On the Alkaloids of Aconitum gigas LEV. et VAN. and the Structure of a New Base, Gigactonine

Sakai, Shin‐ichiro; Shinma, Nobuo; Hasegawa, Sugio; Okamoto, Toshihiko

doi:10.1248/yakushi1947.98.10_1376

Cited by 9 publications

(8 citation statements)

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“…The IR and 1 H 1D NMR spectra of our synthetic sample of 2 were in good agreement with the spectroscopic data for the naturally-occurring alkaloid reported by Sakai et al and by Yu and Das for “lycaconitine” isolated from D .…”

supporting

confidence: 90%

“…In continuation of our efforts to elucidate structure−activity relationships in analogues of 1 , , we turned our attention to lycaconitine ( 2 ), an alkaloid differing from 1 only in the absence of the methyl substituent from the succinimide ring. Although isolations of 2 from several species of Aconitum and Delphinium have been reported, there have been virtually no published reports of modern pharmacological investigations on an authentic sample of this compound ( vide infra ), and there are conflicting sets of spectroscopic data in the literature. − …”

mentioning

confidence: 99%

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Lycaconitine Revisited: Partial Synthesis and Neuronal Nicotinic Acetylcholine Receptor Affinities

et al. 1996

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supporting

confidence: 90%

mentioning

confidence: 99%

Lycaconitine Revisited: Partial Synthesis and Neuronal Nicotinic Acetylcholine Receptor Affinities

et al. 1996

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“…Fraction 10 (11.1 mg) was purified on a Si gel rotor by elution with hexane/CHCl3 and CHC13 with increasing percentages of MeOH to give 6.5 mg of gigactonine [6], Crystallization from Me2CO/C6H6 gave a material with mp 168.5-169.5°[lit. (2,19) mp 168-169°], identical with an authentic sample of gigactonine [6] in its co-tlc behavior and ir, 'H-nmr, and 13C-nmr spectra.…”

mentioning

confidence: 80%

Two New Norditerpenoid Alkaloids from the Roots of Delphinium ajacis

Pelletier¹,

Bhandaru²,

Desai³

et al. 1992

J. Nat. Prod.

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TWO new norditerpenoid alkaloids, ajadelphine 111 and ajadelphinine [2], have been isolated from the roots of Defpbinim ajaris L. The structure of 2 was determined with the aid of 'Hand '3C-nmr spectroscopy, including DEPT, COSY-90, and inverse detected HETCOR (heteronuclear multiplequantum coherence-HMQC) experiments. Ajadelphine [l] is the first lycoctonine-type norditerpenoid alkaloid having a methoxyl group at C-8 and a hydroxyl group at C-18. Ajadelphinine 121 is the first lycoctonine-type norditerpenoid alkaloid having a C-74-8-methylenedioxy group and an 18-OH group. Also isolated were the known norditerpenoid alkaloids delcosine 131, delsoline 141, deltaline {SI, gigactonine [61, 18methoxygadesine m, and delphisine [SI. The latter has not been previously reported in this plant.In continuation of our studies on the alkaloids present in the different plant organs of Delphinium ajacis L. (Ranunculaceae) (1-3), we now report the isolation of two new norditerpenoid alkaloids, ajadelphine 117 and ajadelphinine 121, together with six known ones: delcosine (31, delsoline (41, deltaline 151, gigactonine 161, 18methoxygadesine Trl., and delphisine 181. This is the first time that delphisine 181, an aconitine-type norditerpenoid alkaloid, has been found in this plant. RESULTS AND DISCUSSIONThe air-dried and defatted powdered root material of D . ajacis was extracted exhaustively with 80% EtOH, and the crude alkaloidal mixture was processed as indicated in the Experimental section. Extensive chromatographic separations afforded eight alkaloids, of which three have not been reported previously in this plant.

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“…To study the mechanism of this reaction, the llp-hydroxy epimer (35) of hetisine was prepared. On refluxing (35) in 5% H2S04, (31), (32), (36), and (37) were also obtained. However, the ratio of ( 31) to (32) that was obtained from (30) was greatly different from the ratio of these products from (35).…”

Section: Hetisine (30) R1mentioning

confidence: 90%

“…A re-examination2 of the previously reported22 acid-catalysed rearrangement of hetisine (30) to ( 31) and ( 32) has been presented. In addition to compounds (31) and (32), a new product, of mol. wt 329 and m.pt 295-299 "C, was obtained.…”

Section: Rearrangement Products Of Hetisinementioning

confidence: 99%