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1

Pyrrolizidine alkaloids

100%

Ronczka S., Speer K.

Polish Journal of Food and Nutrition Sciences

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2011

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tom 61

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nr Suppl.1

2

Pyrrolizidine alkaloids in honey from Switzerland

100%

Kast C., Kilchenmann V., Dubecke A., Gallmann P., Beckh G., Lullmann C.

Polish Journal of Food and Nutrition Sciences

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2011

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tom 61

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nr Suppl.1

3

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Content of pyrrolizidine alkaloids in the leaves of coltsfoot (Tussilago farfara L.) in Poland

75%

Adamczak A., Opala B., Gryszczynska A., Buchwald W.

Acta Societatis Botanicorum Poloniae

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2013

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tom 82

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nr 4

Coltsfoot (Tussilago farfara L.) is a common species, widely used in European and Chinese traditional medicine for the treatment of respiratory diseases. However, raw material from this plant contains hepatotoxic pyrrolizidine alkaloids (PAs). The aim of the study was to determine the variability of the level of PAs (senkirkine and senecionine) in leaves of coltsfoot originated from natural populations in Poland. In the phytochemical analysis, 20 samples of T. farfara were used. This plant material was obtained from the Garden of Medicinal Plants in Plewiska near Poznań and originated from different regions of Poland. Coltsfoot leaves were harvested in the middle of July of 2010 and then dried at room temperature. The alkaloid content was detected using the HPLC-DAD method. The amount of PAs in leaves of T. farfara changed in a wide range from 0.06 to 1.04 μg g−1 of dry matter (DM). The content of senkirkine and senecionine was positively correlated (r = 0.68, P = 0.001). There was no statistically significant correlation between the amount of PAs as well as leaf weight and water content in leaves of T. farfara. Our results showed that a medium-sized leaf of coltsfoot (0.33 g DM) may contain from 0.02 to 0.34 μg of PAs (on average 0.14 μg). The level of PAs was not associated with the region of Poland, but phytochemical similarity of samples was usually visible at the local scale. Coltsfoot leaves are characterized by a high variability of the content of toxic PAs, much higher than in the case of the main active compounds, especially flavonoids and mucilage. This phytochemical variability is mainly genetically determined (samples came from a garden collection), and it can be increased by environmental factors. Our investigations indicate that Polish natural populations of T. farfara may provide raw material with a low level of toxic PAs.

4

Pyrrolizidine alkaloids in European honeys and honeys from overseas

75%

Dubecke A., Beckh G., Lullmann C.

Polish Journal of Food and Nutrition Sciences

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2011

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tom 61

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nr Suppl.1

5

Content of pyrrolizidine alkaloids (senecionine and senkirkine) in Tussilago farfara L. plants cultivated in vitro

75%

Dreger M., Krajewska-Patan A., Gorska-Paukszta M., Pieszak M., Opala B., Gryszczynska A., Adamczak A., Mikolajczak P. M., Buchwald W.

Herba Polonica

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2012

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tom 58

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nr 4

Tussilago farfara L. (family Asteraceae) is a valuable medicinal plant that has been used as a cough suppressant and as an antibacterial and anti-inflammatory drug. Mucopolysac charides, flavonoids, sterols, phenolic acids and pyrrolizidine alkaloids (PAs) are the main active compounds of coltsfoot. Due to hepatotoxic properties of some pyrrolizidine alkaloids, raw materials that contain PAs should be monitored and determined. The aim of present work was to establish nodal cultures of Tussilago farfara and to determine the content of senecionine and senkirkine in plants propagated in in vitro conditions. Eleven clones of coltsfoot derived from Polish natural populations were established. Rhizome buds were used as explants for the initiation of in vitro cultures on MS (Murashige and Skooge) medium. Every six weeks the shots and leaves were collected and dried. The HPLC method was applied for the identification and determination of senecionine and senkirkine. Content of pyrrolizidine alkaloids varied significantly depending on origin (population). An average sum of alkaloids (senecionine and senkirkine) ranged from 1.23 to 10.47 mg/100g d.w. that corresponds to 0.0013–0.011%, respectively.

6

Phytochemical, pharmacological and clinical studies of Petasites hybridus (L.) P. Gaertn., B. Mey. and Scherb. A reviev

63%

Ozarowski M., Przystanowicz J., Adamczak A.

