Harmalidine, A β-carboline alkaloid from peganum harmala

Siddiqui, Salimuzzaman; Khan, Obaid Yusuf; Siddiqui, Bina S.; Faizi, Shaheen

doi:10.1016/s0031-9422(00)81861-0

Cited by 17 publications

(12 citation statements)

References 11 publications

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“…In traditional Mongolian medicine it is used as antitussive and antidote and it also eliminates yellow liquorstasis [4]. At the same time, P. harmala is well-known traditional herbal medicine in China and Asian countries for the treatment of a variety of human ailments [5] and skin diseases [6]. Its seeds showed narcotic, anthelmintic and antispasmodic effects and have been employed in the cases of asthma and rhematism treatments [7].…”

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confidence: 99%

Alkaloids from cultivated plant of Peganum harmala L.

et al. 2014

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Alkaloids such as 1H-cyclopenta(b) quinoline, 2.3.5.6.7.8-hexahydro-9-amino-; Vasicinone(1H-Pyrrоlo[2.1-b]quinazolin-9-one,3-hydroxy-2.3-dihydro) and harmine were isolated from cultivated plant of P. harmala. Four unknown alkaloids were isolated from P. harmala for the first time: 2.2.6.6-Tetramethyl-4-piperidone., Quinoline, 2.3.4-trimethyl-., Pyridine, 2-phenoxy-4-amino-and 4-(3-Propynyloxy)-quinazoline. Their structures were determined by GC-MS.

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Section: Introductionmentioning

confidence: 99%

Alkaloids from cultivated plant of Peganum harmala L.

et al. 2014

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“…Yuremamine, isolated from the stem bark of Mimosa hostilis , is another recent interesting example, due to its traditional use promoting hallucinogenic and psychoactive effects . Another psychoactive alkaloid harmalidine and its derivatives have been isolated from the seeds of Pegalum harmala . The pyrrolo[1,2- a ]indole motif can also be found in some non-natural compounds, exhibiting useful biological activities (Figure ). , Due to their interesting properties, these compounds have given rise to various synthetic approaches. , Most of them relied on multistep sequences, especially in the mitomycin area, and any additional convergent and rapid route would be beneficial to this area.…”

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“…This compound could easily be obtained through the Au-catalyzed rearrangement of the simple N -(4-ethoxyphenyl)-2-ethynylazetidine 1k in 85% yield (Table , entry 1). Yet, the psychoactive alkaloid harmalidine seemed to have never been synthesized (Figure ). The present Au-catalyzed rearrangement would offer the first approach to such a compound and analogs, starting from either N -(aryl) 2-(4-hydroxybut-1-ynyl)-3,3-dimethylazetidine 1l or 1m .…”

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“…7 Another psychoactive alkaloid harmalidine and its derivatives have been isolated from the seeds of Pegalum harmala. 8 The pyrrolo [1,2-a]indole motif can also be found in some nonnatural compounds, exhibiting useful biological activities (Figure 1). especially in the mitomycin area, 13 and any additional convergent and rapid route would be beneficial to this area.…”

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Gold(I)-Catalyzed Rearrangement of N-Aryl 2-Alkynylazetidines to Pyrrolo[1,2-a]indoles

et al. 2013

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“…Various parts of the plant are used in folk medicine to treat several illnesses [4]. Researchers from various countries have been studying the chemical composition of this plant since 1841 because of its therapeutic importance [5][6][7][8][9][10][11][12][13]. Mainly the alkaloid composition is studied.…”

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Components of the aerial part of Peganum harmala

et al. 2006

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The genus Peganum (Peganaceae) is represented in the flora of the CIS by the two species P. harmala L. (wild rue) and P. nigellastrum Bge. This genus is broadly represented by wild rue in Kazakhstan [1][2][3]. Various parts of the plant are used in folk medicine to treat several illnesses [4]. Researchers from various countries have been studying the chemical composition of this plant since 1841 because of its therapeutic importance [5][6][7][8][9][10][11][12][13]. Mainly the alkaloid composition is studied. Herein we report experimental results from a study of the component composition of the petroleum-ether extract of the aerial part of wild rue.Extraction with petroleum ether of the air-dried aerial part of P. harmala collected near Karaganda during floweringfruiting produced the total extracted substances (0.96%, 7.0 g).Extract (1 g) was dissolved in diethylether (15 mL) and left overnight in a refrigerator. The resulting precipitate was filtered off and washed with cold (-20°C) ether to produce a substance (0.22 g) that was a mixture of alkaloids (by PMR, mainly peganine and vasicinone). The mother liquor was evaporated. The residue was separated by the standard method [boiled for 10 min in KOH solution (10%) in MeOH. MeOH was evaporated, and the residue was separated between CHCl 3 and H 2 O] into acidic and neutral parts. The acidic part (0.3 g) was methylated and analyzed using GC-MS. The neutral part was evaporated (0.45 g), dissolved in CHCl 3 (10 mL), passed over a silica-gel column (5 g), and eluted with CHCl 3 (20 mL). The combined effluents were evaporated to afford an oil (0.4 g) that was analyzed by GC-MS.GC-MS was performed on a Hewlett-Packard 5890/II MSD gas chromatograph with a quadrupole mass spectrometer (HP MSD 5971) as a detector, a quartz column (30-m, HP-5 MS, copolymer 5%-diphenyl-95%-dimethylenesiloxane) with internal diameter 0.25 mm and thick layer of stationary phase (0.25 µm), temperature 50-280°C, heating rate 4°C/min, 280°C temperature change over 15 min. The percent composition of the components was calculated from peak areas in the plots using correction coefficients. The qualitative analysis was based on comparison of retention times and full mass spectra with those of pure compounds and a library of mass spectrometric data Wiley 275 (275,000 mass spectra) and catalogs [14, 15].Melting points were determined on a Boetius instrument. IR spectra were recorded on a Vektor 22 spectrometer in KBr disks. Table 1 gives the contents of fatty acids and high-molecular-weight alcohols from P. harmala. The results showed that the acidic part contained a significant amount of high-molecular-weight (C 28 -C 30 ) and a few unsaturated acids (principal ones linoleic and linolenic). The principal fatty acids of P. harmala were hexadecanoic (palmitic), octacosanoic, nonacosanoic, and triacontanoic (melissic).The components of the neutral part were high-molecular-weight alcohols (32.183% of the neutral part mass) C 26 H 53 OH, mp 84-85°C (0.053% yield) and C 29 H 59 OH, mp 79-81°C (0.065% yield ...

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Harmalidine, A β-carboline alkaloid from peganum harmala

Cited by 17 publications

References 11 publications

Alkaloids from cultivated plant of Peganum harmala L.

Alkaloids from cultivated plant of Peganum harmala L.

Gold(I)-Catalyzed Rearrangement of N-Aryl 2-Alkynylazetidines to Pyrrolo[1,2-a]indoles

Components of the aerial part of Peganum harmala

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