (Chebouat et al., 2016). ...
... From the plant entire, a wide range of E. alata natural products including alkaloids, tannins, saponins, proanthocyanidins, phenolic acids, flavonoids and essential oils have been mentioned and the plants-derived polyphenols are of great importance for their potential antioxidant activities (Hegazi and El-Lamey, 2011;Moussaoui et al., 2010;Nawwar et al., 1984). Isolation and identification of flavonoid constituents of this species have been early reported including c-glycosylflavones (Wallace et al., 1982), flavonol-3-O-glycosides (Nawwar et al., 1984;Wallace et al., 1982), proanthocyanidins, herbacetin, 8-methyl ether 3-0glucoside-7-0-rutinoside, herbacetin 7-O-(6″-quinylglucoside), vicenin II, lucenin III, kaempferol3-rhamnoside, quercetin-3-rhamnoside and herbacetin-7-glucoside (Nawwar et al., 1984). Fatty acids like hexadecanoic acid, 2-Propenoic acid, benzoic acid,7,2-propenoic acid, benzene-acetic acid, α-hydroxy benzene-dicarboxylic acid and benzene-propanoic acid have been also, identified in the organic extract of this species (Chebouat et al., 2016). ...
Article
Ephedra alata is a medicinal plant with a long history of traditional use for its bronchodilator, anti-asthmatic and cytotoxic effects. In this work, we develop a sensitive and validate LC-ESI/MS method to simultaneously identify and quantify 33 standard phenolic compounds in E. alata methanol (MeOH) crude extract and its derived fractions (Dichloromethane (DCM), Ethyl acetate (EAc), butanol (BuOH) and water). The antioxidant activities were tested using total antioxidant capacity (TAC), DPPH and FRAP assays. Results showed that the validated and reliable LC-ESI/MS method used unambiguously lead to identify and quantify 24 phenolic compounds most of them are present in all extracts. The major components detected were epicatechin, quinic acid, quercetin-3-o-rhamnoside, catechin, trans-cinnamic acid, naringin and trans-ferulic acid which their amounts vary according to the solvent used for the extraction. The DCM extract showed the highest activity when the TAC test was applied, the BuOH and EAc extracts displayed the highest activities with the DPPH test, whereas the DCM and EAc extracts exhibited the strongest activities with the FRAP method. This difference could be attributed to the nature and amounts of phenolic compounds of the extracts. These realized phytochemical and biological analyses could be helpful for the potential use of this plant in novel medicament products.
... The isolation of β-coumaric acid and (f)-2,6-bis-(3,5-dimethoxy-4hydroxyphenyl)-3,7-dioxabicyclo(3,3,0)octane (syringaresinol, 2) from E. alata chloroform extract, the 2,3-digalloylglucopyranose (nilo-citin, 3) from E. alata ethanolic extract and the new alkaloid 7-methoxy-4-quinolone 2-carboxylic acid (ephedralone, 4) from E. alata aqueous extract of the same plant were reported (Nawwar et al. 1984). In addition to the known β-coumaric acid, the furanofuran lignan (f)-syringaresinol and the digalloyl-glucose, nilocitin, were obtained from the whole plant of E. alata. ...
... The known flavonoids vicenin II, lucenin III, kaempferol 3-rhamnoside, quercetin 3-rhamnoside and herbacetin 7-glucoside were also found. The structure of the isolated compounds was determined mostly by FABMS and HNMR spectroscopy (Nawwar et al. 1984). ...
Chapter
With its location in an extensive geographical area that spread from the Mangrove forest in the south to the Sahel savannah in the north, Nigeria has diverse tropical vegetation with varying economic and medicinal significance. The vegetation, among other uses is a source of herbal medicine on which a large proportion of its populace relies for primary health care. Trees have a large repository of phytochemicals, to which the various pharmacological and therapeutic attributes can be ascribed. This article is a concise review of nine trees with medicinal importance belonging to eight families, which are widely used in Nigerian traditional and indigenous medicine. For each plant, information on the taxonomy, morphology, geographical distribution, ecological requirements, major chemical constituents and bioactive compounds, traditional uses and medicinal uses based on biological activities, as well as uses supported by clinical data are provided.
... Furthermore, the presence of apigenin derivatives, such as isovitexin-2-O-rhamnoside and vicenin II, has been reported in the species of E. aphylla [17] . Otherwise, the flavonol glycosides kaempferol-3-O-rhamnoside and quercetin-3-O-rhamnoside were identified previously in E. alata [27] . ...
... Indeed, the number and position of hydroxyl groups in flavonoid structures and the synergistic effects of various bioactive compounds could greatly increase the potency of crude extracts. Studies focused on the antioxidant activity by DPPH of the species from the genus Ephedra such as E. intermedia, E. procera, E. pachyclada and E. sarcocarpa and E. chilensis [27][28][29][30][31] showed differences in their potential. Also, the results of the antioxidant capacity from the plant E. altissima reported previously by Rached et al. [32] indicated a higher activity (IC 50 at 12.0±0.23 ...
... In that paper, we discussed that the active components in the extract might be non-alkaloid substances because ephedrine had no effect on HGF-induced motility. Reports on the constituents in the extract besides ephedrine-type alkaloids are limited, although condensed tannins [5] and flavonoids were found in some Ephedra species [6,7]. In order to explore the active components associated with the antitumor expression shown by Ephedra herb extract, we have investigated the phenolic compounds in the extract, and characterized 10 compounds, including a new flavonoid, which is the subject of this paper. ...
... The EtOAc and n-BuOH extracts, which showed the presence of polyphenolics in HPLC, were chromatographed using Diaion HP-20, Sephadex LH-20, Toyopearl HW-40, MCI-gel CHP-20P, and/or YMC GEL ODS-AQ with aqueous methanol (MeOH) in a stepwise gradient mode. The fractions showing similar HPLC patterns were combined and further purified by column chromatography with aqueous MeOH, to afford a new compound 1, together with the nine known compounds trans-cinnamic acid (2) [8], syringin (3) [9], catechin (4) [10], epicatechin (5) [10], symplocoside (6) [11], pollenitin B (7) [12], herbacetin 7-O-glucoside (8) [6], kaempferol 3-O-rhamnoside 7-O-glucoside (9) [13], and isovitexin 2-O-rhamnoside (10) [14] (Figure 1), which were identified by direct comparison with authentic specimens or by spectral comparisons with data reported in the literature. [12]. ...
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Nine known compounds: trans-cinnamic acid, catechin, syringin, epicatechin, symplocoside, kaempferol 3-O-rhamnoside 7-O-glucoside, isovitexin 2-O-rhamnoside, herbacetin 7-O-glucoside, and pollenitin B and a new flavonoid glycoside, characterized as herbacetin 7-O-neohesperidoside (1) on the basis of spectroscopic analysis and chemical evidence, were isolated from a traditional crude drug, "Ephedra herb extract". Compound 1 had no effects on HGF-induced motility, whereas herbacetin, which is an aglycone of 1, significantly inhibited it.
