Rubiacées d'Océanie: Alcaloïdes de Psychotria oleoides de Nouvelle-Calédonie et de Calycodendron milnei du Vanuatu (Nouvelles-Hébrides)

Libot, Francine; Miet, C; Kunesch, Nicole; Poisson, J; Pusset, J.; Sévenet, Thierry

doi:10.1021/np50051a020

Cited by 54 publications

(47 citation statements)

References 7 publications

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“…[57] Furthermore, psycholeine, [58] meso-pseudophrynamine A [15] and the recently isolated flustramines O (32) and P (33) [9] each have two HPI units (Scheme 2). Natural compounds containing more than two HPI units comprise idiospermuline (34) [59] and the hodgkinsines (35), [50,52,60,61] with three HPI units; psychopentamine [62] and quadrigemines A, B, C (36), and I, [50,52,58,61,63] with four. Quadrigemine C is a weak antagonist of the SRIF (somatostatin) receptor, like psycholeine and meso-pseudophrynamine A. Isopsychotridines A and B (37) [61] and psychotridine, with five; [50,61] oleoidine, [50] with six; and caledonine, [50] with seven.…”

Section: Structure and Bioactivitymentioning

confidence: 99%

Structure, Bioactivity and Synthesis of Natural Products with Hexahydropyrrolo[2,3‐b]indole

Ruiz-Sanchis

Savina

Alberício

et al. 2011

Chemistry A European J

440

199

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Research on natural products containing hexahydropyrrolo[2,3-b]indole (HPI) has dramatically increased during the past few years. Newly discovered natural products with complex structures and important biological activities have recently been isolated and synthesized. This review summarizes the structures, biological activities, and synthetic routes for natural compounds containing HPI, emphasizing the different strategies for assembling this motif. It covers a broad range of molecules, from small alkaloids to complex peptides.

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Section: Structure and Bioactivitymentioning

confidence: 99%

Structure, Bioactivity and Synthesis of Natural Products with Hexahydropyrrolo[2,3‐b]indole

Ruiz-Sanchis

Savina

Alberício

et al. 2011

Chemistry A European J

440

199

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“…Quadrigemines A, 5 C 9 , and E 10 are the three reported members of the [2+2] quadrigemine family. The complex NMR spectra and amorphous nature of these higher-order polypyrrolidinoindoline alkaloids has made determination of their three-dimensional structures particularly difficult.…”

Section: Introductionmentioning

confidence: 99%

“…The relative and absolute configuration of only quadrigemine C ( 1 ) is known with certainty (Figure 2). Sévenet, who initially isolated quadrigemine C from an extract of Psychotria oleoides found in New Caledonia, 9a provided evidence for the R absolute configuration of the two outer quaternary carbons of 1 by chemical correlation with hodgkinsine, whose absolute and relative configuration had been determined by single-crystal X-ray analysis. 9b,11 However rigorous proof of the absolute configuration of the central chimonanthine unit was not secured until the enantioselective total synthesis of (−)-quadrigemine C was reported by our group in 2002.…”

Section: Introductionmentioning

confidence: 99%

“…Sévenet, who initially isolated quadrigemine C from an extract of Psychotria oleoides found in New Caledonia, 9a provided evidence for the R absolute configuration of the two outer quaternary carbons of 1 by chemical correlation with hodgkinsine, whose absolute and relative configuration had been determined by single-crystal X-ray analysis. 9b,11 However rigorous proof of the absolute configuration of the central chimonanthine unit was not secured until the enantioselective total synthesis of (−)-quadrigemine C was reported by our group in 2002. 4 The optical rotations reported for quadrigemines A, C, and E in alcoholic solvents ([α] D A, +32 (EtOH); 5 C, +40 (MeOH); 9d E, +33 (EtOH) 10 are similar; suggesting that these alkaloids, which were isolated by different laboratories, could be identical.…”

Section: Introductionmentioning

confidence: 99%

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Stereocontrolled enantioselective total synthesis of the [2+2] quadrigemine alkaloids

et al. 2015

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A unified strategy for enantioselective total synthesis of all stereoisomers of the 2+2 family of quadrigemine alkaloids is reported. In this approach, two enantioselective intramolecular Heck reactions are carried out at the same time on precursors fashioned in four steps from either meso- or (+)-chimonanthine to form the two critical quaternary carbons of the peripheral cyclotryptamine rings of these products. Useful levels of catalyst control are realized in either desymmetrizing a meso precursor or controlling diastereoselectivity in elaborating C2-symmetic intermediates. None of the synthetic quadrigemines are identical with alkaloids isolated previously and referred to as quadrigemines A and E. In addition, we report improvements in our previous total syntheses of (+)- or (−)-quadrigemine C that shortened the synthetic sequence to 10 steps and provided these products in 2.2% overall yield from tryptamine.

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“…The species of subfamily Rubioideae are divided into 15 tribes, the largest being the Psychotrieae, comprised of approximately 50 genera widely distributed throughout the tropical zone (Libot et al 1987). The Psychotria genus was first described by Linneaus in 1759, and actually is considered as one of the largest plant genera with flowers.…”

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confidence: 99%

Psychotria viridis: Chemical constituents from leaves and biological properties

Soares

Duarte

Cavalcanti

et al. 2017

An. Acad. Bras. Ciênc.

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The phytochemical study of hexane, chloroform and methanol extracts from leaves of Psychotria viridis resulted in the identification of: the pentacyclic triterpenes, ursolic and oleanolic acid; the steroids, 24-methylene-cycloartanol, stigmasterol and β-sitosterol; the glycosylated steroids 3-O-β-D-glucosyl-β-sitosterol and 3-O-β-D-glucosyl-stigmasterol; a polyunsaturated triterpene, squalene; the esters of glycerol, 1-palmitoylglycerol and triacylglycerol; a mixture of long chain hydrocarbons; the aldehyde nonacosanal; the long chain fat acids hentriacontanoic, hexadecanoic and heptadenoic acid; the ester methyl heptadecanoate; the 4-methyl-epi-quinate and two indole alkaloids, N,N-dimethyltryptamine (DMT) and N-methyltryptamine. The chemical structures were determined by means of spectroscopic (IR, 1 H and 13 C NMR, HSQC, HMBC and NOESY) and spectrometric (CG-MS and LCMS-ESI-ITTOF) methods. The study of biologic properties of P. viridis consisted in the evaluation of the acetylcholinesterase inhibition and cytotoxic activities. The hexane, chloroform, ethyl acetate and methanol extracts, the substances 24-methylene-cycloartanol, DMT and a mixture of 3-O-β-D-glucosyl-β-sitosterol and 3-O-β-D-glucosyl-stigmasterol showed cholinesterase inhibiting activity. This activity induced by chloroform and ethyl acetate extracts was higher than 90%. The methanol and ethyl acetate extracts inhibit the growth and/or induce the death of the tumor cells strains B16F10 and 4T1, without damaging the integrity of the normal cells BHK and CHO. DMT also demonstrated a marked activity against tumor cell strains B16F10 and 4T1.

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Rubiacées d'Océanie: Alcaloïdes de Psychotria oleoides de Nouvelle-Calédonie et de Calycodendron milnei du Vanuatu (Nouvelles-Hébrides)

Cited by 54 publications

References 7 publications

Structure, Bioactivity and Synthesis of Natural Products with Hexahydropyrrolo[2,3‐b]indole

Structure, Bioactivity and Synthesis of Natural Products with Hexahydropyrrolo[2,3‐b]indole

Stereocontrolled enantioselective total synthesis of the [2+2] quadrigemine alkaloids

Psychotria viridis: Chemical constituents from leaves and biological properties

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