Cassia alkaloids

Cassia Siamea Lam. Alkaloid, Ci HjgOjN. Toxie. (Wells, Philipp. J. Sci., 1919, 14, 1.)... 

In addition to lupines, poison-hemlock and Nicotiana spp., other plant species of the genera Genista, Prosopis, Lobelia, Cytisus, Sophora, Pinus, Punica, Duboisia, Sedum, Withania, Carica, Hydrangea, Dichroa, Cassia, Ammondendron, Liparia, and Colidium contain potentially toxic and teratogenic piperidine alkaloids. Many plant species or varieties from these genera may be included in animal and human diets (Keeler and Crowe, 1984). 

Alexandre-Moreira, M. S Viegas Jr., C., Palhares de Miranda, A. L. and Bolzani, V. S. 2003. Antinociceptive profile of (—)-spectaline A piperedine alkaloid from Cassia leptophylla. Planta Medica, 69 795-799. 

A number of a, a -disubstituted 3-piperidinol alkaloids have been found in Cassia or Prosopis species,[1] and, quite recently, alkaloids including this structural unit have also been isolated from ascidian.[2] Many of these alkaloids showed interesting pharmacological activities such as anesthetic, analgestic, and antibiotic activities. Clavepictines A and B, and pictamine, isolated from tunicate, by Cardellina, II[3] or Faulkner[4] and co-workers, possess 3-piperidinol structure. Lepadins A, B, and C, isolated from tunicate, by Steffan[5] and Andersen[6] and coworkers, also have this structural unit. We designed lactam 1 as a useful... 

Two new piperidin-3-ol alkaloids have been encountered in the leaves of Cassia spectabilis DC spectaline, which is (+)-2(S)-methyl-6(i )-(13 -oxotetradec-yl)piperidin-3(S)-ol (28), and isocassine, formulated as (—)-2(i )-methyl-6(/ )-(ll -oxodecyl)piperidin-3(i )-ol (29), structures having been settled by spectral study. Their absolute configurations were arrived at by application of the Horeau procedure.24... 

Catecholamine release (CAT-REL) Dopamine release (D-REL) Norepinephrine release (NE-REL) Serotonin release (5HT-REL) Alkaloid Barakol (= 3a,4-Dihydro- Cassia siamea [leaf] 6.2 6.2a D-REL (no effect on D uptake)... 

Total syntheses of racemic cassine (20), an alkaloid of the leaves of Cassia exdelsa Shrad., and of its 3-epimeride have been disclosed (Scheme 4). ... 

In an effort to uncover anticancer active metabolites in Brazilian plants, in early 1993 we initiated active collaboration with several Brazilian natural products chemists. Out of the large number of extracts brought to our laboratory by Dr. Vanderlan da S. Bolzani and screened in our mechanism-based yeast bioassay, extracts derived from two leguminous plants were selected for further studies. Based on preliminary investigation the bioactive methanolic chloroform extract of the leaves of Cassia leptophylla which was shown to contain bioactive alkaloidal constituents was further processed for alkaloids. The alkaloid fraction thus obtained was fractionated by column chromatography on alumina, followed by Silica gel preparative TLC and reversed-phase TLC to afford seven piperidine alkaloids [55] (-)-spectaline (68), (-)-spectalinine (69), canavaline (70), leptophyllin A (71), 3-acetylleptophyllin A (72), iso-... 

Bioactivity data for piperidine alkaloids from Cassia leptophylla. ... 

The new spermidine alkaloid A A -dibenzoylspermidine (86) is one of the metabolites found in the leaves of Cassia floribunda (Leguminosae) (76). 

Outside these two families, however, no other plants have been found to produce real tetrahydro-, dihydro-, and fully aromatic isoquinoline alkaloids in a polyacetate way. Closely related, but chemically a lactam, is siamine (40) from Cassia siamea Lam. (Leguminosae) (42). The structure suggests a biogenesis from a pentaketide precursor 41 (Fig. 2), thus requiring one acetate unit less than each of the naphthyl isoquinoline alkaloid moieties. 

Bolzani VS, Gunatilaka AAL, Kingston DGI. Bioactive and other piperidine alkaloids from Cassia leptophylla. Tetrahedron 1995 51 5929-34. 

A series of substituted piperidine alkaloids have been isolated from the legume genera Cassia (subfamily Caesalpini-oideae) mdProsopis (subfamily Mimosoideae) (Fig. 29.16). (Strunz and Findlay, 1985). Based on the structures of these compounds, it seems possible that they are derived from acetate-malonate precursors. These compounds are quite similar in structure to the venoms of fire ants (Nahrstedt, 1982). Indolizidine alkaloids also have been isolated from Prosopis species (Howard and Michael, 1986). 

Other imidazole alkaloids are known from Alchornea (Euphorbiaceae), Casimiroa (Rutaceae), Cassia absus (Fa-... 

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