Structural characterization of a new steroidal saponin from Agave angustifolia var. Marginata and a preliminary investigation of its in vivo antiulcerogenic activity and in vitro membrane permeability property.

A new furostane steroidal saponin was isolated from the leaves of Agave angustifolia var. marginata. On the basis of chemical conversions and spectroscopic analyses, its structure was established as 3-[O-β-d-glucopyranosyl-(1→3)-O-β-d-glucopyranosyl-(1→3)-O]-[O-6-deoxy-α-l-mannopyranosyl-(1→4)-β-d-xylopyranosyl-(1→2)-O-β-d-glucopyranosyl-(1→4)-β-d-galactopyranosyl)oxy]-(3β,5α,22α,25R)-26-(β-d-glucopyranosyloxy)-22-methoxy-furostane (1).

Ingasaponin, a complex triterpenoid saponin with immunological adjuvant activity from Inga laurina.

As part of our search of bioactive saponins from Brazilian plants, phytochemical study of the seeds of Inga laurina led to the isolation of a new complex triterpenoid saponin, named ingasaponin. It is the first saponin isolated from a species of Inga genus. It was isolated by using chromatographic methods and its structural elucidation was performed using detailed analyses of (1)H and (13)C NMR spectra including 2D-NMR spectroscopic techniques and chemical conversions.

Haemolytic activity and immunological adjuvant effect of a new steroidal saponin from Allium ampeloprasum var. porrum.

A new steroidal saponin was isolated from the bulbs of Allium ampeloprasum L. var. porrum.

A new steroidal saponin with antiinflammatory and antiulcerogenic properties from the bulbs of Allium ampeloprasum var. porrum.

A new steroidal saponin was isolated from the bulbs of Allium ampeloprasum var. porrumL. On the basis of chemical evidence, comprehensive spectroscopic analyses and comparison of known compounds, its structure was established as (3β,5α,6β,25R)-6-[(β-D-glucopyranosyl)oxy]-spirostan-3-yl O-β-D-glucopyranosyl-(1→2)-O-[β-D-glucopyranosyl-(1→3)]-β-D-galactopyranoside.

Modulation of sodium pumps by steroidal saponins.

Costus spicatus, used in Brazilian traditional medicine to expel kidney stones, contains steroidal saponins with different chemical characteristics. In spite of its popular utilization as potent diuretic, no scientific reports correlate this activity with the chemical constituents of the extract. Therefore, two steroidal saponins (3 beta,22 alpha,25R)-26-(beta-D-glucopyranosyloxy)-2-methoxyfurost-5-en-3-yl O-D-apio-beta-D-furanosyl-(1-->2)-O-[6-deoxy-alpha-L-mannopyranosyl-(1-->4)]-beta-D-glucopyranoside (1) and (3 beta,22 alpha,25R)-spirostan-3-yl O-D-apio-beta-D-furanosyl-(1-->2)-O-[6-deoxy-alpha-L-mannopyranosyl-(1-->4)]-beta-D-glucopyranoside (1a), were isolated from the rhizomes of this plant and their effects on the Na+-ATPase and (Na+ + K+)-ATPase activities of the proximal tubule from pig kidney were evaluated.

A new steroidal saponin from Agave shrevei.

A new steroidal saponin was isolated from the leaves of Agave shrevei. Its structure was established as 3-[O-beta-D-glucopyranosyl-(1-->2)-O-[O-beta-D-glucopyranosyl-(1-->4)-O-[O-beta-D-glucopyranosyl-(1-->6)]-O-beta-D-glucopyranosyl-(1-->4)-beta-D-galactopyranosyl)-oxy]-(3beta,5alpha,25R)-spirostane. The structural identification was performed using detailed analyses of 1H- and 13C-NMR spectra including 2D NMR spectroscopic techniques (COSY, HETCOR, HMBC, and HMQC) and chemical conversions.

Isolation and structural elucidation of a novel rotenoid from the seeds of Clitoria fairchildiana.

