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Daturametelins H, I, and J: Three New Withanolide Glycosides from Datura metel L.
Abstract
Three new withanolide glycosides named daturametelins H-J (1-3), together with two known ones, daturataturin A (4) and 7,27-dihydroxy-1-oxowitha-2,5,24-trienolide (5), were isolated from the MeOH extract of the aerial parts of Datura metel L. (Solanaceae). Their structures were determined mainly by spectroscopic techniques including 2D-NMR (HMBC, HMQC, (1)H,(1)H-COSY, NOESY) and MS experiments. Compounds 1-5 were tested for their antiproliferative activity towards the human colorectal carcinoma (HCT-116) cell line. The nonglycosidic compound 5 exhibited the highest activity of the tested withanolides, with an IC(50) value of 3.2+/-0.2 microM (Table 3).
... The structures of isolated withanolides were elucidated by spectral analyses and evaluated for immunosuppressive activity. The structures of three known withanolides (3)(4)(5) were identified as daturametelin J [14], daturataturin A [14] and daturataturin B [15], respectively by comparing spectroscopic data with previously reported (Figure 1 presence of 40 carbons, including four methyl, eight methylene, ten methine, six quaternary carbons and two β-glucosyl moieties ( Table 1). The characteristic downfield signal at δ C 168.7 was due to α, β unsaturated lactone carbonyl and the singlets at δ C 160.3 and 123.7 were attributed to the quaternary vinylic carbons at C-24 and C-25, respectively. ...
... The structures of isolated withanolides were elucidated by spectral analyses and evaluated for immunosuppressive activity. The structures of three known withanolides (3)(4)(5) were identified as daturametelin J [14], daturataturin A [14] and daturataturin B [15], respectively by comparing spectroscopic data with previously reported (Figure 1 presence of 40 carbons, including four methyl, eight methylene, ten methine, six quaternary carbons and two β-glucosyl moieties ( Table 1). The characteristic downfield signal at δ C 168.7 was due to α, β unsaturated lactone carbonyl and the singlets at δ C 160.3 and 123.7 were attributed to the quaternary vinylic carbons at C-24 and C-25, respectively. ...
... were corresponded to C-6, C-7, C-22, C-2/C-3 and C-4/C-5. A comparison of the 13 C NMR data of 2 to those of daturametelin J[14] suggested that compound 2 possessed the same withanolides steroids skeleton except for the without glucose at C-27. The HMBC correlations between H-19 (δ H 1.43) and C-1 (δ C 208.7)/C-10 (δ C 55.2)/C-9 (δ C 42.6)/C-5 (δ C 157.4) confirmed one methyl, one ketone and one vinylic group at C-10, C-1 and C-5.(Figure 2). ...
Two new withanolides, daturafoliside V (1) and daturafoliside W (2) with three known ones, daturametelin J (3), daturataturin A (4) and daturataturin B (5) were isolated from the pericarp of Datura metel L.. The structures of these compounds were identified by the analyses of spectroscopic data. And their inhibitory activities were evaluated by acting on RAW264.7 cells. Moreover, their molecular mechanisms are discussed based on the p-ERK, p-JNK, p-p38 and NF-êBp65 expression levels. As a result, the new one, compound 2 (IC50 38.3 ìM) exhibited the potential immunosuppressive activity. Our datas indicate that studies on the pericarps of D. metel have great potential to discover new compounds and provide new resource for pharmacology research.
... The plant is reported in old literature as early Sanskrit and Chinese literature reveals its narcotics properties. D. stramonium has also been recognized as a remedy for periods problems (Ma et al. 2006). ...
... The D. stramonium is recognized for cytotoxic activity which revealed the presence of withanolide type steroids that assists in preventing humanoid cancer cell growth (Ma et al. 2006). The plant contains two major alkaloids namely Hyoscyamine and Hyoscine which have uses in ophthalmology and also used as preauesthetic agents in surgery. ...
Three new α-glucosidase inhibitory benzo-isochromenes were isolated from the chloroform fraction of Datura stramonium. Their structures were established with the help of modern spectroscopic techniques and were assigned the names as 1,6,8-triimethoxy-2-methyl-3,4-dihydrobenzoisochromene-5,10-diol, 3,6-dimethoxy-5-hydroxy-4-methylbenzoisochromene-9,11-dione and demethylflavasperon for compounds 1-3 respectively. The α-glucosidase inhibiting activity of compound 2 showed strong inhibition with an IC50 value of 27.5 µM, while compound 1 exhibited moderate activity with IC50 value of 60.2 µM compared to positive control (acarbose).
... Though the flower is typically used as the medicinal part of D. metel L., it is limited because of the short flowering season and low yield [8]. The factor of different production areas also plays an important role in the diversity and quality of the chemical components of D. metel L. Recent research has reported that a large number of withanolides are also found in other parts of D. metel L. [9,10]. Given that withanolides possess good physiological activity and are distributed in different parts of the plant, we are very interested in discovering the best parts and the best production areas for D. metel L. The non-flowering parts of the plants could potentially be used as other natural sources of withanolides compounds, rather than being treated as waste. ...
... Some research has confirmed the role of Daturametelin I (64), Daturametelin J (32), and Daturataturin A (65) as a fungicide of charcoal rot fungus, revealing the antiproliferative activity towards the human colorectal carcinoma (HCT-116) cell line of 7α,27-dihydroxy-1-oxowitha-2,5,24-trienolide (69). Daturafoliside O (30), Daturataturin B (55), and 5α,12α,27-trihydroxy-(20S,22R)-6α,7α-epoxy-1-oxowitha-2,24-dienolide (26) also display significant inhibition of nitrite production [5,9]. This gives us some hints that geo-distribution can be an important evaluation indicator when these compounds are required. ...
Withanolides from six parts (flower, leaf, stem, root, seed, and peel) of Datura metel L. (D metel L.) obtained from ten production areas in China were identified and quantified by UPLC-MS/MS. A total of 85 withanolides were characterized for the first time using the UPLC-Q-TOF-MS/MS system. Additionally, a simultaneous, rapid and accurate measurement method was developed for the determination of 22 bioactive withanolides from ten production areas with the UPLC-Q-TRAP-MS/MS system. The results show the total withanolide content is highest in the leaves (155640.0 ng/g) and lowest in the roots (14839.8 ng/g). Compared with other production areas, the total content of plants from Dujiangyan was the highest at 82013.9 ng/g (value range of ten areas: 82013.9–42278.5 ng/g). The results also show significant differences in the distribution of withanolides in the different plant parts, as well as across different production areas. This is a breakthrough report providing a simultaneous qualitative and quantitative analysis of 22 withanolides in D. metel L. It could be the basis for the more rational use of various parts of D. metel L., and the expansion of medicinal resources. This work also lays a solid foundation for research on the quality control of D. metel L.
... In this paper, we present metabolites identification of four compounds with significant bioactivities, including withanolides (daturataturin A and daturametelin I), and amides (N-transferuloyltyramine and cannabisin F) (Figure 1). Daturataturin A and daturametelin I both have been reported to show significant anti-inflammatory and anti-proliferative activities (Ma et al., 2006;Yang et al., 2014a). In addition, daturataturin A showed cytotoxic activity against MDA-MB-435 and SW-620 cell lines, and potential immunosuppressive activity (Alali et al., 2014;Yang et al., 2017). ...
... The separation details are shown in Supplementary Material and its structure was established by NMR analysis (Supplementary Figures S4-S8 and Supplementary Table S1). Its NMR spectra were very similar to those of 2, except that signals for 7-OH disappeared (Ma et al., 2006). A new methyl group appeared at δ H 3.32 and δ C 56.9, and should be connected to C-7 due to its HMBC correlation with C-7 (δ C 74.0) (Supplementary Figure S8). ...
