ArticleLiterature Review

[Alkaloids of Solanaceae (nightshade plants)]

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Abstract

Alkaloids are nitrogen containing compounds found in many plants. They are products of plants secondary metabolism derived from amino acids, purines, pyrimidines or terpene. Most of them are drugs. The biological activity of some alkaloids has led to their intensive exploitation by humans, as pharmaceuticals, narcotics or poisons. During the past 30 years, major technical advances have led to substantial progress in our understanding of alkaloid biochemistry, but since then biosynthetic pathways of some alkaloids are not explained. The nightshade (Solanaceae) are widespread family of plants containing tropane alkaloids or glycoalkaloids. Both of them are naturally produced, as a defense mechanism against insects, predator and disease. On the other hand, most of the species of Solanaceae family have been used by human since several centuries.

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... The Solanaceae family belongs to the most important plant taxa, particularly in terms of food production (e.g., tomatoes and potatoes), and its members are used in medicine (e.g., deadly nightshade, jimson weed) or as drugs (e.g., tobacco) [32]. Solanaceae plants have an enormous potential to deliver new chemicals for crop protection; more and more of these compounds, or mixtures of these compounds, are being identified as pest control agents, especially against insects, fungi and mites [33]. ...
... The broad alkaloid group is divided into a number of subgroups that share similar structures, and closely related plant species generally contain alkaloids with related chemical structures. Solanaceae is a widespread family of species rich in alkaloids, including tropane alkaloids, glycoalkaloids, pyrrolizidine and indole alkaloids, which are naturally produced as a defense mechanism against insects, predators and disease [33]. ...
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Only a small percentage of insect species are pests. However, pest species cause significant losses in agricultural and forest crops, and many are vectors of diseases. Currently, many scientists are focused on developing new tools to control insect populations, including secondary plant metabolites, e.g., alkaloids, glycoalkaloids, terpenoids, organic acids and alcohols, which show promise for use in plant protection. These compounds can affect insects at all levels of biological organization, but their action generally disturbs cellular and physiological processes, e.g., by altering redox balance, hormonal regulation, neuronal signalization or reproduction in exposed individuals. Secondary plant metabolites cause toxic effects that can be observed at both lethal and sublethal levels, but the most important effect is repellence. Plants from the Solanaceae family, which contains numerous economically and ecologically important species, produce various substances that affect insects belonging to most orders, particularly herbivorous insects and other pests. Many compounds possess insecticidal properties, but they are also classified as molluscides, acaricides, nematocides, fungicides and bactericides. In this paper, we present data on the sublethal and lethal toxicity caused by pure metabolites and crude extracts obtained from Solanaceae plants. Pure substances as well as water and/or alcohol extracts cause lethal and sublethal effects in insects, which is important from the economical point of view. We discuss the results of our study and their relevance to plant protection and management.
... The ingestion of particular plants may induce anticholinergic syndrome, which is caused by their alkaloid metabolites (atropine, scopolamine, and hyoscine) as defence mechanism against insects and predators. 3,4 They include Solanaceae family (Mandragora officinarum, "Mandrake"; Mandragora autumnalis, "Devil's herb"; Hyosciamus niger and H. reticularis, known as "henbane"; Burgmansia spp., "Angel's Trumpet"), Datura spp. (Datura inoxia ''Moonfl ower'', Datura stramonium ''Jimson weed'', Datura metel ''Devil's trumpet''); Solanum erianthum, Garryaceae family (Garrya spp.), Bignoniaceae family (Campsis grandiflora), Papaveraceae family (Lamprocapnosspectabilis, "bleeding heart"), 5 and Aquifoliaceae family (Ilex paraguariensis, "Herba mate"). ...
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We report the case of a 32-year-old Italian man admitted to our emergency room for visual disturbances with blurred vision, anisocoria and temporal headache suddenly occurred in absence of other neurological symptoms. A diagnosis of Datura stramoniuminduced anticholinergic toxicity was done. With our work, we want to highlight the importance of a meticulous clinical examination, including papillary diameter and reflexes, combined with a detailed history of the patient in the emergency room. Anticholinergic toxicity is a medical emergency. The diagnosis is always clinical, and it can represent a challenge for the emergency clinicians because it can mimic several neurological diseases, including acute stroke and seizures, but early diagnosis is crucial to avoid severe complications and management errors.