Herba Polonica

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2013

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tom 59

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nr 4

Preparations from rhizomes of Petasites hybridus (L.) Gaertn., B. Mey. & Scherb. (common butterbur) have a long history of use in folk medicine in treatment of several diseases as anti-inflammatory and spasmolytic drugs. Extracts from this species are of interest to researchers in the field of phytopharmacology due to their biologically active compounds, particularly two eremophilane sesquiterpenes (petasin and isopetasin), which are contained not only in rhizomes and roots, but also in leaves. Moreover, P. hybridus contains pyrrolizidine alkaloids, which showed hepatotoxic, carcinogenic and mutagenic properties. Hence, special extracts devoid of alkaloids obtained by sub- and super-critic carbon dioxide extraction were used in the preclinical, clinical studies and phytotherapy. Our review aims to provide a literature survey of pharmacological as well as clinical trials of P. hybridus, carried out in 2000–2013. Also several studies of other species used in non-European countries have been included. Besides, the botanical description of Petasites genus and phytochemical characteristic of P. hybridus and toxicological studies of pyrrolizidine alkaloids as well as chemical profile of patented commercial extracts from rhizomes, roots and leaves of this species used in European phytotherapy have been performed. In this review, attention has also been paid to the promising and potential application of special extracts of P. hybridus not only in the prevention of migraine, treatment of allergic rhinitis symptoms, asthma and hypertension, but also in prevention and slowing the progression of neurodegenerative diseases developing with the inflammatory process in the CNS as a new therapeutic strategy. In fact, there is already an evidence of promising properties of P. hybridus extracts and sesquiterpens – decrease in the prostaglandins and leukotrienes release, inhibition of COX-1 and COX-2 activity, as well as antagonism of L-type voltage-gated calcium channels. In order to explain the new mechanisms of action of P. hybridus extracts in the CNS and their future application in phytotherapy of diseases with neuroinflammatory process, further studies should be performed.

7

The effect of pyrrolizidine alkaloids on the Colorado potato beetle [Leptinotarsa decemlineata Say]

63%

Kropczynska D., Kawka B., Pietrosiuk A., Furmanowa M., Wiedenfeld H.

Acta Biologica Cracoviensia. Series Zoologia

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2004

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tom 46

8

Pyrrolizidine alkaloids - chemistry, biosynthesis, pathway, toxicity, safety and perspectives of medicinal usage

51%

Dreger M., Stanislawska M., Krajewska-Patan A., Mielcarek S., Mikolajczak P. L., Buchwald W.

Herba Polonica

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2009

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tom 55

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nr 4

127-147

Pyrrolizidine alkaloids (PAs) are the class of secondary metabolites that evolved as a powerful tool in the plant defensive interactions against herbivores. The occurrence of PAs in the plant world is scattered in several unrelated botanic families with special abundance in Asteraceae, Boraginaceae and Fabaceae. Homospermidine synthase (HSS) was recognized as a key enzyme that catalyzes homospermidine formation from polyamines. The studies of HSS kinetic and gene sequence revealed that it is of polyphyletic origin and raised as a result of deoxyhypusine synthase (DHS) gene duplication. The ability of PAs production occurred independently at least four times in course of plant evolution. The PAs biosynthesis is tightly correlated with growth phase and biomass production. It is supposed that PAs biosynthesis is individually regulated in different lineages of plants. The PAs with a 1,2 unsaturated necine skeleton show toxic activity (hepatoxicity, carcinogenicity, genotoxicity, teratogenocity and cytotoxicity). It is though that pyrrolic esters formation during the detoxication process in the liver is the main mechanism of PAs toxicity. The pyrrolic esters are highly reactive and tend to bind rapidly with nucleophilic macromolecules including DNA and DNA-protein inducing hepatotoxicity or tumorigenecity. The problem of PAs toxicity cause the restrictions in the production and sale of herbal products. This review encompasses the present status of the pyrrolizidine alkaloids in the plants studies and summarize the topics of chemistry, biosynthesis, evolution including the involved genes, the factors affecting on biosynthesis, accumulation and toxicity of PAs.

Ograniczanie wyników

Pyrrolizidine alkaloids

Pyrrolizidine alkaloids in honey from Switzerland

Content of pyrrolizidine alkaloids in the leaves of coltsfoot (Tussilago farfara L.) in Poland

Pyrrolizidine alkaloids in European honeys and honeys from overseas

Content of pyrrolizidine alkaloids (senecionine and senkirkine) in Tussilago farfara L. plants cultivated in vitro

Phytochemical, pharmacological and clinical studies of Petasites hybridus (L.) P. Gaertn., B. Mey. and Scherb. A reviev

The effect of pyrrolizidine alkaloids on the Colorado potato beetle [Leptinotarsa decemlineata Say]

Pyrrolizidine alkaloids - chemistry, biosynthesis, pathway, toxicity, safety and perspectives of medicinal usage