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Pyrrolizidine alkaloids found in Borago officinalis (borage): (A) Flower of B. officinalis. Young flowers show a bright blue color while older flowers exhibit, because of a lower pH, a slightly reddish coloration. (B) Leaves of B. officinalis contain the supinidine-type PAs amabiline and supinine and the retronecine-type lycopsamine and intermedine as well as their 7-acetylated derivatives. Seeds contain mainly the (-)-isoretronecanol-type PA thesinine and its glucoside thesinine-4′-O-β-D-glucoside.
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Pyrrolizidine alkaloids (PAs) are heterocyclic secondary metabolites with a typical pyrrolizidine motif predominantly produced by plants as defense chemicals against herbivores. They display a wide structural diversity and occur in a vast number of species with novel structures and occurrences continuously being discovered. These alkaloids exhibit...
Citations
... These stretching and bending vibrations indicate the presence of an alkane. As well as noticed the amide II or N-H stretching that located at 1518 cm -1 and 1521 cm -1 and C-N at 1018 cm-1 and 1021 cm -1 due to vibrations of amines (22). Consequently, Olive leaves contain organic functional groups such as alkanes, aromatic compounds, and amide linkages of protein and amine (23). ...
The removal of a high level of cadmium in drinking water by olive leaves as a natural material is a simple way to produce high quality water. The study revealed that olive leaves were able to effectively remove a significant percentage of cadmium. Using a 0.5 gm sample size of ground olive leaves could remove 91.3% of cadmium with an initial concentration of 100 ppm within 120 min. A significant increase in the removal of Cd (II) with an increase in the olive dosage and increase in temperature could be observed.
... They are known to cause severe hepatotoxicity, genotoxicity and neurological damage affecting farm animals, wildlife and humans(Neuman et al., 2015). Pyrolizidine alkaloids can be found mainly in the Boraginaceae and Asteraceae families(Schramm et al., 2019).3.9. Tropane alkaloidsTropane alkaloids are derived from ornithine and have a complex structure(Mao et al., 2014). ...
ZYAZICI ve Doç. Dr. Esra UÇAR'ın yapacağı Ziraat, Orman ve Su Ürünü alanlarında özgün çalışmalar içeren "DIFFERENT PERSPECTIVES IN MEDICINAL AND AROMATIC PLANTS" adlı kitapta yayınlanmaya uygun görülmüştür. Uluslararası olarak yayınlanacak olan kitap çalışmamızda bölümünüzün yer almasını düşünmekteyiz. Çalışmalarınızda başarılar dileriz.
... They are prevalent in the plant families of Asteraceae (tribes Senecioneae, genera Senecio and Eupatorieae), Boraginaceae (genera Heliotropium, Echium, and Symphytum), Apocynaceae, Orchidaceae, one genus of the Fabaceae (genus Crotalaria). Many plant species which accumulate PAs are used in traditional medicine for the treatment of various diseases, others are used as foods or fodder crops [48,49] as seen in Figure 3. ...
... The PA distribution is highly dynamic and the diversification in PA accumulation in different organs may indicate a defensive strategy against herbivores. Furthermore, PA expression is influenced by nutrient and water supply, as well as herbivore infestation [49]. ...
... The PA distribution is highly dynamic and the diversification in PA accumu different organs may indicate a defensive strategy against herbivores. Furtherm expression is influenced by nutrient and water supply, as well as herbivore inf [49]. Asteraceae species synthesize the PAs exclusively in the roots; for example, in the senecionine N-oxide derives from the backbone structure of macrocyclic PA senecionine type, which is biosynthesized in the roots and then translocated to through the phloem, where it is further functionalized to produce species-specific terns [55], while biosynthetic localization of PAs in in the Boraginaceae are more v So far, the site of biosynthesis is species dependent; it can be is located in the enti (e.g., H. indicum), in roots (e.g., S. officinale), or both roots and shoot (e.g., C. officin ...
