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Antonia Garrido Frenich - One of the best experts on this subject based on the ideXlab platform.
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effect of tea making and boiling processes on the degradation of Tropane Alkaloids in tea and pasta samples contaminated with solanaceae seeds and coca leaf
Food Chemistry, 2019Co-Authors: Jesus Marinsaez, Roberto Romerogonzalez, Antonia Garrido FrenichAbstract:Abstract In this study, the degradation of Tropane Alkaloids in pasta under boiling (100 °C during 10 min) and tea making (100 °C and let cool 5 min) conditions has been evaluated for the first time. Pasta and green tea were contaminated with Datura Stramonium and Brugmansia Arborea seeds (pasta and green tea), whereas coca leaf tea was directly analysed. The compounds were extracted using solid-liquid extraction coupled to a preconcentration stage (only for the cooking water), and the compounds were analysed by liquid chromatography coupled to mass spectrometry (Exactive-Orbitrap analyser). Degradation studies indicate that concentration of Tropane Alkaloids decreases, and it depends on the compound, observing the highest degradation for tropinone, Tropane, cuscohygrine and tropine, as well as it was observed that compounds migrated to the aqueous phase during cooking step. Finally, post-targeted analysis was performed and other Tropane Alkaloids were found, as scopine, tigloidine or convolvine, showing a similar behaviour under cooking conditions.
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Degradation of Tropane Alkaloids in baked bread samples contaminated with Solanaceae seeds
Food research international (Ottawa Ont.), 2019Co-Authors: Jesús Marín-sáez, Roberto Romero-gonzález, Antonia Garrido FrenichAbstract:Abstract Solanaceae plant seeds, which contain high concentrations of Tropane Alkaloids, have not been studied in real conditions of proofing and baking processes. In this work both lab vial trials and buckwheat and millet flour samples, contaminated with two species of Solanaceae plants, Datura stramonium and Brugmansia arborea, were undergone to proofing (37 °C) and baking (190 °C) processes. For the determination of Tropane Alkaloids, a simple solid-liquid extraction with methanol:water 2:1 (v/v) containing 0.5% acetic acid was used to extract the targeted compounds, whereas a chromatographic method employing a Zorbax C18 column coupled to an Exactive-Orbitrap analyser was used for their determination. The results indicate that concentrations of Tropane Alkaloids decrease under proofing conditions (degradation between 13 and 95%), while they are almost disappeared under baking conditions (degradation between 94 and 100%). Some degradation pathways have been clarified, showing that most of the compounds degrade into Tropane and tropine, and into tropine and tropinone under proofing and baking conditions respectively.
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Analytical methods, occurrence and trends of Tropane Alkaloids and calystegines: An update.
Journal of chromatography. A, 2018Co-Authors: Ana Romera-torres, Roberto Romero-gonzález, Jose Luis Martinez Vidal, Antonia Garrido FrenichAbstract:Abstract In the last years, the interest in secondary metabolites from plants has been growing, and even more if they have or would have medical applications, as it happens with Tropane Alkaloids and calystegines. Therefore, the number of analytical methods for the analysis of these compounds has been increasing. In this review, the extraction methods as well as the chromatographic separation and detection techniques based on mass spectrometry to determine Tropane Alkaloids and calystegines in plant raw material and food have been described. Finally, a summary of the natural occurrence of Tropane Alkaloids and calystegines in the studied matrices, as well as their accidental presence in food, is presented, highlighting current and future determination trends.
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simultaneous analysis of Tropane Alkaloids in teas and herbal teas by liquid chromatography coupled to high resolution mass spectrometry orbitrap
IEEE Journal of Solid-state Circuits, 2018Co-Authors: Ana Romeratorres, Roberto Romerogonzalez, Jose Luis Martinez Vidal, Antonia Garrido FrenichAbstract:A new method has been developed for the simultaneous determination of 13 Tropane Alkaloids in tea and herbal teas using high-performance liquid chromatography coupled to an Exactive-Orbitrap analyzer. A mixture of methanol, water, and formic acid was used for the extraction of the target compounds followed by a solid-phase extraction step. The validated method provided recoveries from 75 to 128% with intra- and interday precision lower than or equal to 24% (except for apoatropine). Limits of quantification ranged from 5 to 20 μg/kg. Eleven tea and herbal tea samples and two contaminated samples with Datura stramonium seeds were analyzed. Tropane Alkaloids were detected in six samples with concentrations from 5 (apoatropine) to 4340 μg/kg (sum of physoperuvine, pseudotropine, and tropine), whereas concentrations from 5 (apoatropine) to 1725 μg/kg (sum of physoperuvine, pseudotropine, and tropine) were found in the contaminated samples.
