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Terpenes and flavonoids from an Egyptian collection of Cleome droserifolia
Abstract and Figures
Four new sesquiterpene derivatives have been isolated from the aerial parts of Cleome droserifolia. Their structures were established as 6-di(7-hydroxy, 1, 5-epoxy germacrane) (2), 4(15)-guaiane-6-ol (3), 7alpha-germacra-1(10), 4(15)-diene-5beta, 6alpha-diol (4) and 4,7,8-eudesma-triol (5). In addition, a new dolabellane diterpene derivative with the naturally rare peroxy function was identified as methyl ester of 2,18-O-diacetyl-16-O-(3-hydroxy-3-methylglutaryl)-7-hydroperoxydolabella-3,8(17)diene-2,16,18 triol (7). Two known flavonoid derivatives, pinocembrin (6) and quercetin-3-glucoside,7-rhamnoside (1) were isolated from the same source. Structures were established by spectroscopic data.
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Supplementary resource (1)
Data
September 2017
... Phytochemical screening experiments to support the use of this genus for culinary and medicinal purposes [13] C. gynandra, C. viscosa, C. felina L. f. ...
... C. arabica L. Calycopterin [38] C. droserifolia (Forssk.) Delile 5,3 ′ -dihydroxy-3,6,7,4 ′ ,5 ′pentamethoxyflavone, 5-hydroxy-3,6,7,3 ′ ,4 ′ ,5 ′ hexamethoxyflavone, luteolin, 3 ′ -methoxy-3,5,4 ′ -tri-hydroxy flavone-7-neohesperidoside, [13,[39][40][41] [2-amino-9-(4-oxoazetidin-2-yl)]-nonanoic acid. Various other phytoconstituents such as flavonoids, alkaloids, saponins, phenols and amino acids are also found in Cleome species [57,58]. ...
... 1-α-Terpeneol/2-(4-methylcyclohex-3-en-1-yl) propan-2-ol [81] 2-Dodecanone/Dodecan-2-one [81] β-Ionone/(E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl) but-3-en-2-one [81] (+)-Cedrol/(3R,3aS,6R,7R,8aS)-3,6,8,8-tetramethyloctahydro-1H-3a,7-methanoazulen-6-ol. [81] Carvacrol/5-isopropyl-2-methylphenol [81] Pinocembrin/5,7-dihydroxy-2-phenylchroman-4-one [13] Calycopterin/2-(4-hydroxyphenyl)-3,6,7,8-tetramethoxy-4H-chromene-4,5-diol [80] Lactam nonaic acid/2-amino-9-(4-oxoazetidin-2-yl) nonanoic acid [89] Phytol/(E)-3,7,11,15-tetramethylhexadec-2-en-1-ol [82,83] β-Sitosterol/(3S,10R,13R)-17-(5-ethyl-6-methylheptan-2-yl)-10,13-dimethyl-2, 3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol. [80] 5-methyl-5-(4,4,8,10-tetramethyl-3-cabralea lactone/methylenehexadecahydro-1H-cyclopenta[a]phenanthren-17-yl) dihydrofuran-2(3H)-one [72] These phytochemicals were identified as nonaprenol, decaprenol, and undecaprenol, which are composed of a U-terminal isoprene, three internal E-isoprenes, and the remaining Z-isoprene residues, respectively [63]. ...
The species of Cleome genus are taxonomically included in the family of Cleomaceae and in the order of Bras-sicales, representing flowering plants with a long history of use in traditional medicine. Phytochemical screening experiments revealed that Cleome species contain a wide range of beneficial bioactive compounds, including alkaloids, essential oils, fatty acids, flavonoids, terpenes, sterols, and anthocyanins, indicating a therapeutic potential. Furthermore, due to the presence of these phytocompounds, there are various plant species in this genus that have demonstrated a wide range of genotypic, chemo typic, and biological activity in several ecological settings around the world. The potential biological actions and pharmacological effects, such as analgesic, anti-inflammatory, antipyretic, anti-diabetic, antidepressant, antibacterial, anti-arthritic, anticancer, and hepatoprotective are closely related to the active substances contained in various parts of the plants. By centralizing medical data provided by the scientific literature, we offer in the present work a comprehensive perspective on a wide range of bioactive compounds identified from diverse Cleome species, emphasizing the correlation of natural active substances with potential pharmacological activities that can contribute to the improvement of therapeutic management for a range of pathologies. In addition, this review suggests future research perspectives to improve the use of phytochemicals contained in the species of Cleome genus, both in terms of increasing therapeutic efficacy and safety profiles, but also in terms of identifying a possible new pharmacological effect.
... It has been reported that an ethanol extract can treat hyperglycemia in diabetic male albino rats [33]. Phytochemical screening studies on Cleome species have shown that it contains diverse, beneficial secondary products such as terpenoids, flavonoids, phenolics, and alkaloids, and suggest the use of plants from this genus in pharmacological investigations [2]. ...