Datura metel L. is a widely used traditional herbal medicine, and withanolides and amides are the two groups of main bioactive constituents in Datura metel seeds. This study aimed to elucidate the metabolism of four representative bioactive compositions containing daturataturin A (1), daturametelin I (2), N-trans-feruloyltyramine (3), and cannabisin F (4) in rats. After separately oral administration of 20 mg/kg withanolides (1, 2) and amides (3, 4) to rats, a total of 12, 24, and 21 metabolites were detected in the plasma, urine, and fecal samples, respectively. Among them, three hydroxylated metabolites, 1-M3, 2-M2, and 3-M5, were detected in plasma and rat liver microsome incubation system in high abundance. Two metabolites of 1 and 2 were unambiguously identified by comparing with reference standards. Particularly, the methylated metabolite 27α-methoxy-(22R)-22,26-epoxy-27-[(β-D-glucopyranosyl)oxy]ergosta-2,4,6,24-tetraene-1,26-dione (daturametelin L) is a new compound. The withanolides could readily get hydroxylation or methylation metabolism. Meanwhile, the phase II metabolism (glucuronidation or sulfation) was the major reaction for the amides. This is the first study on in vivo metabolism of these active compounds in seeds of Datura metel.
... The methanolic extract also contained two new compound named as daturataturin A and 7,27dihydroxy-1-oxowitha-2,5,24-trienolide. 18 About ten new withanolides namely withametelins I, J, K, L, M, N, O, P, 12β-hydroxy-1,10-seco-withametelin B and 1,10-secowithametelin B, together with seven known withanolides were isolated from methanolic extract of the flowers of D. fastuosa. The structures of these 10 new withanolides compounds were elucidated by means of spectroscopic methods, and the absolute stereochemistry of withametelins I was confirmed by single-crystal X-ray analysis. ...
... µM. 18 Effect on CNS D. fastuosa leaf extract contains important chemical ingredients that can be used to make viable pharmaceutical products with different biological activities on the central nervous system (CNS). The dose most tolerable is 50 ppm so that doses exceeding 100 ppm may be deleterious and may produce side effects. ...
Medicinal plants constitute an effective source of traditional and modern medicines. Traditional system of medicine enlightened the importance of Datura fastuosa Linn (Solanaceae) to have a great medicinal value. The roots, dried leaves and flowering tops have been used in India for their narcotic and antispasmodic properties in the treatment of numerous ailments and conditions. The juice of fresh leaves, or a poultice of them, is used to relieve painful swellings earache. The seeds and root possess antidiarrhoeal, antipyretic properties and are used to treat insanity and fever. The present paper enlightens the chemical profile and pharmacological potential of D. fastuosa and encourages the traditional use to find new therapeutic effects, but under the guidance of a qualified practitioner.
... Withanolide glycosides named daturametelins H-J, together with daturataturin A and 7,27-dihydroxy-1oxowitha-2,5,24-trienolide, were recentlly isolated from Datura metel. The latter nonglycosidic compound showed the highest antiproliferative activity towards the human colorectal carcinoma (HCT-116) cell line [218]. The structures were determined mainly by spectroscopic techniques, including 2D-NMR (HMBC, HMQC, 1 H, 1 H-COSY, NOESY), and MS [218]. ...
... The latter nonglycosidic compound showed the highest antiproliferative activity towards the human colorectal carcinoma (HCT-116) cell line [218]. The structures were determined mainly by spectroscopic techniques, including 2D-NMR (HMBC, HMQC, 1 H, 1 H-COSY, NOESY), and MS [218]. Recently, from the flowers of D. metel, ten new withanolides were isolated: withametelins I-P, 1,10-seco-withametelin B, and 12β-hydroxy-1,10-seco-withametelin B, together with seven known withanolides [219]. ...
The Solanaceae is comprised of some 2500 species of cosmopolitan plants, especially native to the American continent. They have great value as food, like the well-known potato, tomato and eggplants, and medicines, like species of Atropa, Withania and Physalis, but many plants of this family are toxic, and sometimes lethal to mammals, in particular to man. Some of them also produce hallucinations and perceptual changes. The toxic species of this family are characterized by the occurrence of a variety of chemical compounds, some of which are responsible for the toxicity and lethality observed after ingestion, while others are suspected to be toxic. In this review, the following toxic compounds belonging to different members of the Solanaceae family are described: Tropane alkaloids (Atropa, Datura, Hyoscyamus, Mandragora); pyrrolidine and pyrrolic alkaloids (Nierembergia, Physalis, Solanum); protoalkaloids (Nierembergia); glycoalkaloids (Lycopersicon, Solanum); nicotine (Nicotiana); cardenolides (Cestrum, Nierembergia); capsaicinoids (Capsicum); kaurene-type tetracyclic diterpenes (Cestrum); steroidal glycosides (Cestrum, Solanum); 1,25-dihydroxyvitamin D3 and vitamin D3 (Cestrum, Solanum, Nierembergia); and withasteroids, withanolides (Withania), and physalins (Physalis). Other bioactive chemical constituents of members of this family are sugar esters and lectins. Phenylpropanoids are not included in this paper.
... In order to expand the available resources, our group found that the leaves of D. metel have some similarities in chemical constituents with its flowers and significant advantages in terms of high and stable yield. As a result, four new withanolides were isolated and named dmetelins A-D (compounds 1-4), together with one known withanolide, 7α,27-dihydroxy-1-oxowitha-2,5,24-trienolide (5) [19] (Figure 1). The structures of compounds 1-5 were determined by the interpretation of spectroscopic analysis, including 1D and 2D NMR spectroscopy. ...
... In addition, NOEs between Me-19/H-2β and H-2α/H-3α suggested a β orientation of 3-OCH 3 . The configuration of C-20 and C-22 were in good agreement with that of 1. Consequently, compound 2 was identified as 1α,3β,27-trihydroxy-(20S,22R)-1-oxo-witha-4,6,24trienolide and given the common name dmetelin B. (Tables 1 and 2) were very similar to those of 7α,27-dihydroxy-1-oxowitha-2,5,24-trienolide [19], also isolated as compound 5 during this work. A comparison of the 13 C-NMR data of these two compounds indicated that they have the same planar structure. ...
Four new withanolides named dmetelins A-D (compounds 1-4), along with the known compound 7α,27-dihydroxy-1-oxo-witha-2,5,24-trienolide (5) were isolated from the leaves of Datura metel L. (Solanaceae). Their structures were elucidated on the basis of detailed analysis of 1D and 2D NMR and mass spectrometry data. All the compounds were evaluated for their inhibitory effects on lipopolysaccharide (LPS)-induced nitric oxide (NO) production in RAW264.7 cells. Compounds 1, 4 and 5 showed significant inhibitory activities, and compounds 2 and 3 showed moderate inhibitory activities with IC50 values of 17.8, 11.6, 14.9, 33.3 and 28.6 μM, respectively.
... The two major species with allelopathic activities are Datura metel L and Datura stramonium. Ma et al. [117] have identified that the Datura metel contains phytotoxic compounds in the form of withanolide glycosides namely daturametelins H-J, daturataturin-A, and 7,27-dihydroxy-1oxowitha-2,5,24-trienolide present in the aerial parts. Some other allelochemical compounds such as pyrrole compound derivative, 2-(3,4-dimethyl-2,5-dihydro-1H-pyrrol-2-yl)-10 -methyl ethyl pentanoate was extracted and identified from the leaves of Datura metel [118] and sphingosine compound derivatives namely (4E,8Z)-1-O (-D-glucopyranosyl)-N-(20 hydroxyhexadecanoyl)-sphinga-4,8-dienine [119]. ...
Weeds are noxious plants that cause major problems for crop cultivation by interfering with crop growth and development. Due to weed infestation, about 50% of crop yields are reduced. In fact, weed causes more damage than pests and diseases in crop production. In modern agriculture, weeds are managed by using synthetic chemical herbicides. However, in organic farming, weed management is only possible through conventional methods such as manual and mechanical weeding, which are uneconomical and labor-intensive processes. Nowadays, labor shortage is the major problem in agriculture for performing various intercultural operations, especially weed management. In addition, continuous usage of synthetic herbicides can cause contamination to the surroundings thereby resulting in environmental pollution and the evolution of several herbicide-resistant weed species. To address these drawbacks allelopathic potential and allelochemicals can be utilized for weed management. Medicinal plants are rich sources of secondary metabolites with allelopathic potential, which helps to manage weeds by using plants extracts and natural herbicides. Allelochemicals of medicinal plants have the greatest potential for biological weed management by utilizing plant extracts and extracted allelochemicals as natural herbicides. Naturally extracted allelochemicals have almost the same effect as that of using synthetic herbicides in weed management without causing hazards to the environment. Thus, natural herbicides play a vital role in maintaining eco-friendly agriculture and sustainability in soil health. This review will help to create a general view about the allelopathic potential of medicinal plants and also helps to identify future research areas for weed management in organic farming with the help of allelochemicals.
