1-Hydroxyrutaecarpine from Euxylophora paraënsis

The structure of the title compound has been determined on the basis of spectroscopic evidence and synthesis.     

Alkaloids from stem barks of Oricia renieri and Oricia gabonensis

The stem barks of Oricia renieri and O. gabonensis have yielded nine alkaloids, including furoquinolines, acridones, 3,4-pyrano-2-quinolones and a 2-amino-benzophenone. One of the pyranoquinolones isolated from O. renieri, 7-methoxy-N-methylflindersine, is reported for the first time. All alkaloids were identified on the basis of spectral data. The chemotaxonomic significance of the alkaloids of these two species is discussed.     

Bishordeninyl terpene alkaloids and other constituents of Zanthoxylum culantrillo and Z. coriaceum

A new alkaloid, culantraramine, has been found in Zanthoxylum culantrillo, and the known alkaloid, alfileramine, has been identified from Z. coriaceum. Both alkaloids are members of a new structural type, bishordeninyl terpenes. Z. culantrillo was also found to contain eudesmin, epieudesmin, hordenine, N-methylisocorydine, magnoflorine, candicine, skimmianine, synephrine, tembetarine and a dihydroxy-dimethoxytetrahydroprotoberberine. Isolated from Z. coriaceum were N-methylisocorydine, dihydrochelerythrine, chelerythrine, N-methylcanadine and aegiline, in addition to alfileramine.     

Glucosides from the roots of Capparis tenera

Two new lignan glucosides, compounds 2 and 3, two new 1H-indole-alkaloid glucosides, 5 and 6, as well as two new phenolic glucosides, 7 and 10, were isolated from the roots of Capparis tenera, together with five known compounds. Their structures were characterized by chemical and spectroscopic methods. Most of these isolates were obtained for the first time from Capparidaceae. The antioxidant and anti-inflammatory activities of the new compounds were investigated.     

Kokusaginine and evolitrine from Acronychia pedunculata

Kokusaginine and evolitrine are the major alkaloids present in Sri Lankan Acronychia pedunculata. The Indian variety of Acronychia laurifolia collected in Madras does not contain these alkaloids.     

The biochemical systematics of Fagaropsis angolensis and its significance in the Rutales

From the stem bark of Fagaropsis angolensis (Rutaceae) three alkaloids and two limonoids were isolated. The alkaloids were identified as the 6-acetonyl derivatives of the benzophenantridines, dihydrochelerythrine, dihydrosanguinarine and dihydronitidine, the last of these being reported for the first time. The alkaloids did not appear to be artefacts of the corresponding benzophenanthridines. The limonoids were identified as rutaevin and limonin diosphenol. The significance of these compounds in resolving the confused taxonomic position of F. angolensis is discussed. Attention is drawn to the presence of a small group of taxa within the Rutaceae capable of synthesizing 1-benzyltetrahydroisoquinoline-derived alkaloids and the potential of these taxa as a starting point for visualizing biochemical evolution within the order Rutales, and putative relationships between the Rutales and Ranales are examined.     

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.     

Growth and quaternary alkaloid production in differentiating and non-differentiating strains of Ruta graveolens

Cultures of Ruta graveolens have been grown and maintained on Murashige and Skoog's medium supplemented with α-naphthalene acetic acid (1 mg/l.) and kinetin (0.1 mg/l.) or 2,4-dichlorophenoxyacetic acid (1 mg/l.), and glucose (30 g/l.). The production of dihydrofuroquinoline alkaloids has been investigated in these cultures. The present study showed that: (a) cultures of Ruta produced both differentiating and non-differentiating strains; (b) quaternary alkaloids (platydesminium, ribalinium and rutalinium) were present in all the strains and maximum contents were detected at 3-4 weeks growth; (c) high platydesminium and rutalinium content was associated with differentiation and callus formation, respectively; (d) changed concentrations of quaternary alkaloids were recorded in all the five strains grown on media supplemented with tryptophan and precursors (anthranilic acid, 5-methylanthranilic acid and 2,4-dihydroxyquinoline).     

Hydroxytropane tiglates in the roots of Mandragora species

Roots of Mandragora autumnalis and M. vernalis contain hyoscyamine, hyoscine, cuscohygrine, apoatropine 3α-tigloyloxytropane and 3,6-ditigloyloxytropane. Belladonnine is present in the dried roots but could not be detected in fresh roots. No major differences were found in the alkaloids present in the two species. This is the first time the presence of tiglic acid esters has been reported in Mandragora species and the significance of this in the chemotaxonomy of the genus is indicated.     

Structure and synthesis of atalaphylline and related alkaloids

The structure of atalaphylline, (1; 1,3,5-trihydroxy-4-(γ,γ-dimethylallyl)acridone an alkaloid of Atalantia monophylla, was confirmed by oxidative degradation and by total synthesis. The synthesis involved the preparation of 1,3,5-trihydroxy-9-acridone followed by direct prenylation to give atalaphylline and a monoprenylated product.