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Anti-inflammatory activity of Agave intermixta Trel. and Cissus sicyoides L., species used in the Caribbean traditional medicine.

Agave intermixta Trel. and Cissus sicyoides L. are two tropical plants originating from the Dominican Republic. Aqueous extracts from these species are used in traditional medicine. In contrast, biological activity and toxicity of these plants are not yet evaluated systematically. The aim of the present work is to investigate a potential anti-inflammatory activity, and to elucidate the toxicity of the extracts. No lethal effects were produced after oral administration of the extracts. The values of the medium lethal doses after intraperitoneal administration were quite high for both species, although A. intermixta seems to be rather more toxic than C. sicyoides. The anti-inflammatory effects have been investigated in two experimental in vivo models. The carrageenan-induced rat paw oedema was chosen as a model for general inflammation, and the mice ear oedema test using tetradecanoylphorbol acetate as inflammatory agent as a model of topical inflammation. Dry extracts from decoctions of A. intermixta leaves and C. sicyoides stems were administered in doses of 300 and 500 mg/kg (p.o.) in the general model, and in doses of 3 and 5 mg/mouse ear for both plants in the topical model. In the general anti-inflammation assay, the oral administration of both extracts produced a significant anti-inflammatory effect, most pronounced for A. intermixta than for C. sicyoides. In the topical model, the administration of both extracts produced similar inhibitions of the oedema, with a reduction of approximately 50% in comparison with the control group. In homogenated tissue samples from the inflamed areas, a distinct decrease in the level of myeloperoxidase enzyme was noted.

Agave↗

Characterization of volatile compounds of Mezcal, an ethnic alcoholic beverage obtained from Agave salmiana.

Commercial mezcals (white, white with worm, rested, rested with worm, and aged) produced from Agave salmiana were analyzed by solid-phase microextraction-gas chromatography-mass spectrometry (SPME-GC-MS). Thirty-seven compounds were identified, and nine of them were classified as major compounds of mezcal (MCM). Saturated alcohols, ethyl acetate, ethyl 2-hydroxypropanoate, and acetic acid form the MCM group. Minor compounds of mezcal group include other alcohols, aldehydes, ketones, large chain ethyl esters, organic acids, furans, terpenes, alkenes, and alkynes. Most of the compounds found in mezcals in this study are similar to those present in tequilas and other alcoholic beverages. However, mezcals contain unique compounds such as limonene and pentyl butanoate, which can be used as markers for the authenticity of mezcal produced from A. salmiana.

Agave↗

Genetic differentiation in the Agave deserti (Agavaceae) complex of the Sonoran desert.

The Agave deserti complex, comprising A. deserti, A. cerulata and A. subsimplex, represents a group of species and subspecies with a near allopatric distribution and clear differences in morphology. Genetic differentiation and taxonomic status with respect to spatial distribution of 14 populations of the complex were analyzed in an effort to understand the evolution and speciation process within the genus. Allelic frequencies, levels of genetic variation, expected heterozygosity (H(S)), proportion of polymorphic loci (P), and genetic differentiation (theta and Nei's genetic distance) were estimated using 41 putative RAPD loci. All three species show high levels of genetic variation (H(S)=0.12-0.29, P=63.4-95.1), and low genetic differentiation between populations and species (theta populations=0.14+/-0.02 (SE); G(st)=0.11+/-0.02). Accordingly, gene flow among populations was estimated as high by three different methods (N(m)=2.91-6.14). Nei's genetic distances between the three species were low compared to the values obtained from other Agavaceae, and there was no clear correlation with taxonomic divisions. In a UPGMA analysis, A. subsimplex and A. cerulata formed exclusive monospecific clusters, whereas the A. deserti populations appear in more than one cluster together with other species. The results were consistent with a pattern of genetic isolation by distance.

Agave↗

Three new hecogenin glycosides from fermented leaves of Agave americana.

Eight steroidal compounds, including three new hecogenin glycosides, agamenosides D-F, were isolated from the fermented leaves of Agave americana. The structures of the new steroidal saponins were elucidated by spectroscopic data and chemical methods. The activity of the isolated compounds on deformations of mycelia germinated from conidia of Pyricularia oaryzae P-2b was evaluated.

Agave↗

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. The hemolytic activity of the steroidal saponin was evaluated using an in vitro assay.

Agave↗

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. The haemolytic activity of the steroidal saponin was evaluated using an in vitro assay.

Agave↗

Phytochemical analysis and anti-allergic study of Agave intermixta Trel. and Cissus sicyoides L.

