Pyrrolizidine Alkaloids from <i>Echium setosum</i> and <i>Echium vulgare</i>

El-Shazly, Assem M.; Sarg, Taha; Ateya, Abdel-Monem; Aziz, A Abdel; El-Dahmy, S.; Witte, Ludger; Wink, Michael

doi:10.1021/np9600661

Cited by 39 publications

(10 citation statements)

References 17 publications

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“…In the most widespread and investigated species, E. vulgare , 17 compounds were detected. Most of the detected compounds (peaks 1, 3, 5, 6, 9, 10, 12, 16, 17) were previously found in E. vulgare [12,23,27,28] . Several compounds (peaks 7, 8, 13, 14, 19–21) were detected for the first time in our work E. vulgare , but they have been previously found in other Boraginaceae species [29–32] …”

Section: Resultssupporting

confidence: 50%

Assessment of Distribution and Diversity of Pyrrolizidine Alkaloids in the Most Prevalent Boraginaceae Species in Macedonia

Stefova

Cvetanoska

Bogdanov

et al. 2022

Chemistry & Biodiversity

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Systematic study of extraction efficiency of pyrrolizidine alkaloids (PAs) and corresponding pyrrolizidine alkaloid N‐oxides (PANOs) from plant material for subsequent LC/MS analysis was carried out. The optimal extraction was achieved with methanol and one clean up step using SPE C18 column. With the optimized LC‐ESI‐MS/MS method using ion trap, the distribution and diversity of PAs and PANOs in plant material (leaves, flowers and stems) obtained from wild‐growing E. vulgare, E. italicum, S. officinale L., C. creticum and O. heterophylla species from Macedonia was assessed. These widespread Boraginaceae species contain various PAs and PANOs and 25 of them were identified. Based on these qualitative and quantitative analyses, the profiles of 1,2‐unsaturated PAs for each sample were obtained and their toxic potential was estimated. The toxic potential of O. heterophylla and C. creticum were assumed to be highest (containing up to 4753 mg/kg and 3507 mg/kg), followed by E. vulgare (up to 1340 mg/kg), S. officinale L. (up to 479 mg/kg) and E. italicum (up to 16 mg/kg). This method can be used for monitoring the inclusion of these secondary metabolites in the food chain in order to contribute in their risk management.

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Section: Resultssupporting

confidence: 50%

Assessment of Distribution and Diversity of Pyrrolizidine Alkaloids in the Most Prevalent Boraginaceae Species in Macedonia

Stefova

Cvetanoska

Bogdanov

et al. 2022

Chemistry & Biodiversity

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“…Echimidine- N -oxide B ( 13 ) was the most abundant PANO in both species, and has been described as responsible for acute alkaloid toxicity in rats [ 40 ]. Echimidine was previously found in high quantities in E. vulgare and E. setosum [ 47 ]. Rare or less common PAs observed included 7- O -acetyllycopsamine/intermedine ( 7 ) > leptanthine- N -oxide ( 1 ) > echiuplatine- N -oxide ( 12 ).…”

Section: Resultsmentioning

confidence: 99%

Metabolic Profiling of Pyrrolizidine Alkaloids in Foliage of Two Echium spp. Invaders in Australia—A Case of Novel Weapons?

Skoneczny

Weston

Zhu

et al. 2015

IJMS

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Metabolic profiling allows for simultaneous and rapid annotation of biochemically similar organismal metabolites. An effective platform for profiling of toxic pyrrolizidine alkaloids (PAs) and their N-oxides (PANOs) was developed using ultra high pressure liquid chromatography quadrupole time-of-flight (UHPLC-QTOF) mass spectrometry. Field-collected populations of invasive Australian weeds, Echium plantagineum and E. vulgare were raised under controlled glasshouse conditions and surveyed for the presence of related PAs and PANOs in leaf tissues at various growth stages. Echium plantagineum possessed numerous related and abundant PANOs (>17) by seven days following seed germination, and these were also observed in rosette and flowering growth stages. In contrast, the less invasive E. vulgare accumulated significantly lower levels of most PANOs under identical glasshouse conditions. Several previously unreported PAs were also found at trace levels. Field-grown populations of both species were also evaluated for PA production and highly toxic echimidine N-oxide was amongst the most abundant PANOs in foliage of both species. PAs in field and glasshouse plants were more abundant in the more widely invasive species, E. plantagineum, and may provide competitive advantage by increasing the plant’s capacity to deter natural enemies in its invaded range through production of novel weapons.

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“…Essential oils of flower, leave and stem of A. santolina from Egyptian plant have been studied and 44 (97.62 %), 43 (95.62 %) and 37 (96.09 %) compounds identified respectively. Fragranyl acetate (45-52 %), fragranol (11-19 %), borneol (3-5 %), terpin-4-ol (6-7 %) and camphor (3-4 %) were the main constituents in the investigated parts 16 . The principle components in the hexane-ether extract of the aerial parts were fragranyl acetate (50.7 %), fragranol (8.78 %) and camphor (6.6 %).…”

Section: Resultsmentioning

confidence: 95%

Chemical Compositions of Essential Oils of Different Parts and Extract of Achillea santolina L. from Iran

Motavalizadehkakhky¹,

Ebrahimi²,

Emamiyan³

et al. 2013

Asian J. Chem.

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The genus Achillea L. (Asteraceae) is represented by about 115 species found in the northern hemisphere, mostly in Europe and Asia and commonly known as yarrows 1-3. It has been represented in Iran by nineteen species including seven endemics, among this genus, Achillea santolina L. (it has been known as Bomadaran in Iran) is represented in Iran 4. The Achillea L. species belong to the oldest medicinal plants that are used both for pharmaceutical purposes and in folk medicine. These plants contain a complex of different pharmacological compounds, for example, terpenes, flavonoids, alkaloids, bitters, tannins, lignans 5. Achillea species are diuretic, emmenagog agents, wound healing, for curing stomachache, diarrhea and antichloristic, antispasmodic, antiseptic and infection preventing properties and have been used to reduce sweating and to stop bleeding, amarum, stomachicum, cholagolum and carminativum, too 3,6-13. The Achillea genus has a wide distributional range 14 and the differences in oil composition may be affected by different environmental factors, plant genetic type, seasonality and developmental stage, because of a chemically polymorphic and perennial 15. Terpenoids (1,8-cineole, camphor, borneol, pinenes, artemisia ketone, santolina alcohol, farnesane, caryophyllene

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Pyrrolizidine Alkaloids from Echium setosum and Echium vulgare

Cited by 39 publications

References 17 publications

Assessment of Distribution and Diversity of Pyrrolizidine Alkaloids in the Most Prevalent Boraginaceae Species in Macedonia

Assessment of Distribution and Diversity of Pyrrolizidine Alkaloids in the Most Prevalent Boraginaceae Species in Macedonia

Metabolic Profiling of Pyrrolizidine Alkaloids in Foliage of Two Echium spp. Invaders in Australia—A Case of Novel Weapons?

Chemical Compositions of Essential Oils of Different Parts and Extract of Achillea santolina L. from Iran

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