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Study of the occurrence of Tropane Alkaloids in animal feed using LC-HRMS
Analytical Methods, 2018Co-Authors: Ana Romera-torres, Roberto Romero-gonzález, Jose Luis Martinez Vidal, Antonia Garrido FrenichAbstract:The consumption of animal products is rapidly increasing and, therefore, the use of feedstuffs in farms is in demand in developing countries. Feed cereals represent more than 48% of total feed material and they might be contaminated by Solanaceae plants, which contain toxic metabolites such as Tropane Alkaloids. A wide-scope analysis of Tropane Alkaloids in feed, including atropine, scopolamine, tropinone, anisodamine, Tropane, homatropine, tropine, littorine, physoperuvine, pseudotropine, apoatropine and aposcopolamine, has been performed using liquid chromatography coupled to an Exactive-Orbitrap analyzer. An extraction method based on pressurized liquid extraction with methanol/water/formic acid (75/25/0.4; v/v/v) as a solvent extraction, followed by a solid phase extraction step using Strata-X-C cartridges and a clean-up step with chitosan has been used. The method was fully validated and recoveries from 70 to 109% with an intraday precision lower than or equal to 15% were achieved and limits of quantification (LOQs) ranged from 5 to 25 μg kg−1 for all the compounds. More than 40 samples belonging to several classes of animal feed (cow, rabbit, sheep, chicken and pig) were analysed, showing the occurrence of Tropane Alkaloids in 18 out of 45 samples, with concentration ranging from 5 (atropine) to 222 μg kg−1 (scopolamine), highlighting the need of analytical methods for the control of TAs in animal feeds.
Myungsuk Choi - One of the best experts on this subject based on the ideXlab platform.
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production of Tropane Alkaloids during de differentiation of scopolia parviflora calli
Journal of Natural Products, 2010Co-Authors: Seung Mi Kang, Won Kyun Choi, Mi Jin Jeong, C. S. Karigar, Myungsuk ChoiAbstract:The production of Tropane Alkaloids during differentiation and de-differentiation of Scopolia parviflora calli was studied. Tropane alkaloid production drastically decreased during calli de-differentiation. Scopolamine (1) production decreased after 10 days of culture, whereas that of hyoscyamine (2) decreased during de-differentiation of root to calli. The production of 1 was enhanced in calli undergoing differentiation to shoot after 60 days of culture, reaching a maximum by 80 days. However, production of hyoscyamine in regenerated plants was lower. The expression level of hyoscyamine 6β-hydroxylase (H6H), a key biosynthetic enzyme for Tropane Alkaloids, was significantly increased in 4-week-old calli. This study suggests that the biosynthesis of Tropane Alkaloids is regulated inversely in de-differentiating Scopolia parviflora calli.
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Production of Tropane Alkaloids during de-differentiation of Scopolia parviflora calli.
Journal of natural products, 2010Co-Authors: Yong Duck Kim, Seung Mi Kang, Won Kyun Choi, Mi Jin Jeong, C. S. Karigar, Ji Yun Min, Myungsuk ChoiAbstract:The production of Tropane Alkaloids during differentiation and de-differentiation of Scopolia parviflora calli was studied. Tropane alkaloid production drastically decreased during calli de-differentiation. Scopolamine (1) production decreased after 10 days of culture, whereas that of hyoscyamine (2) decreased during de-differentiation of root to calli. The production of 1 was enhanced in calli undergoing differentiation to shoot after 60 days of culture, reaching a maximum by 80 days. However, production of hyoscyamine in regenerated plants was lower. The expression level of hyoscyamine 6beta-hydroxylase (H6H), a key biosynthetic enzyme for Tropane Alkaloids, was significantly increased in 4-week-old calli. This study suggests that the biosynthesis of Tropane Alkaloids is regulated inversely in de-differentiating Scopolia parviflora calli.
