Alkaloid studies—L

Gilbert, B.; Duarte, Apparicio Pereira; Nakagawa, Y.; Joule, J. A.; Flores, Sonia; Brissolese, J. Aguayo.; Campello, Jayr de Paiva; Carrazzoni, E.P.; Owellen, Richard J.; Blossey, Erich C.; Brown, Keith S.; Djerassi, Carl

doi:10.1016/0040-4020(65)80057-6

Cited by 84 publications

(25 citation statements)

References 41 publications

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“…The nuclear inagiletic resonance spectrum confirms the presence of four aromatic protons (multiplet: 6.55 to 7.50 6), but absorption typical of olefinic protons and of methyl groupings of any type is absent. A two-proton quartet (centered a t 3.98 6), which has also been observed in other dihydroindolic aspidosperma allialoids, has been shown to be characteristic of the -0-CI-12-grouping as found in aspidoalbine (V) (4) and aspidoliinidine (IV) (5). This region of the nuclear nlagnetic resonance spectrum of fcndleridine is striliingly similar to that of 0-nlethyl-N-despr~pion~laspidoalbine (6)…”

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confidence: 72%

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Alkaloids of the Seeds of Aspidosperma Fendleri Woodson

Burnell¹,

Medina²,

Ayer³

1966

Can. J. Chem.

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The s t r u c t~~r e s of three new allcaloids fro111 the seeds of A. fendleri have been elucidated and two of the bases have been converted into aspidolimidine. A fourth base has been shown to be present in small anlouilts but its nature remains unknown.Extraction of the seeds of the Venezuelail tree Aspidosperma fefzdleri (I) has yielded four alkaloids, of which fendlerine, CnaHaoNsOa, is the most abundant; this alkaloid is also found in large quantities in the trunlc and root bark. The structures of fendlerine and the minor base fendleridine have been discussed in preliininary reports (2, 3).Fendleridine, CI9HnaN20, is the simplest of the bases present and, on the basis of its ultraviolet spectrum, belongs to the unsubstituted dihydroindole group of allialoids. T h e infrared spectrum reveals peaks characterizing the dihydroindole imino group and the aromatic ring but gives no information concerning the nature of the oxygen atom, which is probably ethereal. The nuclear inagiletic resonance spectrum confirms the presence of four aromatic protons (multiplet: 6.55 to 7.50 6), but absorption typical of olefinic protons and of methyl groupings of any type is absent. A two-proton quartet (centered a t 3.98 6), which has also been observed in other dihydroindolic aspidosperma allialoids, has been shown to be characteristic of the -0-CI-12-grouping as found in aspidoalbine (V) (4) and aspidoliinidine (IV) (5). This region of the nuclear nlagnetic resonance spectrum of fcndleridine is striliingly similar to that of 0-nlethyl-N-despr~pion~laspidoalbine (6)(except for the methoxyl bands in the latter). A plausible structure for fendleridine is that sho~vn by I ; this is supported by the mass spectron~etric fragmentation pattern (Fig. I).Confirination of the analytical figures was shown by the molecular ion pealc a t 296 m / e ; the typical aspidosperlnine type RI-28 pealc (a) arising from the loss of ethylene is also present. Rupture of the C-10-C-11 bond (at x in a) gives rise to fragment b, which is responsible for the base peak a t 138 m/e. This fragment has also been observed in the 'Present address: Chenlistry Deparl,ne,lt, Latlal Unioersity, Quebec 10, Q~iebec.

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confidence: 72%

“…fragmentation of aspidoalbine (V) (4) and aspidolimidine (IV) (5). The indolic portion of the inolecule gives rise to weaker peaks a t 144 m/e (rupture a t y) and 130 m/e (rupture a t x).…”

mentioning

confidence: 99%

Alkaloids of the Seeds of Aspidosperma Fendleri Woodson

Burnell¹,

Medina²,

Ayer³

1966

Can. J. Chem.

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“…dasycarpon [90][91][92]104 ; A. parvifolium 93 ; A. subincanum 85,115 Dasicarpidona (232) A. dasycarpon 83,91,92 ; A. multiflorum 52 ; A. pyricollum 51,116 ; A. subincanum 81 Diidrodasicarpidona (dasicarpidol; 233) A. dasycarpon 83,91,92 Des-N-metildasicarpidona (234) A. dasycarpon 83,91,92 Diidrouleína ( A Tabela 20 apresenta o levantamento dos alcalóides indólicos isolados por espécie e por série de Aspidosperma. Pelos resultados obtidos pôde-se constatar que as espécies do gênero Aspidosperma são caracterizadas pela incidência de uma grande quantidade e diversidade estrutural de alcalóides indólicos.…”

Section: Des-n-metiluleína (231)unclassified

Alcalóides indólicos isolados de espécies do gênero Aspidosperma (Apocynaceae)

Pereira¹,

Jácome²,

Alcântara³

et al. 2007

Quím. Nova

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Recebido em 20/7/06; aceito em 11/9/06; publicado na web em 28/5/07 INDOLE ALKALOIDS FROM SPECIES OF THE Aspidosperma (Apocynaceae) GENUS. Species from genus Aspidosperma (Apocynaceae) are popularly employed to treat various diseases. This genus is characterized by the occurrence of indole alkaloids. Taking into account the various biological activities attributed to these alkaloids, the description of the chemical diversity in genus Aspidosperma is important. A review of simple carbolinic alkaloids isolated from species of various genera was published in 1979. In 1987, it was published another one dealing with the relationships between the chemical structures of the indole alkaloids and the evolution of Aspidosperma species. This work updates the information about the indole alkaloids isolated from Aspidosperma species.

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“…跟 Edward 的方法相同, Kametani 等 6 Apparicine 的合成 Apparicine 是 1965 年从粗毛果白坚木分离得到的 [30,31] , 具有强壮剂和抗脊髓炎病毒活性 [32] . 该化合物的合成工作一直未开展, 直到 2006 年报道了其仿生合成 [33] .…”

Section: -Epiuleine 1dunclassified

Progress in the Synthesis of Indole Alkaloid Uleine and Its Derivatives

Wang¹,

Liu²,

Huang³

et al. 2012

Chin. J. Org. Chem.

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Uleine and its derivatives belong to the monoterpenoid indole alkaloids based on their structures. The characteristic of their structures is only one carbon atom which separates the indole nucleus and the basic nitrogen atom, as opposed to the normal two-carbon bridge of tryptamine and most monoterpenoid indole alkaloids. Their natural contents are extremely low, and their synthetic work has attracted generations of chemists. The synthetic methods of uleine and its derivatives are reviewed according to the types of structure building methodology. The indole and pyridine derivatives were used as the starting material in most tetracyclic synthesis. Several simple and convenient routes are succeeded.

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Alkaloid studies—L

Cited by 84 publications

References 41 publications

Alkaloids of the Seeds of Aspidosperma Fendleri Woodson

Alkaloids of the Seeds of Aspidosperma Fendleri Woodson

Alcalóides indólicos isolados de espécies do gênero Aspidosperma (Apocynaceae)

Progress in the Synthesis of Indole Alkaloid Uleine and Its Derivatives

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