Norditerpenoid and Diterpenoid Alkaloids from Turkish<i> Consolida orientalis</i>

Meriçli, Filiz; Ah, Meriçli; Ulubelen, Ayhan; Hk, Desai; Pelletier, S. W.

doi:10.1021/np0005558

Cited by 19 publications

(9 citation statements)

References 12 publications

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“…This was consistent with the presence of an N-CH 2 -CHO group [4,5]. Through-space 1 H-13 C coupling of the resonance for the tertiary methyl protons at 0.96 (3H, s) and resonances for atoms at 32.7 (C-4), 40.0 (C-3), 43.9 (C-5), and 58.1 (C-20) confirmed that an 18-methyl was present.…”

supporting

confidence: 77%

Alkaloids from two species of the genus Aconitum

Usmanova

Aisa

et al. 2011

Chem Nat Compd

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We investigated the aerial part of Aconitum leucostomum Worosch collected in the Altai Mountains of XinjiangUyghur Autonomous Region of the PRC. Extraction by CHCl 3 of the aerial part of the plant (2.9 kg) afforded total bases (13.26 g, 0.45%). Part of the total alkaloids (6.7 g, pH 6) was chromatographed over a column of Al 2 O 3 with elution by hexane:acetone (5:1, 1:1), CHCl 3 , and CHCl 3 :MeOH (5:1, 1:1). The first hexane:acetone effluents afforded lappaconitine (2.09 g) and N-deacetyllappaconitine (0.13 g). Part of the total bases (6.36 g, pH 10) was chromatographed over a column of Al 2 O 3 with elution by hexane:acetone (5:1, 1:1), acetone, and acetone:MeOH (10:1, 5:1, 1:1). The hexane:acetone effluents afforded lappaconitine (1.16 g) and ranaconitine (0.06 g). Base 1 (0.04 g), mp 234°C, was isolated from the acetone fractions.In continuation of the investigation of the alkaloid composition of A. septentrionale (Ranunculaceae) roots collected in the Russian Federation in the Republic of Bashkortostan, we chromatographed the mother liquor of lappaconitine (64 g) over a column of silica gel (290 g) [1]. The column was eluted with CHCl 3 and CHCl 3 :MeOH (100:1, 50:1, 25:1) A total of 460 100-mL fractions was collected. Work up of the initial CHCl 3 effluents (fractions 1-5) with acetone separated lappaconitine (2.66 g), mp 216-218°C; of subsequent fractions (6-35), N-deacetyllappaconitine (0.18 g), mp 208-211°C. The CHCl 3 :MeOH effluents (100:1) (fractions 131-151) were worked up with acetone:EtOH to afford sepaconitine (0.06 g), mp 253-255°C. The CHCl 3 :MeOH effluents (50:1) (fractions 190-206) were rechromatographed over a column of silica gel. Elution by CHCl 3 and CHCl 3 :MeOH (50:1) isolated songorine (0.02 g), mp 201-203°C. Then, CHCl 3 :MeOH (25:1) gave fractions 385-425 that were rechromatographed over a column of silica gel with elution by CHCl 3 :MeOH (50:1 and 25:1). Fractions of 10 mL were collected. Fractions that were identical with respect to R f were combined and worked up with EtOH to isolate 1, C 22 H 33 NO 2 , mp 236°C (EtOH). Base 1 was insoluble in acetone, MeOH, and EtOH; slightly soluble in CHCl 3 and Py; and soluble in DMSO. Its IR spectrum (mineral oil) exhibited absorption bands at 3375 (OH), 3066, 1651, 893 (=CH 2 ), 2910 and 1678 cm -1 (CHO). The mass spectrum (EI-MS) showed peaks for ions with m/z 343 (72%) [M] + , 342 (100) [M -1] + , 328 (12.8) [M -CH 3 ] + , 314 (6.4) [M -CHO] + , 300 (12.8) [M -COCH 3 ] + , 257 (The mass spectral fragmentation of 1 was identical to that of chellespontine [2]with the exception of the intensity of several peaks. Because a sample of chellespontine was not available for direct comparison with 1, we used its spectral data (PMR, 13 C NMR, HSQC, HMBC) (Table 1). According to the data, 1 did not contain resonances for methoxyls and acetoxyls characteristic of norditerpenoid alkaloids. The data indicated that 1 was a C 20 atisane-type diterpenoid alkaloid [2]. The 13 C NMR spectrum exhibited resonances for 22 C atoms. Of these, three were quaterna...