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enhanced production of Tropane Alkaloids in scopolia parviflora by introducing the pmt putrescine n methyltransferase gene
In Vitro Cellular & Developmental Biology – Plant, 2005Co-Authors: Youngmin Kang, Seung Mi Kang, C. S. Karigar, Heeyoung Jung, Jung Dong Bahk, Theertha D Prasad, Myungsuk ChoiAbstract:In wild-type Scopolia parvilfora (Solanaceae) tissues, only the roots express the enzyme putrescine N-methyltransferase (PMT; EC 2.1.1.53), which is the first specific precursor of the Tropane Alkaloids. Moreover, the tropanane alkaloid levels were the highest in the root (0.9 mg g−1 on a dry weight basis), followed by the stem and then the leaves. We metabolically engineered S. parviflora by introducing the tobacco pmt gene into its genome by a binary vector system that employs disarmed Agrobacterium rhizogenes. The kanamycin-resistant hairy root lines were shown to bear the pmt gene and to overexpress its mRNA and protein product by at least two-fold, as determined by polymerase chain reaction (PCR) and Northern and Western blottings, respectively. The transgenic lines also showed higher PMT activity and were morphologically aberrant in terms of slower growth and the production of lateral roots. The overexpression of pmt markedly elevated the scopolamine and hyoscyamine levels in the transgenic lines that showed the highest pmt mRNA and PMT protein levels. Thus, overexpression of the upstream regulator of the Tropane alkaloid pathway enhanced the biosynthesis of the final product. These observations may be useful in establishing root culture systems that generate large yields of Tropane Alkaloids.
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overexpression of hyoscyamine 6 beta hydroxylase h6h gene and enhanced production of Tropane Alkaloids in scopolia parviflora hairy root lines
Journal of Microbiology and Biotechnology, 2005Co-Authors: Youngmin Kang, Seung Mi Kang, C. S. Karigar, Heeyoung Jung, Theertha Prasad, Jung Dong Bahk, Myungsuk ChoiAbstract:The hyoscyamine 6I²-hydroxylase (h6h) gene was introduced into the genome of Scopolia parviflora through the Agrobacterium rhizogenes binary vector system. The enzyme was expressed ally and tissue specific selectively in roots, resulting in five transgenic hairy root lines. The presence of the h6h gene in kanamycin-resistant hairy roots and its overexpression were confirmed by polymerase chain reaction (PCR), Northern blotting, and Western blotting, respectively. In the transgenic hairy root lines which constitutively expressed the H6H enzyme, hyoscyamine and scopolamine accumulated in high concentration. Among the transgenic hairy root lines that expressed the H6H enzyme, only two were more productive. The levels of Tropane Alkaloids in transgenic hairy root varied greatly: The best transgenic line (#5) contained 8.12 mg of scopolamine per g dry weight, which produced the compound three times more than wild-type root. These results suggest a possibility of improving the yield of Tropane Alkaloids in hairy root lines by genetic and metabolic engineering. © The Korean Society for Microbiology and Biotechnology.
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growth pattern and content of Tropane Alkaloids of metabolic engineered scopolia parviflora hairy root lines
The Korean Journal of Medicinal Crop Science, 2004Co-Authors: Youngmin Kang, Myungsuk ChoiAbstract:Hyoscyamine and scopolamine are two most common Tropane Alkaloids found in the Solanaceae. The pEB expression vector carrying Nspmt gene was transformed to Agrobacterium rhizogenes. The growth of transgenic hairy roots were approximately to 80% of the wild type root. Transgenic hairy roots are less developed on only their branch roots than those of the wild type root. The extracts from Nspmt transgenic hairy root lines, 3 and 5 contained between 3.52 and 4.23 mg/g dry weight as hyoscyamine and did between 5.23 to 6.40 mg/g dry weight as scopolamine. These results showed that the overexpression of the pmt gene enhanced Tropane Alkaloids production of S. parviflora transformed roots and this improvement affected both hyoscyamine and scopolamine production.
Anthony Richard Carroll - One of the best experts on this subject based on the ideXlab platform.
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Tropane Alkaloids from the australian plant triunia montana proteaceae
Tetrahedron Letters, 2017Co-Authors: Fan Yang, Huijun Zhao, Anthony Richard CarrollAbstract:Four Tropane Alkaloids, including a new compound triuniamine A (3) a known compound 2,3-dihydrodarlingine (4) with previously unassigned relative configuration and two known compounds darlingine (1), 10-hydroxydarlingine (2) were obtained from the stems of the endemic Australian plant Triunia montana (Proteaceae). The structure and relative configuration of the stereogenic centers in triuniamine A was elucidated on the basis of 1D and 2D NMR spectroscopy and high-resolution mass spectrometry. The relative configuration of the four stereogenic centers in 2,3-dihydrodarlingine were established from ROESY correlations, and its absolute configuration assigned from comparison of its ECD spectrum with that of (+)-darlingine.