... The bathochromic shift of band I in AlClR 3R together with hypsochromic shift experimental after adding of HCl confirmed the occurrence of ortho-dihydroxyl groups at C-3` and C-4` in ring B, still the bathochromic shift in band II relative to MeOH continued after adding of HCl designated the occurrence of a free 5-OH group. On explanation of the given above data and the chromatographic properties, compound 2 was expected to be 5,3`,4`trihydroxy glycosyl flavone [34,35]. Negative ESI/MS spectrum exhibited the molecular ion peak at m/z 623 [M-H]P -P , corresponding to molecular weight of 624 and molecular formula CR 28RHR32ROR16R, to support evidence of methyl luteolin-di-hexoside structure. ...
... 3). This structure is confirmed by comparison with previous published reports [34][35][36][37]. Hence, compound 2 was identified as 7-O-methyl-luteolin 8-C-β-glucopyranosyl-(1```→4``)-Oβ-D-glucopyranoside or (4``-glucopyranosyl-7-O-methylorientin), which was isolated for the first time from nature ( fig. 3). ...
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Objective: Cancer is considered as one of the top reasons of death and the number of cases increasing gradually. Cancer is severe clinical difficulty to the health caution system. This study explored two novel polyphenols of Afrocarpus gracilior Pilger growing in Egypt and evaluated their cytotoxic activity. Methods: Methanolic (80%) extract of the leaves of A. gracilior was subjected to column chromatography; the chemical structures of the isolated compounds were established by advanced spectral techniques: UV, 1H, 13C NMR, two dimensional NMR (2D NMR) and electron spray ionization mass spectroscopy (ESI-MS). Compounds 1 and 2 were studied for their cytotoxic activity against hepatocellular carcinoma (Hep-G2) using sulforhodamine B (SRB) assay. Furthermore the pharmacokinetics profiles of these molecules were accessed by employing Petra/Osiris/Molinspiration (POM) analyses. Results: Two novel C-flavonoid glycosides were isolated [1: Apigenin 8-C-β-D-glucopyranosyl-(1```→4``)-O-β-D-glucopyranoside] and [2: 7-O methyl-luteolin 8-C-β-glucopyranosyl-(1```→4``)-O-β-D-glucopyranoside]. They exhibited significant cytotoxic activity (IC50 = 9.02 and 15.61 µg/ml, respectively) against Hep-G2 cells. The POM analyses revealed that the activity of these two compounds depends on the presence of glucosyl and alkyl groups at the internal and terminal atmosphere of the compounds. Conclusion: These findings demonstrated that the leaves of A. gracilior contain a series of bioactive polyphenolic compounds with significant cytotoxic properties against hepatocellular carcinoma and may be used as alternative anticancer agents for doxorubicin. On the basis of POM calculations, it will be interesting to develop some alternative flavones because the deglucosylated derivatives have a better drug score than parent molecules. This preliminary study will be extended to other strains of cancer.
... Ephedra Herb has long been used as an antitussive and expectorant in traditional Japanese medicine [2,3]. The terrestrial stems of E. sinica are well known to contain ephedrine alkaloids, (-)-ephedrine and ( + )-pseudoephedrine, and tannins ephedrannin A and B [4][5][6]. The ephedrine alkaloids in Ephedra Herb are mainly responsible for exerting pharmaceutical effects as well as adverse effects [7,8]. In addition, only a few bioactive constituents of Ephedra Herb, except for ephedrine alkaloids, have been reported [9]. ...
... Thus, the MeOH and EtOH-soluble fractions were passed through column chroma-tography on silica gel and octadecylsilanized (ODS) silica gel producing compounds 1-10. Compounds 1-9 were identified as β-sitosterol (1) [10], 7β-hydroxysitosterol (2) [11], 7α-hydroxysitosterol (3) [11], kaempferol-3-O-rhamnoside (4) [12], kaempferol-3-O-(4″-trans-p-coumaroyl)-rhamnopyranoside (5) [13], kaempferol-3-O-(4″-cis-p-coumaroyl)-rhamnopyranoside (6) [14], herbacetin-7-O-glucopyranoside (7) [6], mahuanin A (8) [15], and ephedrannin A (9) [16], respectively (▶Fig. 1). ...
Article
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Bioassay-guided fractionation of the MeOH extract of Ephedra sinica terrestrial stems, using a PPAR-γ ligand binding assay, resulted in the isolation of 10 compounds, including one new bisabolane-type sesquiterpenoid (10). The structure of the new compound was determined by extensive spectroscopic analysis, including two-dimensional (2D) NMR. Among the isolated compounds, the sitosterol derivatives (1 and 2), flavonoid glucoside (7), and the new sesquiterpenoid (10), showed significant PPAR-γ ligand-binding activity.
... The isolation of β-coumaric acid and (f)-2,6-bis-(3,5-dimethoxy-4hydroxyphenyl)-3,7-dioxabicyclo(3,3,0)octane (syringaresinol, 2) from E. alata chloroform extract, the 2,3-digalloylglucopyranose (nilo-citin, 3) from E. alata ethanolic extract and the new alkaloid 7-methoxy-4-quinolone 2-carboxylic acid (ephedralone, 4) from E. alata aqueous extract of the same plant were reported (Nawwar et al. 1984). In addition to the known β-coumaric acid, the furanofuran lignan (f)-syringaresinol and the digalloyl-glucose, nilocitin, were obtained from the whole plant of E. alata. ...
... The known flavonoids vicenin II, lucenin III, kaempferol 3-rhamnoside, quercetin 3-rhamnoside and herbacetin 7-glucoside were also found. The structure of the isolated compounds was determined mostly by FABMS and HNMR spectroscopy (Nawwar et al. 1984). ...
Chapter
In the twentieth century, science makes substantial breakthrough in management and cure of diseases by chemotherapy due to discovery of antibiotics and other chemotherapeutic agents. In the twenty first century, man and other animals are still, however being challenged by emergence of new infectious and non-infectious diseases that have proven to be resistant to the available novel therapeutic drugs. The available orthodox medications have either been ineffective against some causative agents of these diseases; too costly or basically unavailable to the average citizen of developing countries like Nigeria. The use of herbal remedies for prevention, management and cure of diseases is as old as antiquity, yet still common practice among the African population. A number of plants used in traditional herbal medicine have been evaluated by different researchers. This book chapter provides a concise review of traditional use, phytochemical contents, pharmacognostic and biological activities of some wild herbaceous plants that of medicinal importance in Nigeria. Plants including; Cuminium cyminum Linn, Rauwolfia vomitoria Afzel, Cassia sieberiana D.C, Piliostigma thonningii (Schumach.) Milne-Redh, Guiera senegalensis J.F.Gmel, Acalypha indica Linn, Euphorbia hirta Linn, Euphobia unispina N.E.Br, Phyllantus muellerianus (Kuntze) Exell, Senna occidenatlis Linn and Grewia mollis Juss are comprehensively reviewed. Phytochemicals like glycosides, alkaloids, polyphenols, flavonoids, phytosterols, terpenoids, saponins etc are widely reported to be present in various parts of these plants. The traditional herbal use of the plants in management and cure of ailments, as well as reported biological and pharmacological activities were linked to the presence of these phytochemicals. Based on the information reviewed, it is concluded that these wild herbaceous plants are potential sources of new natural bioactive substances that could be explored and exploited for their therapeutic and industrial applications.
