Some New Vallesamine-Type Alkaloids

Zèches, Monique; Ravao, Thérèse; Richard, Bernard; Massiot, Georges; Men‐Olivier, L. Le; Verpoorte, Robert

doi:10.1021/np50052a023

Cited by 42 publications

(30 citation statements)

References 4 publications

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“…Identification by GC-MS established that the detected alkaloid, eluted at 54.5 min, had a pattern of mass fragmentation similar to that of the monoterpenoid indole alkaloid, 19-E-vallasamine (Fig. 8C), based on the comparison with the NIST libraries (NIST 2011) and the mass data reported previously (340 M+, 310, 267, 208, 180, 169, 154, 143, 130) (Nielsen et al, 1994;Zeches et al, 1987).…”

Section: Transcription Profile Analysis Of Cyp76f45 and Cpr I And Detsupporting

confidence: 62%

“…Interestingly, the resulting alkaloid preparation appeared to contain essentially a single type of alkaloid that could be visualized as a major band on TLC after spraying with the alkaloid-specific Dragendorff's reagent. This alkaloid band was subsequently analyzed by GC-MS and was found to have a mass spectrum that was similar to the known compound, 19-E-vallasamine (Nielsen et al, 1994;Walser and Djerassi, 1964;Zeches et al, 1987). Although complete elucidation is still needed to confirm the structure, its inclusion in the group of monoterpenoid indole alkaloids is highly possible.…”

Section: Discussionmentioning

confidence: 95%

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Functional expression of a putative geraniol 8-hydroxylase by reconstitution of bacterially expressed plant CYP76F45 and NADPH-cytochrome P450 reductase CPR I from Croton stellatopilosus Ohba

et al. 2015

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Section: Transcription Profile Analysis Of Cyp76f45 and Cpr I And Detsupporting

confidence: 62%

Section: Discussionmentioning

confidence: 95%

Functional expression of a putative geraniol 8-hydroxylase by reconstitution of bacterially expressed plant CYP76F45 and NADPH-cytochrome P450 reductase CPR I from Croton stellatopilosus Ohba

et al. 2015

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“…Part) showed a total of 22 separate Catom resonances, comprising two Me, five CH 2 , eight CH groups, and seven quaternary C-atoms, in agreement with the molecular formula. The observed quaternary Cresonance at d(C) 120.1 provided additional confirmation for the presence of the CN substituent [21] [22]. The 1 H-NMR spectrum (cf.…”

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confidence: 79%

“…Besides the ibogan derivatives discussed above, other examples include the 21-substituted aspidofractinine compounds, lahadinines A and B from Kopsia [21], a CNsubstituted seco-stemmadenine derivative from Alstonia [22], and the N-cyanostrychnine derivatives from Strychnos species [25].…”

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confidence: 99%

Biologically Active Ibogan and Vallesamine Derivatives from Tabernaemontana divaricata

Kam

Pang

Choo

et al. 2004

Chemistry & Biodiversity

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Six new indole alkaloids, viz., (3S)-3-cyanocoronaridine (2), (3S)-3-cyanoisovoacangine (3), conolobine A (5), conolobine B (6), conolidine (7), and (3R/3S)-3-ethoxyvoacangine (8), in addition to 36 known ones, were obtained from the stem-bark extract of the Malayan Tabernaemontana divaricata. The structures were determined by NMR and MS analysis. The CN-substituted alkaloids showed appreciable cytotoxicity towards the KB human oral epidermoid carcinoma cell-line.

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“…Azocinoindoles containing two pharmacophore fragments are a part of many alkaloids [1,2]. However, only few methods for the synthesis of azocinoindoles have been described, with multiple stages and low yields of the target products [3].…”

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confidence: 99%

Synthesis of 6-aryl-Substituted Azocino-[5,4-b]indoles from 1-aryl-Substituted 2-Ethyltetrahydro-β-Carbolines

Voskressensky

Борисова

Chervyakova

et al. 2014

Chem Heterocycl Comp

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We optimized the reaction of tetrahydropyridine ring expansion in 1-aryl-substituted tetrahydro-β-carbolines by the action of activated alkynes and achieved higher than 70% yields of the target indoloazocines. The substituents in the 1-aryl ring and at the indole nitrogen atom were shown to affect the rate and selectivity of this transformation.Indoles fused with medium-sized rings attract the attention of synthetic and medicinal chemists due to their remarkable and diverse biological activity. Azocinoindoles containing two pharmacophore fragments are a part of many alkaloids [1,2]. However, only few methods for the synthesis of azocinoindoles have been described, with multiple stages and low yields of the target products [3]. We have previously proposed a method for the synthesis of tetrahydroazocino[5,4-b]-and tetrahydroazocino[4,5-b]indoles based on a domino reaction of the tetrahydropyridine fragment expansion in β-and γ-carbolines, by using activated alkynes [4,5]. The yields of 6-methyl(isopropyl, benzyl)tetrahydroazocino [5,4-b]indoles in acetonitrile were 40-50%. The reaction in methanol was accompanied by cleavage of the carboline tetrahydropyridine ring with the participation of a methanol molecule [5]. The 6-aryl-substituted tetrahydroazocino[5,4-b]indoles gave only 6-(2-fluorophenyl)-and 6-(4-fluorophenyl)tetrahydroazocinoindoles in the aforementioned domino reaction.In the case of 1-(m-fluorophenyl)-substituted β-carboline transformation by the action of dimethyl ester of acetylene dicarboxylic acid (DMAD) in the presence of indole or 5-methoxyindole, the initial ammonium zwitterion А was shown to undergo cleavage at the С(1)-N bond, giving an "open" cation В. The electrophilic substitution of the latter in indole "trap" produced a diindolylarylmethane [6].Initial biological screening showed that the azocino[5,4-b]-and azocino [4,5-b]indoles are effective inhibitors of acetyl-and butyrylcholine esterases, and can be further developed as drugs against neurodegeneration [5]. Azocines condensed with 4-aminopyrimidine fragment exhibited high cytotoxic activity during the initial screening. However, no chemical transformations of tetrahydroazocinoindoles have been studied thus far.

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Some New Vallesamine-Type Alkaloids

Cited by 42 publications

References 4 publications

Functional expression of a putative geraniol 8-hydroxylase by reconstitution of bacterially expressed plant CYP76F45 and NADPH-cytochrome P450 reductase CPR I from Croton stellatopilosus Ohba

Functional expression of a putative geraniol 8-hydroxylase by reconstitution of bacterially expressed plant CYP76F45 and NADPH-cytochrome P450 reductase CPR I from Croton stellatopilosus Ohba

Biologically Active Ibogan and Vallesamine Derivatives from Tabernaemontana divaricata

Synthesis of 6-aryl-Substituted Azocino-[5,4-b]indoles from 1-aryl-Substituted 2-Ethyltetrahydro-β-Carbolines

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