Kanji Ishimaru - One of the best experts on this subject based on the ideXlab platform.
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Tropane Alkaloids in root cultures of solanaceous plants
Studies in natural products chemistry, 2007Co-Authors: Koichiro Shimomura, Kanji Ishimaru, Kayo Yoshimatsu, Martina SauerweinAbstract:Publisher Summary Solanaceous plants, such as genus Atropa, Datura, Duboisia, Hyoscyamus, and Scopolia are regarded as rich sources of Alkaloids, namely of the pharmaceutically interesting Tropane derivatives. The principal Alkaloids of medicinal interest in this group are hyoscyamine and scopolamine, which act as anticholinergic agents in parasympathetic nervous system. They are used as mydriatics and spasmolytics. Although the chemical synthesis of these Alkaloids has been described in this chapter, the drugs are still produced exclusively from plant materials. This chapter demonstrates the establishment of the adventitious and the hairy root cultures of several solanaceous plant species including Datura, Duboisia, Hyoscyamus, and Scopolia for the production and biosynthetic studies of Tropane Alkaloids. In addition, the isolation and structural elucidation of the new Tropane alkaloid 7β-hydroxyhyoscyamine and the piperidone alkaloid hyalbidone from them is also presented.
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Tropane Alkaloids in auxin-independent root cultures of Physochlaina physaloides.
Kokuritsu Iyakuhin Shokuhin Eisei Kenkyujo hokoku = Bulletin of National Institute of Health Sciences, 2002Co-Authors: Koichiro Shimomura, Kayo Yoshimatsu, Makoto Hirose, Shinsaku Natori, Motoyoshi Satake, Kanji IshimaruAbstract:Adventitious and hairy root cultures of Physochlaina physaloides were established. These roots grew well and produced high amounts of Tropane Alkaloids (particularly hyoscyamine and 6 beta-hydroxyhyoscyamine) in auxin-free culture medium. The effects of basal media and temperature on the growth and alkaloid production of these roots were investigated. Both root cultures produced highest amount of Tropane Alkaloids in B5 medium though the optimum temperature for hairy roots were lower than that for adventitious roots.
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Tropane Alkaloids in the adventitious and hairy root cultures of solanaceous plants
Phytochemistry, 2001Co-Authors: Koichiro Shimomura, Martina Sauerwein, Kanji IshimaruAbstract:Abstract Adventitious and hairy root cultures of several solanaceous plant species were established. The highest content of Tropane Alkaloids was obtained in the adventitious roots of Hyoscyamus albus cultured in hormone-free 1/2 MS liquid medium. On the other hand the hairy roots of H. albus transformed with A. rhizogenes strain MAFF 03-01724 grew very fast and yielded over 5 mg/100 ml flask of hyoscyamine within 22 days of culture. The alkaloid content in the hairy roots of H. niger was higher than that of its adventitious roots. 7β-Hydroxyhyoscyamine, recently isolated, was produced in the hairy roots of Scopolia tangutica and Datura innoxia , while it could not be detected in their adventitious root cultures.
Seung Mi Kang - One of the best experts on this subject based on the ideXlab platform.
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production of Tropane Alkaloids during de differentiation of scopolia parviflora calli
Journal of Natural Products, 2010Co-Authors: Seung Mi Kang, Won Kyun Choi, Mi Jin Jeong, C. S. Karigar, Myungsuk ChoiAbstract:The production of Tropane Alkaloids during differentiation and de-differentiation of Scopolia parviflora calli was studied. Tropane alkaloid production drastically decreased during calli de-differentiation. Scopolamine (1) production decreased after 10 days of culture, whereas that of hyoscyamine (2) decreased during de-differentiation of root to calli. The production of 1 was enhanced in calli undergoing differentiation to shoot after 60 days of culture, reaching a maximum by 80 days. However, production of hyoscyamine in regenerated plants was lower. The expression level of hyoscyamine 6β-hydroxylase (H6H), a key biosynthetic enzyme for Tropane Alkaloids, was significantly increased in 4-week-old calli. This study suggests that the biosynthesis of Tropane Alkaloids is regulated inversely in de-differentiating Scopolia parviflora calli.