... This compound together with kynurenic acid (10) and 6-methoxykynurenic (12) acid were isolated from E. pachyclada Boiss [65]. Transtorine (13), a 4-quinolone containing a 2-carboxylic acid moiety, was isolated from E. transitoria Riedl [66] while ephedralone (14) a 7-methoxylated analog of 13 was isolated from E. alata Decne [67]. From the "mao-kon" crude drug, macrocyclic spermine alkaloids ( Figure 1) were isolated, represented by ephedradines A-D (15)(16)(17)(18) [68][69][70] that possess hypotensive activity in animal models [71]. ...
... and named herbacetin 8-methyl ether 3-O-glucoside-7-O-rutinoside (74) and herbacetin 7-O-(6"-quinylglucoside) (75). Other molecules such as vicenin 2 (66), lucenin 3 (71), kaempferol-3-O-rhamnoside (72), quercetin 3-O-rhamnoside (73) and herbacetin 7-O-glucoside (63) were also isolated and identified from E. alata Decne [67]. The latter compound was also reported from E. lomatolepis Schrenk [80] and compound 74 from E. equisetina Bunge [77]. ...
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Ephedra is one of the largest genera of the Ephedraceae family, which is distributed in arid and semiarid regions of the world. In the traditional medicine from several countries some species from the genus are commonly used to treat asthma, cold, flu, chills, fever, headache, nasal congestion, and cough. The chemical constituents of Ephedra species have been of research interest for decades due to their contents of ephedrine-type alkaloids and its pharmacological properties. Other chemical constituents such as phenolic and amino acid derivatives also have resulted attractive and have provided evidence-based supporting of the ethnomedical uses of the Ephedra species. In recent years, research has been expanded to explore the endophytic fungal diversity associated to Ephedra species, as well as, the chemical constituents derived from these fungi and their pharmacological bioprospecting. Two additional aspects that illustrate the chemical diversity of Ephedra genus are the chemotaxonomy approaches and the use of ephedrine-type alkaloids as building blocks in organic synthesis. American Ephedra species, especially those that exist in Mexico, are considered to lack ephedrine type alkaloids. In this sense, the phytochemical study of Mexican Ephedra species is a promising area of research to corroborate their ephedrine-type alkaloids content and, in turn, discover new chemical compounds with potential biological activity. Therefore, the present review represents a key compilation of all the relevant information for the Ephedra genus, in particular the American species, the species distribution, their ecological interactions, its ethnobotany, its phytochemistry and their pharmacological activities and toxicities, in order to promote clear directions for future research.
... alenda (Stapf) Trab., a dioecious species, is the most important pioneer plant of the moving and semi-stable sand dunes in the deserts and steppes of south Tunisia and occurs naturally in the Grand Erg Oriental (Nabli, 1989) and grows up to 5 m tall near Rjim Mâatoug, Tunisa (Chaieb and Boukhris, 1998). Other than its sand stabilization value, E. alata has gained popularity because of its secondary product chemistry-it is an important source of pharmaceutical compounds (Smith, 1977;Nawwar et al., 1984Nawwar et al., , 1985Abourashed et al., 2003;Hayashi et al., 2010). Local nomadic populations also use it for pasture and for fuel, but overuse in this respect has contributed to its decrease (Nabli, 1989;Chaieb and Boukhris, 1998). ...
... The data presented demonstrate that coordination of water loss and carbon gain, combined with proline accumulation function as mechanisms behind its successful distribution across arid regions. Most previous studies on the genus Ephedra have focused on the pharmacological and medical aspects of the species (Smith, 1977;Nawwar et al., 1984Nawwar et al., , 1985Abourashed et al., 2003;Hayashi et al., 2010), and studies on the ecophysiology of Ephedra have long been needed to improve the basis for management of this important regional plant species. Analysis of the relationship between water relations and gas exchange characteristics of this xerophytic species in this study provide a tool for understanding how plants cope with extreme drought, and how the mechanisms of adaptation to dry conditions may affect its prospects for cultivation, restoration, and persistence in natural ecosystems in the face of climate change. ...
... The probable explanation of this difference is that a subspecies of Ephedra alata was included in our investigation, and the different solvent, used for extraction process can also be the reason of the different activities. The presence of alkaloids, including ephedrine and pseudoephedrine, lignans, flavonoids and other phenolic compounds were referred in the extracts of E. alata, but the compounds responsible for the antibacterial activity has not been yet identified [22,23]. The antimicrobial effects of other Ephedra species were also described earlier. ...
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The aim of the present study was the evaluation of the antimicrobial and antiproliferative activities of selected Saharan species, which are applied in the traditional medicine but not studied thoroughly from chemical and pharmacological point of view. The studied plants, namely Anthyllis henoniana, Centropodia forskalii, Cornulaca monacantha, Ephedra alata var. alenda, Euphorbia guyoniana, Helianthemum confertum, Henophyton deserti, Moltkiopsis ciliata and Spartidium saharae were collected from remote areas of North Africa, especially from the Tunisian region of Sahara. After drying and applying the appropriate extraction methods, the plant extracts were tested in antimicrobial screening assay, performed on 19 Gram-positive and -negative strains of microbes. The inhibition zones produced by plant extracts were determined by disc-diffusion method. Remarkable antibacterial activities were exhibited by extracts of Ephedra alata var. alenda and Helianthemum confertum against B. subtilis, M. catarrhalis and methicillin-resistant and non-resistant S. aureus. Minimum inhibitory concentrations of these two species were also determined. Antiproliferative effects of the extracts were evaluated against 4 human adherent cell lines (HeLa, A431, A2780 and MCF7). Notable cell growth inhibition was found for extract of Helianthemum confertum and Euphorbia guyoniana. Our results provided data for selection of some plant species for further detailed pharmacological and phytochemical examinations.
... The probable explanation of this difference is that a subspecies of Ephedra alata was included in our investigation, and the different solvent, used for extraction process can also be the reason of the different activities. The presence of alkaloids, including ephedrine and pseudoephedrine, lignans, flavonoids and other phenolic compounds were referred in the extracts of E. alata, but the compounds responsible for the antibacterial activity has not been yet identified [22,23]. The antimicrobial effects of other Ephedra species were also described earlier. ...
Article
The present work is the first phytochemical investigation of Euphorbia davidii Subils. After multistep separation process, three flavonoid glycosides were obtained from the ethyl acetate soluble fraction of the methanol extract of the whole plant. The structures of the isolated compounds were determined as kaempferol 3-O-rhamnoside, myricetin 3-O-rhamnoside, and quercetin 3-O-rhamnoside. Aqueous and organic extracts of the plant were screened in vitro for antiproliferative activity against HeLa (cervix epithelial adenocarcinoma), A431 (skin epidermoid carcinoma), A2780 (ovarian carcinoma) and MCF7 (breast epithelial adenocarcinoma) cells, using the MTT assay. n-Hexane and chloroform extracts demonstrated moderately dose-dependent cell growth inhibitory activity against all four cell lines.
... It naturally produces toxins such as microcystin-AR, microcystin-LR, microcystin-RR , etc. [5]. The root of Ephedra equisetina (Mongolian Ephedra or Ma Huang in TCM) is recognized as a 'poisonous but safe' material in TCM primarily due to its alkaloid content [8]. The root of Ephedra equisetina is often used in cooking or home décor in China. ...
