tropane alkaloids

Members of the genus Atropa contain various tropane alkaloids, including atropine ((±)-hyoscyamine) and scopolamine, which possess medicinal properties. Preserving the diverse genetic background of wild populations via optimal plant production from seeds could be essential for avoiding the loss of potential uses. We analyzed the germination ecology of two Atropa species comprising the threatened A. baetica and widespread A. belladonna to determine the: (1) influence of temperature, light, and seed age on germination patterns; (2) effects of cold stratification and gibberellic acid (GA3 ); (3) phenology of seedling emergence in outdoor conditions; (4) phenology of dormancy break and loss of viability in buried seeds; and (5) ability to form persistent soil seed banks...

Alkaloids are naturally occurring compounds containing basic nitrogen atoms. They are biosynthesized mainly by plants but also by some fungi species. Many alkaloids are toxic to humans and animals, and they have been classified as food contaminants. Among them, ergot, tropane, and pyrrolizidine alkaloids have maximum levels in foods, established by the Commission Regulation (EU) 2023/915. In this study, an analytical method was successfully developed and validated for the simultaneous determination of 42 ergot, tropane, and pyrrolizidine alkaloids and their N-oxides in cereal-based food...

In recent years, the monitoring of tropane alkaloids, specifically hyoscyamine and scopolamine, in food has become a pressing concern. This is due to increasing reports of food contamination with these compounds worldwide, raising awareness about the potential risks associated with their consumption. A novel method is proposed here for the determination of the sum of (+)-hyoscyamine, (-)-hyoscyamine, and (-)-scopolamine in buckwheat-based matrices, using solid-liquid extraction at low temperature and quantification by bidimensional chromatography coupled to tandem mass spectrometry...

This study assessed the levels of environment and food-related exposures in urine of Austrian school children aged six to ten (n = 85) focusing on mycotoxins, phytoestrogens, and food processing by-products using two multi-analyte LC-MS/MS methods. Out of the 55 biomarkers of exposure reported in this study, 22 were quantified in the first void urine samples. Mycotoxins frequently quantified included zearalenone (detection rate 100%; median 0.11 ng/mL), deoxynivalenol (99%; 15 ng/mL), alternariol monomethyl ether (75%; 0...

Epigallocatechin gallate (EGCG) is a main component in green tea extract, which possesses multiple bioactivities. The present research studied the effects of EGCG on the laying performance, egg quality, immune status, antioxidant capacity, and hepatic metabolome of Linwu laying ducks reared under high temperature. A total of 180 42-w-old healthy Linwu laying ducks were allocated into control or EGCG-treated groups. Each treatment had 6 replicates with 15 ducks in each replicate. Diets for the two groups were basal diets supplemented with 0 or 300 mg/kg EGCG, respectively...

Tropane alkaloids are an important class of biologically active small molecules characterized by their 8-azabicyclo[3.2.1]octane core. Because of their numerous medicinal applications, microbial biosynthesis and a variety of chemical syntheses have been designed for individual family members. However, current approaches are not amenable to late-stage structural diversification at N8, C3, C6, or C7, positions that are critical for modulating the biological properties of these molecules. Here, we describe a general approach to the synthesis of tropane alkaloids and their analogues that relies on the construction of the 8-azabicyclo[3...

This case report reveals a rare incident of unintended Jimson weed ( Datura stramonium ) exposure within a family in the United States. In this narrative, a pregnant 36-year-old Asian woman and her family unknowingly ingested homemade soup infused with Jimson weed leaves. This led to symptoms such as vomiting, dry mouth, blurred vision, flushed skin, breathing difficulties, and hallucinations. While the woman and her daughter quickly recovered, the husband's severe hallucinations required intensive care. The episode underscores the vital importance of accurate plant identification, particularly in homegrown produce...

TAs, including hyoscyamine and scopolamine, were used to treat neuromuscular disorders ranging from nerve agent poisoning to Parkinson's disease. Tropinone reductase I (TR-I; EC 1.1.1.206) catalyzed the conversion of tropinone into tropine in the biosynthesis of TAs, directing the metabolic flow towards hyoscyamine and scopolamine. Tropinone reductase II (TR-II; EC 1.1.1.236) was responsible for the conversion of tropinone into pseudotropine, diverting the metabolic flux towards calystegine A3. The regulation of metabolite flow through both branches of the TAs pathway seemed to be influenced by the enzymatic activity of both enzymes and their accessibility to the precursor tropinone...

Pyrrolizidine alkaloids are secondary metabolites produced by plants as a defense against insects. These can cause acute or chronic toxicity in humans. Therefore, avoiding potential poisoning from the consumption of tea and culinary plants contaminated with pyrrolizidine alkaloids (PAs), pyrrolizidine alkaloids N-oxides (PANOs), and tropane alkaloids (TAs) is important for human health and food safety. Therefore, it is important to determine the levels of these substances with reliable and highly accurate methods...

The transmission of insect-borne viruses involves sophisticated interactions between viruses, host plants, and vectors. Chemical compounds play an important role in these interactions. Several studies reported that the plant virus tomato spotted wilt orthotospovirus (TSWV) increases host plant quality for its vector and benefits the vector thrips Frankliniella occidentalis . However, few studies have investigated the chemical ecology of thrips vectors, TSWV, and host plants. Here, we demonstrated that in TSWV-infected host plant Datura stramonium , (1) F...

