Conpropine, a new alkaloid from the aerial part of Convolvulus subhirsutus from Uzbekistan

Gapparov, A. M.; Aripova, S. F.; Razzakov, N. A.; Khuzhaev, V. U.

doi:10.1007/s10600-009-9187-3

Chem Nat Compd

2008

DOI: 10.1007/s10600-009-9187-3

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Conpropine, a new alkaloid from the aerial part of Convolvulus subhirsutus from Uzbekistan

A. M. Gapparov

S. F. Aripova

N. A. Razzakov

et al.

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“…It has been established that convolinine is an N-hydroxyethyl derivative of convolvine and has the structure (±)-3D-(3,4-dimethoxybenzoyl)-Nhydroxyethylnortropane based on spectral data and an x-ray crystal structure. ) were isolated from the aerial part of Convolvulus subhirsutus growing in Uzbekistan [1,2]. In continuation of the study of C. subhirsutus roots collected in Tashkent Oblast, a new alkaloid (mp 128-129°C, [D] D 0°) was isolated from total alkaloids of the non-phenolic part after isolation of convolvine and convolamine by column chromatography over Al 2 O 3 of the mother liquor of the non-phenolic part of total bases from the benzene:CHCl 3 fractions.…”

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Convolinine, a new alkaloid from Convolvulus subhirsutus of Uzbekistan flora

et al. 2010

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957.944/945 M. G. Levkovich, and O. AripovSeveral alkaloids of known structure and the new base convolinine were isolated from total alkaloids from the aerial part of Convolvulis subhirsutus growing in Uzbekistan. It has been established that convolinine is an N-hydroxyethyl derivative of convolvine and has the structure (±)-3D-(3,4-dimethoxybenzoyl)-Nhydroxyethylnortropane based on spectral data and an x-ray crystal structure. ) were isolated from the aerial part of Convolvulus subhirsutus growing in Uzbekistan [1,2]. In continuation of the study of C. subhirsutus roots collected in Tashkent Oblast, a new alkaloid (mp 128-129°C, [D] D 0°) was isolated from total alkaloids of the non-phenolic part after isolation of convolvine and convolamine by column chromatography over Al 2 O 3 of the mother liquor of the non-phenolic part of total bases from the benzene:CHCl 3 fractions. The physicochemical properties and chromatographic mobility differed from those described in the literature for tropane bases. We called it convolinine (1).The alkaloid had the formula C 18 H 25 NO 5 . The IR spectrum of the base contained absorption bands for active H at 3290 cm -1 ; ester carbonyl, at 1749; 3,4-disubstituted benzene, at 1601, 1516, 878, and 821; stretching and bending vibrations of CH 3 -, CH 2 -, and CH-, at 29222 -, and CH-, at , 28542 -, and CH-, at , 14632 -, and CH-, at , 14192 -, and CH-, at , 12842 -, and CH-, at , and 1274; and ether -C-O-C-, at 1074 and 1021.The PMR spectrum exhibited resonances for protons of two aromatic methoxyls as two 3H singlets at 3.87 and 3.89 ppm. An 8H multiplet was found in the range 1.85-2.85 that is characteristic of tropane bases for four CH 2 groups of a tropane ring in the C-2, C-4, C-6, and C-7 positions. A 2H multiplet probably for CH 2 protons bound to a N atom was observed at 3.77. A 2H multiplet for two methine protons of C-1 and C-5 in a tropane ring that is characteristic of tropane alkaloids occurred at 3.59. A 1 H triplet for H 3E that is diagnostic for tropane bases esterified on the C-3 hydroxyl was located at 5.23. Resonances for three aromatic protons with characteristic structure of meta-and para-substitution were seen at 7.60-6.80. The isolated D-proton appeared as a doublet with J = 2.0 Hz at 7.50. The other aromatic -proton gave a doublet of doublets (meta-constant J = 2.0 Hz and ortho-constant J = 8.5 Hz) at 7.58. Finally, the E-proton resonated at 6.84 as a doublet (J = 8.5 Hz). A 2H multiplet for protons of CH 2 bonded to oxygen was noted at 2.75.Based on these spectral characteristics, IR spectra (absorption bands for active H), PMR spectra, and taking into account the molecular weight of the alkaloid (M + 335) with an unsubstituted N-containing tropane core, it can be hypothesized that convolinine has a substituted N atom and that the substituent is -C 2 H 4 OH. The PMR spectra suggest that this could be a -CH 2 -CH 2 -OH group on the N atom.

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Convolinine, a new alkaloid from Convolvulus subhirsutus of Uzbekistan flora

et al. 2010

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“…The mixture was heated on a water bath at 60-70°C for 1 h and left at room temperature for 2 h. The resulting precipitate was filtered off and recrystallized from acetone:MeOH (4:1) to afford crystals (0.12 g, 81.5%) with mp 240-241°C, R f 0. 3.85 (3H, s, Ar-OCH 3 ), 4.03 (2H, d, J = 6, NCH 2 ), 4.23 (2H, m, H-1, 5), 5.23 (1H, t, J = 2, H-3E), m,.…”