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An aqueous extract of Ephedra equisetina root was found to induce cyanobacterial cell death. The extract displayed no negative effects on the fish populations but instead, improved the habitat conditions for the growth of macrophytes, zooplankton and bacteria because the inhibiting effects of the extracts on cyanobacteria helped clear up the water column. The removal kinetics of cyanobacteria by E. equisetina extract appears to be a first order process with the rate constant being extract-dose-dependent. Compounds including the flavonoids found in E. equisetina root kill the cyanobacteria in vitro at a dose of 5.0 µg extract per 100 mL water or above. The extract constituents act to disrupt the thylakoid membrane, interrupt the electronic transport, decrease the effective quantum yield, and eventually lead to the failure of photosynthesis in Microcystis aeruginosa. This study presents an easily-deployed, natural and promising approach for controlling cyanobacterial blooms as an emergency measure, and also provides insight into the dynamics and mechanism of the extract consisting of multiple compounds synergistically removing algae.
... The probable explanation of this difference is that a subspecies of Ephedra alata was included in our investigation, and the different solvent, used for extraction process can also be the reason of the different activities. The presence of alkaloids, including ephedrine and pseudoephedrine, lignans, flavonoids and other phenolic compounds were referred in the extracts of E. alata, but the compounds responsible for the antibacterial activity has not been yet identified [22,23]. The antimicrobial effects of other Ephedra species were also described earlier. ...
Article
The landscape of southern Tunisia areas is dominated by shrubs and woody plant species. Their morphological and physiological features being suitable for arid and Saharan bioclimate. It can be estimated that their phytochemical characteristics and metabolic activities are in accordance with the environment, and the plants have special spectrum of secondary metabolites, and offer a great medical and pharmaceutical potential. The present study aims the investigation of the biological activities on some plant species from the Tunisian region of Sahara. The studied species were: Anthyllis henoniana (Coss.), Centropodia forskalii (Vahl.), Cornulaca monacantha (Delile), Ephedra alata var. alenda (Stapf.) Trabut, Euphorbia guyoniana (Boiss. & Reut.), Helianthemum confertum (Dunal), Henophyton deserti (Coss. & Durieu), Moltkiopsis ciliata (Forssk.) and Spartidium saharae (Coss. & Durieu). The antibacterial activity was evaluated on 19 strains of microbes by disc-difussion method with determination of the values of inhibition zones (7 – 14,5 mm) and minimum inhibitory concentrations (MIC = 0,1 – 5 mg/mL). Amoxicilin+clavulanic acid and vancomycin were applied as positive controls in the experiments. In vitro antiproliferative effect of the extracts was evaluated against 4 human adherent cell lines (HeLa, A431, A2780 and MCF7) using the MTT assay and cisplatin as reference compound. The aqueous-ethanolic (1:1) extracts of six desert plants showed antimicrobial activity against Bacillus subtilis, Moraxella catarrhalis, Staphylococcus aureus or methicillin-resistant Staphylococcus aureus. Extracts of E. guyoniana and H. confertum showed antiproliferative activity on breast adenocarcinoma (MCF7), and ovarian carcinoma (A2780) cell lines. Our screening study proved that Saharan plant species are promising sources of potential antibacterial and antitumor agents. Our findings serve as starting points for selection of plant species for further investigation.
... These flavonoids have been isolated as major constituents of Ephedra alata by Nawwar et. al. [32,33]. Our results showed that pure ephedrine as the main alkaloid of Ephedra species had no effect on growth and AFB 1 production by A. parasiticus even at concentration of 1000 lg/ml (data are not shown in details). ...
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This study was undertaken to evaluate the effect of Ephedra major Host, an important medicinal plant with various biological activities, on growth and aflatoxin (AF) production by Aspergillus parasiticus NRRL 2999. The fungus was cultured in yeast extract-sucrose (YES) broth, a conductive medium that supports AF production, in the presence of various concentrations of essential oil (EO), hexanic and methanolic extracts of plant aerial parts, fruits, and roots using microbioassay technique. After incubating for 96 h at 28 degrees C in static conditions, mycelial dry weight was determined as an index of fungal growth, and aflatoxin B(1) (AFB(1)) was measured using HPLC technique. Based on the obtained results, EO of plant aerial parts significantly inhibited fungal growth at the highest concentration of 1000 microg/ml without any obvious effect on AFB(1) production at all concentrations used. Among plant extracts tested, only methanolic extract of aerial parts and roots were found to inhibit fungal growth and AFB(1) production dose-dependently with an IC(50) value of 559.74 and 3.98 microg/ml for AFB(1), respectively. Based on the GC/MS data, the major components of E. major EO were bis (2-ethylhexyl) phthalate (42.48%), pentacosane (20.94%), docosane (14.64%), citronellol (5.15%), heptadecan (4.41%), cis-3-Hexen-1-ol benzoate (4.07%), and 7-Octen-2-ol (3.25%). With respect to the potent inhibition of fungal growth and AF production by E. major, this plant may be useful in protecting crops from both toxigenic fungal growth and AF contamination.
... The results of the phytochemical analysis carried out on the aqueous extracts of the aerial part of Ephedra alata showed the presence of certain active compounds Tannins, Flavonoids, Anthocyans, Saponins, Alkaloids, Terpenoids and Leucoanthocyans when sterols and Cardinolids are absent, these results are compatible with the literate [20][21][22] Phenolic compounds are considered important contributors to the biological activities of plants [23]. These compounds possess various biological activities such as Antibacterial [24]. ...
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Plants have been a source of important chemical compounds that can be used for treatment of different disease. Natural products in plants also are a source of active compounds and can be considered an alternative to synthetic molecules with high antioxidant potential. Objective of this study was to determine the antioxidant and antibacterial potential of Ephedra alata extract. Methods: Phytochemical values namely, total phenolic, DPPH radical scavenging effect were studied by established methods. Antimicrobial properties of Ephedra alata was tested using cup-plate diffusion method and disc diffusion. 17 Results showed numerous secondary metabolic products including in plant Ephedra alata extract such as Flavonoids, Saponins, Tannins were detected. And other metabolic products such as Steroids and Cardinolids are absent. The yield for the aqueous extract was 9.89%. However, the polyphenols extract content was equal to 0.004243 (mg GAE/ml extract. Effectiveness of antioxidant plant using DPPH free root was estimated at IC 50 = 0.901 mg/ml for aqueous extract. In antibacterial screening, the extract showed antibacterial power with zone of inhibitions compared to positive controls Penicillin against multi-resistant germs such as: Pseudomonase aeruginosa and Serratia fonticola responsible of many infectious. Growth inhibition varies with bacterial species and concentration of Ephedra alta extract.
... However, the presence of the myricetin derivatives, such as myricetin 3-rhamnoside have been also reported in the hydroethanolic extract of E. alata from Palestine (Al-rimawi et al., 2017). The isoflavones biochanin A and the diazein, as well as the quercitin were also previously detected in many ephedracontaining dietary supplements purchased from the market in arkansas-United states (Grippo, Capps, Rougeau, & Gurley, 2007).Whilst, kaempferol-3-O-rhamnoside and quercetin-3-O-rhamnoside were identified in E. alata growing in the Egyptian desert (Nawwar, El-sissi, & Barakat, 1984). ...