... However, toxic alkaloids such as tropane alkaloids or glycoalkaloids are of particular interest because of their reported antimicrobial, anti-rheumatic and antioxidant activities [145]. They have also demonstrated antitumour activity against several types of cancer, including prostate, breast and colon cancer [146,147]. Tropane alkaloids such as atropine, hyoscyamine and scopolamine have a characteristic bicyclic structure, and particularly high concentrations have been found in Datura stramonium, Datura ferox and Datura innoxia. Atropine is a racemic mixture of two enantiomeric forms of hyoscyamine, with the L-enantiomeric form being the active one. ...
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Many of the anticancer agents that are currently in use demonstrate severe side effects and encounter increasing resistance from the target cancer cells. Thus, despite significant advances in cancer therapy in recent decades, there is still a need to discover and develop new, alternative anticancer agents. The plant kingdom contains a range of phytochemicals that play important roles in the prevention and treatment of many diseases. The Solanaceae family is widely used in the treatment of various diseases, including cancer, due to its bioactive ingredient content. The purpose of this literature review is to highlight the antitumour activity of Solanaceae extracts—single isolated compounds and nanoparticles with extracts—and their synergistic effect with chemotherapeutic agents in various in vitro and in vivo cancer models. In addition, the biological properties of many plants of the Solanaceae family have not yet been investigated, which represents a challenge and an opportunity for future anticancer therapy.
... Many of the members of this family have medicinal properties, as well as hallucinogenic, narcotic, and even poisonous activities. Such properties are due to the fact that many members of this family contain tropane alkaloids and glycoalkaloids naturally produced by defense mechanisms of the plant itself against insect predation, herbivory, and attacks by pathogenic organisms (Jerzykiewicz, 2007). Despite being highly diverse, only a few species of the Solanaceae are food crops of economic importance: potatoes, tomatoes, Capsicum peppers, eggplants, pepino melons, naranjillas, and tamarillos (tree tomatoes) (Gebbhardt, 2016). ...
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This review focus on the use of elicitors of plant defense for shelf life extension of the four main Solanaceae food crops: potatoes (Solanum tuberosum), tomatoes (S. lycopersicum), eggplants (S. melongena), and Capsicum peppers (chillies and peppers). An overview of worldwide production and losses of these cultures from 2006 onwards is provided, along with the current proposals for the mechanisms of plant colonization by pathogens and the induced resistance in the host, as well as the physiology and biochemistry involved in the use of elicitors during the postharvest phase. A search was made on the patents and published papers on this subject from 2015 to 2020. On average, worldwide losses in storing operations may reach 14.16%, 18.96%, and 1.31% for potatoes, tomatoes, and chilli peppers, respectively, while for eggplants, the losses reach 9.85% along distribution phase. In spite of the increase of elicitor utilization, their mechanisms of action and large-scale applicability are still under investigation. It is noteworthy that the number of published research articles is greater than the number of patents related to the subject, which reflects the difficulties involved in technological developments. Biological agents and natural compounds are indistinctly used as elicitors, according to the literature and patents reviewed. The integrated management of the losses during the postharvest phase has seen the successful inclusion of the use of elicitors of plant defense as a promising trend for sustainable agriculture now and in the next years.
... The extract of E. pavonii, a species endemic to western Ecuador, showed presence of alkaloids and flavonoids. Alkaloids are characteristic compounds of the Solanaceae family (Jerzykiewicz, 2007). Erythrochiton giganteus and Erythroxylum patens have a moderate presence of alkaloids, flavonoids, tannins and terpenes. ...