Agave intermixta Trel. (Maguey) and Cissus sicyoides L. (Bejuco caro) are Caribbean plant species from the Dominican Republic used locally in traditional popular medicine that have shown an antiinflammatory effect in experimental animal models. A phytochemical analysis on these species allowed us the isolation and identification of the steroidal sapogenins hecogenin and diosgenin from Maguey and the hydroxystilbene resveratrol from Bejuco caro. The effects of these plant extracts and their isolated constituents on compound-48/80-induced histamine release from peritoneal mast cells were investigated. Significant inhibition was produced by 0.5 mg mL(-1) of a methanolic extract of Bejuco (41.1%) and by its constituent resveratrol (82.4%) at a dose of 250 microM. However, none of the steroidal sapogenins from A. intermixta showed a significant inhibitory effect on histamine release from mast cells. From these results, it can be deduced that the in-vitro anti-allergic activity towards the release of histamine from mast cells shown by the methanolic extract of C. sicyoides may be mediated by its constituent resveratrol and might contribute to the antiinflammatory activity shown by this species.

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Four new steroid constituents from the waste residue of fibre separation from Agave americana leaves.

Three new steroidal saponins, named agamenosides H-J (1-3), and a new cholestane steroid agavegenin D (4) were isolated from the waste residue of fibre separation from Agave americana leaves, together with six known steroids. Structures of the new compounds 1-4 were deduced to be (22S,23S,24R,25S)-24-[(beta-D-glucopyranosyl)oxy]-5alpha-spirostane-3beta,6alpha,23-triol 6-O-beta-D-glucopyranoside (1), (22S,23S,24R,25S)-5alpha-spirostane-3beta,23,24-triol 24-O-beta-D-glucopyranoside (2), (22S,23S,25R,26S)-23,26-epoxy-5alpha-furostane-3beta,22,26-triol 26-O-beta-D-glucopyranoside (3), and (22S,25S)-5alpha-cholestane-3beta,16beta,22,26-tetrol (4), respectively, by means of spectroscopic analysis, including extensive 1D and 2D NMR data, and the results of hydrolytic cleavage.

Agave↗

Steroidal glycosides from Agave utahensis.

Three new spirostanol glycosides (1-3) and a new furostanol glycoside (4), together with two known spirostanol glycosides (5 and 6) were isolated from the whole plants of Agave utahensis (Agavaceae). The structures of the new compounds were determined by spectroscopic analysis and the results of hydrolytic cleavage.

Agave↗

A new bioactive steroidal saponin from Agave attenuata.

A new steroidal saponin was isolated from the leaves of Agave attenuata Salm-Dyck. Its structure was established as (3beta,5beta,22alpha,25S)-26-(beta-D-glucopyranosyloxy)-22-methoxyfurostan-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. The haemolytic potential of the steroidal saponin was evaluated and the anti-inflammatory activity was performed using the capillary permeability assay.

Agave↗

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. The steroidal saponin showed absence of haemolytic effects in the in vitro assay, but demonstrated a significant inhibition of the capillary permeability activity.

Agave↗

A new steroidal saponin from AGAVE brittoniana and its biphasic effect on the Na+-ATPase activity.

A new steroidal saponin, 3-{(O-6-deoxy-a-L-mannopyranosyl-(1 --> 4)-O-beta-D-glucopyranosyl-(1 --> 3)-O-[O-beta-D-glucopyranosyl-(1 --> 3)-beta-D-glucopyranosyl-(1 --> 2)]-O-beta-D-glucopyranosyl-(1 --> 4)-beta-D-galactopyranosyl)oxy}-6-hydroxy-(3beta,5alpha,6alpha,25R)-spirostan-12-one, was isolated from Agave brittoniana Trel. The structure was determined by extensive NMR spectroscopy studies and chemical conversions. Its effects on the Na+-ATPase and (Na+ + K+)-ATPase activities of the proximal tubule from pig kidney were evaluated. It was observed that this steroidal saponin exerts a biphasic effect on the Na+-ATPase activity. It is concluded that the effect of the aqueous extract as a diuretic is due, at least in part, to the action of saponin on the ouabain-insensitive Na+-ATPase.

Agave↗

New steroidal saponins from Agave lophantha Schiede and their pharmacological evaluation.