... They state that this plant was successfully publicized as effective. Several pharmacological studies have concerned E. alata sensu lato (Al-rimawi et al., 2017;Borhane et al., 2018;Ghanem and El-magly, 2008;Nawwar et al., 1984). Kmail et al. (2015) investigated the plant's activity in mono and co-cultures of HepG2 and human THP-1 derived macrophages. ...
Article
This study is the first ethnobotanical investigation of Tuareg communities from the region of Illizi in the Algerian Sahara. The study aims to highlight the unique floristic diversity used in their traditional medicine. Ethnobotanical surveys were conducted with 120 Tuareg nomads, mostly old and illiterate men, using free listing and structured interviews. Field data were organised in Use Reports (URs) and analysed using the Informant Consensus Factor. We identified 118 medicinal plants belonging to 43 botanical families dominated by Asteraceae, Fabaceae and Poaceae. The Tuareg use leaves in infusion as the most common preparation method. The species most often mentioned in the surveys are Salvadora persica L., Peganum harmala L. and Anvillea garcinii subsp. radiata (Coss. & Durieu) Anderb. Gastrointestinal system disorders are the ailments most commonly treated with herbal medicine. The treatment of cancer has the highest consensus among the community. This pathology is treated only by Ephedra alata subsp. alenda (Stapf) Trab. The analysis of the results in comparison with the available literature in Algeria and neighbouring countries led us to identify 21 new medicinal plants as well as 65 plants with new uses. We evaluated the originality of the ethnobotanical knowledge of the Tuareg community using a comparative approach with two populations geographically close, the Arabic-speaking nomads of the Algerian steppe and the Egyptian Bedouins with whom they share a nomadic way of life. Plants shared with Algerian nomad neighbours are those available in markets and used also for culinary and aromatic purposes, but plants shared with Bedouin communities are mostly non-cultivated desert plants. We conclude that Tuareg use medicinally many plants specific to their environment in unique ways.
... Compounds 1 and 2 were identified as rhodiosin and herbacetin, respectively, based on the comparison of their 1 H and 13 C spectral data with those in the literature (Nawwar et al. 1984;Jeong et al. 2009). ...
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Context: Rhodiola rosea L. (Crassulaceae) is well-known to contain flavonoids such as the herbacetin derivative rhodiosin. However, flavonoids are not typically used in quality control. Objective: This study analyses two flavonoids of R. rosea rhizomes and roots for their potential as analytical markers. Materials and methods: Two constituents were isolated from ethanolic extracts via HPLC, identified via NMR and quantified via RP-HPLC. Presence and content variation was investigated according to extraction (solvent and repetitions), drying (temperature and duration) and sample origin (homogenously cultivated plants of different provenance, commercial samples). Results: Rhodiosin was identified as a main flavonoid, accompanied by 10-fold lower concentrated herbacetin. Both compounds were best extracted with 70–90% ethanol, but were also detectable in more aqueous extracts. Different drying conditions had no effect on the flavonoid content. These two flavonoids were consistently identified in rhizome and root extracts of over 100 R. rosea samples. Rhizomes tend to contain less flavonoids, with average ratios of rosavins to flavonoids of 1.4 (rhizomes) and 0.4 (roots). Provenance differences were detected in the range (rhodiosin plus herbacetin) of 760–6300 µg/mL extract corresponding to a maximum of approximately 0.5–4.2% (w/w) in the dry drug. Conclusions: For the first time, two main flavonoids present in R. rosea were quantified systematically. Rhodiosin and herbacetin can be detected simultaneously to phenylpropenoids or salidroside in authentic samples, influenced by the plant part examined and the plant origin. Rhodiosin and herbacetin may serve as additional marker to guarantee a consistent content of R. rosea products.
... The total phenolic content was highest in the methanolic extract (47.62 mg gallic acid equivalent/g of extract powder), while in ethanolic extract, the total phenolic content was 19.175 mg GAE/g of extract powder. The total flavonoid content of the plant was 0.519 mg rutin /g in the aqueous extract and 5.44 mg RU/g in the ethanolic extract while was the highest in the methanolic extract 54.66 mg rutin /g (367)(368)(369)(370) . ...
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The use of dietary or medicinal plant based natural compounds to disease treatment has become a unique trend in clinical research. Polyphenolic compounds, were classified as flavones, flavanones, catechins and anthocyanins. They were possessed wide range of pharmacological and biochemical effects, such as inhibition of aldose reductase, cycloxygenase, Ca+2-ATPase, xanthine oxidase, phosphodiesterase, lipoxygenase in addition to their antioxidant, antidiabetic, neuroprotective antimicrobial anti-inflammatory, immunomodullatory, gastroprotective, regulatory role on hormones synthesis and releasing…. etc. The current review was design to discuss the medicinal plants contained phenolics and flavonoids, as natural ingredients for many therapeutic purposes.
... The decoction of E. alata aerial parts has been reported in folk medicine to relieve nasal decongestion, in the treatment of asthma, digestive system disorders and as a general respiratory decongestant. The hot broth of the dried green stems is used in traditional medicine, as hot tea, after abortion and to treat bacterial and fungal infections (Gupta et al., 2008;Nawwar et al., 1984). Previous in vitro and in vivo studies showed that E. alata extracts have several biological properties including antiinflammatory, anticancer, antibacterial, antioxidant, antidiabitic, antiobesity and antiviral effects (Hyuga et al., 2016). ...
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In the current study the potential use of aqueous and methanolic extracts of Ephedra alata aerial parts as biological control agent against pathogenic bacteria and especially Staphylococcus aureus methicillin resistant isolated from auricular infections was evaluated. Chemical tests and spectrophotometric methods were used for screening and quantification of phytochemicals. The assessment of the antioxidant activity was accomplished by DPPH and ABTS radicals scavenging assays. Extracts were evaluated for their antibacterial efficacy by diffusion and microdilution methods. Biofilm inhibition was tested using XTT assay and the cytotoxicity of extracts was carried out on Vero cell line. The GC-FID analysis revealed that E.alata was rich in unsatured fatty acids. In addition, the aqueous extract had the highest flavonoid and protein contents (30.82 mg QE /g dry extract and 98.92 mg BSAE/g dry extract respectively). However, the methanolic extract had the highest phenolic, sugars and tannins. The antioxidant activity demonstrated that the aqueous extract exhibited the strong potency (IC50 ranged between 0.001 and 0.002 mg/mL). Both extracts displayed antimicrobial activity on Gram negative and positive strains. They were effective against S.aureus isolated from auricular infections. The tested extracts were able to inhibit biofilm formation with concentration-dependent manner. Moreover, no cytotoxic effect on Vero cells line was demonstrated for the extracts. Overall, our findings highlight the potential use of E. alata extract as a novel source of bioactive molecules with antioxidant, antibacterial and antiobiofilm effects for the control of infectious disease especially those associated to S. aureus methicillin resistant.
... The spectral data of the known compounds were in accordance with the published data. They were identified as apigenin 6,8-di-C-β-D-glucopyronoside (vicenin 2), [16] apigenin-7 methyl ether 4′glucoside, [17] apigenin-4`-methyl ether 7-O-rutino-pyranoside, [18] apigenin 7-O-β-Dglucopyranoside, [19] and apigenin. [19] Bioassay Table 4]. ...