... This supports the antidiabetic potential of D. parasiticum observed in this study. Daturametelin H is a naturally occurring substance found in Datura metel containing an α, β-unsaturated ketone that could contribute to its bioactivity [41], while Stigmastane-3,6-dione is found in Piper nigrum and Metasequoia glyptostroboides [42]. The structures of these identified active components in D. parasiticum leaf extracts are presented in Figure 1. ...
The medicinal plant Dysoxylum parasiticum (Osbeck) Kosterm. (Meliaceae) is native to Indonesia, but its bioactive potential has been little explored. This study de- termined the phenolic content, antioxidant, and antidiabetic activities of D. parasitic- cum leaf extracts. Dried, powdered leaves were sequentially extracted with hexane, ethyl acetate, and methanol. Total phenolic and flavonoid contents were quantified by colorimetric assays. The ethyl acetate extract had the highest phenolic content at 21.54 mg gallic acid equivalents/g dry weight. Antioxidant capacity was evaluated by DPPH radical scavenging assay, while antidiabetic activity was assessed as inhibition of α-glucosidase enzyme. The ethyl acetate extract showed potent antioxidant (IC50 30.72 μg/mL) and α-glucosidase inhibitory (IC50 16.32 μg/mL) activities compared to standard controls. Putative bioactive components were identified by LC-MS/MS, including stylosin, capillartemisin A, 19β-glucosyl-14-deoxy-11,12- didehydroandrographoside, daturametelin H, stigmas-3,6-dione, 2α,3β,4α-trihy- droxy nortropane and arnebinone. The traditional use of D. parasiticum is validated by its antioxidant and anti-diabetic potential, which is associated with its phenolic content.
... Compound 54 showed cytotoxicity in the sub-micromolar range against several tested cell lines. This activity was unusual for the withanolides with a glucosylated moiety as compared with other withanolide glycosides [10,82]. To determine the effect of the glucosyl group on the activity, compound 55 was generated from 54. ...
Natural products are a major source of biologically active compounds that make promising lead molecules for developing efficacious drug-like molecules. Natural withanolides are found in many flora and fauna, including plants, algae, and corals, that traditionally have shown multiple health benefits and are known for their anti-cancer, anti-inflammatory, anti-bacterial, anti-leishmaniasis, and many other medicinal properties. Structures of these withanolides possess a few reactive sites that can be exploited to design and synthesize more potent and safe analogs. In this review, we discuss the literature evidence related to the medicinal implications, particularly anticancer properties of natural withanolides and their synthetic analogs, and provide perspectives on the translational potential of these promising compounds.
... The nonglycosidic compound exhibited the highest activity of the tested with anolides, with an IC50 value of 3.2±0.2 μM (Ma et al., 2006). ...
Anticancer activity against selected herbal plants, biosynthesize, characterization and optimization
... The above analysis depicted the structure of 1 as 3β-hydroxy-14, 20-epoxy-1-oxowitha-5, 24-dienolide-27-O-β-d-glucopyranoside. The known compounds isolated from W. coagulans, were identified as withanolid J (2) [40], coagulin E (3) [6], withaperuvin C (4) [41], 27-hydroxywithanolide I (5) [42], and ajugin E (6) [43] by comparing spectral data to the reported data in the literature. The structures of the compounds 2-6 are presented in Figure 2. ...
Withania coagulans (W. coagulans) is well-known in herbal medicinal systems for its high biological potential. Different parts of the plant are used against insomnia, liver complications, asthma, and biliousness, as well as it is reported to be sedative, emetic, diuretic, antidiabetic antimicrobial, anti-inflammatory, antitumor, hepatoprotective, antihyperglycemic, cardiovascular, immuno-suppressive and central nervous system depressant. Withanolides present in W. coagulans have attracted an immense interest in the scientific field due to their diverse therapeutic applications. The current study deals with chemical and biological evaluation of chloroform, and n-butanol fractions of W. coagulans. The activity-guided fractionation of both extracts via multiple chromatographic steps and structure elucidation of pure isolates using spectroscopies (NMR, mass spectrometry, FTIR and UV-Vis) led to the identification of a new withanolide glycoside, withacogulanoside-B (1) from n-butanol extract and five known withanolides from chloroform extract [withanolid J (2), coagulin E (3), withaperuvin C (4), 27-hydroxywithanolide I (5), and ajugin E (6)]. Among the tested compounds, compound 5 was the most potent α-glucosidase inhibitor with IC50 = 66.7 ± 3.6 µM, followed by compound 4 (IC50: 407 ± 4.5 µM) and compound 2 (IC50: 683 ± 0.94 µM), while no antiglycation activity was observed with the six isolated compounds. Molecular docking was used to predict the binding potential and binding site interactions of these compounds as α-glucosidase inhibitors. Consequently, this study provides basis to discover specific antidiabetic compounds from W. coagulans.
... Withanolides exert antioxidant effect by scavenging the free radicals which are generated by gentamicin which improves histological architecture of kidney (42). Different researchers have reported the presence of withanolides compounds in D. metel plant (43)(44)(45). Mai et al., 2017, has isolated different flavonoids such as kaempferol from D. metel (11). Kaempferol exhibited antioxidant effect and free radical scavenging activity (18). ...
Datura metel is traditionally used as a remedy for renal toxicity. However, the nephroprotection has not been scientifically validated yet. To evaluate the nephroprotective like effect of methanolic extract of D. metel in gentamicin induced mice model, mice of either sex were divided into groups. One group received normal saline as negative control. The 2nd group received gentamicin 100mg/kg for 8 days as positive control, 3rd group received 50mg/kg silymarin as standard, while the reaming groups received 100, 200 and 300 mg/kg of MEDM and gentamicin 100mg/kg, for 8 days. The blood and urine samples were collected on 9th day, animals were then dissected and whole kidneys were removed and preserved in formalin for later histological examinations. The level of serum creatinine, blood urea nitrogen, urine creatinine and urine urea were significantly (P<0.05) elevated and the renal MDA level was also elevated significantly (P<0.05) by gentamicin in mice. After the treatment of test animals with MEDM, the elevated level of serum and urine biomarkers by gentamicin were reversed by MEDM. The nephroprotective effect was found in dose dependent manner. As the MEDM significantly protected the nephrotoxicity via its antioxidant effect. The findings of our study thus proved the scientific background for the nephroprotective effect of MEDM.
... As far as herbicidal (Table 3) and steroid compounds 5 baimantuoluoline B, D, E, F, and compound 8 (Table 4), as well as sphingosine derivatives and pyrrole derivative isolated from genus Datura are responsible for its herbicidal activity. [36][37][38][39] ...
The genus Datura comprises wild shrub plants that belong to the Solanaceae family. Naturally, they possess both medicinal and poisonous properties due to the presence of many biologically active phytochemical constituents. Traditionally, Datura had been used for mystic and religious purposes, as a natural drug to treat asthma, pain, gout, boils, abscesses, and wounds, and as psychoactive infusions and fumitories. Different Datura species exhibit diverse ethnopharmacological activities against different diseases, and many ancient and traditional cultures have used various forms of Datura to treat ailments and to prevent many diseases. In this article, we comprehensively summarize various phytochemical constituents isolated from Datura, their pharmacological properties against different diseases, parts of the plants used as traditional therapeutic agents, regions where they are located, and botanical descriptions of different Datura species. The ethnopharmacological properties of Datura may provide new insights for discovery and development of natural drugs. Further research is needed for the investigation of mechanisms of action and to develop safety profiles of the phytochemical constituents isolated from Datura species.
... Previous pharmacological studies have showed that the D. metel seeds have hypoglycemic activity in normal and alloxan-induced diabetic rats [3], the chloroform extract of D. metel exhibits an antifungal effect toward several pathogenic species of Aspergillus [4], and the seeds and fruit pulps of D. metel show high antioxidant activity [5]. Previous chemical studies have demonstrated that the major chemical components of D. metel are with anolide-type steroids [6-12], which have been shown to suppress NO production in lipopolysaccharide (LPS)-stimulated RAW264.7 cells [11,12] and exhibit cytotoxicity against HCT-116, A549, DLD-1, BGC-823, and K562 cancer cell lines [6,7,10]. In addition, some megastigmane sesquiterpenes and amide alkaloids from D. metel were also reported [13,14]. ...
