Alkaloids of Thermopsis Lupinoides

Ammodendrine, together with seven other known lupin alkaloids, was isolated from Thermopsis lupinoides. (+)-Lupanine (+)-17-oxolupanine occurred together with (?)anagyrine, (?)-baptifoline, (?)-cytisine, (?)-N-methylcytisine (?)N-formylcytisine. These alkaloids have the opposite stereochemistry to that of (+)-lupanine and (+)-17-oxolupanine. The distribution of alkaloids in fresh flowers, leaves, stems roots of this plant was also examined.     

Stereochemistry of tropane alkaloid formation in Datura

Five-month-old Datura innoxia plants were fed via the roots with either d(+)-hygrine-[2′-¹⁴C] or l(?)-hygrine-[2′-¹⁴C]. After 7 days the root alkaloids 3α,6β-ditigloyloxytropane, 3α,6β-ditigloyloxytropan-7β-ol, hyoscine, hyoscyamine and cuscohygrine were isolated from both groups of plants. d(+) but not l(?)-hygrine acts as a precursor for the tropane alkaloids whereas both enantiomers appeared to serve equally well in the biosynthesis of cuscohygrine.     

Alkaloids of Fumaria vaillantii

The aerial parts of Turkish Fumaria vaillantii yielded 26 isoquinoline alkaloids. Of these, oxysanguinarine, (±)-8-acetonyldihydrosanguinarine, (±)-8-methoxydihydrosanguinarine and fumaramidine are reported for the first time from this plant. New alkaloids for the genus Fumaria are dihydrosanguinarine, norsanguinarine, (+)-isocorydine, (?)-corledine and (+)-juziphine. This is the first occurrence of the isoquinolone N-methylcorydaldine in a member of the Fumariaceae. Spectral data are given for the new compound, E-fumaramine.     

Sesquiterpenes and alkaloids from Cleistopholis patens

The root bark of Cleistopholis patens collected in Ghana yielded two sesquiterpenes and five alkaloids. The sesquiterpenes have been characterised as the acyclic methyl-(?)-(trans)-(trans)-10,11-dihydroxyfarnesoate and its monocyclic derivative methyl-(+)-10-hydroxy-6,11-cyclofarnes-7(14)-enoate. The alkaloids were of the unusual aza-polycyclic and naphthyridine groups and included one new member of both classes. Examination of stem bark samples from the same source and from Sierre Leone showed the presence of the sesquiterpenes and the oxoaporphine alkaloid liriodenine but neither of the rarer alkaloid types.     

Three new alkaloids from Buxus papillosa

Three new steroidal alkaloids have been obtained from Buxus papillosa Schneider. These are (?)-cyclobuxupaline-C (IV)(+)-cyclopapilosine-D (VII) and (+)-buxamine-C (IX). A known alkaloid also present is desoxy-16-buxidienine (X).     

Alcaloides d'Araliopsis soyauxii. Isolement d'un nouvel alcaloide,l'Araliopsine

Six alkaloids have been isolated from root bark of Araliopsis soyauxii. Five are known, maculine, flindersiamine, skimmianine, (?) ribalinine, (+) isoplatydesmine and the sixth, araliopsine is new; its structure has been established as hydroxyisopropyldihydrofuro-2-quinolone. From the trunk bark four alkaloids have been isolated: flindersiamine, kokusaginine (?) ribalinine, (+) isoplatydesmine.     

Fumariaceae alkaloids including the biogenetic precursor of cularine

Corydalis claviculata has yielded (+)-crassifoline, the first 7,8,3′,4′-oxygenated benzylisoquinoline and biogenetic precursor of cularine, as well as the new cularine alkaloids (+)-sarcocapnidine, (+)-claviculine and (+)-O-methylcularicine.     

Aporphine alkaloids and lignans formed in response to injury of sapwood in Liriodendron tulipifera

Two new phenolic aporphine alkaloids, (+)-lirioferine and (+)liriotulipiferine, were isolated from discolored sapwood of L. tulipifera. Injury to the tree stem greatly stimulated biosynthesis of glaucine and phenolic alkaloids related to glaucine including thaliporphine, predicentrine, N-methylaurotetanine and corunine as well as the above two compounds. Injury also stimulated synthesis of oxoaporphine related and other polymeric pigments. Corunine was responsible for at least part of the color of discolored sapwood. None of the above compounds except glaucine was detected in normal sapwood or heartwood of L. tulipifera. Thus, formation of alkaloids and lignans in discolored sapwood differs both quantitatively and qualitatively from that observed during the normal transition of sapwood to heartwood in this tree. The compounds formed in response to injury differed substantially from one zone of injury to another within the same tree.     

Indole alkaloids from Hunteria zeylanica

Fourteen indole alkaloids were isolated and identified from the leaves and bark of Hunteria zeylanica: isocorymine, vobasine, (+)-eburnamenine, eburnamine, isoeburnamine, O-ethyleburnamine, O-methyleburnamine, O-methylisoeburnamine, pleiocarpamine, dihydrocorynantheol, yohimbol, epiyohimbol, tuboxenine and hydroxy-17-decarbomethoxy-16-dihydroepiajmalicine. O-Ethyleburnamine, O-methylisoeburnamine, epiyobimbol and hydroxy-17-decarbomethoxy-16-dihydroepiajmalicine, although known products, were isolated for the first time from a natural source.     