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Derivatives of the alkaloid convolvine and their pharmacological activity

et al. 2011

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A. Nabiev, and V. U. KhuzhaevA series of new convolvine derivatives based on the alkaloid from Convolvulus subhirsutus and C. pseudocanthabrica were synthesized using alkylhalides and aliphatic and aromatic acid chlorides. Results of biological tests showed that convolvine and its derivatives exhibited pronounced antihypoxic, immunomodulating, and anti-inflammatory activity.The aerial parts of Convolvulus subhirsutus and C. pseudocanthabrica growing in Uzbekistan [1] have previously yielded 10 alkaloids [2-7] that were tropane derivatives, the principal ones being convolvine and convolamine with a content of 45-50% of the total alkaloids. A quantitative determination found that the content of the alkaloid mixture in the aerial part was 0.6%; in the roots, 1.6% of the dry plant weight.The convolvine content in C. subhirsutus and C. pseudocanthabrica reaches 0.3% in the aerial part; 0.7%, in roots. As a result of the availability of convolvine, a series of its derivatives were prepared. Their pharmacological properties were studied in a search for compounds with valuable pharmacological activity. For this, convolvine (1) was reacted with alkyl halides (methyliodide, hexylbromide, amylbromide, nonylbromide, benzylchloride) to produce the corresponding derivatives N-methylconvolvine hydroiodide (2), N-amylconvolvine hydrobromide (3), N-hexylconvolvine hydrobromide (4), N-nonylconvolvine hydrobromide (5), and N-benzylconvolvine (6) according to the scheme:Convolvine was also reacted with aliphatic and aromatic acid chlorides to produce N-benzoylconvolvine (7), N-chloroacetylconvolvine (8), and N-4c-nitrobenzoylconvolvine (9), reduction of 9 produced N-4c-aminobenzoylconvolvine (10), and N-naphthoylconvolvine (11):

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Phytochemical study of Convolvulus subhirsutus growing in Uzbekistan

et al. 2009

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Eight alkaloid derivatives of tropane, among which the major ones were convolvine and convolamine; the minor ones, phyllalbin, convolidine, nortropine, phyllalbin N-oxide, convolvidine, and conpropine, have been isolated previously from the aerial part of Convolvulus subhirsutus growing in Uzbekistan [1,2]. Quantitative analysis found 0.6% total bases in the aerial part; 1.6%, in the roots. The contents of the major alkaloids convolvine and convolamine were 45-50% of the total mixture. In continuation of research on alkaloids of this plant collected near Tepar, Tashkent Oblast′, a base (15 mg) with mp 144-145°C that was identified as the known alkaloid convolicine was isolated by chromatography over a column of Al 2 O 3 from the non-phenol part of total alkaloids after removal of convolvine and convolamine [3]. The benzene eluates contained an alkaloid (10 mg) with mp 178-179°C that was identified as confolidine.The extract was neutralized to pH 7 after removal of the alkaloids, diluted with water in a 1:1 ratio, and treated successively with hydrocarbons, EtOAc, and CHCl 3 . Paper chromatography and comparison with authentic samples detected in the remaining aqueous phase D-mannose, D-glucose, and D-galactose. Crystals with mp 136°C that were identified as β-sitosterol were isolated from the hydrocarbon fraction. The mother liquor was treated with acetone, evaporation of which produced crystals with mp 81-82°C that were identified as acetamide. Treatment of the mother liquor with acetone:MeOH isolated veratric acid with mp 181-182°C.The CHCl 3 fraction was also treated with acetone, evaporation of which produced crystals with mp 201-202°C, R f 0.5 (system 1). The IR spectrum of the compound contained absorption bands for active H (3115 cm −1 , -OH), -CH (3045), an aromatic ring (1605, 1562, 1506), and a conjugated carbonyl (1702) [4,5]. The UV spectrum showed absorption maxima at 297 and 345 nm that were characteristic of 6,7-dihydroxycoumarins [6]. The PMR spectrum of the coumarin had resonances for aromatic protons at 6.15 and 7.79 ppm as two doublets (J = 9.6 Hz) for the C-3 and C-4 protons; at 7.05, a singlet for the C-5 proton; at 6.71, a singlet for the C-8 proton. A 3H singlet for the aromatic methoxyl was observed at stronger field (3.85). Resonances for H-4 and H-8 were broadened due to through-space spin-spin coupling between them with J of H-4 and H-8 <1 Hz [7].The molecular weight of the coumarin was confirmed by a peak with mass 192 in the GC/MS. These spectral properties indicated that the isolated coumarin was scopoletin [8], which was isolated for the first time from a plant of the genus Convolvulus.Chromatography of the EtOAc fraction over a column of silica gel produced from EtOAc:hydrocarbon fractions a compound with mp 140-141°C, R f 0.46 (system 1). GC/MS of it gave MW 208 amu. The UV spectrum exhibited maxima at 218, 245, and 330 nm that were characteristic of a conjugated aromatic system. The IR spectrum had absorption bands for a 1,3,4-trisubstituted benzene ring at 1682, 1588, 870, and 8...

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Conpropine, a new alkaloid from the aerial part of Convolvulus subhirsutus from Uzbekistan

Cited by 3 publications

References 0 publications

Convolinine, a new alkaloid from Convolvulus subhirsutus of Uzbekistan flora

Convolinine, a new alkaloid from Convolvulus subhirsutus of Uzbekistan flora

Derivatives of the alkaloid convolvine and their pharmacological activity

Phytochemical study of Convolvulus subhirsutus growing in Uzbekistan

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