Chemical investigation of an acidic methanol extract of the whole plants of D. metel resulted in the isolation of five compounds, including kaempferol 3-O-beta-D-glucosyl(1->2)-beta-D-galactoside 7-O-beta-D-glucoside (1), kaempferol 3-O-beta-glucopyranosyl(1->2)-beta-glucopyranoside-7-O-alpha-rhamnopyranoside (2), pinoresinol O-beta-D-glucopyranoside (3), (7R,8S,7'S,8'R)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-D-glucopyranoside (4), and (7S,8R,7'S,8'S)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-D-glucopyranoside (5). Their structures were elucidated by 1D and 2D NMR and MS spectroscopic analyses as well as comparing with the data reported in the literature. The absolute configurations of compounds 4 and 5 were determined by CD spectra. It is noted that (7R,8S,7'S,8'R)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-D-glucopyranoside and (7S,8R,7'S,8'S)-4,9,4',7'-tetrahydroxy-3,3'-dimethoxy-7,9'-epoxylignan-4-O-beta-D-glucopyranoside were isolated for the first time from the Datura genus.
... This antifungal potential may probably be due to the presence of several phytochemical compounds in the extracts. Phytochemical analysis of the methanolic extracts of D. metel aerial parts revealed the presence of five withanolide glycosides namely, daturataturin A, daturametelins H-J and 7, 27-dihydroxy-1-oxowitha-2, 5, 24-trienolide (Ma et al., 2006). In addition, Gupta et al. (1991) identified a hexa cyclic withanolide namely withametelin B which was obtained from D. metel leaves. ...
The present study was undertaken to assess the in vitro antifungal activity of petroleum ether, chlo-roform, methanol and aqueous extracts of Datura metel L. leaves and flowers, against two Trichoderma species (Trichoderma harzianum and Trichoderma viride) and three formae speciales of Fusarium oxysporum, that is, Fusarium oxysporum f. sp. melonis, Fusarium oxysporum f. sp. lycopersici and Fusarium oxysporum f. sp. tuberosi. Radial growth of the pathogen on PDA plates was recorded after 3 to 7 days of incubation at 25°C. Results revealed an important antifungal activity of D. metel leaf and flower aqueous extracts at all concentrations tested (1, 2, 3 and 4%) against pathogenic fungus.How-ever, the extent of response to extracts was species specific. In fact, the highest inhibition (69%) of T. viride mycelial growth was observed with flower aqueous extracts. Indeed, F. oxysporum f. sp. melonis was found to be more susceptible than the other fungal species to organic extract; radial growth inhibition varied from 24 to 76% and from 31 to 76% in the presence of leaf and flower organic extracts, respectively. In addition, the radial growth of F. oxysporum f. sp. Lycopersici was reduced by all organic extracts. The fungicidal activity of leaf extracts was more effective against F. oxysporum f. sp. tuberosias compared to flower extracts. Both Trichoderma species were less sensitive to D. metel organic extracts than Fusarium species. Our findings showed that D. metel extracts can be used as potential source of fungicides to control the phytopathogenic fungi tested.
Key words: Antifungal activity, aqueous and organic extracts, Datura metel, Fusarium, Trichoderma, radial growth.
... Withanolides [105] Daturametelins H-J [106] Cytotoxic activities agains A549 (lung), BGC-823 (gastric) and K562 (leukemia) cancer cell lines [105] 26 Euphorbia neriifolia L(Indain spurge tree) ...
Ayurveda, “life knowledge”, is an ancient Indian traditional medical system, which has been practiced for >5000 years and still in use with the same importance among many cultural tribes in Indian sub-continents. Ayurvedic medicine is a unique holistic approach to treatment where herbal medicines, special diets, yoga and relaxation methods, and lifestyle management are key strategies for curing various chronic diseases like diabetes, cancer, cardiovascular, neurological disorders and many other. Cancer is biologically complex disease, causing local damage and inflammation of cells due to lack of full response in a specific tissue that is responsible to maintain cellular differentiation, survival, proliferation and death. Studies have suggested that bioactive phytochemicals present in Ayurvedic plants (fruits, vegetables and herbs) mediate their effects by inhibiting some of the recently identified inflammatory pathways. Nevertheless, for successful implementation of Ayurvedic principles to drug discovery, major concerns relating to proportion, practicality, safety and drug interactions and possible side effects of newly developed Ayurvedic drugs and formulations need to be addressed. Systematic investigations of Ayurvedic drugs, employing contemporary scientific tools and methods, are expected to lead to the discoveries of major significance. Explorations involving studies of bioactive phytochemicals, their side effects, the specific potential targets and the mechanisms of action would transform this traditional therapeutic approach to standard Ayurvedic drug discovery which would be accepted and embraced by global populations. Current review focuses on the importance of anti-cancer drug discovery from Ayurvedic medicines in the modern context, ongoing improvements and major achievements in the field over the past decade or two.
... The withonilides which are steroidal lactones present in the plant have a have been reported to have a high anticancer activity against colorecto carcinoma (HCT-116) cell line [31, 32]. Many solanaceae species are rich in calystegines, which have glycosidase inhibiting properties against cancer [6].The results obtained hence confirm that the plant has signifcant anticancer potential as stated in the other reports about the species2627282930. Many other phytocomponents extracted can also be expected to contribute to the anticancer activity. ...
Objective: Current clinical trends involve the usage of plants as therapeutic agents in a wide range of applications. Present investigation is focused on the anticancer activity of the methanolic extract of Datura metel against MCF-7 cell line. Materials & Methods: The study was facilitated by collecting the plant sample and subjected to methanol extraction using Soxhlet apparatus. The anticancer activity of the extracted sample against MCF-7 cell line was examined by MTT assay. Results: The study confirms that the leaf extract of Datura metel has pronounced anticancer potential against MCF-7 cell lines while compared to that of the stem extract. Conclusion: The plant investigated possesses remarkable anticancer activity and hence isolation of the compound contributing to the activity may lead to develop at a novel and natural phytomedicine for the disease.
... In Aconitum pendulum, alkaloids, steroids and glycosides have been isolated and determined1617181920. Alkaloids, iridoids and fatty acids were isolated from Strychnos nux-vomica212223. Datura stramonium is rich in alkaloids, flavanoids, withanolides as well as sesquiterpenes24252627. The alkaloids have also been extracted from Anisodus tanguticus [28]. ...
Tibetan ethnomedicine is famous worldwide, both for its high effectiveness and unique cultural background. Many poisonous plants have been widely used to treat disorders in the Tibetan medicinal system. In the present review article, some representative poisonous plant species are introduced in terms of their significance in traditional Tibetan medicinal practices. They are Aconitum
pendulum, Strychnos nux-vomica, Datura
stramonium and Anisodus tanguticus, for which the toxic chemical constituents, bioactivities and pharmacological functions are reviewed herein. The most important toxins include aconitine, strychnine, scopolamine, and anisodamine. These toxic plants are still currently in use for pain-reduction and other purposes by Tibetan healers after processing.
... The nonglycosidic compound exhibited the highest activity of the tested withanolides, with an IC50 value of 3.2±0.2 µM (Ma et al., 2006). ...
Plants have been an exemplary source of medicine. Ayurveda, traditional medicine, tribal medicine and other Bangladeshi literatures mention the use of plants in the treatment of various human ailments. Bangladesh has about 6,000 plant species and among them, around five thousands have been claimed to possess medicinal properties. Researches conducted in the last few decades on exploring plants mentioned in ancient literature or used traditionally for treating diseases is increasing. Datura metel is well known for its insecticidal, herbicidal, anti-fungal, anti-bacterial, anti-cancer, anti-inflammatory and anti-rheumatoid activity. Datura is also rich in Alkaloidal compounds. The present paper summarizes the phyto-chemistry, traditional uses and pharmacological actions of the plant Datura metel.