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Production of Tropane Alkaloids during de-differentiation of Scopolia parviflora calli.
Journal of natural products, 2010Co-Authors: Yong Duck Kim, Seung Mi Kang, Won Kyun Choi, Mi Jin Jeong, C. S. Karigar, Ji Yun Min, Myungsuk ChoiAbstract:The production of Tropane Alkaloids during differentiation and de-differentiation of Scopolia parviflora calli was studied. Tropane alkaloid production drastically decreased during calli de-differentiation. Scopolamine (1) production decreased after 10 days of culture, whereas that of hyoscyamine (2) decreased during de-differentiation of root to calli. The production of 1 was enhanced in calli undergoing differentiation to shoot after 60 days of culture, reaching a maximum by 80 days. However, production of hyoscyamine in regenerated plants was lower. The expression level of hyoscyamine 6beta-hydroxylase (H6H), a key biosynthetic enzyme for Tropane Alkaloids, was significantly increased in 4-week-old calli. This study suggests that the biosynthesis of Tropane Alkaloids is regulated inversely in de-differentiating Scopolia parviflora calli.
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enhanced production of Tropane Alkaloids in scopolia parviflora by introducing the pmt putrescine n methyltransferase gene
In Vitro Cellular & Developmental Biology – Plant, 2005Co-Authors: Youngmin Kang, Seung Mi Kang, C. S. Karigar, Heeyoung Jung, Jung Dong Bahk, Theertha D Prasad, Myungsuk ChoiAbstract:In wild-type Scopolia parvilfora (Solanaceae) tissues, only the roots express the enzyme putrescine N-methyltransferase (PMT; EC 2.1.1.53), which is the first specific precursor of the Tropane Alkaloids. Moreover, the tropanane alkaloid levels were the highest in the root (0.9 mg g−1 on a dry weight basis), followed by the stem and then the leaves. We metabolically engineered S. parviflora by introducing the tobacco pmt gene into its genome by a binary vector system that employs disarmed Agrobacterium rhizogenes. The kanamycin-resistant hairy root lines were shown to bear the pmt gene and to overexpress its mRNA and protein product by at least two-fold, as determined by polymerase chain reaction (PCR) and Northern and Western blottings, respectively. The transgenic lines also showed higher PMT activity and were morphologically aberrant in terms of slower growth and the production of lateral roots. The overexpression of pmt markedly elevated the scopolamine and hyoscyamine levels in the transgenic lines that showed the highest pmt mRNA and PMT protein levels. Thus, overexpression of the upstream regulator of the Tropane alkaloid pathway enhanced the biosynthesis of the final product. These observations may be useful in establishing root culture systems that generate large yields of Tropane Alkaloids.
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overexpression of hyoscyamine 6 beta hydroxylase h6h gene and enhanced production of Tropane Alkaloids in scopolia parviflora hairy root lines
Journal of Microbiology and Biotechnology, 2005Co-Authors: Youngmin Kang, Seung Mi Kang, C. S. Karigar, Heeyoung Jung, Theertha Prasad, Jung Dong Bahk, Myungsuk ChoiAbstract:The hyoscyamine 6I²-hydroxylase (h6h) gene was introduced into the genome of Scopolia parviflora through the Agrobacterium rhizogenes binary vector system. The enzyme was expressed ally and tissue specific selectively in roots, resulting in five transgenic hairy root lines. The presence of the h6h gene in kanamycin-resistant hairy roots and its overexpression were confirmed by polymerase chain reaction (PCR), Northern blotting, and Western blotting, respectively. In the transgenic hairy root lines which constitutively expressed the H6H enzyme, hyoscyamine and scopolamine accumulated in high concentration. Among the transgenic hairy root lines that expressed the H6H enzyme, only two were more productive. The levels of Tropane Alkaloids in transgenic hairy root varied greatly: The best transgenic line (#5) contained 8.12 mg of scopolamine per g dry weight, which produced the compound three times more than wild-type root. These results suggest a possibility of improving the yield of Tropane Alkaloids in hairy root lines by genetic and metabolic engineering. © The Korean Society for Microbiology and Biotechnology.
