Some alkaloids of Alstonia undulata

Sixteen indole alkaloids have been identified in the root bark and in the leaves of Alstonia undulata from New Caledonia. They are vincamedine, tetrahydroalstonine, alstonidine, deplancheine, fluorocarpamine, pleiocarpamine, 11-methoxyakuammicine, cabucraline, desoxycabufiline, cabucraline-N(4)-oxide, 11-methoxyakuammicine N(4)-oxide, gentiacraline, plumocraline, vincorine, cathafoline and pericyclivine. Five bis indoles of unknown structure have been isolated. The root bark alkaloid mixture contains gentiacraline the first alkaloid made up of an indole and a pyridine alkaloid.     

Isolation and structural characterization of new piperidine alkaloids from Prosopis affinis

The isolation of three new N-methylated piperidine-3-ol alkaloids from the bark of Prosopis affinis Spreng. (Ñandubay) is described. Together with MS and IR data, results from 1D and 2D NMR experiments allowed for the identification of N‑methyl-2-isocassine, N‑methyl-6-isocassine, and N‑methyl-6-isocarnavaline. Inspection of 1D-NOESY spectra and coupling constant data revealed that the heterocyclic moiety of the alkaloids is in fast conformational equilibrium in solution, and this behavior had to be taken into account in order to determine the relative configuration of the chiral centers of the piperidine rings.     

Alcaloïdes de Zanthoxylum decaryi: la decarine,nouvel alcaloide dérivé de la benzophénanthridine

Four alkaloids have been isolated from the stem bark of Zatithoxylum decaryi. Three are known, dictamnine skimmianine, 4-methoxy-1- methyl-2-quinolone. The fourth decarine is new; its structure has been established as 9-methoxy-10-hydroxy-2,3-methylenedioxybenzophenanthridine.¹     

Alcaloïdes des ecorces de racines de Crioceras dipladeniiflorus

Eight alkaloids have been isolated from the root bark of Crioceras dipladeniiflorus. Five of them are new: Δ¹⁴-vincamine (I) epi-16 Δ¹⁴-vincamine (II) 12-methoxy-δ ¹⁴-vincamine (V) apo Δ¹⁴- vincamine (VI), and ditabersonine (VII), a dimeric alkaloid; the three others are known, voaphylline (III), tabersonine, (IV), and vobtusine (VIII).     

Additional alkaloids from Laurelia philippiana and L. novae-zelandiae

Asimilobine, anonaine, noreorydine, nornantenine, (+)-reticuline and the new alkaloid, 4-hydroxyanonaine, were isolated from Laurelia philippiana bark. The biogenetically related obovanine, oxoputerine and (?)-romneine, not known as a natural product, were obtained from the bark of L. novae-zelandiae. The occurrence of (R)-norlaudanosoline-derived alkaloids in L. novae-zelandiae is a distinctive feature of this tree. Neither L. novae-zelandiae nor L. philippiana accumulate dimeric benzylisoquinoline alkaloids to any appreciable extent in the trunk bark, differing in this respect from L. sempervirens, the only other Laurelia species.     

N-isobutyl-trans-2-trans-4-eicosadienamide and other alkaloids of fruits of Piper guineense

A novel alkaloid, N-isobutyl-trans-2-trans-4-eicosadienamide, has been isolated from the fruits of Piper guineense and fully characterized. The structure of the compound has been confirmed by an unambiguous synthesis of the tetrahydro derivative. The known alkaloid, δαβ-dihydropiperine has also been isolated and the position of the double bond in this compound confirmed by the use of an NMR shift reagent.     

A novel tryptophan-derived alkaloid and other constituents from Guettarda speciosa (Rubiaceae: Cinchonoideae–Guettardeae)

Phytochemical examination of two Thai accessions of the widespread paleotropical Guettarda speciosa (Rubiaceae: Cinchonoideae–Guettardeae) led to the isolation of the hitherto undescribed tryptophan-derived alkaloid 5α-carboxystrictosidinic acid together with 5α-carboxystrictosidine, the iridoid glucoside loganic acid and 5-O-caffeoylquinic acid from the root bark extract. The leaf extract further yielded 3-O-caffeoylquinic acid and 4,5-di-O-caffeoylquinic acid. The structures of the isolated compounds were established by NMR and MS techniques and compared to other species of Guettarda. In addition, the structural differentiation of alkaloids within this genus is discussed with special emphasis on 5α-carboxy derivatives suggesting a pathway apart from the strictosidine biosynthetic route.     