Invasive plant species pose a significant threat to global biodiversity and ecosystems. Climate changes favor the spread of non-native plants, whether voluntary or accidentally introduced into a new environment, as these plants possess a greater ability to adapt to changing environments. The spreading of these alien species has a negative impact also on agro-ecosystems, on agricultural yields, and on the nutritional quality of food crops. The high metabolic plasticity of these plants helps them to adapt to new ecosystems, enabling them to succeed in competing with crops. In particular, many alien plants are producers of alkaloids. These molecules represent the main chemical defense to biotic stressors and also the major risk for human health. In this review, we focused on invasive plants producing tropane alkaloids (TAs) and pyrrolizidine alkaloids (PAs). We explored the potential role of these molecules in the fitness of invasive plants in the context of climate change and reviewed the knowledge regarding their biosynthesis steps and examined the mechanism of toxicity when accidentally ingested. Finally, we summarized the most efficient analytical and molecular methods to detect either alkaloid contamination or the presence of invasive plant contaminants, which are the source of these molecules, in food crops. Possible solutions and precautions to ensure food safety have been also proposed.
... Ficus benjamina has a rich content of pyrrolizidine alkaloids which are compounds that are secondary metabolites of plants (Singh and Sharma, 2023). These pyrrolizidine alkaloids have been reported to cause neurotoxicity in animals (Schramm et al., 2019). The neurotoxicity is believed to occur due to cellular adducts formed from interaction between pyrrole esters and cellular proteins. ...
Ficus benjamina has been shown proven to have medicinal potential, especially in alleviating some brain pathologies but there are few works on its neurotoxic effect. This study investigated the acute toxicity and effect of ethanol crude leaf extract of Ficus benjamina on the histology of some parts of the brain. Twenty-nine (29) Wistar rats weighing 123g -190g were used for the study. LD50was determined with nine (9) rats using Lorke’s method. Twenty (20) rats were divided into four (4) groups of 5 animals each. The control group was administered water and feed. Low dose (500 mg/kg), medium dose (1000 mg/kg), and high dose (1500 mg/kg) of extract were administered for twenty-one (21) days. On the 21st day, all the animals were weighed and sacrificed and the brains were harvested and processed histologically by the formalin-fixed-paraffin wax embedding method. The tissue blocks were sectioned and stained using haematoxylin and eosin, Periodic acid Schiff, and GFAP (glial fibrillary acidic protein). The results showed that the LD50 was ≤5000 mg/kg. There was no statistical significant difference in the body weights of the animals before and after the experiment (p=). Histopathological changes showed normal histology of cells in the choroid plexus, hippocampal CA3 area, and cerebral frontal cortex, normal glycogen, and normal astrocytes in the control. The low-dose group had mild reactive astrogliosis. There was mild atrophy, vacuolation, and mild reactive astrogliosis in the medium-dose group. The high-dose group had marked hypertrophy/hyperplasia, blood vessel dilation, vacuolation, necrosis, and mild reactive astrogliosis. The results suggest that prolonged consumption of the medium and high dose of the leaf extract of Ficus benjamina may cause marked neurotoxicity. The low dose is safer for administration.
... It also makes them beautiful and charismatic species, as they sport bright aposematic colors, and are widely used for popularizing Lepidoptera among broader audiences (e.g., Sourakov and Warren Chadd 2022). Although there are published reviews on PA toxicity, biosynthesis, and the role of PAs in plant-insect interactions (Fu et al. 2004;Macel 2011;Schramm et al. 2019), to our knowledge, a comprehensive qualitative and quantitative review of pyrrolizidine alkaloid research on tiger moths has yet to be conducted. ...
Insects and plants have been part of an evolutionary arms race that has led plants to produce toxins as defense and insects to sequester these chemical compounds. Pyrrolizidine alkaloids (PAs) are secondary plant chemical metabolites, and some herbivorous insects have evolved biochemical mechanisms to tolerate, sequester, and use PAs against predators and parasitoids. Several tiger moth species (Erebidae: Arctiinae) have gone one step further by transferring PAs acquired during mating to their eggs or using them as precursors of sexual pheromones, thereby making PAs an essential element in sexual selection. Although tiger moths are well known to use PAs for defense, a comprehensive qualitative and quantitative systematic review of PA research on tiger moths has yet to be conducted. To identify areas of past research focus and future research potential, we analyzed 108 studies retrieved from an exhaustive search on the Web of Science. Through a scientometric analysis, we synthesized available literature, examining authors, journals, countries and keywords with the aim of providing researchers tools to navigate the current literature more effectively. Using a systematic review approach, we evaluated the frequency of moth species studied and host plant diet, along with their research topic, allowing us to identify major knowledge gaps. We show that the number of publications decreased after 2015, and most research has focused on a few moth species and research topics. Our results provide valuable insights that can help direct research efforts to further the development of knowledge about PAs in Arctiinae.