... l are polar in nature, while n-hexane is non-polar. This reveals that only the polar compounds in the shoots of D. metel are toxic against the germination and growth of parthenium . Various withanolide compounds have been isolated from D. metel which may be responsible for the herbicidal activity of this medicinal plant against the parthenium weed. Ma et al. (2008) isolated five withanolide glycosides named daturataturin A, daturametelins H–J and 7,27-dihydroxy-1-oxowitha-2,5,24-trienolide from the MeOH extract of the aerial parts of D. metel. In addition, sphingosine derivatives (Sahai et al.,1999) and a pyrrole derivative, have also been isolated from leaves of D. metel (Dabur et al., 2004), whi ...
The present study was designed to evaluate herbicidal activity of Withania somnifera and Datura metel against noxious weed parthenium (Parthenium hysterophorus L.). In laboratory bio-assays, the effect of aqueous, methanol and n-hexane shoot and root extracts of 5, 10, 15 and 20% w/v concentrations (on fresh weight bases) of both the plant species was tested against germination and seedling growth of parthenium. In general, aqueous and methanol extracts markedly suppressed germination, and root and shoot growth of parthenium. Shoot extracts were more inhibitory than the root extracts. In foliar spray bioassay, aqueous and methanol shoot extracts of 10% w/v (on dry weight bases) concentrations were sprayed on 1-week and 2-weeks old pot grown parthenium seedlings. Two subsequent sprays were carried out after 5 and 10 days of the first spray. Both types of extracts significantly reduced length and biomass of parthenium shoots. In a soil amendment bioassay, crushed dried leaves of W. somnifera were incorporated in the soil at 1, 2,…5% w/w. Parthenium seeds were sown one week after residue incorporation and plants were harvested 40 days after sow-ing. The various soil amendment treatments of W. somnifera and D. metel reduced parthenium seed germination by 43–89% and 7-89%, respectively. Residues of 4 and 5% concentrations significantly suppressed plant biomass. The present study concludes that foliar spray of aqueous and methanol extracts, and soil amendment with leaf residue of W. somnifera and D. metel can control the germina-tion and growth of parthenium weed.
... Further increase in extract concentration to 15% adversely affected the plant biomass resulting in 45% suppression in plant biomass (Fig.-2D,Table-2). Five withanolide glycosides named daturametelins H-J, daturataturin A and 7,27- dihydroxy-1-oxowitha-2,5,24-trienolide, have been isolated from the methanol extract of the aerial parts of D. metel (Ma et al., 2006), which may be responsible for herbicidal activity of this plant. Methanol root extract was more toxic to P. minor than shoot extract. ...
Present study was undertaken to investigate the herbicidal potential of aqueous and organic solvent (methanol and n-hexane) extracts of shoot and root of Datura metel L. (Syn, Datura alba Nees.) against Phalaris minor Retz., one of the most problematic weeds of wheat in Pakistan. In laboratory bioassays, aqueous, methanol and n-hexane extracts of 0, 5, 10 and 15% (w/v) were applied. Extracts in different solvents exhibited markedly variable herbicidal activities against the target weed species. Germination was significantly reduced by methanol root extract of 5-15% concentrations. Similarly, 15% n-hexane root extract also significantly decreased germination. Root length was significantly suppressed by all the employed concentrations of aqueous as well as organic solvent extracts. Shoot length was significantly declined by all the concentrations of methanol and n-hexane root extracts. The highest concentration of 15% of aqueous and methanol shoot extracts also reduced shoot length significantly. Aqueous shoot extracts were proved highly toxic to plant biomass where all the employed extract concentrations significantly reduced biomass.. The present study concludes that root and shoot extracts of D. metel contain herbicidal constituents. Further studies are suggested to isolate and identify the effective herbicidal constituents from D. metel which can be used as structural lead for the preparation of natural product based herbicide for the management of P. minor.
The interest in using the Datura stramonium plant is due to its natural products, which are used in many pharmaceutical industries. The objective of the current study was to assess the therapeutic and cytotoxic effects of the D. stramonium plant on two types of human cancer cell models (MCF7 and HT29) in vitro. A soxhlet apparatus was used to obtain methanolic extract from dried plant leaves. The recovered crude, after the solvent had evaporated, was then dispersed at varied concentrations of extract 100, 50, 20, and 0.0 µg/mL and tested to see how the cells responded. Also, the cancer-testis antigen (CTA) gene transcription in the two cell types exposed to the plant extract was examined using a semi-quantitative real-time polymerase chain reaction. Gas chromatography–mass spectrometry (GC-MS) results produced the significant main metabolites Nonanoic acid, Tropine N-Oxide, 3,6-Ditigloyloxy-7-hydroxytropane, Hexadecanoic acid, 2-Pentadecanone,6,10,14-trimethyl-, Carvenone, methyl ester, Phytol, Aposcopolamine, Hyoscyamine, 4,8,12,16-Tetramethylheptadecan-4-olide, Scopolamine, Alpha.-Tocospiro A, 1,2-Cycloheptanedione, 3,3,7,7-tetramethyl-, dihydrazone, Campesterol, Stigmasterol, Gamma -Sitosterol and dl-.alpha.-Tocopherol. The results showed that the two types of cell lines impacted by D. stramonium extract, through untreated type 1 cells (MCF7) gave a highly significant transcription according to all applicable genes. All implemented analyses cleared the strong genetic impacts of Datura extract on cancer cells’ genomes. TGIF2LY and C2orf63 transcript accumulation were also significantly elevated when exposed to plant extract at a level of 50 µg/mL in cell line type 2 (HT29), but TGIF2LY and P53 had the lowest relative expression at a level of 100 µg/mL when treated the same cell line type.
Six novel withanolides, along with nine known related compounds were isolated from the leaves of Datura stramonium L. The structures and absolute configurations of the new withanolides were elucidated by employing various spectral techniques and comparing them with those previously reported in the literature. In addition, four withanolides demonstrated interesting cytotoxic activity on LN229 cells with IC50<20 μM.
Toxic compounds can induce the formation of free radicals (reactive oxygen species (ROS)) which can trigger damage and decrease cell viability. Clove (Syzygium aromaticum) contains phenolic compounds that are useful as antioxidants which can reduce ROS toxicity. However, little is known about the antitoxin activity of clove extract. Therefore, this study is aimed at determining the effect of ethanolic clove extract as an antitoxin agent against malachite green (MG) mutagen using the yeast Saccharomyces cerevisiae as a model. The methods used to analyze the ability of ethanolic clove extract as antitoxin were decolorization assay and cell viability test towards MG. The phenol contents of leaf and bud extract were 441.28 and 394.73 mg GAE g-1 extract, respectively. Clove leaf extract has strong antioxidant activity in vitro (IC50 9.29 ppm for 1,1-diphenyl-2-picrylhydrazyl (DPPH) and 29.57 for 2,2 ′ -azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS)). Liquid chromatography quadrupole-mass spectrometry (LC-MS/MS) analysis showed the presence of 4-O-caffeoylquinic acid and several other bioactive compounds, in which these compounds had bioactivity against toxic compound. The addition of extract reduced the ability of S. cerevisiae to decolorize malachite green but increased cell viability. Based on the data, clove leaf extract shows the potential antitoxin activity. This research should facilitate a preliminary study to investigate the antitoxin agent derived from cloves leaf extract. Further research to analyze the antitoxin mechanism of this extract in yeast model is interesting to do to provide a comprehensive insight into the potential antitoxin agents of clove leaf extract.
Three new steroids (1-3) and 13 reported analogs (4-16) were extracted from Datura metel L. pericarps. Structure analysis of these extracted compounds was performed by 1 D-NMR and 2 D-NMR spectroscopy, and their spectra were compared with those of similar compounds previously described in the literature. The extracted steroids (1-3) and known compounds (4-16) were evaluated for anti-inflammatory activity against LPS-activated RAW 264.7 cells. Compounds 5, 7, 9, 12 and 15 showed potential anti-inflammatory activity with IC50 less than 35 μM, while compounds 3 and 11 showed weak anti-inflammatory activity with IC50 less than 100 μM.
