A revised structure for the piperidine alkaloid andrachamine

Mill, Sibel; Hootelé, Claude

doi:10.1139/v96-272

Cited by 28 publications

(18 citation statements)

References 19 publications

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“…inflata . However, Andrachamine, cis ‐8,10‐di‐ n ‐propyllobelidiol, was isolated from Andrachne aspera (Euphorbiaceae) and together with its ethyl homologue from Siphocampylus verticillatus (Campanulaceae) …”

Section: Resultsmentioning

confidence: 99%

“…This is the first identification of propyl homologue piperidine alkaloids in L. inflata. However, Andrachamine, cis-8,10-di-npropyllobelidiol, was isolated from Andrachne aspera (Euphorbiaceae) [22,23] and together with its ethyl homologue from Siphocampylus verticillatus (Campanulaceae). [21] Peak 24 was tentatively identified as 8-methyl-10phenyllobelionol.…”

Section: Identification Of Piperidine Alkaloids In the Aerial Parts Omentioning

confidence: 99%

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HPLC‐ESI‐MS/MS of brain neurotransmitter modulator lobeline and related piperidine alkaloids in Lobelia inflata L

Kursinszki

Szöke

2015

J. Mass Spectrom.

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There is a renewed interest in lobelia alkaloids because of their activity on the central nervous system. Lobeline, the most active of them, a nicotinic receptor ligand and neurotransmitter transporter inhibitor, is a candidate pharmacotherapy for metamphetamine abuse. In the present work, high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry in positive ion mode was used for investigating the alkaloid profile in Lobelia inflata L. Chromatographic separations were achieved on a Gemini C6-phenyl reversed-phase column providing good peak shape and improved selectivity. Being mostly 2,6-disubstituted piperidines, lobelia alkaloids presented abundant [M + H](+) ions with typical fragmentation. Identification was possible from a few specific ions, especially those resulting from excision of one of the substituents. Based on fragmentation pattern of lobeline as reference compound, 52 alkaloids were identified in the aqueous methanolic extract of L. inflata in contrast to the previously known some 20. Structural variability of these alkaloids identified arises basically from their substituents which can be phenyl-2-ketoethyl- or phenyl-2-hydroxyethyl units as well as their methyl-, ethyl- or propyl- homologues attached in different combinations. Several propyl homologue lobelia alkaloids and five hydroxypiperidine derivatives were found in the plant at the first time. In addition to 8-O-esters of 2-monosubstituted piperidine alkaloids previously reported by us in L. inflata, a 3-hydroxy-3-phenylpropanoic acid ester of hydroxyallosedamine ring-substituted was also identified as a new natural product. High-performance liquid chromatography-electrospray ionization tandem mass spectrometry can be successfully applied to Lobeliacae plant samples in the routine screening for new and known bioactive constituents, quality control of the crude drug, lobelia herba, alkaloid production studies, breeding and chemotaxonomy.

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Section: Resultsmentioning

confidence: 99%

Section: Identification Of Piperidine Alkaloids In the Aerial Parts Omentioning

confidence: 99%

HPLC‐ESI‐MS/MS of brain neurotransmitter modulator lobeline and related piperidine alkaloids in Lobelia inflata L

Kursinszki

Szöke

2015

J. Mass Spectrom.

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“…Therefore, it would be of great interest to realize the successive addition of two nucleophiles directly onto isoxazololactam 3; a high level of stereoselectivity should be induced by the shape of the bicyclic framework. [11] Scheme 1. [7] The NÀO bond would, in fact, act as a protecting group and, more importantly, as an activating and stabilizing group.…”

mentioning

confidence: 99%

“…[10] The presence of the cyclic isoxazolidine would force the side chain at position C3a of the alkoxypiperidinium unit in a pseudoequatorial position, and the stereoelectronically preferred axial attack of a nucleophile should lead diastereoselectively to 9. [11] Scheme 1. Ring-rearrangement metathesis of nitroso Diels-Alder cycloadducts and our previous synthesis of porantheridine (6 Such a strategy is inspired by the pioneering work of Kibayashi et al, who realized the successive addition of a Grignard reagent and sodium borohydride to related tetrahydroxazino[2,3-a]piperidin-8-ones to obtain 4a,8-cistetrahydroxazino[2,3-a]piperidines.…”

mentioning

confidence: 99%

Stereodivergent Synthesis of Substituted N,O‐Containing Bicyclic Compounds by Sequential Addition of Nucleophiles to N‐Alkoxybicyclolactams

2010

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In control! N‐alkoxybicyclolactams derived from the ring‐rearrangement metathesis of nitroso Diels–Alder cycloadducts were subjected to the successive addition of two nucleophiles to yield substituted piperidine or pyrrolidine precursors with good to excellent stereoselectivity. The relative configuration of the newly formed stereocenter can be controlled by the order of addition of the two nucleophiles.

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“…Hootelé and co-workers 25 Lhommet and co-workers 26 carried out a systematic study on the alkylation to 2,6-trans-disubstituted piperidines via bicyclic N-acyliminium ions ( Table 1.…”

Section: Alkylations Of Bicyclic N-acyliminium Ions To 26-trans-disumentioning

confidence: 99%

Lewis acid-mediated alkylations of N,O-acetals and applications to the total syntheses of alkaloids

Lu¹

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LIST OF ABBREVIATIONS CHAPTER 1: INTRODUCTION 1.1. Alkylations of monocyclic iminium ions to 2,6-cisdisubstituted-piperidine rings. 1.1.1. Alkylations of monocyclic N-iminium ions arising from oxazolopiperidone synthon. 1.1.2. Alkylations of monocyclic N-acyliminium ions arising from α-alkyloxyl carbamates. 1.1.3. Alkylations of monocyclic N-acyliminium ions arising from imino glycal. 1.1.4. Alkylations of monocyclic N-sulfonyliminium ions. 1.2. Alkylations of monocyclic iminium ions to 2,6-transdisubstituted-piperidine rings. 1.3. Alkylations of bicyclic iminium ions to 2,6-trans-disubstitutedpiperidine rings.

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A revised structure for the piperidine alkaloid andrachamine

Cited by 28 publications

References 19 publications

HPLC‐ESI‐MS/MS of brain neurotransmitter modulator lobeline and related piperidine alkaloids in Lobelia inflata L

HPLC‐ESI‐MS/MS of brain neurotransmitter modulator lobeline and related piperidine alkaloids in Lobelia inflata L

Stereodivergent Synthesis of Substituted N,O‐Containing Bicyclic Compounds by Sequential Addition of Nucleophiles to N‐Alkoxybicyclolactams

Lewis acid-mediated alkylations of N,O-acetals and applications to the total syntheses of alkaloids

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