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supporting

confidence: 77%

Alkaloids from two species of the genus Aconitum

Usmanova

Aisa

et al. 2011

Chem Nat Compd

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“…H-15b H-16, OCH 3 -14 C-7, C-16 C5, and consorientealine (Desai et al, 1993;Meriçli F. et al, 2001). Except for the aldehyde group, there were six O-bearing C atoms present as shown by the signals at δ C 87.…”

Section: Resultsmentioning

confidence: 99%

Diterpenoid Alkaloids of Aconitum vulparia Rchb.

Kurtoğlu

Şen

Melikoğlu

et al. 2012

Zeitschrift Für Naturforschung C

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From the roots of Aconitum vulparia Rchb., collected in Prüm (Germany), a new norditerpenoid alkaloid, named alexhumboldtine, has been isolated along with the known norditerpenoid alkaloids lappaconitine, anthranoyllycoctonine, lycoctonine, puberaconitine, ajacine, and septentriodine. The structure of alexhumboldtine was established on the basis of 1H, 13C, DEPT, homonuclear 1H COSY, NOESY, HSQC, and HMBC NMR studies. From the aerial parts of the plant another norditerpenoid alkaloid, aconorine, has been isolated

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“…Delphinium anthriscifolium Hance is composed of alkaloids, fixed oils, lipoids, and glycosides. Delsoline and eldeline are the two main alkaloids of D. anthriscifolium Hance [ 3 – 5 ]. Delsoline has a curare-like effect and a ganglion-blocking effect and can be used to relieve muscle tension or hyperkinesia.…”

Section: Introductionmentioning

confidence: 99%

Pharmacokinetics and UPLC-MS/MS of Delsoline in Mouse Whole Blood

Shao

Jin

et al. 2018

Journal of Analytical Methods in Chemistry

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Delsoline, a major alkaloid of Delphinium anthriscifolium Hance, has both a curare-like effect and a ganglion-blocking effect and is used to relieve muscle tension or hyperkinesia. A ultraperformance liquid chromatography-tandem mass spectrometry (UPLC-MS/MS) method was established for the determination of delsoline in mouse blood, and the pharmacokinetics of delsoline after intravenous administration (1 mg/kg) and intragastric administration (9, 6, and 3 mg/kg) were studied. Gelsenicine served as an internal standard, and a UPLC BEH C18 chromatographic column was used. The mobile phase consisted of acetonitrile and 0.1% formic acid; the gradient elution flow rate was 0.4 mL/min. The MRM model was used for the quantitative analysis of delsoline m/z 468.3⟶108.1 and the internal standard m/z 327.1⟶296.1. Mouse blood samples were treated with acetonitrile precipitation to remove proteins. In the concentration range of 0.1–1000 ng/mL, delsoline in mouse blood showed a good linearity (r2 > 0.995), and the lower limit of quantitation was 0.1 ng/mL. The intraday precision relative standard deviation (RSD) was below 14%, and the interday precision RSD was below 15%. The accuracy ranged between 94.3% and 110.1%, the average recovery was above 90.8%, and the matrix effect ranged between 97.0% and 102.5%. The UPLC-MS/MS method was sensitive, rapid, and selective in the study of pharmacokinetics of delsoline. The absolute bioavailability of delsoline was 20.9%.

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Norditerpenoid and Diterpenoid Alkaloids from Turkish Consolida orientalis

Cited by 19 publications

References 12 publications

Alkaloids from two species of the genus Aconitum

Alkaloids from two species of the genus Aconitum

Diterpenoid Alkaloids of Aconitum vulparia Rchb.

Pharmacokinetics and UPLC-MS/MS of Delsoline in Mouse Whole Blood

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