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The phytochemical screening, total phenolics and flavonoids content and antioxidant activity of plants native to western Ecuador were investigated to provide the basic information for further studies towards the discovery of new compounds. The species studied were Adenostemma platyphyllum Cass., Castilla elastica subsp. gummifera (Miq.) C.C. Berg., Cochlospermum vitifolium (Willd.) Spreng., Ectozoma pavonii Miers, Erythrochiton giganteus Kaastra & A.H. Gentry, Erythroxylum patens Ruiz ex O.E.Schulz, Ficus brevibracteata W.C. Burger, Ficus tonduzii Standl., Grias ecuadorica Cornejo & S.A. Mori, Handroanthus billbergii subsp. ampla (Bureau K. Schum.) S.O. Grose, Morisonia americana L., Operculina codonantha (Benth.) Hallier f., Passiflora macrophylla Spruce ex Mast., Podandrogyne jamesonii (Briq.) Cochrane, Pradosia montana T.D. Penn., Tecoma castaneifolia (D.Don) Melch, Urera baccifera (L.) Gaudich. ex Wedd., and Xanthosoma sagittifolium (L.) Schott. The highest percentage of inhibition of DPPH• was found in E. patens (92.41%). Most of the extracts evaluated exhibited antioxidant activity.
... The role of alkaloids as defense matabolites, extensively studied in alkaloid-containing plants in general, 734 in Solanaceae plants, 44,45,735 and specifically in Datura stramonium, 84 are well known and published. But I. Shonle and J. Bergelson published an interesting research, which actually proposes that D. stramonium alkaloids have another opposite role. ...
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Solanaceae is one of the most studied among all plant families. Plants of this family are very rich with medicinally active natural products, some of them, with nutritional importance. Some of these compounds are psychoactive and mind altering. Alkaloids, physalins and withanolides are the major notable active natural products present in these plants. In this review article, we will present the vast majority of published research about these plants. This work will include biological and medicinal activities, extended presentation of natural products, their activities and in some cases, their synthesis, biosynthesis and production, along with other chemical aspects. Despite all the wideness of this article, we have introduced limited (but not ignored. presentations of two important aspects of this plant family, mainly due to the large size of this article. One, ethnobotany and ethnomedicine uses of these plants, and two, the influence of various cultivation conditions on these plants, and the results of these conditions.
... Eggplant (S. melongena L.) is the 2nd most essential vegetable crop after tomato (S. lycopersicum L.) which belongs to the enormous and species-rich genus S. L. (Solanaceae) (Knapp et al. 2013). Solanaceae plants have acquired an immense potential to deliver new chemicals for crop stability especially against detrimental insects, fungi, and mites (Chowański et al. 2016;Jerzykiewicz 2007). The adverse consequence of pesticide on seed germination has been studied by several researchers so far. ...
Article
Eggplant (Solanum melongena L.cv. Longai) is an essential vegetable crop grown during November to January in Karimganj district of Assam. However, these crops suffer from biotic stress like insect, pests, and rodents, which curtail the quality of fruits yield. In the present study, the effect of excessive use of insecticide like malathion (PM) and tatafen (PTF) with different concentrations viz. 50, 100, 150 and 200 ppm were exposed once and observations were recorded after 7 days of treatment. The obtained results affirmed that seedling growth, relative water content, fresh and dry weight was reduced and had a steady phytotoxicity response by the higher concentration of both insecticide and effect was more prominent at early stage of treatment. The activity levels of hydrogen peroxide (H2O2) and proline content were analyzed. To cope with a detrimental impacts of insecticide-induced oxidative stress, low levels of insecticide provide enhance results than the higher concentration as compared to the control plant.
... It has been reported that species belonging to the Solanaceae family can present a prominent toxicity attributable to the presence of a wide repository of alkaloids, including tropanealkaloids, glycoalkaloids, pirrolizidin and indol alkaloids, which are produced as a natural defense mechanism against insects, predators and infectious agents [47]. Alkaloids typical of Solanaceae plants, including α-tomatine, α-chaconine and α-solanine have been reported as displaying insecticidal activity against species of economic and medical importance [48,49]; therefore, it seems plausible that the lethal effect observed in the present study is, at least partially, due to the presence of these chemicals in the S. mammosum aqueous extract. ...
