Pyrrolizidine and tetrahydroisoquinoline alkaloids from Echium humile

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

doi:10.1016/0031-9422(95)00847-0

Cited by 36 publications

(21 citation statements)

References 16 publications

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“…Whereas echimidine dominated the alkaloid extract after reduction (42% ), 7-angeloyllycopsamine and echimidine were the major components before reduction with 29 and 25% , respectively. Our results are in agreement with a recent ex amination of other Echium species (El-Shazly et al, 1996a;1996b) which showed that all pyrroli zidine alkaloids in Echium derive from the retronecine base. All the toxic PAs are esters of 1,2-unsaturated pyrrolizidine nucleus (necines) (Bull et al, 1968;Mattocks, 1986;Hartmann and Witte, 1995;Röder, 1995).…”

Section: Resultssupporting

confidence: 93%

Pyrrolizidine Alkaloids from Echium rauwolfii and Echium horridum (Boraginaceae)

El-Shazly

Abdel-All²,

Tei³

1999

Zeitschrift Für Naturforschung C

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Echium rauwolfii, Echium horridum, Boraginaceae, Pyrrolizidine Alkaloids, Capillary GLC Echimidine was isolated from Echium rauwolfii and Echium horridum and identified by MS, *H-and 13C NMR as a major alkaloid. In addition, structures of 12 minor alkaloids were inferred from GLC and GLC-M S analyses: 7-angeloylretronecine, 7-tigloylretronecine, lycopsamine, 7-acetyllycopsamine, uplandicine, 7-angeloyllycopsamine, 7-tigloyllycopsamine, tigloyl isomer of echimidine, 7-angeloyl-9-(2-methylbutyryl)retronecine, 7-tigloyl-9-(2-methylbutyryl)retronecine, 7-angeloyl-9-(2,3-dihydroxybutyryl)retronecine, and 7-tigloyl-9-(2,3-dihydroxybutyryl)retronecine. Both species had similar alkaloid profiles. Alkaloid extracts exhibited antibacterial effects with a MIC of 1.7 mg/ml in E. coli. Microscopic examination of E. coli treated with different subtoxic alkaloid concentrations (1 3 -5 2 ng/ml) revealed extensive filamentation.

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Section: Resultssupporting

confidence: 93%

Pyrrolizidine Alkaloids from Echium rauwolfii and Echium horridum (Boraginaceae)

El-Shazly

Abdel-All²,

Tei³

1999

Zeitschrift Für Naturforschung C

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“…PAs with 1,2-unsaturated necines but without a hydroxyl group at C-7 (as in supinidine type) with an esterification at C-9 results in a base peak m/z 122, while the saturated necine of the same type (trachelanthamidine, isoretroncanol, lindelofidine) shows a base peak at m/z 124. 1,2-unsaturated diester PAs esterified with angelic, tiglic or senecioic at C-7 shows a base peak at m/z 220 [40,42,59,67,70,90,91,96,163,193,200,201]. The fragmentation pathway of this type of PAs starts with the cleavage of the weak allylic ester bond at C-9.…”

Section: Mass Spectrometrymentioning

confidence: 99%

“…and Trichodesma incanum [46]. For analytical purposes high-resolution capillary GLC alone or in combination with mass spectrometry is the method of choice for free PA bases [40,59,67,70,90,91,96,163,[191][192][193][194][195]. HPLC and HPLC-MS are also helpful but less sensitive than GLC and GLC-MS [60,93,[196][197][198][199].…”

Section: Phytochemical Analysis Of Pasmentioning

confidence: 99%

“…High resolution Gas-liquid chromatography coupled with mass spectrometry (GLC-MS) has become a valuable and highly sensitive means for separation, convenient identification and quantification of complex PA mixtures, even in minute quantities or in diasteroisomeric forms [40,59,67,70,90,91,96,163,[191][192][193][194][195]. The combination of molecular weight, group mass fragmentation pattern and Kovats retention indices, enables an unequivocal identification of most of PA tertiary bases even in trace amounts or of closely related isomers.…”

Section: R1 R2mentioning

confidence: 99%

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Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties

2014

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Among the diversity of secondary metabolites which are produced by plants as means of defence against herbivores and microbes, pyrrolizidine alkaloids (PAs) are common in Boraginaceae, Asteraceae and some other plant families. Pyrrolizidine alkaloids are infamous as toxic compounds which can alkylate DNA und thus cause mutations and even cancer in herbivores and humans. Almost all genera of the family Boraginaceae synthesize and store this type of alkaloids. This review reports the available information on the present status (literature up to early 2014) of the pyrrolizidine alkaloids in the Boraginaceae and summarizes the topics structure, distribution, chemistry, chemotaxonomic significance, and biological properties.

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“…reported literature (El-Shazly et al, 1996;Zhu et al, 2015). The series of ions at m/z 136, 120, 119, 93, 94 and 80, are characteristic of 1, 2-unsaturated pyrrolizidine diesters.…”

Section: Discussionmentioning

confidence: 89%

Phytochemical and biological investigation of Eugenia uniflora L. cultivated in Egypt

Bakr¹,

Mohamed²,

Waly³

2017

J. Pharmacognosy Phytother.

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Eugenia uniflora L. (Myrtaceae) is a plant species used in folk medicine for treatment of various disorders. This study aims to quantify the phenolic and flavonoid contents of E. uniflora aqueous methanolic extract (AME), identification of its major constituents, as well as the evaluation of its biological activity. Quantification was performed using colorimetric assays. Column chromatographic separation was used for isolation of the major phenolic constituents while their structures were elucidated by 1D-and 2D Nuclear magnetic resonance spectroscopy (NMR) spectra. Alkaloids were identified using gas chromatography-mass spectrometry (GC-MS) analysis. The antidepressant activity of E. uniflora AME in mice was evaluated using the tail suspension test (TST). The weight control effect was evaluated by serial weighing. The results showed high phenolic and flavonoid contents of E. uniflora AME. The chromatographic investigation identified a new flavonoid, myricetin 3-O-(4'', 6''-digalloyl) glucopyranoside, for first time in this genus, along with four flavonoids and phenolic acids. Integerrimine alkaloid was identified through GC/MS analysis. Administration of E. uniflora AME significantly reduced the immobility time in mice (P value of < 0.0001) in a dose-dependent manner for doses of 1, 10, 50 and 100 mg/kg. Also, a non-significant weight reduction in mice chronically treated with the E. uniflora AME was observed. Our study reports the isolation of myricetin 3-O-(4'', 6''-digalloyl) glucopyranoside from E. uniflora. It confirms that E. uniflora leaf extract has an antidepressant and anti-obesity effect.

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Pyrrolizidine and tetrahydroisoquinoline alkaloids from Echium humile

Cited by 36 publications

References 16 publications

Pyrrolizidine Alkaloids from Echium rauwolfii and Echium horridum (Boraginaceae)

Pyrrolizidine Alkaloids from Echium rauwolfii and Echium horridum (Boraginaceae)

Diversity of Pyrrolizidine Alkaloids in the Boraginaceae Structures, Distribution, and Biological Properties

Phytochemical and biological investigation of Eugenia uniflora L. cultivated in Egypt

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