Isolation and 2D NMR Studies of Alkaloids from<i>Comptonella sessilifoliola</i><sup>1</sup>

Pusset, J.; López, J. L.; Païs, M.; Neirabeyeh, M. Al; Veillon, Jean‐Marie

doi:10.1055/s-2006-960053

Cited by 50 publications

(30 citation statements)

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“…In addition to these units, the 13 C-NMR spectrum of 1 (Table 1), analyzed with the aid of heteronuclear multiple quantum coherence (HMQC) and heteronuclear multiple-bond correlation spectroscopy (HMBC) experiments, exhibited signals due to one carbonyl carbon (d 190.8) and eight quaternary carbons (d 101.9, 113.4, 147.7, 154.5, 155.1, 156.9, 160.3, 164.5). On the aromatic ring, the 1 H-and 13 C-NMR spectral data of 1 were in close agreement with those of evolitrine (5) 5,6) and other 7-O-substituted-4-methoxyfuroquinolines, 7,8) suggesting that 1 is a 7-O-substituted-4-methoxyfuroquinoline alkaloid containing a C 10 side-chain. No.…”

supporting

confidence: 63%

Three New Furoquinoline Alkaloids from the Leaves of Boninia glabra

Inada

Ogasawara

Koga

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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Boninia glabra Planchon, which belongs to the family Rutaceae, is indigenous to the Bonin Islands in Japan.1) No phytochemical study of the plant has been made to date. As part of our phytochemical studies on the Bonin Islands, 2) the chemical components of an MeOH extract obtained from the leaves of B. glabra were investigated. As a result, three new furoquinoline alkaloid oxogeranyl ethers (1-3) were isolated, along with a known furoquinoline alkaloid (4). This paper describes the isolation and structural elucidation of these components. After column chromatography and HPLC separation of the CHCl 3 -soluble part of the MeOH extract, compounds (1-3) were isolated together with a known furoquinoline alkaloid, skimmianine (4).3,4) Identification of the known compound was achieved by comparisons with previously reported physical and spectral data.Compound 1 exhibited a molecular formula of C 22 H 23 NO 4 by HR-EI-MS and had IR absorption at 1670 cm Ϫ1 (conjugated ketone). The 1 H-NMR spectrum of 1 ( (d 101.9, 113.4, 147.7, 154.5, 155.1, 156.9, 160.3, 164.5). On the aromatic ring, the 1 H-and 13 C-NMR spectral data of 1 were in close agreement with those of evolitrine (5) 5,6) and other 7-O-substituted-4-methoxyfuroquinolines, 7,8) suggesting that 1 is a 7-O-substituted-4-methoxyfuroquinoline alkaloid containing a C 10 side-chain. Three novel furoquinoline alkaloid oxogeranyl ethers (1-3) and one known furoquinoline alkaloid (4) were isolated from the leaves of Boninia glabra, an endemic plant of the Bonin Islands. Their structures were elucidated on the basis of spectroscopic analysis.

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supporting

confidence: 63%

Three New Furoquinoline Alkaloids from the Leaves of Boninia glabra

Inada

Ogasawara

Koga

et al. 2008

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The observed correlations between the methine hydrogen signal at δ 6.77 and the The methanolic extract from stems afforded skimmianine, 11 8-methoxyflindersine (2) 12 and dictamnine. 13,14 As no carbon shifts of 2 could be found in the literature, these data are listed in Table 1. Complete and unambiguous 13 C NMR assignments for 2 were made using the HSQC and HMBC techniques and using 1 and haplophytin A (3) 15 as a models.…”

Section: Resultsmentioning

confidence: 99%

Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)