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The family of mosquitoes (Diptera: Culicidae) contains several species of major public health relevance due to their role as vectors of human disease. One of these species, Aedes aegypti, is responsible for the transmission of some of the most important vector-borne viruses affecting humankind, including dengue fever, chikungunya and Zika. Traditionally, control of Ae. aegypti and other arthropod species has relied on the use of a relatively small diversity of chemical insecticides. However, widespread and intensive use of these substances has caused significant adverse environmental effects and has contributed to the appearance of pesticide-resistant populations in an increasing number of locations around the world, thereby dramatically reducing their efficiency. Therefore, it becomes urgent to develop novel alternative tools for vector control. In that context, our study aimed at evaluating the insecticidal activity against Ae. aegypti of aqueous extracts obtained from the fruits of Solanum mammosum L., as well as silver nanoparticles synthesized using aqueous extracts from this plant species (SmAgNPs). To perform the test, third instar Ae. aegypti larvae were exposed to increasing concentrations of plant extract and SmAgNPs for 24 h. Our results suggest that both the aqueous extract and SmAgNPs were toxic to the larvae, with SmAgNPs displaying a much higher level of toxicity than the extract alone, as reflected in their LC50 values (0.06 ppm vs 1631.27 ppm, respectively). These results suggest that both S. mammosum extracts and SmAgNPs exhibit noteworthy larvicidal activity, and should be further explored as potential source of alternative tools in the fight against insect vectors of human disease.
... Caffeine is one of the well-known alkaloids. The large group of alkaloid is classified into a number of subclasses that have similar configuration, and closely related plant varieties commonly contain alkaloids with similar molecular structures (Jerzykiewicz, 2007). ...
... Solanceae family constitutes a large, widespread group of plant species with a remarkable high concentration of alkaloids, which are secondary metabolic products that form a defense mechanism against insects, predator and disease. [14] Alkaloids are pharmacologically active, nitrogen-containing compounds that are divided in several subgroups. An important subgroup of alkaloids, commonly found in plants of the Solonceae family, is tropane alkaloids. ...
... Aerial part of Acnistus arborescens (Solanaceae) showed major content of alkaloids and tannins, while steroles were present in less proportion. Some species of Solanaceae, are knows due to the biosynthesis of different kinds of alkaloids which present very important pharmacologic properties (Jerzykiewicz, 2007). However, alkaloids isolated from A. arborescens has not been reported. ...
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Phytochemical screening of ethanolic extracts of Acnistus arborescens (L.) Schltdl. (Solanaceae); Albizia multiflora (Kunth) Barneby & J.W. Grimes (Fabaceae); Capparidastrum petiolare (Kunth) Hutch. (Capparaceae); Colicodendron scabridum (Kunth) Seem. (Capparaceae); Gronovia scandens L. (Loasaceae); Gustavia angustifolia Benth. (Lecythidaceae); Piscidia carthagenensis Jacq. (Fabaceae); Psidium rostratum Mc Vaugh (Myrtaceae); Psidium guayaquilense Landrum & Cornejo (Myrtaceae); Psidium cf. rostratum Mc Vaugh (Myrtaceae); Salicornia fruticosa L. (Amaranthaceae); Simira ecuadorensis (Standl.) Steyerm. (Rubiaceae); Ruellia floribunda Hook. (Acanthaceae) were assayed. Alkaloids, tannins and terpenoids were the secondary metabolites most frequently found, while flavonoids, quinones, anthraquinones, steroids and saponins were present in less proportion. Folin-Ciocalteu method was used to quantify the total phenolic content in the ethanolic extracts using a calibration curve of gallic acid. The range between 941.97 ± 30.69 and 241.54 ± 15.54 GAE/mg dry extract, has been observed for Psidium guayaquilense and Acnistus arborescens, respectively. On the other hand, antibacterial activity of the ethanolic extracts was evaluated using the disk diffusion agar method against Staphylococcus aureus ATCC 25923, Escherichia coli ATCC 25922 and Vibrio parahaemolyticus ATCC 17802. P. rostratum, P. guayaquilense, P. cf. rostratum, R. floribunda and S. ecuadorensis were the most active extracts against the bacterial assays with minimal inhibitory concentration (MIC) values ranging between 20 and 100 ppm. According to literature, it is most likely that this is the first report on phytochemical screening, total phenolic content and antibacterial activity of ethanolic extracts of these species.
... La primera es endémica del Perú, y junto a la segunda constituyen parte de la diversidad vegetal de las lomas costeras. 5,6 Numerosos estudios han demostrado que los alcaloides de la familia Solanaceae, exhiben diversas propiedades biológicas, sea el caso de la hiosciamina, atropina y escopolamina, ya usados en medicina. También alcaloides como tomatina, solanina, solasodina, β-solamarina, desacetoxi-solafilidina y 2a-hidroxisoladulcidina, han demostrado poseer propiedades antinociceptivas y antibacterianas frente a bacterias gram positivas y gram negativas. ...