... While the root has been used medicinally for over 2000 years, especially topically for wound healing, it is known to contain genotoxic constituents, namely pyrrolizidine alkaloids (PAs) [97]. PAs are heterocyclic organic compounds made by plants as a defense mechanism from predators [98]. In comfrey, some of the known PAs are lycopsamine (DTXSID60145542) and 7-acetyllycopsamine (DTXSID50223742). ...
Areas covered:
This paper outlines the selection of NAMs, including in vitro assays using primary rat cortical neurons, zebrafish embryos, and Caenorhabditis elegans. These assays aim to assess neurotoxic endpoints such as neuronal activity and behavioral responses. Microelectrode array recordings of rat cortical neurons provide insights into the impact of botanical extracts on neuronal function, while the zebrafish embryos and C. elegans assays evaluate neurobehavioral responses. The paper also provides an account of the selection of botanical case studies based on expert judgment and existing neuroactivity/toxicity information. The proposed battery of assays will be tested with these case studies to evaluate their utility for neurotoxicity screening.
Expert opinion:
The complexity of botanicals necessitates the use of multiple NAMs for effective neurotoxicity screening. This paper discusses the evaluation of methodologies to develop a robust framework for evaluating botanical safety, including complex neuronal models and key neurodevelopmental process assays. It aims to establish a comprehensive screening framework.
... Therefore, it becomes the subject of numerous discussions, research projects, reports, and legal regulations. Numerous aspects of PA chemistry, metabolism, and toxicity were discussed in high-quality review articles [8,15,[19][20][21][22][23][24][25][26][27][28][29][30]. The occurrence of PAs in food and herbal products is a very important problem, and due to the health hazards, There were hundreds of structurally different PAs discovered. ...
... So far, more than 500 PAs have been found and their structures determined [5 Taking into account the form of N-oxides, over 900 structures are known. PAs are het ocyclic compounds, they include a group of basic ester compounds (mono-and diester which structurally include a combination of amino alcohols with mono-or dicarboxy acids [22]. They are pyrrolizidine or necine derivatives, esters, and diesters [21]. ...
... Taking into account the form of N-oxides, over 900 structures are known. PAs are heterocyclic compounds, they include a group of basic ester compounds (mono-and diesters), which structurally include a combination of amino alcohols with mono-or dicarboxylic acids [22]. They are pyrrolizidine or necine derivatives, esters, and diesters [21]. ...
Pyrrolizidine alkaloids (PAs) are toxic compounds that occur naturally in certain plants, however, there are many secondary pathways causing PA contamination of other plants, including medicinal herbs and plant-based food products, which pose a risk of human intoxication. It is proven that chronic exposure to PAs causes serious adverse health consequences resulting from their cytotoxicity and genotoxicity. This review briefly presents PA occurrence, structures, chemistry, and toxicity, as well as a set of analytical methods. Recently developed sensitive electrochemical and chromatographic methods for the determination of PAs in honey, teas, herbs, and spices were summarized. The main strategies for improving the analytical efficiency of PA determination are related to the use of mass spectrometric (MS) detection; therefore, this review focuses on advances in MS-based methods. Raising awareness of the potential health risks associated with the presence of PAs in food and herbal medicines requires ongoing research in this area, including the development of sensitive methods for PA determination and rigorous legal regulations of PA intake from herbal products. The maximum levels of PAs in certain products are regulated by the European Commission; however, the precise knowledge about which products contain trace but significant amounts of these alkaloids is still insufficient.
... For example, berberine, an alkaloid found in plants such as goldenseal (Hydrastis canadensis) and Oregon grape (Berberis spp.), exhibits these properties. It has been shown to have antiviral effects against several viruses, including herpes simplex virus (HSV), respiratory syncytial virus (RSV), and influenza viruses [104] . Pyrrolizidine alkaloids, found in plants like comfrey (Symphytum spp.) and coltsfoot (Tussilago farfara), demonstrate antibacterial properties against bacteria such as Staphylococcus aureus and Escherichia coli [105] . ...