Alkaloids,limonoids and furocoumarins from three Mexican Esenbeckia species

The chemical constituents of three Mexican Esenbeckia species have been determined. Rutaevin was the main limonoid present in the seeds of all three species, E. litoralis, E. flava and E. berlandieri. The husks, leaves, wood and bark contained a wide array of known furocoumarins and furoquinoline alkaloids. In addition, 1-hydroxy-3-methoxy-N-methylacridone was obtained from E. litoralis bark and a new natural 2-quinolone alkaloid, formulated as 3,3-diisopropyl-N-methyl-2,4-quinoldione, was obtained from E. flava wood. The structure was assigned from spectroscopic considerations and conversion to N-methylhaplofoline.     

Polyavolinamide,an indolosesquiterpene alkaloid from Polyathia suaveolens

A new indolosesquiterpene alkaloid, polyavolinamide, has been identified in the stem of Polyathia suaveolens accompanied by the three previously isolated indolosesquiterpene alkaloids, polyavolensin, polyavolensinol, polyavolensinone, as well as an unidentified triterpene and an aporhine alkaloids. Polyavolinamide was also the major component of the root bark. Its structure was assigned on the basis of ¹¹H and ¹³C NMR, and mass spectrometry.     

Na-formylechitamidine,an alkaloid from Alstonia boonei

A known alkaloid, echitamidine, and a new alkaloid, N_a-formylechitamidine, have been isolated from the stem bark of Alstonia boonei. The structure of this new alkaloid was assigned on the basis of chemical and spectroscopic data.     

Zanoxyline—a new alkaloid from stem bark of Zanthoxylum oxyphyllum

The EtOH extract of stem bark of Zanthoxylum oxyphyllum yielded rhetsinine and a new alkaloid 1-(4′methoxy benzyl)-6,7-dimethoxy N:N dimethyl 1,2,3,4 tetrahydroisoquinolinium hydroxide provisionally named zanoxyline.     

Erythrinoid and indol alkaloids isolated from the seeds of Erythrina rubrinervia Kunth: Chemotaxonomic significance

In the present work, we report the isolation of five alkaloids from the seeds of Erythrina rubrinervia. Four of the isolated alkaloids are erythrinoid type alkaloids which were identified as erysodine (1), erysovine (2), erythraline (3) and erysotrine (4), plus an indolic alkaloid which was identified as hypaphorine (5). The analysis of spectroscopic data for the alkaloid l-hypaphorine shows that the published structure (5a) must be revised, and the correct structure is that depicted as the structure 5c. The chemical structures were elucidated by full spectroscopic analysis. The chemotaxonomic significance of those findings in the genus Erythrina is also discussed.     

Directed biosynthesis of unnatural alkaloids in Dolichothele sphaerica

Using appropriate precursors, the two unnatural alkaloids 4(5)-[N-isocaproylaminomethyl]imidazole and 3-[2-N-isovalerylaminoethyl]pyrazole were produced by Dolichothele sphaerica. The former compound represents an unnatural alkaloid formed by the simultaneous introduction of two unnatural precursors, namely isocaproic acid and 4(5)-aminomethylimidazole. The latter compound represents an aberrant alkaloid formed by the introduction of a precursor of different heterocyclic entity, 3-aminoethylpyrazole.     

Dimeric bisindole alkaloids from the stem bark of Strychnos nux-vomica L.

Strychnos nux-vomica L. (Loganiaceae) is famous for its monomeric alkaloid content, such as strychnine, a convulsant poison. The stem bark of the tree is traditionally used to treat intermittent fever in South East Asia. In various studies, it appeared that dimeric indolo-monoterpenic alkaloids possess a promising activity on Plasmodium falciparum. Three bisindolomonoterpenic alkaloids together with strychnochrysine, previously identified in the root bark of S. nux-vomica, were isolated from the stem bark. The structures of these compounds were established using NMR spectroscopy and mass spectrometry.Stereochemistry of the compounds was confirmed by molecular modelling. This then allowed the structural determination of strychnoflavine, a coloured bisindole alkaloid previously isolated from the root bark of the tree. Moreover, the conformational inversion in alkaloids possessing an ether bond in the strychnane moiety could be easily predicted by specific δ ¹³C NMR values.These longicaudatine-type alkaloids were found to display in vitro antiplasmodial activity against a chloroquine resistant strain and a chloroquine sensitive strain. The most interesting was strychnochrysine showing an IC₅₀ value at around 10 μM.     