Wild plants from the desert of Egypt have been traditionally used to treat many microbes. These medicinal plants can overcome the resistance and toxicity of commercial drugs. However, little is known about the antiprotozoal efficacy of these plants. In this study, we evaluated the activity of some Egyptian plant extracts against Toxoplasma gondii and Neospora caninum in vitro. The cytotoxic potentials of these extracts were also evaluated against human foreskin fibroblast (HFF) cells. From 12 plant extracts screened, the methanolic extracts from Artemisia judaica, Cleome droserifolia, Trichodesma africanum, and Vachellia tortilis showed potent activity against T. gondii growth, with half-maximal inhibitory concentrations (IC50, µg/ml) of 2.1, 12.5, 21.8, and 24.5, respectively. Their mean selectivity index (SI) values were 150.8, 29.6, 18.9, and 22.6, respectively. The previously mentioned extracts and the ethanolic extract of P. undulata were further evaluated against N. caninum, with mean IC50 (µg/ml) of 1.0, 3.0, 3.1, 8.6, and 17.2, respectively. Their mean SI values were 370.9, 18.5, 13.2, 36.8, and 32.2, respectively. Our data suggests that these extracts can be used as an alternative source to treat both T. gondii and N. caninum infections.
... [6,7] Phytochemical screening studies carried out on Cleome species revealed the presence of different important secondary products including flavonoids, saponins, coumarins, terpenoids, phenolics and alkaloids. [7][8][9] The ...
The pivotal Cleome arabica L. species belongs to the Cleome genus with fascinating secondary metabolites consisting of main classes of phenols, flavonoids, and glucosinolate derivatives. The current study was carried out on three crude extracts of Cleome arabica L. plant of Jordanian origin. In terms of the valuable resources for natural new drugs development. The phytochemical contents, antioxidants and antibacterial activities, in addition to the oil composition of this species were identified. 46 compounds representing 96.98% of the total composition were detected from the essential oil obtained by hydrodistillation (0.06%). The oil composition was dominated by nitrogen-sulfur-containing compounds (35.66%), esters (19.64%), and oxygenated sesquiterpenes (11.92%). Butanol extract had significantly the best scavenging activities of DPPH (P<0.0001), ABTS (P<0.0001), and hydroxyl radicals (P<0.0001) while the Aq.MeOH extract exhibits the highest flavonoid content (173.5 ± 0.002 mg Quercetin/g dry extract) and had significantly the most ferrous chelating effect (P=0.0011). Also, most of the tested extracts showed antibacterial activities against bacterial strains. Our findings exhibited that the Cleome arabica L. plant from Jordan origin might be a good candidate as potential biologically compounds that could be used as a source of natural antioxidants and antibacterial agents.
... It has been reported that an ethanol extract can treat hyperglycemia in diabetic male albino rats [33]. Phytochemical screening studies on Cleome species have shown that it contains diverse, beneficial secondary products such as terpenoids, flavonoids, phenolics, and alkaloids, and suggest the use of plants from this genus in pharmacological investigations [2]. ...
Wild medicinal plants have been traditionally used as antimicrobial agents. Here, we evaluated the in vitro activity of extracts from wild Egyptian desert plants against Toxoplasma gondii and Neospora caninum. From 12 plant extracts tested, the methanolic extracts from Artemisia judaica, Cleome droserifolia, Trichodesma africanum, and Vachellia tortilis demonstrated potent activity against the growth of T. gondii, with half-maximal inhibitory concentrations (IC50s) of 2.1, 12.5, 21.8, and 24.5 µg/ml, respectively. C. droserifolia, an ethanolic extract of P. undulata, T. africanum, A. judaica, and V. tortilis demonstrated potent efficacy against N. caninum, with mean IC50s of 1.0, 3.0, 3.1, 8.6, and 17.2 µg/ml, respectively. Our data suggest these extracts could provide an alternative treatment for T. gondii and N. caninum infections.
... Regarding its medicinal uses, it has an immediate effect on abdominal and rheumatic pain, is anti-inflammatory, and is also effective for improving wound healing and treating snake bites and scorpion stings [43][44][45][46]. These effects are attributed to the rubefacient, antimicrobial, analgesic, antipyretic, antioxidant, and anti-inflammatory activities of its components [45][46][47][48][49], which include flavonoids, glycosides, carbohydrates, buchariol, teucladiol, daucosterol, cardenolides, saponins, sterols, tannins, catechins, triterpenes and sesquiterpenes as well as a newly described alkaloid found in its aerial parts [50][51][52][53]. C. droserifolia was previously reported to have an antibacterial effect [54], but little is known about its antiprotozoal efficacy. ...
