Alkaloids of fumaria officinalis

Mardirossian, Z.H.; Kiryakovt, H.G.; Ruder, Jean-Pierre; MacLean, David B.

doi:10.1016/s0031-9422(00)86978-2

Cited by 22 publications

(7 citation statements)

References 12 publications

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“…From the observation of demethylation, decarbonylation, and deformaldehydation (Supplementary Scheme S1(D), see Supporting Information), vicinal methoxyl groups could be present on the A‐ring. This compound was already observed in an extract of Fumaria officinalis but the identification of N ‐methylsinactine needs further investigation.…”

Section: Resultsmentioning

confidence: 91%

Identification of structurally diverse alkaloids in Corydalis species by liquid chromatography/electrospray ionization tandem mass spectrometry

Jeong

Lee

et al. 2012

Rapid Comm Mass Spectrometry

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RATIONALE Alkaloids with significant therapeutic effects are the main active constituents of Corydalis (C.) species. There are several kinds of alkaloids in C. species associated with diverse alkaloid metabolism in plants, but they are rarely identified. This study aimed to identify diverse alkaloids in C. species by liquid chromatography/electrospray ionization tandem mass spectrometry (LC/ESI‐MS/MS). METHODS Several types of alkaloids were extracted from C. species using ultrasonication with 70% CH3OH, and the extract was partitioned at pH 2 and 12. Separation of alkaloids was achieved by C18 high‐performance liquid chromatography (HPLC), and MS/MS analysis was conducted by electrospray ionization triple‐quadrupole mass spectrometry. For further confirmation, LC/Fourier transform ion cyclotron resonance (FTICR)‐MS was used to obtain accurate mass data and gas chromatography (GC)/MS combined with trimethylsilyl derivatization was applied for identification of the minor alkaloids. RESULTS Thirty‐three alkaloids among three different C. species were successfully separated and identified by LC/ESI‐MS/MS and LC/FTICR‐MS. Structural assignment of individual alkaloids was performed according to MS/MS spectral patterns. For further confirmation, accurate mass data of alkaloids by LC/FTICR‐MS were obtained within 5 ppm and the GC/MS data for the trimethylsilyl alkaloids were also obtained. Among 33 alkaloids identified from this study, 13 alkaloids were reported for the first time in the investigated C. species. CONCLUSIONS The LC/ESI‐MS/MS technique was effective in obtaining structural information and yielded diagnostic ions for diverse alkaloids. Based on the identified 33 alkaloids, marker compounds were suggested for the three C. species with different geographic origins. This study may also be useful for elucidating unknown alkaloids in herbal medicines. Copyright © 2012 John Wiley & Sons, Ltd.

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Section: Resultsmentioning

confidence: 91%

Identification of structurally diverse alkaloids in Corydalis species by liquid chromatography/electrospray ionization tandem mass spectrometry

Jeong

Lee

et al. 2012

Rapid Comm Mass Spectrometry

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“…As a model system, we were attracted to indanone-derived β-ketoesters due to their potential for elaboration into conformationally constrained tyrosine analogues (CCTAs) such as 5-hydroxy-2-aminoindan-2-carboxylic acid (Hai) ( 4 ), 9 spirohydantoin-derived CGRP antagonists investigated for treatment of migraine headaches ( 5 ), 10 and amino-indane natural products such as dihydroparfumidine 11 ( 6 ) ( Fig. 1c ).…”

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confidence: 99%

“…Challenged by low levels of enantioselectivity using common chiral phosphate scaffolds, we undertook efforts to design novel CAPT catalysts. We were drawn to the BINAM-derived phosphoric acids (BDPAs, Table 1, 13-16) rst prepared by Ishihara and coworkers, 13 as they offer two potential improvements over BINOL-derived phosphates (7)(8)(9)(10)(11): rst, we hypothesized that the nitrogen lone pairs would improve hydrogen-bonding interactions with the substrates relative to traditional chiral phosphoric acid catalysts (7)(8)(9)(10)(11)(12). 14 Second, increased resonance donation from the nitrogens could improve ion-pairing with the diazonium cation.…”

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confidence: 99%

Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst

et al. 2015

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Chiral anion phase-transfer of aryldiazonium cations was utilized to achieve highly enantioselective α-amination of carbonyl compounds. A broad scope of indanone- and benzosuberone-derived substrates was amenable to this strategy. Critical to obtaining high levels of enantioselectivity was the use of BINAM-derived phosphoric acids. The utility of this transformation was demonstrated through facile conversion of diazene products to valuable α-amino acid derivatives.

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“…seems to be undesirable to water buffaloes. This can be attributed either to their morphological structure (thorns) or the presence of toxic substances, such as alkaloids, saponins, cumarin, glycosides etc (Mardirossian et al 1983, Todd et al 1995, Al-Sultan et al 2003). It appears that the water buffaloes tended to test the numerous available plant species on the wet grassland awaiting for a post-ingestive response (Provenza et al 2003).…”

Section: Discussionmentioning

confidence: 99%

Seasonal variation in water buffaloes’ diet grazing in wet grasslands in Northern Greece

2019

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Seasonal variability in grasslands’ vegetation affects animals’ diet selection. We studied the seasonal changes in water buffaloes’ diet during grazing in wet grasslands in Northern Greece. We recorded each month the plant species of the vegetation and the species consumed by buffaloes. We categorized the former into three functional groups (graminoids, legumes, and forbs) and the latter into five groups (graminoids, legumes, forbs, shrubs, and trees). There were significant differences in the proportions (%) of functional groups in the vegetation and in buffaloes’ diet between seasons (χ2 test, P<0.05). Graminoids, legumes, and forbs participated in buffaloes’ diet in all seasons, while the less preferred functional groups were trees and shrubs. Buffaloes consumed ten species in all seasons but we observed the most diverse diet, in terms of plant species, in spring. The most frequently consumed species in each functional group were Cynodon dactylon (graminoids), Trifolium repens (legumes), Cichorium intybus (forbs), Rubus sp. (shrubs), and Populus sp. (trees). However, the majority of plant species in buffaloes’ diet was in very low proportions (<1%), while buffaloes did not sample at all 38 herbaceous species. Researchers need to conduct further research to understand water buffaloes’ foraging strategy regarding plants’ anti-quality characteristics.

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Alkaloids of fumaria officinalis

Cited by 22 publications

References 12 publications

Identification of structurally diverse alkaloids in Corydalis species by liquid chromatography/electrospray ionization tandem mass spectrometry

Identification of structurally diverse alkaloids in Corydalis species by liquid chromatography/electrospray ionization tandem mass spectrometry

Enantioselective α-amination enabled by a BINAM-derived phase-transfer catalyst

Seasonal variation in water buffaloes’ diet grazing in wet grasslands in Northern Greece

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