Alkaloids of Delphinium dictyocarpum

Narzullaev, A. S.; Yunusov, M. S.; Yunusov, S. Yu.

doi:10.1007/bf00563677

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Chem Nat Compd

1972

DOI: 10.1007/bf00563677

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Alkaloids of Delphinium dictyocarpum

A. S. Narzullaev¹,

M. S. Yunusov²,

S. Yu. Yunusov³

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Cited by 6 publications

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“…They established structure 3 for dictyocarpine on the basis o^H-nmr and mass spectral studies (5). The study also involved chemical correlation of 1-3 with the alkaloid delpheline [4]. Later the structure of dictyocarpine [33 was confirmed by a single crystal X-ray analysis of its acetone complex (6).…”

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confidence: 99%

Revised ¹³C Nmr Assignments for Norditerpenoid Alkaloids with 7,8-Methylenedioxy and 10β-OH Groups

Desai¹,

Pelletier²

1993

J. Nat. Prod.

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13C-nmr chemical shift assignments for the norditerpenoid alkaloids deltaline[1], deltamine [2], dictyocarpine [3], and 14-acetyldictyocarpine [51 have been revised on the basis of a study of their ID, 2D, and selective INEPT nmr spectra. These revisions suggest that the I3C-nmr chemical shift assignments for twenty-eight other norditerpenoid alkaloids possessing 7,8-methylenedioxy and 1 ßgroups may have to be revised. Complete -nmr chemical shift assignments for compounds 1-3 and 5 are also reported.The alkaloid deltaline [1] was isolated from Delphinium occidentale S. Wats (Ranunculaceae) in 1936 by Couch (1). Deltaline (eldeline) [1] and deltamine (eldelidine)[2] were isolated by Rabinovich (2) from Delphinium elatum L. in 1952. The structures of 1 and 2 were established by Kuzovkov and Platonova in 1959 (3).Dictyocarpine {3} was first reported from Delphnium dictyocarpum by Narzullaev et al. (4) in 1972. They established structure 3 for dictyocarpine on the basis o^H-nmr and mass spectral studies (5). The study also involved chemical correlation of 1-3 with the alkaloid delpheline [4]. Later the structure of dictyocarpine [33 was confirmed by a single crystal X-ray analysis of its acetone complex (6).13C-nmr chemical shift assignments for compounds 1-3 and 5 were reported from this laboratory in 1980 (7). The assignments were based on the determination of the noise-decoupled and single-frequency off-resonance decoupled (SFORD) spectra. The 13C-nmr signals were assigned with the help of the single-frequency proton off-resonance decoupling technique, application of the known chemical shift rules for OH substitution and acetylation shifts, and steric effects, and from comparisons of spectra from compound to compound.A growing need for the complete and unambiguous nmr chemical shift assignments for the naturally occurring complex diterpenoid alkaloids prompted us to examine the 1 R=Ac (deltaline)3 R=H (dictyocarpine) 2 R=H (deltamine) 5 R=Ac (14-acetyldictyocarpine) 4 (delpheline) 6 (delcorine)

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confidence: 99%

Revised ¹³C Nmr Assignments for Norditerpenoid Alkaloids with 7,8-Methylenedioxy and 10β-OH Groups

Desai¹,

Pelletier²

1993

J. Nat. Prod.

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“…The location of one of the three methoxyls in the C-18 position was confirmed by the presencee in the 13 C NMR of 1 of a triplet at δ 78.5 ppm. The presence in the PMR of 1 of a 1H singlet for H-6α at δ 4.37 ppm placed a β-OH group on C-6 [7]. Furthermore, a 1H triplet (J = 4.5 Hz) was observed at δ 3.71 ppm, indicating that C-14 contained an α-methoxyl [8].…”