Background: Medicinal plants have been successfully used as an alternative source of drugs for the treatment of microbial diseases. Finding a novel treatment for malaria is still challenging, and various extracts from different wild desert plants have been reported to have multiple medicinal uses for human public health, this study evaluated the antimalarial efficacy of several Egyptian plant extracts. Methods: We assessed the cytotoxic potential of 13 plant extracts and their abilities to inhibit the in vitro growth of Plasmodium falciparum (3D7), and to treat infection with non-lethal Plasmodium yoelii 17XNL in an in vivo malaria model in BALB/c mice. Results: In vitro screening identified four promising candidates, Trichodesma africanum, Artemisia judaica, Cleome droserifolia, and Vachellia tortilis, with weak-to-moderate activity against P. falciparum erythrocytic blood stages with mean half-maximal inhibitory concentration 50 (IC 50) of 11.7 μg/ml, 20.0 μg/ml, 32.1 μg/ml, and 40.0 μg/ml, respectively. Their selectivity index values were 35.2, 15.8, 11.5, and 13.8, respectively. Among these four candidates, T. africa-num crude extract exhibited the highest parasite suppression in a murine malaria model against P. yoelii. Conclusion: Our study identified novel natural antimalarial agents of plant origin that have potential for development into therapeutics for treating malaria.
Pinocembrin (5,7-dihydroxyflavone) is a major flavonoid found in many plants, fungi and hive products, mainly honey and propolis. Several in vitro and preclinical studies revealed numerous pharmacological activities of pinocembrin including antioxidant, anti-inflammatory, antimicrobial, neuroprotective, cardioprotective and anticancer activities. Here, we comprehensively review and critically analyze the studies carried out on pino-cembrin. We also discuss its potential mechanisms of action, bioavailability, toxicity, and clinical investigations. The wide therapeutic window of pinocembrin makes it a promising drug candidate for many clinical applications. We recommend some future perspectives to improve its pharmacokinetic and pharmacodynamic properties for better delivery that may also lead to new therapeutic advances.
Three diterpenoid dolabellane esters were isolated from Cleome droserifolia. The chemical structures of the isolated
compounds were determined by spectral as well as chemical methods. These dolabellanes (I, II and III) are ester derivatives of
3-hydroxy-3-methyl glutaric acid (3-HMGA). Compounds I and II have the second (3HMGA) carboxyl function free, while
compound III is the methyl ester of compound I. This is the first report of the isolation of this class of compounds from the
genus Cleome and is the first report of the isolation of compound III from a natural source. In addition, eight flavone
derivatives were isolated.
The aerial parts of four Cleome and three Capparis species were investigated for their flavonoid constituents. Thirteen flavonoid glycosides were isolated and identified as kaempferol 7-rhamnoside, kaempferol 3-rutinoside, kaempferol 3,7-dirhamnoside, kaempferol 3-glucoside-7-rhamnoside, kaempferol 3-rhamnoside-7-glucoside, quercetin 7-rhamnoside, quercetin 3-rutinoside, quercetin 7-rutinoside, quercetin 3,7-dirhamnoside, quercetin 3-glucoside-7-rhamnoside, isorhamnetin 3-rutinoside, isorhamnetin 3,7-dirhamnoside, and apigenin 6,8-di-C-glucoside.
Hypoglycemic activity of a multicomponent plant tea widely used in Egypt was studied in normal and diabetic rats. No acute toxic effect was observed after oral administration up to 25 g/kg of the preparation. The drug was administered once daily at doses of 0.5-1.5 g/kg by gavage for one month. Serum glucose, creatinine and total bilirubine were reduced significantly, while serum transaminasis (AST, ALT) activities were not altered by the treatment.
Three guaiane derivatives have been isolated from the aerial parts of Teucrium leucocladum. Their structures [1alpha,5beta-guai-10(14)-ene-4beta,6beta-diol (teucladiol), 1alpha,5beta-guaiane-4beta,6beta,10alpha-triol (teuclatriol) and 1alpha,5beta-guaiane-4beta,6beta,10beta-triol (10-epiteuclatriol)] were established by H-1 and C-13 NMR spectroscopic studies and by comparison with closely related compounds. In addition, the already known neo-clerodane diterpene montanin C has also been isolated from the same source.
The aerial parts of four Cleome species (Capparaceae) were investigated for their surface flavonoids. Ten methylated flavonoids were isolated and identified as 5,7,4′-trihydroxy-3-methoxyflavone (isokaempferide), 5,7,4′-trihydroxy-3,3′-dimethyoxyflavone, 5,7,4′-trihydroxy-6,3′-dimethoxyflavone (jaceosidin), 5,4′-dihydroxy-3,6,7-trimethoxyflavone (penduletin), 5,7,3′,4′-tetrahydroxy-3,6-dimethoxyflavone (axillarin), 5,7,4′-trihydroxy-6,3′-5′-trimethoxyflavone, 5,4′-dihydroxy-3,6,7,3′-tetramethoxyflavone (chrysosplenetin), 5,3′-dihydroxy-3,6,7,4′,5′-pentamethoxyflavone, 5,4′-dihydroxy-3,6,7,8,3′-pentamethoxyflavone and 5-hydroxy-3,6,7,3′,4′,5′-hexamethoxyflavone.
A new monoterpene-glycoside (2-exo-β-D-glucopyranosyl-1,8-cineol) named bucharioside from the methanol-soluble part and a new sesquiterpenoid (4,10-epoxy-6α–hydroxyguaiane) named buchariol from the hexane-soluble part of Salvia bucharica were obtained. Their structures were elucidated with the help of NMR spectroscopy including 1D and 2D experiments.