Acetylated alkaloids from Narcissus pseudonarcissus

Kreh, Mirko; Matusch, Rudolf; Witte, Ludger

doi:10.1016/0031-9422(95)00465-j

Cited by 27 publications

(12 citation statements)

References 2 publications

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“…The most of the compounds studied in the present work have been isolated in the Group of Natural Products at the Faculty of Pharmacy, University of Barcelona, from various plant species of the Amaryllidoideae subfamily and identified by 1D and 2D NMR, CD, EIMS and HRMS spectrometry. Exceptions are compounds 9 , 15 11 , 19 13 , 20 14 15,21 and 19 , 22 which have been identified in plant samples by comparison of their MS spectra in the NIST 98 mass spectral database (NIST#: 111590 for 9 , 413489 for 11 , 111405 for 14 , 111512 for 19 ; The National Institute of Standards and Technology, Gaithersburg, MD 20899) and their original description in the literature. Methanol solutions with concentrations of 250–500 μg/ml were used for GC–MS analyses.…”

Section: Experimental Methodsmentioning

confidence: 99%

“…07 displays a MS spectrum similar to that of anhydrolycorine(19) with ions clusters shifted with −2 amu and a [M − H] + at m/z 248 as a base ion. The neutral losses [M − 31] + , S C H E M E 4 Proposed fragmentation of lycorine-type alkaloids with a Δ 4,11 double bond F I G U R E 5 GC-MS spectrum of dihydrolycorine with saturated rings C and D [M − 59] + and [M − 86] + are as in compound 19, indicating a lycorinetype compound with aromatic ring C and 2 protons at C6.…”

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confidence: 97%

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GC–MS of some lycorine‐type Amaryllidaceae alkaloids

Berkov

Torras-Claveria²,

Viladomat³

et al. 2021

J Mass Spectrom

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The search for novel bioactive compounds and the identification of known ones in the plant kingdom are a challenge for the scientists working in different fields of plant science. In the recent years, mass spectrometry is the most frequently applied method for analysis of complex mixtures of plant metabolites. Twenty‐two alkaloids of different lycorine skeleton subtypes (with a Δ3,4 double bond, with a Δ4,11 double bond, with saturated rings C and D, and with aromatic ring C) were subjected to separation with gas chromatography and studied with electron impact mass spectrometry including single quadropole (GC‐EIMS), tandem mass (GC‐EIMS/MS) and high resolution mass (EI‐HRMS) detectors in order to determine their fragmentation pattern. The compounds showed excellent separation and specific MS fragmentation allowing structural determination. The GC–MS can be successfully applied for searching new and identification of known bioactive molecules, chemotaxonomical and chemoecological studies, among others, within the Amaryllidoideae subfamily.

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Section: Experimental Methodsmentioning

confidence: 99%

mentioning

confidence: 97%

GC–MS of some lycorine‐type Amaryllidaceae alkaloids

Berkov

Torras-Claveria²,

Viladomat³

et al. 2021

J Mass Spectrom

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“…The juice of N. pseudonarcissus L. is recommended for rhinitis, bronchitis and whooping (Zalesova & Petrovskaya, 1898-1901. N. pseudonarcissus contain alkaloids: norpluvine, 10-norpluvine and oxy-acetylgalanthamine (Kreh et al, 1995). The decoction of B. Longicaula L. dry seeds is used against piles and also given for renal colic and hepatitis.…”

Section: The Plant and Their Uses Amaryllidaceaementioning

confidence: 99%

Plants of the Republic of Azerbaijan with Potential Medicinal Applications. Part III

Mir-Babayev¹,

Houghton²

2002

Pharmaceutical Biology

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“…Narcissus belongs to the Amaryllidaceae family and is well known for its ornamental flower value but also for its alkaloids, an important group of compounds for drug development [1]. Several alkaloids are found in Narcissus such homolycorine, lycorenine [2], galanthamine, narwedine [3,4], norgalanthamine [5], haemanthamine lycoramine [6], narciclasine [7] as well as other minor alkaloids. The Narcissus alkaloid, galanthamine, is the most wellknown bioactive compound because of its anticholinesterase activity [8].…”

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confidence: 99%

“…The analysis was done in scan mode (m/z 50-350) using electron ionization at 70 eV. Identification was accomplished by comparing the measured mass spectral fragmentation data with the authentic compound (galanthamine) or with the data from the literature[2][3][4]6,16,23,24].…”

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confidence: 99%

The Effect of Acids on Alkaloid Yield in Pressurized Water Extraction of Narcissus Pseudonarcissus

Rachmaniah

Spronsen

Verpoorte

et al. 2021

J. Eng. Technol. Sci.

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Pressurized water (PW) extraction of galanthamine from Narcissus pseudonarcissus bulbs was performed. The obtained yield was compared with the yield from conventional acidified water extraction and methanolic Soxhlet extraction. Both PW and conventional acidified water extraction were followed by a subsequent purification step for the alkaloids. The PW extraction (70 °C, 150 bar, 45 min) yielded as much galanthamine as methanolic-Soxhlet extraction (ca. 3.50 mg/g). Meanwhile, acid-base extraction with 1% of HBr (v/v) at 65 °C for 3 h gave a lower yield (ca. 2.65 mg/g). A higher PW temperature did not significantly increase the galanthamine yield. Pressure increase is not necessary since more water-soluble compounds such as proteins and polysaccharides are co-extracted, resulting in high viscosity of the water extract solution, which hampers the filtration process. Hence, the acidity of the solution is highly important both in the case of PW extraction and acidified water extraction. Besides galanthamine, the total alkaloid profile following Narcissus alkaloids was also obtained. Lycoramine, O-methyloduline, norgalanthamine, epi-norgalanthamine, narwedine, oduline, haemanthamine, O-methyllycorenine, and a haemanthamine derivate were identified. Although a high yield was obtained from PW extraction, the further purification needs to be improved to obtain an economically feasible industrial extraction process.

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Acetylated alkaloids from Narcissus pseudonarcissus

Cited by 27 publications

References 2 publications

GC–MS of some lycorine‐type Amaryllidaceae alkaloids

GC–MS of some lycorine‐type Amaryllidaceae alkaloids

Plants of the Republic of Azerbaijan with Potential Medicinal Applications. Part III

The Effect of Acids on Alkaloid Yield in Pressurized Water Extraction of Narcissus Pseudonarcissus

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