Alkaloids are a group of secondary metabolites that generate great interest since ancient times. Numerous Solanaceae plants are rich sources of tropane alkaloids as hyoscyamine and scopolamine which are obtained mainly from Hyoscyamus niger, Datura stramonium, Atropa belladonna, Mandragora officinarum . In the present study it was developed an HPLC-DAD using an XBridge Phenyl column for the quantification of scopolamine and hyoscyamine, molecules used in pharmaceutical industry to treat stomach or intestinal disorders...

This study aimed to investigate the effects of clinorotation induced by 2-D clinostat on the growth, tropane alkaloid production, gene expression, antioxidant capacity, and cellular defense responses in the callus tissue of Hyoscyamus niger. Callus induction was conducted by putting hypocotyl explants in the MS culture medium supplemented with 1 mgL-1 2,4-D and 1 mgL-1 BAP growth regulators. The sub-cultured calli were placed on a clinostat for 0, 3, 7, and 10 days (2.24 × 10-5 g on the edge of the callus ring)...

RATIONALE: Tropane alkaloids represent an important class of secondary metabolites, but many of these compounds are already described in the scientific literature, so the use of guided identification and isolation strategies, such as dereplication, represent a fast and safe alternative. METHODS: For the annotation of the tropane alkaloids the chloroform phases of the four Erythroxylum species were analyzed by high-performance liquid chromatography coupled to mass spectrometry with positive-mode electrospray ionization, then the ions of their protonated molecules, molecular formulas and fragmentation patterns were observed and a comparison of the obtained data with those present in the scientific literature was performed...

BACKGROUND: A growing body of evidence has demonstrated that a high-fat and high-protein diet (HFHPD) causes constipation. This study focuses on understanding how the use of Zhishi Daozhi decoction (ZDD) affects the intricate balance of intestinal microorganisms. The insights gained from this investigation hold the potential to offer practical clinical approaches to mitigate the constipation-related issues associated with HFHPD. MATERIALS AND METHODS: Mice were randomly divided into five groups: the normal (MN) group, the natural recovery (MR) group, the low-dose ZDD (MLD) group, the medium-dose ZDD (MMD) group, and the high-dose ZDD (MHD) group...

Liquid-state fermentation (LSF) of tea leaves is a promising way to obtain tea-based nutraceutical products rich in various bioactive compounds. In the study, the changes of bioactive compounds, tea pigments and complex metabolites from LSF of primary dark tea, green tea and white tea infusions with Aspergillus cristatus were determined. Chemical analyses revealed that soluble sugars, monosaccharide composition, total polyphenols, total flavonoids, free amino acids, soluble proteins and tea pigments were changed in different ways...

ETHNOPHARMACOLOGICAL RELEVANCE: Tangchong (ཐང་ཕྲོམ།), a term in the Tibetan language, encompasses a diverse group of plants belonging to different genera of the Solanaceae family. These plants have been utilized in traditional Tibetan medicine for centuries and are currently still employed to treat a variety of ailments, including acute and severe abdominal pain, intestinal obstruction, epilepsy, ascariasis, lung abscess, and other diseases...

Tropane alkaloids (TAs) are large secondary metabolite alkaloids that find extensive applications in the synthesis of antidotes, anesthetics, antiemetics, motion sickness drugs, and antispasmodics. The current production method primarily depends on extraction from medicinal plants of the Solanaceae family. Elicitation, as a highly effective biotechnological approach, offers significant advantages in augmenting the synthesis of secondary metabolites. The advantages include its simplicity of operation, low cost, and reduced risk of contamination...

A quantitative ultra-high performance liquid chromatography-tandem mass spectrometry (UHPLC-MS/MS) method was developed and validated for the determination of tropane alkaloids (TAs), atropine and scopolamine, in a variety of food products. The sample preparation of cereal-based food, oilseeds, honey, and pulses consisted of a solid-liquid extraction with an acidified mixture of methanol and water, while an additional step of solid-phase extraction on a cation-exchange sorbent was introduced in the treatment of teas and herbal infusions, aromatic herbs, spices and food supplements...

Following the implementation of the European regulation limiting the presence of tropane alkaloids in certain foods, a survey was conducted in Serbia on 103 maize products (grits, polenta and semolina) to determine atropine and scopolamine content using liquid chromatography with tandem-mass spectrometry analysis (LC-MS/MS). The probability of exceeding the Acute Reference Dose (ARfD; 0.016 μg/kg bw/day) of the sum of atropine and scopolamine by consuming these products was tested. Overall, across age categories - children, younger and older adolescents, and adults, the group ARfD was exceeded by 21...

Tropane alkaloids (TAs), which are anticholinergic agents, are an essential class of natural compounds. There is a growing demand for these compounds with anesthetic, analgesic, and spasmolytic effects. Anisodus acutangulus is a TA-producing plant (family Solanaceae) that was used as an anesthetic in ancient China. In this study, a high-quality chromosome-scale A. acutangulus genome was assembled, with a contig N50 of up to 7.4 Mb. In A. acutangulus, a recent whole-genome duplication event occurred after the divergence from other Solanaceae plants, which resulted in the duplication of the ADC1 and UGT genes involved in TA biosynthesis...