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Nothing is reported on Amphilophium paniculatum (L.) Kunth. This study aimed at investigation of chemical constituents of the leaves of Amphilophium paniculatum, grown in Egypt, in addition to pharmacological evaluation. Isolation of a new compound, along with 5 known flavonoids. Pharmacological activities were carried out on different extracts of A. paniculatum leaves. Identification of a new flavone glycoside, acacetin 8-C-β-D- glucopyranosy l-(1→2)-α-L-rhamnopyranoside (1) in addition to 5 known flavonoids. The 70% ethanol crud extract and its successive chloroform, ethyl acetate, and 100% ethanol extracts showed significant anti-inflammatoryactivity,analgesic effect, antipyretic activity, antioxidant activity, and anti-hyperglycemic activity. Determination of the median lethal dose (LD50) revealed that the different extracts were safe.
Article
A new naphthalene derivative, 1-methyl-2,3-methylenedioxy-6-naphthalenecarboxylic acid methyl ester (1), and a new alkaloid, ( +/- )-1-phenyl-2-imido-1-propanol (2), together with the four known compounds, ephedrine, pseudoephedrine, N-methylephedrine, and 6-methoxykynurenic acid, have been isolated from the stems of Ephedra sinica, a famous traditional Chinese herbal medicine. The structures of 1 and 2 were determined by spectroscopic methods, including 1D- and 2D-NMR experiments as well as HR-EI-MS analysis.
Article
In addition to the known p-coumaric acid, the furanofuran lignan (±)-syringaresinol and the digalloylglucose, nilocitin, were obtained from the whole plant of Ephedra alata. A new natural alkaloid, ephedralone, was also isolated. The structures were determined mostly by mass, 1H and 13CNMR spectroscopy.
Article
In the extreme north, Papaver radicatum s.l. occurs in a yellow and in a white-flowered type. The more severe the weather conditions the higher the frequency of the white phenotype. The colouring agents in the petals are all flavonol glucosides; in the yellow flowers gossypitrin (1) and herbacitrin (2), in the white ones the kaempferol glucoside astragalin (3). Only astragalin shows UV reflection, which is valuable in attracting insect pollinators, so very likely the presence of astragalin may be responsible for the success of the white-flowered type under suboptimal weather conditions. We were unable to confirm the hypothesis that the yellow colouring agents, gossypitrin and herbacitrin, should be more costly to produce than the white one, astragalin, as an investment in order to obtain the higher temperature observed in yellow flowers. The distribution pattern with high frequency of the yellow-flowered poppies where the likelihood of sunshine is high, may have other reasons than carbon allocation to the colouring agents. Yellow flowers are more showy than white ones, and although this in general benefits pollination it may also increase the risk of herbivory. White flowers are at the same time believed to escape herbivory and obtain a better pollination under dull weather conditions, due to the UV-reflection by astragalin.
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In addition to rutin, quercetin 3-O-glucoside and quercetin 3-O-glucoside-7-O-rhamnoside, the methanolic extract of the aerial parts of Capparis spinosa yielded the new flavonoid quercetin 3-O-[6'"-alpha-L-rhamnosyl-6"-beta-D-glucosyl]-beta-D-glucoside (1).
Article
The new flavone diglycoside 7-O-[6-O-(alpha-L-arabifuranosyl)-beta-D-glucopyranosyl]-gossypetin, named as pyrropetioside, along with 13 known compounds (including 3 artifacts) have been isolated from Pyrrosia petiolosa. Their structures have been elucidated by means of chemical and spectroscopic methods including IR, MS, 1D and 2D NMR techniques.
Article
Four new dihydrostilbenes, alpha,alpha'-dihydro-3,5-dihydroxy-4'-acetoxy-5'-isopentenylstilbene (1), alpha,alpha'-dihydro-3,3',4'-trihydroxy-5-O-isopentenyl-6-isopentenylstilbene (2), alpha,alpha'-dihydro-3,5,3'-trihydroxy-4'-methoxystilbene (3), and alpha,alpha'-dihydro-3,3'-dihydroxy-5beta-d-O-glucopyranosyloxy-4'-methoxystilbene (4), together with seven known flavonoids, glabranin isomer, naringenin, lupiwighteone, pinocembrin 7-O-glucoside, astragalin, isoquercitrin, vicenin II, and the inositol, pinitol, were isolated from the leaves of Glycyrrhiza glabra grown in Sicily. The structures of 1-4 were elucidated by spectroscopic methods.
Article
Eggplant and related Solanum species contain abundant caffeoylquinic acid (CQA) derivatives. Fruit of the invasive species Solanum viarum Dunal contain numerous complex CQA derivatives, but only a few have been identified. The structures of two new compounds isolated from methanolic extracts of S. viarum fruit by C(18)-HPLC-DAD were determined using 2D NMR and MS data. Both include two 5-CQA molecules joined by glucose via ester and glycosidic linkages. The structures of compounds 1 and 2 (viarumacids A and B) are, respectively, 5-caffeoyl- and 3-malonyl-5-caffeoyl-[4-(1β-[6-(5-caffeoyl)quinate]glucopyranosyl)]quinic acid. The antioxidant activities determined by ABTS(•+) and DPPH(•) assays were in the order 1 > 2 > 5-CQA.
Article
The novel flavonol 8-methoxykaempferol 3-O-(2″-β-d-glucopyranosyl-β-d-glucopyranoside) has been found as a yellow pigment in almond pollen. In addition, trace amounts of kaempferol and quercetin 3-diglucosides have been detected. These compounds have been isolated from almond bee pollen, which is a convenient source for the study of flavonoids from natural pollen. HPLC studies show no differences in the flavonoid patterns of pollen and bee pollen, and demonstrate that 8-methoxykaempferol 3-sophoroside is the main flavonoid in almond pollen, while other flower and leaf tissues are devoid of this pigment. This compound is also absent from other botanically related pollens (plum, apple, cherry, and pear).
Chapter
By 1975, some 360 flavone and flavonol glycosides were known to occur in the plant kingdom (Harborne and Williams, 1975). In the following five years, this number doubled so that some 720 structures were listed in our first supplement (Harborne and Williams, 1982). The pace of discovery during 1981–1985 has not slowed down and we now list at the end of this book nearly a thousand substances. This is a conservative estimate in the sense that a number of partly characterized glycosides, which probably differ in mode of linkage or in the type of sugar configuration from those reported here, have been described but are not included in our lists. It is to be regretted that some investigators still do not characterize their glycosides with the necessary rigour to establish the structures unambiguously. As before, the term ‘glycoside’ is used in its widest sense and we include here flavones and flavonols which are acylated and sulphated as well as glycosylated.
Article
C-glycosylflavones appear to be a unifying biochemical feature for Ephedra, Gnetum and Welwitschia, the three genera of the Gnetopsida. The present study reinforces the occurrence of C-glycosylflavones, based on apigenin and luteolin, within the genus Ephedra. All examined species were found to accumulate di-C-glycosylflavones.