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confidence: 90%

Uraphine, a new norditerpene alkaloid from the aerial part of Delphinium uralense

et al. 2008

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The new norditerpene alkaloid uraphine, for which the structure 1α, 6β-dihydroxy-7,8-methylenedioxy-14α,16β,18β-trimethoxy-N-ethylaconitane was proposed based on PMR, 13 C NMR, IR, and mass spectral data, was isolated from the aerial part of Delphinium uralense N. The known alkaloids dehydrodelcorine, delpheline, deltaline, deltamine, elasine, deacetylelasine, gigactonine, and lycoctonine were also isolated from the total alkaloids.The plant Delphinium uralense Nevski has a limited distribution and belongs to the complex D. aggr. dictyocarpum DC. (section Delphinastrum DC) [1]. We reported previously on the isolation from the aerial part of this plant collected during the start of budding in the Southern Urals (Zilair Plateau) of methyllycaconitine, delcorine, and grandiflorine (uraline) [2].In continuation of research on the alkaloid composition of the aerial part of D. uralense, we isolated from the benzene extract of the moderately basic fraction (A, pH 6) [2] by column chromatography and semi-preparative HPLC the known alkaloids dehydrodelcorine, delpheline, deltaline, deltamine, and elasine, and alkaloid 1, which has not previously been described and which we called uraphine. We also isolated deacetylelasine, which was isolated by us for the first time from plant material and has been prepared previously via alkaline hydrolysis of elasine [3]. We isolated the known alkaloids gigactonine and lycoctonine from the strongly basic fraction (B, pH 12).According to IR spectroscopy, 1 contained hydroxyls (3300-3500 cm −1 ). The high-resolution mass spectrum gave molecular weight 465.2715 for 1, which corresponded to the empirical formula C 25 H 39 NO 7 . The fact that the peak for the ion [M -17] + was the base peak suggested that C-1 had an OH group [4]. Peaks for ions [M -56] + and [M -87] + also suggested that there was a hydroxyl in the 1-position and a methoxyl in the 18-position [5,6]. The location of one of the three methoxyls in the C-18 position was confirmed by the presencee in the 13 C NMR of 1 of a triplet at δ 78.5 ppm. The presence in the PMR of 1 of a 1H singlet for H-6α at δ 4.37 ppm placed a β-OH group on C-6 [7]. Furthermore, a 1H triplet (J = 4.5 Hz) was observed at δ 3.71 ppm, indicating that C-14 contained an α-methoxyl [8].

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“…A 1H singlet at G 5.38 ppm in addition to a 3H singlet at 2.04 in the PMR spectrum of 1 indicated that C-6 contained a E-OAc group [5]. A weak-field shift of the characteristic triplet for H-14E (4.13, J = 4.8 Hz) suggested that C-14 had an D-methoxyl; C-10, a E-OH group [6].…”

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confidence: 95%

19-Oxodeltaline, a norditerpene alkaloid from the aerial part of Delphinium uralense

et al. 2010

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Alkaloids of Delphinium dictyocarpum

Cited by 6 publications

References 2 publications

Revised ¹³C Nmr Assignments for Norditerpenoid Alkaloids with 7,8-Methylenedioxy and 10β-OH Groups

Revised ¹³C Nmr Assignments for Norditerpenoid Alkaloids with 7,8-Methylenedioxy and 10β-OH Groups

Uraphine, a new norditerpene alkaloid from the aerial part of Delphinium uralense

19-Oxodeltaline, a norditerpene alkaloid from the aerial part of Delphinium uralense

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Alkaloids of Delphinium dictyocarpum

Cited by 6 publications

References 2 publications

Revised 13C Nmr Assignments for Norditerpenoid Alkaloids with 7,8-Methylenedioxy and 10β-OH Groups

Revised 13C Nmr Assignments for Norditerpenoid Alkaloids with 7,8-Methylenedioxy and 10β-OH Groups

Uraphine, a new norditerpene alkaloid from the aerial part of Delphinium uralense

19-Oxodeltaline, a norditerpene alkaloid from the aerial part of Delphinium uralense

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Product

Resources

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Revised ¹³C Nmr Assignments for Norditerpenoid Alkaloids with 7,8-Methylenedioxy and 10β-OH Groups

Revised ¹³C Nmr Assignments for Norditerpenoid Alkaloids with 7,8-Methylenedioxy and 10β-OH Groups