Lycopodium Alkaloids: X. The Structure of Lycopodine

Harrison, W. A.; Curcumelli-Rodostamo, M.; Carson, David; Barclay, L. R. C.; MacLean, David B.

doi:10.1139/v61-277

Cited by 27 publications

(13 citation statements)

References 10 publications

(12 reference statements)

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“…Bioactive hexahydro-1 0 ,10 0 -dimethyl-spiro[cyclobutane-1,8 0 (7 0 H)-[1H-5,8a]propane-quinolin]-7 0 -one (3) is a derivative of licopodine, and it was present in extract of Lycopodium species [16]. Unusual tetramethyl-N,Nbis(2,6-dimethyl-phenyl)-cyclobutane-1,3-diimine (4), triacontanol, and tricin were reported from Arundo donax, and showed significant antifeedant activity against the boll weevil Anthonomus grand [17].Structures of compounds (1)-(4) are shown in Fig.…”

Section: Terrestrial Cyclobutane-containing Alkaloidsmentioning

confidence: 99%

Bioactive cyclobutane-containing alkaloids

2007

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The present review describes research on novel natural cyclobutane-containing alkaloids and synthetic compounds isolated from terrestrial and marine species. More than 210 compounds have been confirmed to show antimicrobial, antibacterial, anticancer, and other activities. Structures, origins, biosynthesis, photodimerization, and biological activities of a selection of cyclobutane-containing alkaloids and selected synthetic analogs of natural alkaloids are reviewed.

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Section: Terrestrial Cyclobutane-containing Alkaloidsmentioning

confidence: 99%

Bioactive cyclobutane-containing alkaloids

2007

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“…The spectra of lycopodine, dihydrolycopodine (2,9), anhydrodihydrolycopodine (2, 9), and acetyldih~rdrolycopodine (2,9) are shown in Fig. I.…”

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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 spectrum of lycodoline IV, which carries a hydroxy group a t Ci differs froin that of lycopodine (2) in much the same way as the spectrum of hydroxy-des-N-methyl-aobscurine differs from t h a t of des-N-methyl-a-obscurine. T h e spectrum of lycodoline has been discussed in detail elsewhere (11) and i t is only necessary t o indicate the points of similarity with the spectrum of hydroxy-des-N-methyl-a-obscurine.…”

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confidence: 93%

Lycopodium Alkaloids: Xv. Structure and Mass Spectra of Some Minor Alkaloids of L. Flabelliforme

Alam¹,

Adams²,

MacLean³

1964

Can. J. Chem.

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Hydroxy-des-N-methyl-a-obscurine, C I~H~~O ?~\ T ? , has been isolated froin L . fEabelliforme and a structure assigned to it on the basis of physical evidence. A s t r i l c t~~r e is assigned t o Lycopodium allraloid L.5, which we have named flabellidine, on the basis of physical evidence and its chemical derivation from lycodine. The mass spectra of hydroxy-des-N-methy1-aobscurine, flabellidine, and flabelline are discussed.The alltaloids of L. flabelliforme were first investigated by i\/Ianslte and Marion ( I ) , who isolated lycopodine (the major alkaloid), nicotine, and six bases, which they designated by number only. Alkaloid L.1 is now ltnown t o be dihydrolycopodine (2), L.2 t o be acetyldihydrolycopodine (3), and L.6 t o be a mixture of a-and P-obscurine (4). The structures of lycopodine and its derivatives (2) and of a-and p-obscurine (5) are now known. The structure of alkaloid L.5, t o which we have assigned the trivial name flabellidine, is discussed in this paper, leaving alkaloids L.3 and L.4 of the original six still uninvestigated.By using chromatographic and countercurrent distribution methods, an additional seven alltaloids have been isolated from L.flabell.iforme in this laboratory. Thus Young (6) has reported the isolation of two new alltaloids, flabelliformine and flabelline, t o each of which a structure has been assigned (7,8). Alam (9) has found four alkaloids of ltnown structure (clavolonine, lycodine, annotinine, and des-N-methyl-a-obscurine) and a new base hydroxy-des-N-methyl-a-obscurine, the structure of which is discussed in this paper.The structure assigned t o hydroxy-des-N-methyl-a-obscurine I rests on physical evidence as insufficient material was available t o investigate its chemistry.The presence of a hydroxyl group in I is inferred from its infrared spectrum, which, in Nujol and in chloroform, shows a pealt a t 3510 cm-l. The position of this peak in chloroform solution is not shifted upon dilution, thereby indicating that the hydroxyl group is intrainolecularly hydrogen bonded. Aside from the pealt in the hydroxyl region, the spectrum of this compound is remarkably similar t o that of a-obscurine (11) and des-Nmethyl-a-obscurine (111). The spectra of the three are reproduced in Fig. 1 for the region 3600-1500 cm-I.The ultraviolet spectrum of I (l:f:;OH 255 mp, log E = 3.78) is almost identical with that of I1 (~::i~~ 255 mp, log E = 3.75) and I11 (l:f:{OH 255 mp, log E = 3.81). From the spectral evidence i t appears that I must have the same chromophoric system as I1 and 111.The mass spectrum of the hydroxy compound shows a molecular weight of 276, corresponding t o the molecular formula C16H2402b?2. This formula differs in colnposition from I11 (C16H240N2) by one oxygen atom, suggesting t h a t the new base may be a simple hydroxy derivative of the latter. T h e fragmentation pattern of I , discussed later, is in agreement with this proposition.The nuclear magnetic resonance (n.m.r.) spectrum of I shows a three proton doublet For personal use only.

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Lycopodium Alkaloids: X. The Structure of Lycopodine

Cited by 27 publications

References 10 publications

Bioactive cyclobutane-containing alkaloids

Bioactive cyclobutane-containing alkaloids

Lycopodium Alkaloids Xiii. Mass Spectra of Representative Alkaloids

Lycopodium Alkaloids: Xv. Structure and Mass Spectra of Some Minor Alkaloids of L. Flabelliforme

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