Article
A new di-C-glucosylflavone, 2″2‴-di-O-β-glucopyranosyl-vicenin II and a new flavonol di-O-glycoside, herbacetin 3-O-α-rhamnopyranoside-8-O-β-glucopyranoside, were isolated from the aerial parts of Ephedra aphylla. Vicenin II, the 7-methoxy-4-quinolone 2-carboxylic acid, ephedralone, p-hydroxybenzoic, p-coumaric, protocatechuic acids and herbacetin 7-methyl ether were also isolated. The 13C NMR spectrum of the latter compound has been assigned for the first time. © 1997 Elsevier Science Ltd. All rights reserved
Article
Extraction of phenolic compounds of grape leaves after flavour extraction has been studied. Fractionation of these compounds was done using thin-layer and column chromatography and the compounds were identified by NMR analysis. A remarkable variation in the concentration of these phenolic compounds of all the varieties was observed. when subjected to flavour extraction. Einfluß der Geruchsstoffextraktion auf die phenolischen Bestandteile von Weinblättern Nach der Geruchsstoffextraktion wurden phenolische Bestandteile aus Weinblättern isoliert. Die Fraktionierung dieser Bestandteile cr-folgte mit Hilfe der Dunnschicht- und Säulenchromatographic, und zur Identifizierung dieser Komponcnten dicnte die NMR-Spektroskopie. Eine deutliche Variation in der Konzentration dieser phenolischen Komponcnten wurde bei alien untersuchten Sortcn von Weinblattern nach Anwendung der Geruchsstoffextraktion festge-stellt.
Article
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This study designed to evaluate antioxidant activity, screen the existence of phytogenic chemical compounds and to determine the total flavonoid and phenol contents of the Ephedra alata. to prove its utilization in the Palestinian folk medicine for treatment of cancer. Total flavonoid contents of the plant were determined by using rutin reference standard method and total phenols determined by using Folin Ciocalteu method while antioxidant activity evaluated by using 2, 2-diphenyl-1-picryl-hydrazyl-hydrate assay. Phytochemical analyses indicated the presence of cardiac glycosides, reducing sugars, flavonoids, phenolic compounds and alkaloids. The total phenolic content in the ethanolic extract was 19.175 mg gallic acid while was the highest in the methanolic extract which was 47.62 mg gallic acid equivalent/g of extract powder. The total flavonoid content of the plant was 0.519 mg RU/g in the aqueous extract and 5.44 mg RU/g in the ethanolic extract while was the highest in the methanolic extract 54.66 mg RU/g. In the same time the E. alata methanolic extract showed that it has high antioxidant activity and powerful oxygen free radical scavenging abilities as well as the IC50 for the plant was almost equivalent to the Trolox standard antioxidant which justified its uses in the Palestinian traditional medicines and could represented as a good candidate for further biological and chemical analysis, and can be further subjected for isolation of the therapeutically active compounds with anticancer activity and also for further pharmacological evaluations.
Chapter
The last five years have seen a steady growth of the number of C-glycosylflavonoids known to occur in plants, which now amounts to a little more than three hundred. New natural C-glucosyl-, C-galactosyl-, C-xylosyl-, C-arabinosyl- and C-rhamnosyl-flavonoids have been reported to occur either as free compounds or as O-glycosides or O-acyl derivatives. The C-β-L-arabinopyranosyl residue (Fig. 3.1) has been identified in the ‘neo’ isomer of schaftoside as the result of the characterization of the four 6-C-α and β-L-arabinopyranosyl and furanosylacacetins produced by the acid isomerization of synthetic 6-C-α-L-arabinopyrano-sylacacetin (Besson and Chopin, 1983; Besson et al., 1984). Several new types of C-glycosylflavonoids have been described: C-glycosyl-α- and β-hydroxydihydro-chalcones, C-glycosylquinochalcone, C-glycosylflavanol, C-glycosylprocyanidin, di-C-glycosylflavanone, di-C-glycosylquinochalcone.
Chapter
The gymnosperms form a relatively small group of about 800 species of mainly evergreen trees or shrubs. They have been fairly well investigated for phenolic constituents and often appear to accumulate a rich variety of flavonoids. Most attention has been paid to the leaves or leafy twigs, mainly with the object of determining the distribution from species to species. Flavonoid biochemistry has proven its worth in solving various taxonomic problems. The now classic example of heartwood flavonoid patterns being correlated with the morphological subdivision of the genus Pinus into Haploxylon and Diploxylon pines (Erdtman, 1963) has been followed by many others (Section 13.3). Exploration of flavonoid patterns at the populational level has also received recent attention, revealing for example interesting correlations with plant geography (Section 13.4).
Chapter
Für die Bände I bis VI der „Chemotaxonomie“ dienten die Klassifikationen von Smith (1955) und Engler (Syllabus, 11. Aufl., 1.Band, 1954) als Richtlinien der Sippenabgrenzung und -anordnung. Dementsprechend wurden 16 Abteilungen und bei den Samenpflanzen (XV Gymnospermae + XVI Angiospermae) 6 Klassen besprochen. Vgl. Bd. I, S. 25–28.
Chapter
Tunisian has a high diversity of plants as a result of the variation in topography climate and edaphic conditions of the country. Among these plants several aromatic and medicinal species are traditionally used in folk medicines to treat and/or manage common ailments. Some others species are used in foods as spices and/or in aromatherapy. The present chapter endeavors to highlight the botanical description, geographical distribution, ethno pharmacological uses of 45 species spread over 22 botanical families among those the most used in traditional medicine. Information on the chemical composition and biological activities of these species are also included in this chapter.
Article
The genus Ephedra of the Ephedraceae family contains more than 60 species of nonflowering seed plants distributed throughout Asia, America, Europe, and North Africa. These Ephedra species have medicinal, ecological, and economic value. This review aims to summarize the chemical constituents and pharmacological activities of the Ephedra species to unveil opportunities for future research. Comprehensive information on the Ephedra species was collected by electronic search (e.g., GoogleScholar, Pubmed, SciFinder, and Web of Science) and phytochemical books. The chemical compounds isolated from the Ephedra species include alkaloids, flavonoids, tannins, polysaccharides, and others. The in vitro and in vivo pharmacological studies on the crude extracts, fractions and few isolated compounds of Ephedra species showed anti-inflammatory, anticancer, antibacterial, antioxidant, hepatoprotective, anti-obesity, antiviral, and diuretic activities. After chemical and pharmacological profiling, current research is focused on the antibacterial and antifungal effects of the phenolic acid compounds, the immunosuppressive activity of the polysaccharides, and the antitumor activity of flavonoids.
Article
Ephedra herb is a traditional Chinese medicine with a long history. Conventionally, it was used as a folk phytomedicine in many ancient medical books and traditional prescriptions. Up to date, a variety of specific ingredients have been found in Ephedra herb, mainly including alkaloids, flavonoids, tannins, polysaccharides, organic acids, volatile oils, and many other active compounds. These components from Ephedra herb account for its use as the accurate treatment of cold, cough, cardiovascular and immune system disease, cancer, microbial infection, and other diseases. Moreover, with the fast development of novel chemistry and medicine technology, new chemical constituents and pharmacological effects of Ephedra herb are increasingly identified, demonstrating their great potential for various diseases treatment. Therefore, further detailed understanding and investigation of this ancient herb will offer new opportunities to develop novel therapeutics. This study systematically reviews its progress of phytochemistry, traditional and modern pharmacology based on research data that have been reported, aiming at providing useful insight for commercial exploitation, further study and precision medication of Ephedra herb in future.