The seeds of Clitoria fairchildiana provided a new rotenoid, 6-hydroxy-2,3,9-trimethoxy-[1]benzopyrano[3,4-b][1]benzopyran-12(6H)-one. The structural elucidation was performed using detailed analyses of H- and 13C-NMR spectra including 2DNMR spectroscopic techniques (1H-13CHETCOR) and by comparison with spectrometric data from the literature. The anti-inflammatory activity was investigated using a capillary permeability assay.

A new bioactive steroidal saponin from Agave shrevei.

A new steroidal saponin was isolated from the leaves of Agave shrevei Gentry. Its structure was established as 26-(beta-D-glucopyranosyloxy)-22-methoxy-3-(O-beta-D-glucopyranosyl-(1-->2)O-[O-beta-D-glucopyranosyl-(1-->4)-O-[O-beta-D-glucopyranosyl-(1-->6)]-O-beta-D-glucopyranosyl(1-->4)-beta-D-galactopyranosyl]oxy)-(3beta,5alpha,25R)-furostane. The structural identification was performed using detailed analyses of 1H and 13C NMR spectra including 2D NMR spectroscopic techniques (COSY, HETCOR, and COLOC) and chemical conversions.

Pulcherrimasaponin, from the leaves of Calliandra pulcherrima, as adjuvant for immunization in the murine model of visceral leishmaniasis.

A novel triterpenoidal saponin, called pulcherrimasaponin (CP05), isolated from the leaves of Calliandra pulcherrima Benth. shows remarkable similarities to the previously described potent adjuvant, QS21 saponin (Quillaja saponaria Molina). On the basis of chemical and physicochemical evidence, its structure was established as [3beta,16alpha,28[2E,6S[2E,6S(2E,6S)]]]-olean-12-en-28-oic acid 3-[[O-alpha-l-arabinopyranosyl-(1-->2)-O-alpha-l-arabinopyranosyl-(1-->6)-2-(acetylamino)-2-deoxy-beta-d-glucopyranosyl]oxy]-16-hydroxy-O-beta-d-glucopyranosyl-(1-->3)-O-[O-beta-d-xylopyranosyl-(1-->3)-beta-d-xylopyranosyl-(1-->4)-O-6-deoxy-alpha-l-mannopyranosyl-(1-->2)-6-O-[6-[[2-O-2,6-dimethyl-1-oxo-6-(beta-d-xylopyranosyloxy)-2,7-octadienyl]-[(6-deoxy-beta-d-glucopyranosyl)oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-beta-d-xylopyranosyl]oxy]-2,6-dimethyl-1-oxo-2,7-octadienyl]-beta-d-glucopyranosyl ester.

A new steroidal saponin from Agave attenuata.

A new steroidal saponin was isolated from the leaves of Agave attenuata. Its structure was established as (3beta,beta,25S)-spirostan-3-yl O-beta-D-glucopyranosyl-(1 --> 2)-beta-D-glucopyranosyl-(1 --> 2)-O-[beta-D-glucopyranosyl-(1 --> 3)]-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranoside. The structural identification was performed using detailed analyses of 1H- and 13C-NMR spectra including 2D NMR spectroscopic techniques (COSY, HETCOR, and COLOC) and chemical conversions.

A new bioactive steroidal saponin from Sansevieria cylindrica.

A new steroidal saponin was isolated from the leaves of Sansevieria cylindrica. Its structure was established as (3beta,12beta,15alpha,25S)-26-(beta-D-glucopyranosyloxy)-22-hydroxyfurost-5-en-3-yl 12-O- (6-deoxy-alpha-L-mannopyranosyl)-15-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-glucopyranoside. The structural identification was performed using detailed analyses of (1)H and (13)C NMR spectra including 2D NMR spectroscopic techniques (COSY, HETCOR, HMBC and HMQC) and chemical conversions.

Antiinflammatory activity of rotenoids from Clitoria fairchildiana.

Five structurally related rotenoids were isolated from the roots of Clitoria fairchildiana. The antiinflammatory activity was investigated using a capillary permeability assay. The protective effect was measured as the inhibition in vascular permeability produced by acetic acid in the peritoneal cavity.