The structure of selagine

Valenta, Z.; Yoshimura, Hitomi; Rogers, Edward F.; Ternbah, M.; Wiesner, K.

doi:10.1016/s0040-4039(01)99300-1

Cited by 34 publications

(24 citation statements)

References 5 publications

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“…the next most abundant group; annotinine (5,6) ; and selagine (7,8). At the time of writing, annotinine and selagine are the sole reported representatives of their groups.…”

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confidence: 99%

Lycopodium Alkaloids Xiii. Mass Spectra of Representative Alkaloids

MacLean¹

1963

Can. J. Chem.

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The mass spectra of a number of Lycofiodium alkaloids are recorded and schemes proposed for their fragmentation. The loss of the bridge dominates the fragmentation process in the structural types examined.The Lycopodium alkaloids have been the subject of many studies in the past few years, but there are still many alkaloids of unknown constitution. Those alkaloids whose structures have been elucidated are, for the most part, the most abundant while those whose structure still await solution have been found in smaller quantity. The mass spectrometric method, which has been used in many recent investigations, is particularly well suited to structural studies on substances available in small a m o~n t .~ I t was of interest, therefore, to record the spectra of the Lycopodium alkaloids of known structure and t o study their fragmentation in order that the information so obtained might be applied t o the study of those alkaloids whose structures are yet unresolved and to those alkaloids yet to be isolated.The Lycopodium alkaloids which are now known may be conveniently classified for the purposes of this discussion into four groups: those related in skeletal structure to lycopodine ( 2 ) , by far the largest group; those related in skeletal structure to lycodine (3, 4),

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“…the next most abundant group; annotinine (5,6) ; and selagine (7,8). At the time of writing, annotinine and selagine are the sole reported representatives of their groups.…”

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confidence: 99%

Lycopodium Alkaloids Xiii. Mass Spectra of Representative Alkaloids

MacLean¹

1963

Can. J. Chem.

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“…Huperzine A (1) is isolated from the Chinese folk medicinal plant Huperzia serrata (= Lycopodium serrata) (1) and has been shown to be identical with the alkaloid selagine, which had previously been isolated from L. selago and incorrectly assigned structure 2 (4,5). Huperzine A is reported to increase efficiency for learning and memory in animals (1) and to show promise in the treatment of Alzheimer's disease and myasthenia gravis ( 6 8 ) .…”

Section: Resultsmentioning

confidence: 99%

Macleanine, a unique type of dinitrogenous Lycopodium alkaloid

Ayer¹,

Ma²,

Liu³

et al. 1994

Can. J. Chem.

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. Can. J. Chem. 72, 128 (1994).The structure of macleanine, a unique type of Lycopodium alkaloid, was deduced from its spectroscopic (especially 'H and 13c nuclear magnetic resonance) properties and from biogenetic considerations. The structure was verified by an X-ray crystallographic study of the hydroperchlorate. On a dCduit la structrure de la macleanine, un type unique d'alcaloi'de du Lycopodiurn, en se basant sur ses propriCtCs spectroscopiques (spkcialement la rksonance magnktique nuclCaire du 'H et du I3c) et sur des considCrations biogCnCtiques. On a vCrifiC la structure par une Ctude de diffraction des rayons X sur son perchlorate.[Traduit par la redaction]

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“…A nuclear Overhauser enhancement (nOe) experiment confirmed the proximity of the C-10 methyl (6 1.70) to the allylic C-7 hydrogen (6 3.60) and spin decoupling experiments revealed that this allylic hydrogen was coupled (J = 5 Hz) to the C-8 alkenic hydrogen. This coupling was not detected in the 60-MHz spectrum of selagine recorded by the earlier workers (1,2). The stereochemistry at C-11 was not proposed in the original papers on selagine (1, 2) but was assigned as shown in 1 on the basis of a study of the rate of methiodide formation (5).…”

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confidence: 81%

“…The use of huperzine A (2) in the 1 2 treatment of myasthenia gravis and Alzheimer's disease is currently under clinical investigation in China (4). Because of the structural similarity of selagine (1) and huperzine A (2), the % 3 H3ci 4g \ OH Alberta group has reinvestigated the alkaloids of L. selago to H3C obtain selagine in order to determine its anticholinesterase activ-H2N NH H2N / NH ity. We report herein the isolation of selagine and the finding \ that selagine is identical with huperzine A (2).…”

Section: H2nmentioning

confidence: 99%