Horticultural plants contain various secondary metabolites (SMs), including flavonoids, terpenoids, and alkaloids. These compounds play a critical role in plant growth, helping the plants adapt to different types of stress and providing numerous health benefits to humans. Advances in detection methods, such as liquid phase mass spectrometry and spatial metabolomics, have enabled the identification and characterization of a growing variety of SMs and their unique functions in horticultural plants. Recent studies have investigated the effects of SMs on horticultural plants under different biotic and abiotic stresses. This article offers a detailed review of the functions of key representative SMs in horticultural plants, focusing on their responses to biotic and abiotic stresses and their impact on human health. Furthermore, we explore the potential of using these compounds to improve the resistance of horticultural plants through future breeding efforts.
... Various compounds have been identi ied from T. farfara, which are sesquiterpenoids, triterpenoids, lavonoids, phenolic acids, chromones, and pyrrolizidine alkaloids [18][19][20]. Pyrrolizidine alkaloids (PAs) are heterocyclic organic compounds synthesized by plants and T. farfara has had uses in traditional medicine, but the discovery of toxic pyrrolizidine alkaloids in the plant has resulted in liver health concerns [21]. Nevertheless, the effect of the aerial part extracts of T. farfara in mice by FD has not been reported. ...
Fine Dust (FD) in the respiratory air generates a variety of human disease issues throughout the earth. This study aimed to investigate whether (1) Tussilago farfara extracts (TF) decrease neutrophils accumulation, typical pathological features, and goblet cell hyperplasia in mice following exposure to fine dust (FD); (2) inflammatory cytokines result from FD exposure; and (3) asymmetric dimethyl-arginine (ADMA) and symmetric dimethyl-arginine (SDMA) levels in the mice following exposure to FD. Seven-week-old male Balb/c mice (n = 5/group) were instilled two times by intra-nasal-trachea (INT) injection for 3 days and 6 days to the mice four groups; normal, control, FD + dexamethasone (Dexa, positive control), and FD + TF groups. TF suspended in 0.5% carboxymethyl cellulose (CMC) was administered orally to the mice daily for 10 days (100 mg/kg). Neutrophil accumulation, typical pathological features, goblet cell hyperplasia, ADMA, and SDMA levels were assessed on day 10 in FD-induced mice. Results indicated FD significantly reduced neutrophil accumulation in BALF, typical pathological features containing goblet cell hyperplasia in lung tissues, and inflammatory cytokines [interleukin (IL)-17 and tumor necrosis factor-α (TNF-α), macrophage inflammatory protein-2 (MIP-2) and C-X-C motif chemokine 1 (CXCL-1)]. Furthermore, TF significantly decreased levels of elevated ADMA and SDMA by FD exposure. Collectively, TF decreased the counts of neutrophils in BALF, histological changes in lung tissues due to downstream secretion of inflammatory cytokines, and levels of ADMA and SDMA. Therefore, TF may be a potential therapeutics for treating FD-associated diseases.
... [4] Around 6000 known species contain pyrrolizidine alkaloids, resembling roughly 3 % of the world's flowering plants. [5] Many pyrrolizidine alkaloids are highly hepatotoxic and have shown to be genotoxic and show anti-tumor activities. [6] In the last decades, numerous synthetic approaches have been developed that often involve 1,3-dipolar cycloadditions, [7] ringclosing meta-thesis, [8] or proline-based structure modifications. ...
The triplet‐sensitized (by the solvent acetone) as well as the direct (λex=300–320 nm) photochemical decarboxylation of N‐phthaloylated γ‐aminobutyric acid (GABA) derivatives are versatile and high‐yielding routes to benzopyrrolizidines via intramolecular electron transfer initiated decarboxylation followed by radical coupling. The ß‐mono‐ and ß,ß'‐disubstituted N‐phthaloyl GABA derivatives 7 a–7 g, respectively, were applied as substrates. Decarboxylative photocyclization yielded hydroxy benzopyrrolizidines 8 a–8 g in high chemical yields and with moderate diastereoselectivities from the ß‐monosubstituted substrates. The analogous α‐substituted GABA derivatives 11 a–11 c were also applied as potential substrates for memory of chirality effects. The reaction quantum yields of the photodecarboxylation reactions for the parent GABA derivative 13 and for the new substrates 7 h and 11 a were determined by the quantum yield determination system (QYDS) and showed a remarkable concentration dependency indicating aggregation at higher substrate concentrations. Inhibition studies on the atherogenic human serine hydrolase cholesterol esterase showed derivatives 8 a and 8 d to exhibit a hyperbolic mode of inhibition with moderate IC50 values of about 60–80 μM.