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The aim of this work is a phytochemical study, antioxidant activity and Chromatographic Analysis by HPLC of extracts of the female cones of Ephedra alata DC. Which grows in Oued Souf region (South East of Algeria). According to the results obtained from the estimation of polyphenols and flavonoids content, the methanolic extract has the best content of polyphenols (158.34±2.71mg GAE/g Extract), and the best values of flavonoids (88.50±1.12mg QE/g Extract). The chromatographic analysis by HPLC has identified eight phenolic compounds, which are Gallic Acid, Chlorogenic acid, Vanillic Acid, Vanillin, p-Coumaric acid, Rutin, Naringenin and Quercitin. The antioxidant activity was evaluated by three tests: DPPH• free-radical scavenging, Hemolysis and Reducing power, the results of test scavenging the free-radical DPPH• show the tannins extract had the best activity capacity than the other extracts (IC50: 14.94±1.34μg/mL), But, in the hemolysis test, all the extracts were proximity except for the aqueous extract that was shown protected of the erythrocytes (50±0.5% of hemolysis percentage). Finally, in the reducing power assay, its results showed that the tannins extract has a best reducing power 27.16±0.25μg/mL in Abs700= 0.5 compared to other extracts.
Thesis
The descriptions of dubious new species that lack robust taxonomic rigor create more confusion rather than bridging the Linnean shortfall in biodiversity. In an era of biodiversity crisis, it becomes urgent to undertake integrative taxonomic revisions to resolve taxonomic confusions in several plant taxa, even if that leads to drastic decline in the species number. Here I resolve the taxonomic conundrum of Ephedra in India by adopting an integrative taxonomic approach and using comprehensive set of characters from multiple lines of evidence (morphology, anatomy, palynology, seed micromorphology and molecular data). I reduce the number of Ephedra species in India from the currently known 16 to only 4 well-defined species: E. foliata, E. gerardiana, E. intermedia and E. regeliana. I provide proper species delimitations, detailed descriptions, taxonomic keys, photoplates of diagnostic characters, regional distributions and phylogenetic relationships of Ephedra in India, validated by robust empirical evidence. Our studies reveal that the previously reported three species: E. nebrodensis, E. pachyclada and E. przewalskii do not occur in India. The recently described four species (E. sumlingensis, E. pangiensis, E. khurikensis and E. yangthangensis) are synonymized with E. intermedia, and another E. kardangensis synonymized with E. gerardiana. Five recent designations viz. E. sheyensis, E. yurtungensis, E. yurtungensis var. lutea, E. lamayuruensis and E. khardongensis are recognized as nomen nodums due to lack of descriptions, diagnosis and type specimens. Our study provides a robust and reliable set of 16 morphological characters, validated by significant statistical support, which can prove useful for species delimitation in Ephedra. I also recorded few novel characters of evolutionary significance in Ephedra, which merit further investigation in future. Looking ahead, I believe that the methodological and data analytical learnings from this study can guide the future research direction in designing integrative taxonomic studies on such complex plant taxa elsewhere in the world.
Article
The collected information is an attempt to cover the more recent developments in the phytochemistry and pharmacology of this genus. During the past years, alkaloids, flavonoids, volatile oils, organic acids, polysaccharides, tannins and phenolic constituents have been isolated from Ephedra. Pharmacological studies are described according to hypoglycemic effects, anticoagulated blood properties, depressurization, immunosuppressive activity, antioxidation and antivirus activity and so on. The information summarized here is intended to provid a rational foundation for the futher development and utilization of Ephedra which is rich in China.
Article
C-Glycosylflavones have been identified in Ephedra antisyphilitica, Gnetum gnemon and Welwitschia mirabilis. The C-glycosidic moieties of apigenin and luteolin derivatives have been identified as glucose and/or xylose for these species.
Article
The new natural product gossypetin 8-O-β-D-glucuronide-3-sulphate was isolated as a minor flavonoid constituent from the leaves of Malva sylvestris. The structure was established by chromatographic behaviour and acid hydrolysis yielding gossypetin, glucuronic acid and sulphate and confirmed by 1H NMR and 13C NMR spectroscopy.
Article
Die Flavan–3–ole (+)–Catechin, (–)–Epicatechin, (+)–Gallocatechin und (–)–Epigallocatechin sowie die Flavan–3,4–diole (+)–Leukopelargonidin, Leukocyanidin und Leukodelphinidin in den einjährigen und zweijährigen Zweigen sowie in der Rinde einer männlichen Pflanze von Ephedra helv. C. A. Mey. wurden im Verlaufe einer Vegetationsperiode quantitativ durch Absorptionsmessungen direkt von der DC–Platte bestimmt. Dabei ergab sich, daß in den jungen Geweben vorwiegend die (–)–Epi–Verbindungen der Flavan–3–ole gebildet werden, während in den älteren Geweben die entsprechenden (+)–Isomeren entstehen. Auch ist das junge Gewebe der Bildungsort der 3',4',5'–Hydroxyflavan–3–ole, während die 3',4'–Hydroxy-flavan–3–ole in älteren grünen Zweigen gebildet werden. Die Leukoanthocyanidine werden anscheinend in der Wurzel synthetisiert und von dort in die älteren oberirdischen Gewebe transportiert. Der höchste Gesamtgerbstoffgehalt war in den grünen Zweigen im Juli festzustellen, zu einem Zeitpunkt, wo der Gehalt der 3',4',5'–Hydroxyflavan–3–ole stark abnimmt.
Article
Four yellow flavonol pigments earlier reported in the Leguminosae, Ericaceae and Papaveraceae as quercetagetin glycosides have now been found to be the isomeric gossypetin derivatives. Reliable methods are outlined for distinguishing between these isomeric 6- and 8-hydroxyquercetin derivatives on a microscale, including a simple colour test which can be carried out on chromatograms. The yellow flavonol monomethyl ether reported in Lotus corniculatus flower is now shown to be gossypetin 7-methyl ether. Gossypetin, besides occurring in Rhododendron petals, is also widespread in the leaves of this (in 76 of 103 species examined) and nine related genera of the Ericaceae. It also occurs as a leaf constituent in the related Empetrum (Empetraceae). In a survey of legume leaves, gossypetin was only detected once, in Acacia constricta. Surveys indicate that herbacetin, the kaempferol analogue of gossypetin, is much less common, but it has been detected as principal flower pigment in Meconopsis paniculata (Papaveraceae). Consideration of the known natural distribution of the two yellow flavonols indicates that they are of most interest as taxonomic markers at the generic and subfamilial levels.
Article
13C NMR spectra for a variety of flavonoid glycosidcs are presented and analysed. Evidence is presented which demonstrates that 13C NMR spectroscopy is a valuable technique for distinguishing the sites of methylation, glycosylation and acylation in flavonoid glycoiides, and in some cases the nature and sites of specific sugars and acyl groups. Shifts observed in the spectrum on derivization of the 5-OH group are unusual. The ring size and C-1 configuration in glycosidic sugars are also evident from the spectra. Structural assignments are made for several glycoides.