Moraes

Tomazela

Ferracin

et al. 2003

J. Braz. Chem. Soc.

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Nosso interesse quimiotaxonômico sobre Neoraputia nos estimulou a examinar N. paraensis, visando a busca de alcalóides. As frações foram monitoradas via RMN 1 H e ESI-EM/EM e foram analisadas somente aquelas cujos espectros apresentavam características de alcalóides do ácido antranílico e flavonóides não isolados anteriormente. Foram isolados do caule os alcalóides flindersina, skimmianina, 8-metoxiflindersina e dictamnina; das folhas os flavonóides 3',4',7,8-tetrametoxi-5,6-(2",2"-dimetilpirano)-flavona, 3',4',5,7,8-pentametoxiflavona, 5-hidroxi-3',4',6,7-tetrametoxiflavona, 3',4'-metilenodioxi-5,6,7-trimetoxiflavona e 5-hidroxi-3',4'-metilenodioxi-6,7-dimetoxiflavona,. Os alcalóides do ácido antranílico não foram encontrados em dez anos.Vários flavonóides isolados de N. paraensis, N. magnifica, Murraya paniculata, enxerto de Citrus sinensis (Rutaceae) e Lonchocarpus montanus (Leguminosae) foram testados frente a gliceraldeído-3-fosfato desidrogenase de Trypanosoma cruzi, visando verificar seus potenciais em inibir a atividade da enzima. Os flavonóides polimetoxilados e um isoflavonóide foram os mais ativos.Our taxonomic interest in the Neoraputia stimulated an investigation of N. paraensis searching for alkaloids. Fractions were monitored by 1 H NMR and ESI-MS/MS and only those which showed features of anthranilate alkaloids and flavonoids absent in the previous investigations were examined. Stems afforded the alkaloids flindersine, skimmianine, 8-methoxyflindersine and dictamnine; leaves yielded 3',4',7,8-tetramethoxy-5,6-(2",2"-dimethylpyrano)-flavone, 3',4',5,7,8-pentamethoxyflavone, 5-hydroxy-3',4',6,7-tetramethoxyflavone, 3',4'-methylenedioxy-5,6,7-trimethoxyflavone and 5-hydroxy-3',4'-methylenedioxy-6,7-dimethoxyflavone. The alkaloids have remained undiscovered for 10 years.A number of flavonoids isolated from N. paraensis, N. magnifica, Murraya paniculata, Citrus sinensis graft (Rutaceae), Lonchocarpus montanus (Leguminosae) were evaluated for their ability to inhibit the enzymatic activity of the protein glyceraldehyde-3-phosphate dehydrogenase from Trypanosoma cruzi. Highly oxygenated flavones and isoflavone were the most actives.

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“…1) of alkaloids have been elucidated by 1 H NMR, 13 C NMR and MS spectroscopic methods [17]. All the NMR data were identical to those of the corresponding known compounds previously reported in the literature [18][19][20]. In our previous study, the above seven alkaloids were all select ed as markers for assessment of quality of P. chinense [21].…”

Section: Introductionmentioning

confidence: 56%

Simultaneous determination of six alkaloids inPhellodendron amurenseby high-performance liquid chromatography

Li¹,

Liu²,

Shi

2013

Acta Chromatographica

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Summary.A high-performance liquid chromatography (HPLC) method has been developed for simultaneous determination of six alkaloids, i.e., (−)-(R)-platydesmin, noroxyhydrastinine, berberine, skimmianine, canthin-6-one, and pteleine in the herbal medicine of Phellodendron amurense Rupr. The optimal condition for extraction and separation was achieved with a linear mobile phase gradient prepared from 0.1% phosphoric acid and acetonitrile. The LODs and LOQs for the analytes ranged from 0.06 to 0.22 μg mL −1 and from 0.25 to 0.80 μg mL −1 , respectively. The optimized method was applied to the determination of alkaloids in P. amurense Rupr. and was found to be efficient. This method can provide a scientific and technical platform to the manufacturers for setting up a quality control standard as well as to the public for quality and safety assurance of the proprietary traditional Chinese medicines.

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Isolation and 2D NMR Studies of Alkaloids fromComptonella sessilifoliola¹

Cited by 50 publications

References 3 publications

Three New Furoquinoline Alkaloids from the Leaves of Boninia glabra

Three New Furoquinoline Alkaloids from the Leaves of Boninia glabra

Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)

Simultaneous determination of six alkaloids inPhellodendron amurenseby high-performance liquid chromatography

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Isolation and 2D NMR Studies of Alkaloids fromComptonella sessilifoliola1

Cited by 50 publications

References 3 publications

Three New Furoquinoline Alkaloids from the Leaves of Boninia glabra

Three New Furoquinoline Alkaloids from the Leaves of Boninia glabra

Enzymatic inhibition studies of selected flavonoids and chemosystematic significance of polymethoxylated flavonoids and quinoline alkaloids in Neoraputia (Rutaceae)

Simultaneous determination of six alkaloids inPhellodendron amurenseby high-performance liquid chromatography

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Isolation and 2D NMR Studies of Alkaloids fromComptonella sessilifoliola¹