Alkaloids from leaves and root bark ofErvatamia hirta

Clivio, Pascale; Richard, Bernard; Deverre, Jean-Robert; Sévenet, Thierry; Zèches, Monique; Men-Oliver, Louisette Le

doi:10.1016/0031-9422(91)80111-d

Cited by 67 publications

(55 citation statements)

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“…They [36]. Fragment ions characteristic of iboluteine [35,37] were obtained at m/z 122.2 These mass spectra concur with the results published by Clivio et al [37] and Taylor [35]; but due to the unavailability of reference substances for these compounds, their structures were not confirmed. Using a 8-g aliquot of blood sample (accurately weighed), concentrations found (SIM mode, Fig.…”

Section: Application Of the Methods In A Poisoning Case Involving The supporting

confidence: 85%

“…Under the same chromatographic conditions, four additional compounds apart from ibogaine and noribogaine were detected, one of which was identified as ibogamine. Among the three non-identified compounds, two could be attributed to the oxidation products, iboluteine and desmethoxyiboluteine, due to the similarity of their mass spectra with the literature data [35,37]. The concentrations of ibogaine and noribogaine found in the blood sample in the Tabernanthe iboga poisoning case were 10-20 times greater than those reported by Mash et al [38] after a single oral dose of 800 mg of ibogaine in humans.…”

Section: Discussioncontrasting

confidence: 63%

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Liquid chromatography–electrospray mass spectrometry determination of ibogaine and noribogaine in human plasma and whole bloodApplication to a poisoning involving Tabernanthe iboga root

Kontrimaviciūte¹,

Breton

Mathieu

et al. 2006

Journal of Chromatography B

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Section: Application Of the Methods In A Poisoning Case Involving The supporting

confidence: 85%

Section: Discussioncontrasting

confidence: 63%

Liquid chromatography–electrospray mass spectrometry determination of ibogaine and noribogaine in human plasma and whole bloodApplication to a poisoning involving Tabernanthe iboga root

Kontrimaviciūte¹,

Breton

Mathieu

et al. 2006

Journal of Chromatography B

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“…m/z 150.1 characteristics of the iboluteine moiety. [16] Moreover, the UV spectrum found for this compound was in accordance with the paper of Goutarel et al [17] A representative chromatogram is presented in Figure 5A. After exposure to 254 nm, another compound with a retention time of 5.7 min was detected.…”

Section: Ibogaine and Noribogaine 1083 Stability Resultssupporting

confidence: 70%

Ibogaine and Noribogaine: Structural Analysis and Stability Studies. Use of LC‐MS to Determine Alkaloid Contents of the Root Bark of Tabernanthe Iboga

Kontrimavičiūtė

Mathieu

Balas

et al. 2007

Journal of Liquid Chromatography & Related Technologies

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The aim of this study was: i) to carry out a structural analysis of ibogaine and noribogaine, ii) to identify products formed under light exposure (daylight or 254 nm, 208C) of the two drugs in methanolic solutions, and iii) to examine the alkaloid contents of a specimen of root bark of the Tabernanthe iboga shrub using liquid chromatography-electrospray mass spectrometry. After daylight exposure, two oxidation products were detected: ibochine and iboluteine from ibogaine, and desmethoxyibochine and desmethoxyiboluteine from noribogaine. After exposure to 254 nm of the ibogaine solution, another compound that could possibly be the analogous lactam of iboluteine was detected. From the liquid chromatography electrospray-mass spectrometry analysis of the root barks of a specimen of the Tabernanthe iboga shrub, seven alkaloids were detected: ibochine (m/z 325), ibogaline (m/z 341), iboluteine (m/z 327), ibogaine (m/z 311), ibogamine (m/z 281) and voacangine (m/z 369). The last compound characterized by the protonated species (M þ H) þ at m/z 309 has not been identified. In all samples, ibogaine was the principal alkaloid observed; its concentration ranged from 1.8 to 5.93 mg/g. For the other indole alkaloids, the peak areas of ibogaline, ibogamine and voacangine represent 11.9, 21.5, and 30.5% of that of ibogaine, respectively.

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“…The spectroscopic data of all compounds were in good agreement with the literature data [4][5][6][7][8][9][10][11][12][13][14]. All these structures are isolated from E. flabellformia for the first time.…”

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confidence: 72%

Indole alkaloids from Ervatamia flabellformia

Liang

Chen

et al. 2008

Chem Nat Compd

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Ervatamia flabellformia Tsiang (Apocynaceae) [1] is a common plant cultivated in Yunnan and Guanxi provinces of China, and its chemical constituents have not been reported yet. As a part of our continuous research on anti-addictive constituents from the genus Ervatamia [2, 3], thirteen indole alkaloids were isolated from the stems of Ervatamia flabellformia.The stems of E. flabellformia were collected in October 2002 in Xishuangbanna, Yunnan province and identified by senior engineer Wang Hong, Xishuangbanna Tropical Botanic Garden of the Chinese Academy of Science. A voucher specimen (No. 200210-1) has been deposited in the Herbarium of the School of Pharmacy, Second Military Medical University, Shanghai.The air-dried and powdered stems (12 kg) were extracted with 95% EtOH (50 L) under reflux. After removal of EtOH by evaporation under reduced pressure, the residues were extracted with 2% HCl. The aqueous layer was basified with NH 4 OH and partitioned with CHCl 3 . The CHCl 3 layer was dried over Na 2 SO 4 and evaporated under reduced pressure to give 45 g of crude alkaloid fraction, which was submitted to repeated column chromatography over silica gel and Sephadex LH20 (MeOH) to yield 13 indole alkaloids.All compounds were identified by spectroscopic methods, including NMR and mass spectrometry (NMR spectra were acquired on a Bruker DRX-500 spectrometer with TMS as internal standard, operating at 500 MHz for 1 H and 13 C; ESIMS data were obtained on a Q-Tof micro mass spectrometer; silica gel H (10-40 μm) for column chromatography and HPTLC plates precoated with silica gel HF 254 (5-7 μm) were supplied by Zhifu Huangwu Silica Gel D & R Plant, Yantai, China; Sephadex LH-20 and ODS were purchased from Pharmacia and Merck, respectively. The spectroscopic data of all compounds were in good agreement with the literature data [4][5][6][7][8][9][10][11][12][13][14]. All these structures are isolated from E. flabellformia for the first time.Dihydroperivine (1), colorless cubic crystal (methyl acetate), C 20 H 24 N 2 O 3 . 1 H and 13 C NMR data are shown in Tables 1 and 3 [4].3-(R)-Hydroxyvoacangine (2), white powder, C 22 H 28 N 2 O 4 . EI-MS m/z (%): 368

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Alkaloids from leaves and root bark ofErvatamia hirta

Cited by 67 publications

References 16 publications

Liquid chromatography–electrospray mass spectrometry determination of ibogaine and noribogaine in human plasma and whole bloodApplication to a poisoning involving Tabernanthe iboga root

Liquid chromatography–electrospray mass spectrometry determination of ibogaine and noribogaine in human plasma and whole bloodApplication to a poisoning involving Tabernanthe iboga root

Ibogaine and Noribogaine: Structural Analysis and Stability Studies. Use of LC‐MS to Determine Alkaloid Contents of the Root Bark of Tabernanthe Iboga

Indole alkaloids from Ervatamia flabellformia

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