Indole monoterpene alkaloids from leaves of Psychotria suterella Müll. Arg. (Rubiaceae)
Section snippets
Subject and source
Psychotria suterella Müll. Arg. (Rubiaceae) is a shrub or small tree of up to 2 m in height, that is found in coastal tropical forests of Southern Brazil, ranging from Rio de Janeiro to Rio Grande do Sul (Dillemburg and Porto, 1985). Plants were collected in the rural area of the city of Três Forquilhas, RS, Brazil, in the summer of 1999 and identified by botanist Marcos Sobral (Faculty of Pharmacy, Universidade Federal do Rio Grande do Sul-UFRGS). A voucher specimen (ICN 98870) has been
Previous work
Psychotria (Rubiaceae) is a complex genus, with estimates of 1000–1650 species (Nepokroeff et al., 1999). Segregation of species into new genera has been proposed based on molecular and morphological analyses (Nepokroeff et al., 1999; Taylor, 1996). Psychotria is known for its alkaloid producing species. Chemical investigations may aid in the establishment of new limits for the genus.
Present study
Leaves (1.8 kg) were dried in the shade for a week, ground and extracted at room temperature in EtOH 5% NH4OH. Classical acid/base extraction yielded 3.77 g of total alkaloid extract; 1.5 g was submitted to CC using a CHCl3/MeOH gradient. The fraction eluted with CHCl3/MeOH (9 : 1) (500 mg) was again submitted to CC to yield 200 mg of lyaloside eluted with CHCl3/MeOH (9 : 1). Another 500 mg of the total alkaloid extract were subjected to vacuum liquid chromatography to yield two main fractions, F1 (168
Chemotaxonomic significance
The three indole monoterpene alkaloids isolated from P. suterella leaves, lyaloside, naucletine and strictosamide, had not been previously reported for the genus. Lyaloside was previously isolated from Pauridiantha lyallii (Rubiaceae) (Levesque et al., 1983). Naucletine, a pyridino-indoloquinazoline alkaloid directly derived from strictosidine, was previously reported in Strychnos (Quentin-Le Clercq et al., 1984), Nauclea (Erdelmeier et al., 1992) and Pauridiantha (Jacquesy and Levesque, 1987).
Acknowledgments
This work was funded by CNPq (PADCT), CAPES and FAPERGS (Brazil). We are grateful to Dr. Paulo Moreno (Instituto de Quı́mica, USP, Brazil) for help in obtaining some NMR spectra, and Marcos Sobral (UFRGS) for assistance in plant identification.
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