Quaternary alkaloids of Thalictrum foliolosum

The isolation and identification of eleven alkaloids from the quaternary alkaloid fraction of a root extract of Thalictrum foliolosum are described     

Two Delphinium ramosum chemotypes,their biogeographical distribution and potential toxicity

Larkspurs (Delphinium, Ranunculaceae) are poisonous plants found on rangelands throughout Western North America. Two main structural groups of norditerpene alkaloids, the N-(methylsuccinimido) anthranoyllycoctonine type (MSAL-type) and the non-MSAL type, are responsible for larkspur-induced poisoning. Information on the alkaloid composition is lacking for a number of Delphinium species, including D. ramosum. Delphinium ramosum grows throughout parts of Colorado and northern New Mexico. The objective of this study was to profile the alkaloid composition of D. ramosum throughout its geographical distribution using both field and herbarium specimens. Two alkaloid profiles were identified, one that contained significantly greater concentrations of the MSAL-type alkaloids than the other. Plants containing each respective alkaloid profile were unique in their geographical distribution. Populations of these two chemotypes will likely differ in their toxic potential and consequently pose different risks of poisoning when grazed by livestock species. This information has important implications in grazing management decisions on D. ramosum-infested rangelands and demonstrates that botanical classification alone is not an adequate indicator of relative risk of toxicity.     

Alkaloids of Uncaria attenuata from Thailand

The major alkaloids of a sample of leaves of Uncaria attenuata obtained from Thailand have been identified as the pentacyclic heteroyohimbine alkaloids tetrahydroalstonine, rauniticine and the novel 14-β-hydroxy-3-iso-rauniticine. Evidence for the structure of the new alkaloid was obtained from a study of UV, IR, MS, ¹H NMR and ¹C NMR spectra.     

Minor indolopyridoquinazoline alkaloids from Euxylophora paraënsis

Four new indolopyridoquinazoline alkaloids were isolated in small amount from the bark of Euxylophora paraänsis Hub. Chemical reactions and spectroscopic evidence indicated that euxylophorine-C has structure (Ia), which was confirmed by synthesis. The structures of the other alkaloids, euxylophorine-D (IIa), euxylophoricine-D (IIIa) and euxylophoricine-E (IVa), were determined through correlation with (Ia).     

Alkaloids of Toddalia asiatica (Rutaceae)

Phytochemical investigation of the alkaloidal extract of the roots of Toddalia asiatica led to the isolation of a new seco-benzophenanthridine alkaloid (1) and twelve known alkaloids (2–13). The new structure was elucidated by means of spectroscopic analysis, and the known alkaloids were identified by comparison with the literature. Among these alkaloids, 1 and 5–7 were reported from the genus Toddalia for the first time. The distribution of the isolated alkaloids at genus/family level was presented via network analysis and their chemotaxonomic significance was also discussed.     

Isoquinoline-derived alkaloids from the bark of Guatteria olivacea (Annonaceae)

Phytochemical investigation of the bark of Guatteria olivacea R. E. Fries (Annonaceae) led to the isolation and identification of ten isoquinoline-derived alkaloids, including three phenanthrenes, atherosperminine, argentinine, and atherosperminine N-oxide; three aporphines, asimilobine, puterine, and discoguattine; two oxoaporphines, liriodenine and oxoputerine; and two tetrahydroprotoberberines, corypalmine and discretine. All these alkaloids are described for the first time in G. olivacea and their chemotaxonomic significance was discussed. The structure elucidation of these isolated alkaloids was established by extensive analyses of 1D and 2D NMR spectroscopy in combination with MS. The NMR data for atherosperminine, argentinine, and atherosperminine N-oxide were reviewed.