Mass spectra of amaryllidaceae alkaloids. The structure of narcissidine.

Kinstle, Thomas H.; Wildman, W. C.; Brown, Clifford

doi:10.1016/s0040-4039(00)72920-0

Cited by 27 publications

(27 citation statements)

References 2 publications

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“…A final proof of the natural origin of jonquailine was found by extracting the bulbs of N. jonquilla quail described above but using ethanol and analyzing the crude extract by GC/MS as detailed in the experimental for alkaloids and corresponding isocarbostyril content. Lycorine, haemanthamine and narciclasine, the main components, as well as the new alkaloid jonquailine ( t R = 24.59 min) were identified also by co-injection with their standards and by comparing the mass spectral fragmentation with standard reference spectra reported in literature [41,42]. Minor components were identified as deoxytazettine, epi-macronine, trisphaeridine and tazettine [41,42].…”

Section: Resultsmentioning

confidence: 99%

“…Lycorine, haemanthamine and narciclasine, the main components, as well as the new alkaloid jonquailine ( t R = 24.59 min) were identified also by co-injection with their standards and by comparing the mass spectral fragmentation with standard reference spectra reported in literature [41,42]. Minor components were identified as deoxytazettine, epi-macronine, trisphaeridine and tazettine [41,42]. In addition no peak corresponding to the 8- O -ethylpretazettine was observed and thus the acetalization of the lactol at C-8 did not occur during the extraction process.…”

Section: Resultsmentioning

confidence: 99%

“…The split ratio was 1:20. The alkaloids and narciclasine were identified by applying co-chromatography with standards previously isolated from N. jonquilla quail bulbs and other Amaryllidaceae plants, by comparing the mass spectral fragmentation with standard reference spectral data from NIST (NIST Mass Spectral Database, PC-Version 5.0 (2005), National Institute of Standardization and Technology, Gaithersburg, MD, USA), and by comparing mass spectral data with those of literature [41,42]. …”

Section: Methodsmentioning

confidence: 99%

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Jonquailine, a new pretazettine-type alkaloid isolated from Narcissus jonquilla quail, with activity against drug-resistant cancer

Masi¹,

Frolova²,

Yu³

et al. 2015

Fitoterapia

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A new alkaloid, belonging to the pretazettine group of Amaryllidaceae alkaloids, was isolated from dried bulbs of Narcissus jonquilla quail and named jonquailine. Its structure, including the absolute configuration, was elucidated using various NMR, ECD and ESI MS techniques. Initial biological evaluation revealed significant antiproliferative effects against glioblastoma, melanoma, uterine sarcoma and non-small-cell lung cancer cells displaying various forms of drug resistance, including resistance to apoptosis and multi-drug resistance. Jonquailine was also found to synergize with paclitaxel in its antiproliferative action against drug-resistant lung cancer cells. The results obtained compared with literature data also showed that the hydroxylation at C-8 is an important feature for the anticancer activity but this seems unaffected by the stereochemistry or the acetalization of the lactol.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Jonquailine, a new pretazettine-type alkaloid isolated from Narcissus jonquilla quail, with activity against drug-resistant cancer

Masi¹,

Frolova²,

Yu³

et al. 2015

Fitoterapia

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“…Alkaloid 26, which lacks the 3,4-unsaturation, possesses the base peak at m/z 332 (M-1) instead of the typical base peak after the retro-Diels Alder process. 34 The EI-MS fragmentation of the tazettine-type skeleton, represented by compounds 18, 19 and 28, is strongly supported by the stereochemistry of the substituent at C-3. The b-orientation of the C-3 substituent induces a retro-Diels Alder process at ring C followed by the loss of the neutral fragment [C 5 H 8 O], which yields the base peaks at m/z 247 and 245 for compounds 18 and 28, respectively (Table 2).…”

Section: Cgc-ms Dereplicationmentioning

confidence: 96%

Identification of Alkaloids from Hippeastrum aulicum (Ker Gawl.) Herb. (Amaryllidaceae) Using CGC-MS and Ambient Ionization Mass Spectrometry (PS‑MS and LS-MS)

Bessa

Andrade

Domingos

et al. 2016

J. Braz. Chem. Soc.

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Amaryllidaceae alkaloids are well-known isoquinolines which have demonstrated a wide range of biological activities such as antiviral, anticancer, acetylcholinesterase inhibition, antimalarial, among others. Mass spectrometry (MS) studies based on capillary gas chromatography (CGC), paper spray (PS), and leaf spray (LS) ionization were carried out for alkaloid investigation of the native Brazilian species Hippeastrum aulicum, along with nuclear magnetic resonance (NMR) techniques. Thirty-one alkaloids were identified including the new compound haemanthamine N-oxide. The results from PS-and LS-MS techniques were consistent with those observed in CGC-MS analysis. To the best of our knowledge, it is the first study combining NMR, CGC-MS and the ambient ionization-mass spectrometry (PS-and LS-MS) on Amaryllidaceae plants.

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“…Alkaloid profiles of different parts of L. martinezii plants in vegetative, flowering and ripening stages were studied for the first time. Lycorine-type compounds show intensive molecular M þ and [M À H] þ peaks [24]. Twenty-two were left unidentified due to a lack of reference spectra.…”

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confidence: 99%

Biogeographical Patterns and Phenological Changes in Lapiedra martineziiLag. Related to Its Alkaloid Diversity

Ríos

Berkov

Martínez-Francés

2013

Chemistry & Biodiversity

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The aim of this work was to investigate the alkaloid patterns of Lapiedra martinezii and their relation to biogeography and phenology focused in a phylogenetic comparison. Plants from 14 populations of L. martinezii, covering almost its entire distribution area, were subjected to morphological, ecological, and phytochemical analysis. Experiments for different alkaloid-type content are proposed as a new tool for analysis of plant distribution. Several plants were transplanted for weekly observation of their phenological changes, and alkaloids from different plant organs were extracted, listed, and compared. The alkaloid pattern of L. martinezii comprises 49 compounds of homolycorine, lycorine, tazettine, haemantamine, and narciclasine types. The populations located in the north and south margins of the distribution area displayed alkaloid patterns different from those of the central area. Changes in these patterns during their phenological cycle may be related to a better defence for plant reproduction. L. martinezii is an old relict plant, and it has maintained some of the more primitive morphological features and alkaloid profiles of the Mediterranean Amaryllidaceae. The variations in alkaloid content observed could be interpreted in a phylogenetic sense, and those found in their phenological changes, in an adaptive one.

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Mass spectra of amaryllidaceae alkaloids. The structure of narcissidine.

Cited by 27 publications

References 2 publications

Jonquailine, a new pretazettine-type alkaloid isolated from Narcissus jonquilla quail, with activity against drug-resistant cancer

Jonquailine, a new pretazettine-type alkaloid isolated from Narcissus jonquilla quail, with activity against drug-resistant cancer

Identification of Alkaloids from Hippeastrum aulicum (Ker Gawl.) Herb. (Amaryllidaceae) Using CGC-MS and Ambient Ionization Mass Spectrometry (PS‑MS and LS-MS)

Biogeographical Patterns and Phenological Changes in Lapiedra martineziiLag. Related to Its Alkaloid Diversity

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