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Introducción: Solanum multifidum Lam., y Lycianthes lycioides (L.) Hassl. son dos especies características de las lomas costeras del Perú. Ambas pertenecen a la familia Solanaceae, conocida por su elevado contenido de alcaloides con diversas actividades terapéuticas, lo que motivó su estudio. Objetivo: evaluar la actividad antinociceptiva y antibacteriana de los alcaloides totales de las hojas de Solanum multifidum Lam., y Lycianthes lycioides (L.) Hassl. Métodos: los alcaloides totales se extrajeron de las hojas secas de las especies estudiadas, mediante el método descrito por Peña. La actividad antinociceptiva se evaluó in vivo utilizando el test de las contorciones abdominales, mientras que la actividad antibacteriana in vitro se evalúo utilizando la técnica de difusión en agar con discos impregnados y se determinó la concentración mínima inhibitoria mediante el método de dilución en agar. Resultados: los alcaloides totales de ambas especies presentaron actividad antinociceptiva a las dosis de 2,5 mg/kg, 5 mg/kg y 10 mg/kg., mostrando mayor porcentaje de inhibición, a dosis de 10 mg/kg., con diferencias estadísticamente significativas (p< 0,05). Asimismo, estos alcaloides inhibieron el crecimiento de Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 25992), y Pseudomona aeruginosa (ATCC 27853), a las concentraciones de 2 mg/mL y 4 mg/mL, mostrando mayor bioactividad frente a Staphlylococus aureus. En términos generales, los alcaloides totales Lycianthes lycioides (L.) Hassl., resultaron ser más activos como antinociceptivos y antibacterianos. Conclusiones: se demostró la actividad antinociceptiva y antibacteriana de los alcaloides totales de ambas especies. Este trabajo constituye el primer reporte de la bioactividad de estas especies vegetales, y resulta una opción atractiva para el desarrollo de nuevos fármacos.
Article
Introduction: Solanum multifidum Lam. and Lycianthes lycioides (L.) Hassl. are two species typical of coastal hills of Peru. Both belong to the Solanaceae family, and are renowned for their high content of alkaloids with a variety of therapeutic activities. That was the reason why the present study was conducted. Objective: evaluate the antinociceptive and antibacterial activity of total alkaloids from leaves of Solanum multifidum Lam. and Lycianthes lycioides (L.) Hassl. Methods: total alkaloids were extracted from dry leaves of the study species following the method described by Peña. Antinociceptive activity was evaluated in vivo using the writhing test, whereas in vitro antibacterial activity was evaluated with the agar diffusion technique with impregnated discs. Minimum inhibitory concentration was determined by the agar dilution method. Results: in both species total alkaloids showed antinociceptive activity at doses of 2.5 mg/kg, 5 mg/kg y 10 mg/kg, with the greatest inhibition percentage at 10 mg/kg and statistically significant differences (p< 0.05). The alkaloids also inhibited the growth of Staphylococcus aureus (ATCC 25923), Escherichia coli (ATCC 25992) and Pseudomona aeruginosa (ATCC 27853) at concentrations of 2 mg/mL and 4 mg/mL, exhibiting greater bioactivity against Staphlylococus aureus. In general terms, total alkaloids Lycianthes lycioides (L.) Hassl. showed the greatest antinociceptive and antibacterial activity. Conclusions: it was demonstrated that total alkaloids from both species have antinociceptive and antibacterial activity. The present paper is the first report about bioactivity of these plant species, an attractive option for the development of new drugs.
Plants from the genus Physalis L. (family Solanaceae), native to warm and subtropical regions of Central and South America, are particularly rich in secondary metabolites, e.g.: withanolides, physalins, calystegines, tropane and nortropane alkaloids. Due to the high biological activities of these compounds, in the tropics Physalis plants have been used for centuries as medicinal herbs in the treatment of urinary and skin diseases, gonorrhea, ulcers, sores and as a vermicidal drug. This review describes the main categories of secondary metabolites, their distribution, chemistry, biosynthesis as well as biological activities. Particular attention is given to their potent anticancer activities.
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