The structures of one new monodesmosidic spirostanoside and one new bisdesmosidic furanostanol glycoside isolated from leaves of Agave lophantha Schiede have been determined by means of spectroscopic and chemical methods as (25R)-5 beta-spirostan-3 beta-ol-3-O-(beta-D-apiofuranosyl(1-->4)beta-D -glucopyranosyl(1-->3)[beta-D-glucopyranosyl(1-->2)]beta-D -galactopyranoside) and 26-O-beta-D-glucopyranosyl(25R)-5 beta-furost-20(22)-ene-3 beta, 26-diol-3-O-(beta-D-xylopyranosyl(1-->3)-[beta-D-glucopyranosyl(1--2)] beta-D-galactopyranoside), respectively. The 1H and 13C NMR resonances of the two compounds were assigned by NMR (1H, 13C, HOHAHA, 1H-1H COSY, HMQC, HMBC, NOE difference) studies. The pharmacological activities of the saponin containing fraction are discussed.

Agave↗

[A new steroidal glycoside from fermented leaves of Agave americana].

OBJECTIVE: To investigate the constituents of fermented leaves of Agave americana, and discover new compounds. METHOD: Compounds were purified with silica gel and C8 reverse--phase silica gel column chromatography. The structures were elucidated by chemical and spectroscopic evidence. RESULT: Three steroidal compounds were obtained and their structures were identified as (25R)-5 alpha-spirostan-3 beta, 6 alpha, 23 alpha-triol 6-O-beta-D-glucopyranoside(1), (25R)-5 alpha-spirostan-3 beta, 6 alpha, 23 alpha-triol-3, 6-di-O-beta-D-glucopyranoside (cantalasaponin-1) (2) and (25R)-5 alpha-spirostan-3 beta, 6 alpha, 23 alpha-triol(hongguanggenin) (3). CONCLUSION: Compound 1 is new compound, named agamenoside C.

Agave↗

Molluscicidal activity and clinico-pathological effect of Agave lophantha.

Dry powder and different extracts of Agave lophantha were tested against Biomphalaria alexandrina. The results showed that the butanol extract has high molluscicidal activity. The activity of the dry powder has been found to be stable under the effect of some simulated field conditions. Also the toxicological effect of the plant on mice was tested through determination of certain parameters such as total protein, aspartate aminotransferase, alanine aminotransferase, alkaline phosphatase and acid phosphatase enzymes as well as histopathological study on liver and kidney.

Animals↗

Steroidal glycosides from Agave cantala.

Two new steroidal glycosides, agaveside A and B, isolated from the fruits of Agave cantala were characterized as 3 beta-O-[beta-D-xylopyranosyl-(1----2),beta-D-xylopyranosyl-(1----3), beta-D-glucopyranosyl-(1----3)-[beta-D-xylopyranosyl-(1----3)-beta-D- galactopyranosyl-(1----2)]-beta-D-glucopyranosyl]-(25R)-5 alpha-spirostane and 3 beta-O-[beta-D-xylopyranosyl-(1----2), beta-D-xylopyranosyl-(1----3)-beta-D-glucopyranosyl-(1----3)- [beta-D-galactopyranosyl-(1----2)]-beta-D-glucopyranosyl]-(25R)-5 alpha-spirostane. The structures were elucidated by a combination of 13CNMR spectroscopy, chemical degradation and fast atom bombardment mass spectrometry.

Carbohydrate Conformation↗

A spirostane hexaglycoside from Agave cantala fruits.

A new steroidal glycoside, agaveside D, isolated from the fruits of Agave cantala was characterized as 3 beta-(alpha-L-rhamnopyranosyl-(1----2),beta-D-glycopyranosyl- (1----3)-beta-D-glucopyranosyl[beta-D-xylopyransoyl-(1----4)-alpha -L-rhamnopyranosyl-(1----2)]-beta-D-glucopyranosyl)-25R-5 alpha-spirostane on the basis of chemical degradation and spectrometry.

Carbohydrate Sequence↗

A comprehensive evaluation of Agave attenuata, a candidate plant molluscicide in South Africa.

Dried leaf material of a Mexican plant, Agave attenuata, was found to be highly toxic to the target snail, Bulinus africanus, intermediate host of Schistosoma haematobium in South Africa. The molluscicidal potency of the plant underwent seasonal variation, but remained stable over a range of pH values, after exposure to sunlight and organic matter, and during dry storage. It was unstable in aqueous suspension. The toxicity of the molluscicide to crop plants, invertebrates, fish and mammals was lacking or low. Given these properties, A. attenuata may provide a substitute for niclosamide and be used safely for snail control by rural communities.

Animals↗