The genus Datura has been used as an important traditional medicine in China, as well as in other countries worldwide. This review summarizes the latest progress and perspective of the genus Datura, from the aspects of botany, traditional uses, phytochemistry, pharmacology, and toxicology. Up to May 2022, literatures were collected from online scientific databases, including Google Scholar, PubMed, SciFinder, CNKI, ACS, and Web of Science, and information was also obtained from “Flora Republicae Populairs Sinicae”, Chinese Pharmacopoeia, Chinese herbal classic books, and Ph.D. and M. Sc. dissertations. Studies on chemical constituents, pharmacological activities, and toxicity are mainly focused on D. metel, D. stramonium, and D. inoxia. Furthermore, 496 compounds have been discovered from the genus Datura, including withanolides, alkaloids, flavonoids, terpenoids, phenylpropanoids, steroids, amino acids, aromatics, and aliphatics. Among them, withanolides and alkaloids are two main active constituents. Pharmacological activities of extracts and compounds have been studied from the aspects of antitumor, antiinflammation, antioxidant, antimicrobial, antispasmodic, anticoagulant, analgesic, hypoglycemic and xanthine oxidase inhibitory activities, as well as the effects on central nervous system and immune system. Modern pharmacological studies have provided more clues to elucidate the traditional usages. The toxicity of the genus Datura is noteworthy, especially the potential toxicity on organs. This review would provide a comprehensive and constructive overview for new drug development and utilization of the genus Datura.
Schedule E1 is an important part of Drugs and Cosmetics Act (Government of India) that comprises the list of poisonous drugs from plant, animal and mineral origins to be consumed under medical supervision. Ayurveda, the world's oldest medicinal system has a list of drugs represented in schedule E1 that are used since thousands of years. This review reports the anti-cancer activities of fifteen toxic ayurvedic drugs from plant origin represented in Drugs and Cosmetics Act, 1940. The information was collected from the various authentic sources, compiled and summarised. The plant extracts, formulations, phytoconstituents and other preparations of these drugs have shown effective activities against mammary carcinoma, neuroblastoma, non-small cell lung carcinoma, lymphocytic leukaemia, colorectal adenocarcinoma, Ehrlich ascites carcinoma, prostate adenocarcinoma, glioblastoma asterocytoma and other malignancies. They have various mechanisms of action including Bax upregulation, Bcl2 downregulation, induction of cell cycle arrest at S phase, G2/M phase, inhibition of vascular endothelial growth factors, inhibition of Akt/mTOR signalling etc. Certain traditional ayurvedic preparations containing these plants are reported beneficial and the possibilities of these drugs as the alternative and adjuvant therapeutic agents in the current cancer care have been discussed. The studies suggest that these drugs could be utilised in future for the critical care of malignancies.
Extraction of Datura metel L. leaves with ethanol as a solvent gave a group of steroids, including two unique 1,10-seco-withanolides (1, 4), an unusual nitrogen-containing withanolides (2), one undescribed saponin (3), two withanolides with a carbohydrate (5, 6), and one C21 steroid (7). These compounds' structures were identified based on HR-ESI-MS and ¹H, ¹³C-NMR data analyses, also compared with data from the document. Some compounds showed moderate inhibition on NO production in lipopolysaccharide-stimulated RAW 264.7 cells.
This research aimed to screen potential α-glucosidase inhibitors (AGIs) from Sargassum pallidum, Ecklonia kurome, Hizikia fusiforme and Undaria pinnatifida Suringar. Acetone was the best solvent to extract polyphenolic compounds in brown seaweeds with high total phenolic content. After concentrating with AB-8 macroporous resin, the enriched EtOH extract of Hizikia fusiforme extracts (HFEE) had the highest total phenolic content with 60.2 mg GAE/g E. The enriched acetone extract of Sargassum pallidum (SPEA) indicated the best α-glucosidase inhibitory effect with IC50 value of 270.7 μg/mL. A total of 21 potential α-glucosidase inhibitors were separated from four brown seaweed extracts by ultrafiltration, and included 2 phenolic acids, 5 terpenes, 4 flavonoids, 5 fatty acids, 3 simple phenolic compound, 1 ester and 1 other compound. The main constituents were palmitic acid (0.40–1.21 mg/g), poricoic acid A (0.58–1.62 mg/g), n-hexacosyl caffeate-hexose (0.92–2.37 mg/g), quercetin-3-O-glucuronide (1.02 mg/g in SPEA) and 6- gingerol (1.06–1.87 mg/g). Molecular docking has showed that poricoic acid A and quercetin-3-O-glucuronide could bind the active sites of α-glucosidase and form 4 and 6 hydrogen bonds in ligand-enzyme complex, and then caused the inhibition activity on α-glucosidase. The results showed the significant potential of Sargassum pallidum to be explored as AGIs.
Four new indole alkaloids, daturametelindoles A-D (1-4) were isolated from the EtOAc soluble partition of the ethanol extract of the Datura metel seeds. The structures of the new compounds were determined based on spectroscopic evidence, including their 1D- and 2D-NMR spectra and mass spectrometry. In particular, compounds 1-4 were all racemes, confirmed by the optical rotations and CD spectra. Unfortunately, the chiral monomers were not obtained due to the amount, but the developments of their chiral separation and chiral resolution were completed. All isolated compounds were evaluated for cytotoxic effects against human gastric adenocarcinoma cells (SGC-7901), human hepatoma (Hepg2), and human breast cancer (MCF-7).
Five Exodeconus species were phytochemically analyzed. From the aerial parts of E. pusillus, the 7α,27-dihydroxy-1-oxo-22R-witha-2,5,24-trienolide and three other previously unreported normal-type withanolides were isolated. All the studied species had normal type and/or ring-D aromatic withanolides, and some had already been isolated from other Solanaceae genera, and therefore, these compounds are not chemotaxonomic markers at the generic level. The chemical composition of an undescribed Exodeconus species analyzed here supports the designation of this taxon as a new entity. The integral chemical profile of Exodeconus can be evaluated for its taxonomic implication when a more robust phylogeny of Solanaceae is available that allows the phylogenetic relationships with its closest genera to be clarified.
Twenty three undescribed withanolides, daturmetelides A-W (1-23), were isolated from 70% EtOH extract of the leaves of Datura metel L. The structural characterizations and relative configurations of 1-23 were elucidated by extensive spectroscopic analysis as well as by comparison with literature values. The absolute configurations of 1 and 3 were determined by X-ray crystallography. Bioassay results showed that 1 and 7 exhibited moderate inhibitory effects against NO production in lipopolysaccharide-stimulated RAW 264.7 cells (IC50 values of 13.74 μM and 13.92 μM, respectively). In addition, 1 and 7 showed significant anti-inflammatory activities against the production of TNF-α, IL-1β, IL-6 and COX-2. Western blot analysis was further performed to reveal the mechanism of anti-inflammatory action via inhibition of the NF-κB activation.
One new C 21 -steroid, pregnane A (1), and two new anolides daturafolisides X and Y (2 and 3), together with six known with anolides (4–9), were isolated from the roots of Datura metel L. The structures of these compounds were established by 1D and 2D NMR spectra and mass spectroscopy by comparing our results with the literature values. Compounds 1–9 were evaluated for inhibition against nitric oxide production in lipopolysaccharide-induced RAW 264.7 macrophages. It was found that the isolated compounds showed the different levels of anti-inflammatory activities with IC 50 values ranging from 24.2 to 43.4 μmol/L.
Two new steroids meteloside F (1) and meteloside G (2), together with six known ones (3–8), were isolated and identified from the seeds of Datura metel L. The chemical constituents were isolated by silica gel, ODS chromatogram columns. and preparative HPLC. The structures of these compounds were established by one- and two-dimensional NMR spectra and HR-ESI-MS. The compounds exhibited inhibition on the nitric oxide release of lipopolysaccharide-induced RAW 264.7 cells with IC50 values from 30.2 to 44.8 μM.