Minor alkaloids of Heliotropium curassavicum

Isolation and structure determination of the minor alkaloids of Heliotropium curassavicum are described. These include the new pyrrolizidine alkaloids, heliocurassavine [isoretronecanol (?) curassavine], heliocoromandaline [isoretronecanol (+) viridiflorate], heliocurassavicine [isoretronecanol (?) trachelanthate], heliocurassavinine [laburnine (?) trachelanthate], curassavinine [supinidine (?) curassavate], coromandalinine [supinidine (+) viridifloratel, heliovinine [supinidine (?) trachelanthate] and curassanecine [1-(α-hydroxy-methyl)-8α pyrrolizidin-1β-ol]. Structures were established by high resolution ¹H NMR, mass spectrometry and paper electrophoresis of the alkaloids and their hydrolysis products.     

Iridoids,iridoid-triterpenoid congeners and lignans from Desfontainia spinosa

The leaves of Desfontainia spinosa; were found to contain the three known seco-iridoids secoxyloganin, dimethyl secologanoside and sweroside in addition to the three iridoids loganin, loganetin and loganic acid previously reported. In addition a novel loganin derivative 7-O-(p-coumaroyl)-loganin was isolated. The leaves were also found to contain a novel type of compound consisting of ester-linked triterpene and seco-iridoid congeners between 24-hydroxytormentic acid and secoxyloganin. These were named desfontainic acid, a monoglucoside, and desfontainoside, the corresponding diglucoside. Desfontainoside only could be detected in the stems. The stem contained the same iridoids and also the known furofuran lignans (+)-syringaresinol, (+)-syringaresinol O-β-D-glucopyranoside and liriodendrin. The iridoids present provide chemotaxonomic evidence for retaining Desfontainia in the Loganiaceae as a separate tribe the Desfontaineae. None of the compounds present forms a basis for the reputed hallucinogenic activity.     

Alkaloids and other constituents of Zanthoxylum williamsii,Z. monophyllum and Z. fagara

Zanthoxylum williamsii (Rutaceae) was found to contain (+)-asaranin, (+)-sesamin, esculetin dimethyl ether, nitidine, chelerythrine, magnoflorine, laurifoline, skimmianine and edulinine. The quaternary alkaloid fraction of Z. monophyllum contained berberine, magnoflorine, chelerythrine and a 1,2,9,10-substituted dihydroxydimethoxy-N,N-dimethylaporphinium salt. Leaves of Z. fagara were found to contain synephrine. Leaves of each species were examined for the presence of bishordeninyl terpene alkaloids, but none was found. Some chemotaxonomic relationships among Zanthoxylum species are 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.     

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.     

Five new alkaloids from Aconitum apetalum (Ranunculaceae)

Twenty-one alkaloids, including five new ones, acoapetaldines A–E (1–5), were isolated from the whole plants of Aconitum apetalum. Among them, 1 is an aconitine-type diterpenoid alkaloid, 2 and 3 are aporphine alkaloids and 4 and 5 are napelline-type diterpenoid alkaloids. The structures of the new alkaloids were elucidated by spectroscopic data analysis and that of acoapetaldine D (4) was confirmed by single crystal X-ray crystallography. Acoapetaldine A (1) and aconorine (12) exhibited moderate anti-tobacco mosaic virus (anti-TMV) activity, while corydine (15) displayed moderate antimicrobial activity against Pseudomonas aeruginosa.     

Lignans and aporphine alkaloids in bark of Liriodendron tulipifera

Lirionol, a novel tetracyclic lignan, has been isolated from the bark of Liriodendron tulipifera and its structure determined by spectroscopic analysis. In addition, syringic acid methyl ester, (+)-pinoresinol, (+)-syringaresinol, N-(2-hydroxy-2-phenylethyl)benzamide and O-methyl-N-norlirinine have also been isolated. The structures of lirinine and related compounds isolated from the leaves of this tree-species by Yunusov et al. are also discussed.     

New alkaloids from Strychnos icaja

The alkaloids of Strychnos icaja (Loganiaceae) have been studied. An extract from Zaire leaf material yielded nine alkaloids, comprising novacine, the new base 21,22-α-epoxy-4,14-dihydroxy-3-methoxy-N-methyl-sec.-pseudostrychnine, and seven others of known structure previously obtained from the plant. Cameroun leaf material gave five alkaloids, of which one, 21,22-α-epoxy-3,4-dimethoxy-N-methyl-sec.-pseudostrychnine, is new. Fruits from Gabon afforded eight alkaloids; two of them are new and are formulated as 21,22-α-epoxy-4-methoxy-N-methyl-sec.-pseudostrychnine and the corresponding 14-hydroxy derivative.     

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.     

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.     

Alkaloid profiles of Dermatophyllum arizonicum,Dermatophyllum gypsophilum,Dermatophyllum secundiflorum,Styphnolobium affine,and Styphnolobium japonicum previously classified as Sophora species

Sophora arizonica, Sophora gypsophila, Sophora secundiflora, Sophora affinis, and Sophora japonica were recently reclassified as Dermatophyllum arizonicum, Dermatophyllum gypsophilum, Dermatophyllum secundiflorum, Styphnolobium affine, and Styphnolobium japonicum, respectively. Some legumes of the sub family Papilionoideae including Sophora species are reported to contain a variety of quinolizidine alkaloids. The quinolizidine alkaloid profiles of D. arizonicum, D. gypsophilum, D. secundiflorum, S. affine, and S. japonicum were investigated qualitatively and quantitatively using field collections and herbarium specimens throughout their range of geographical distribution for the native species. This is the first report of the alkaloid profiles of D. arizonicum and D. gypsophilum. Alkaloid profiles of the other species were compared to previous reports. The Dermatophyllum species contain quinolizidine alkaloids, and the teratogen anagyrine (11), while the Styphnolobium species do not contain quinolizidine alkaloids. The chemotaxonomic data are consistent with the reclassification of each species.