Chemical investigation of an acidic methanol extract of the whole plants of Datura metel resulted in the isolation of two new guainane sesquiterpenes, 1β,5α,7β-guaiane-4β,10α,11-triol (1) and 1α,5α,7α-11-guaiene-2α,3β,4α,10α,13-pentaol (2), along with eight known compounds: pterodontriol B (3), disciferitriol (4), scopolamine (5), kaempferol 3-O-β-D-glucosyl(1 → 2)-β-D-galactoside 7-O-β-D-glucoside (6), kaempferol 3-O-β-glucopyranosyl(1 → 2)-β-glucopyranoside-7-O-α-rhamnopyranoside (7), pinoresinol 4′′-O-β-D-glucopyranoside (8), (7R,8S,7′S,8′R)-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxy-lignan-4-O-β-D-glucopyranoside (9), and (7S,8R,7′S,8′S)-4,9,4′,7′-tetrahydroxy-3,3′-dimethoxy-7,9′-epoxylignan-4-O-β-D-glucopyranoside (10). Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D NMR and MS spectra. Compounds 2-4 and 6-10 were shown to have modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated BV cells.
Datura metel L. (Solanaceae) is an annual herb that has been widely used in the traditional medicine for the treatment of coughs, bronchial asthma, and rheumatism. Chemical investigation of an acidic methanol extract of the whole plants of D. metel resulted in the isolation of five new steroidal saponins (1-3, 5, and 6), named metelosides A-E, and four known compounds (4, 7-9). Their structures were elucidated by extensive spectroscopic methods, including 1D and 2D NMR and MS spectra. The structures of metelosides A and B were found to be unusual among the reported spirostane-type steroidal saponins due to the presence of the acetamide groups in the molecules. Compounds 2, 4, 5, and 6 were shown to be cytotoxic against three cancer cell lines, including HepG2, MCF-7, and SK-Mel-2 cells. Furthermore, compounds 3, 4, and 7 exhibited modest anti-inflammatory effects through inhibition of NO production in LPS-stimulated BV cells.
Withanolides are highly oxygenated natural products. These C28 steroids with ergostane-based skeletons functionalized at C-22 and C-26 form six-membered δ-lactone rings. Withanolides containing a δ-lactone side chain often occur in Solanaceae and have a variety of biological activities because of their complicated structures. Characteristic spectroscopic behaviors and biosynthesis of withanolides are conducive to their structural elucidation and “biomimetic synthesis”, respectively. However, the last review to summarize their spectroscopic features and biosynthesis was in 1996. Since then, many withanolides with novel structures have been described by their spectra with biosynthesis investigated with many bioassays. This review surveys δ-lactone withanolides and emphasizes their spectral features, configurations and biosynthetic genes. The period reviewed includes through January 2014. We also include phytochemical species.
Objective: Many therapeutic drugs used for the treatment of Alzheimer's disease are acetylcholinesterase inhibitors. This work was carried out to find out the acetylcholinesterase inhibitory properties of the withanolides of Datura metel. Method: We used modified in vitro assay method of Ellman using acetylcholinesterase from Electropus electricus (electric eel). Methanolic extract of D. metel particularly the withanolide rich fraction of the extract inhibited acetylcholinesterase in a dose dependent manner. Results: Four withanolides e.g. 12-deoxywithastramonolide [IC50 value = 4.6 ± 0.27 (9.775μM)], lycium substance B [IC50 value = 13.61 ± 0.18 (29.978 μM)], withametelin [IC50 value = 21.03 ± 0.51 (48.234 μM)], secowithametelin [IC50 value = 22.97 ± 0.06 (45.039 μM)], had acetylcholinesterase inhibitory property. Conclusion: The results suggest that the acetylcholinesterase inhibitory property of D. metel is due to the presence of these withanolides.
Datura metel Linn., a traditional medicinal plant belonging to the family Solanaceae, is a poisonous herb that grows wild in the tropics. It is now being widely planted due to its chemical and decorative characteristic. In Malaysia, D. metel is locally known as "kecubung", while the Chinese recognized it as "yáng jīn huā" and in other parts of the world it is also known as datura, devil's trumpet as well as raving nightshade. This plant is one of the fifty fundamental herbs in Chinese medicine. Traditionally, the Chinese has been using this herb to treat asthma; in which the dried leaves are rolled and smoked as a cigar. It has also been used for centuries in witchcraft rituals due to its hallucinogenic effects. The present work is aimed to evaluate the cytotoxic property of the methanolic extract of D. metel leaves against two isogeneic human tumour cell lines namely, HCT116 derived from human colorectal cancer and MCF 7 derived from estrogen dependent human breast cancer cells. The cell proliferation assay was performed using tetrazolium (MTT) method. The methanolic extract exhibited significant cytotoxicity against HCT 116 cells with an IC 50 28.4µg/mL. Similarly, it exerted potent cytotoxicity towards MCF7 cells (IC 50 28.77µg/mL). These results highlight the potential of D. metel in the treatment of breast and colorectal cancer. In conclusion, the results showed that D. metel has a potential as an alternative in the treatment of breast and colorectal cancer.
Nine new withanolides, named daturafolisides A-I (1-9), along with six known compounds (22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide-27-O-β-D- glucopyranoside, daturataturin A, daturametelin J, daturataurin B, baimantuoluoside B, 12-deoxywithastramonolide (10-15), were isolated from the leaves of Datura metel L. The structures and absolute stereochemistry of these compounds were elucidated by means of spectroscopic methods including 1D and 2D NMR techniques, mass spectrometry and circular dichroism (CD) analyses. All isolates were evaluated for in vitro anti-inflammatory potential using LPS-stimulated RAW 264.7 murine macrophages. Among them, compounds 1, 2, 14, and 15 exhibited significant inhibition of nitrite production with values of IC50 at 20.9, 17.7, 17.8, and 18.4 μM. Compounds 3, 4, 6, and 13 presented moderate inhibitory activities with values of IC50 at 59.0, 52.8, 71.2, and 53.1 μM, while the rest compounds displayed weak suppressive effect.
Two new withanolides baimantuoluoside H (1) and baimantuoluoline K (2), and one known withanolide glycoside (3) were isolated and identified from the ethyl acetate-soluble fraction of ethanol extract of Datura metel seeds. The structures of the new compounds were determined using 1D and 2D NMR spectroscopy, and mass spectrometry. All isolated compounds were evaluated for their antiproliferative activity against human gastric adenocarcinoma (SGC-7901), human hepatoma (Hepg2), and human breast cancer (MCF-7) cells, as well as their immunosuppressive properties. It was determined that compounds 1-3 exhibited medium antiproliferative and potential immunosuppressive effects.
Toxic plants, regarded as unusual natural resources, are important sources for novel bioactive chemical entities and even new clinical drugs, and are receiving increasing attention. The present review summarizes more than 550 constituents with considerable bioactivities from about 120 toxic seed plant species in the last fifteen years (1998–2012), as well as follow-up studies on structural modification, SAR and action mechanisms, building on the foundations of the first monograph “Toxic plants in China” edited by Chen and Zheng in 1987. A thorough study on bioactive constituents from toxic plants could benefit proper utilization and improve the therapeutic index. It is hoped to lay an available foundation for future drug research and development. On the other hand, bioactive constituents could be used as probes to discover new targets and explore the mysteries of organisms.
The integrated whitefly control systems are based on the contribution of chemical and biological control fostered by conservation of natural enemies. This study attempts to establish the integrated impact of the parasitoid Encarsia inaron Walker (Hymenoptera: Aphelinidae) in junction with the biorational imidacloprid against the greenhouse whitefly, Trialeurodes vaporariorumWestwood (Homoptera: Aleyrodidae), feeding on bean plants cv. Contender under greenhouse condition. Experiments were carried out to establish the individual and combined effects of the parasitoid and insecticide to control the greenhouse whitefly. A synergy effect was observed in the simultaneous use of E. inaron and imidacloprid causing 97.2% mortality in the population of immature whiteflies. There was no significant difference between the application of imidacloprid and the introduction of E. inaron alone which caused 90.1% and 78.7% whitefly mortality, respectively. The application of imidacloprid significantly reduced the percentage of the adult emergence and parasitism of E. inaron to 18% and 25% respectively, compared to control with 47% adult emergence and 57.9% parasitism. The current results suggest that despite some negative impacts of imidacloprid on E. inaron, the combination of these two factors works more efficiently than the use of them separately against the greenhouse whitefly.
Eight steroids, including five withanolides (1-5) and three other ergostane-type steroids (6-8), were isolated from the aerial parts of the halophyte Datura stramonium L., which were collected from the Yellow River Delta in China. Their structures were elucidated on the basis of extensive spectroscopic methods, especially 1D and 2D NMR techniques. Compounds 1 and 2 were new compounds and characterised as (22R)-27-hydroxy-7α-methoxy-1-oxowitha-3,5,24-trienolide and its 27-O-β-d-glucopyranoside. Compound 3 was a new natural product and identified as (22R)-27-hydroxy-1-oxowitha-2,5,24-trienolide and isolated from nature for the first time.
Tassi) Goidanich, the charcoal rot fungus, occurs worldwide and is one of the most economically important fungal pathogens reported to infect about 500 plant species in more than 100 families, including many important crops such as alfalfa, chickpea, maize, sorghum, soybean and sunflower (Wyllie, 1993; Mihail and Taylor, 1995). Charcoal rot disease can be controlled by soil fumigation with methyl Abstract The antifungal activity of leaves of Datura metel for in vitro and in vivo management of Macrophomina phaseoli-na, the causal agent of root rot in mungbean [Vigna radiata (L.) R. Wilczek], was studied. In a laboratory bioassay, methanolic extracts of 0.5, 1.0, 1.5, 2.0 and 2.5 g/100 mL significantly reduced the fungal biomass by 36-47%. In a pot trial, dried powdered leaves of D. metel were mixed in soil at 0.5, 1.0 and 1.5% (w/w) with soil already inocula-ted with the target fungal pathogen. A negative control without fungal inoculation and leaf amendment, and a positi-ve control with M. phaseolina inoculation only, were used for reference. Plant mortality due to M. phaseolina inocu-lation was significantly reduced by 42% and 80% due to 1.0 and 1.5% dry leaves amendments, respectively, as compared to positive control. There was a gradual increase in root and shoot growth of the plants with increase in dose of soil amendment. Generally, 1.5% dose significantly enhanced root and shoot growth as compared to positive control. M. phaseolina root rot in mungbean can effectively be managed by amending the soil with 1.5% dry leaf manure of D. metel. Additional key words: leaf residue; medicinal plants; natural fungicides; Vigna radiata.
Two new C28 steroidal glycosides called daturataturin A (1a) and daturataturin B (2a) were isolated from the methanolic extract of the fresh aerial parts of Datura tatura L. (Solanaceae), and their chemical structures were characterized as (22R)-7α, 27-dihydroxy-1-oxowitha-2, 5, 24-trienolide 27-O-β-D-glucopyranoside and (22R)-1α, 3β, 7α, -27-tetrahydroxywitha-5, 24-dienolide 3-O-β-D-glucopyranoside by spectral analysis.
Two withanolide glucosides, daturametelin A and B, were obtained as major ingredients from the methanol extract of the whole plants of Datura metel L. Their structures were determined by the spectroscopic means.
Minor new withanolides, daturametelins C, D, E, F and G-Ac, have been isolated from the methanolic extract of the fresh aerial parts of Datura metel L. (Solanaceae) and their structures have been determined mainly by spectroscopic means. Daturametelins E anf F are the first withanolides having a 1-one-3β-O-sulfate structure in ring A.
Eight new steroidal lactones of the withanolide series have been isolated from the leaves of Withania somnifera(Solanaceae) growing in North-Western India. This population of W. somnifera differs from those investigated so far and constitutes a new chemotype. The new compounds (IV)—(XI) have been investigated by chemical degradation and interconversion reactions, as well as by analysis of their spectral properties. The following structures have been assigned: 5α,17α-dihydroxy-1-oxo-6α,7α-epoxy-22R-witha-2,24-dienolide (IV); 5α,17α-dihydroxy-1-oxo-22R-witha-2,6,24-trienolide (V); 5α,27-dihydroxy-1-oxo-6α,7α-epoxy-22R-witha-2,24-dienolide (VIa); 4β,17α-dihydroxy-1-oxo-5β,6β-epoxy-22R-witha-2,24-dienolide (VIIa); 17α,27-dihydroxy-1-oxo-22R-witha-2,5,24-trienolide (VIIIa); 7α,27-dihydroxy-1-oxo-22R-witha-2,5,24-trienolide (VIIIa); 7α,27-dihydroxyl-1-oxo-22R-witha-2,5,24-trienolide (IXa); 1α,3β,5α-trihydroxy-6α,7α-epoxy-22R-with-24-enolide (Xa); 4β-hydroxy-5β,6β-epoxy-1-oxo-22R-witha-2,14,24-trienolide (XIa).
The effects of chlordiazepoxide, diazepam and oxazepam on the lethal toxicity and metabolic activation of ifosfamide were investigated in mice. Ifosfamide was administered 24 h after the final injection of chlordiazepoxide, diazepam or oxazepam (100 mg/kg/d for 3 d, i.p.). The prior administration of chlordiazepoxide, diazepam or oxazepam enhanced the toxicity of ifosfamide (778 mg/kg, i.p.) during observation for 6 d after the administration of ifosfamide. In chlordiazepoxide-, diazepam- or oxazepam-treated mice, a higher concentration of active metabolite in the plasma after the administration of ifosfamide (200 or 600 mg/kg, i.p.) was observed as compared with that in mice treated with ifosfamide alone. On the other hand, chlordizepoxide, diazepam or oxazepam markedly enhanced the activity of ifosfamide oxidase in the liver microsomes. These results suggest that the potentiation of ifosfamide toxicity is due to stimulation of the metabolic activation of ifosfamide by chlordizepoxide, diazepam and oxazepam.
Two novel steroids with a cyclopropane ring at C-25 and C-26, 7-oxopetrosterol (1) and 7alpha-hydroxypetrosterol (2), along with two known compounds, petrosterol (3) and 23,24-dihydrocalysterol (4), have been isolated from the Japanese marine sponge Strongylophora corticata. The structures of 1 and 2 were determined as 26, 27-cyclo-24,27-dimethyl-3beta-hydroxycholest-5-en-7-one and 26, 27-cyclo-24,27-dimethylcholest-5-en-3beta,7alpha-diol on the basis of spectroscopic investigations.
Three cytotoxic withanolides, two with new structures, were isolated from the leaves of Acnistus arborescens and their structures determined by a combination of 1D and 2D NMR, mass spectral, and molecular modeling studies. Dereplication analysis of the ethyl ether extract was useful for evaluating the components showing significant cytotoxic activity.
Limonoids have been shown to inhibit the growth of estrogen receptor-negative and -positive human breast cancer cells in culture. The primary objective of this study was to test the antiproliferative activity of limonoids (obacunone 17 beta-D-glucopyranoside, nomilinic acid 17 beta-D-glucopyranoside, limonin, nomilin, and a limonoid glucoside mixture), found in high concentrations in mandarin (Citrus reticulata Blanco), against a series of human cancer cell lines. The human cancer cell lines included leukemia (HL-60), ovary (SKOV-3), cervix (HeLa), stomach (NCI-SNU-1), liver (Hep G2), and breast (MCF-7). The growth-inhibitory effects of the four limonoids and the limonoid glucoside mixture against MCF-7 cells were significant, and the antiproliferative activity of the different citrus limonoids was also dose and time dependent. No significant effects were observed on growth of the other cancer cell lines treated with the four individual limonoids at 100 micrograms/ml. At 100 micrograms/ml, the limonoid glucoside mixture demonstrated a partial inhibitory effect on SKOV-3 cancer cells. With use of flow cytometry, it was found that all the limonoid samples could induce apoptosis in MCF-7 cells at relatively high concentrations (100 micrograms/ml). Considering the high concentration needed to induce apoptosis, it is unlikely that this is the primary mechanism of action for the cytotoxic effects seen with limonoids in this study. Further work is needed in this area to establish the mechanism of action of citrus limonoids on human breast cancer cells.
Activity-guided fractionation of the bark of Nephelium maingayi, collected in Indonesia, led to the isolation of six new saponins (1-6). The aglycon of 4 was determined to be a new compound, 7alpha-methoxyerythrodiol, and those of 1-3 and of 5 and 6 were identified as erythrodiol and maniladiol (16beta-hydroxyamyrin), respectively. The structures of 1-6 were determined on the basis of spectral data interpretation, and the absolute configurations of their component monosaccharides were determined as their thiazolidine derivatives after acid hydrolysis. Of the isolates, only compounds 1 and 5 showed very weak cytotoxic activity against a panel of human tumor cell lines.