Phytotoxic steroidal saponins from Agave offoyana leaves

A bioassay-guided fractionation of Agave offoyana leaves led to the isolation of five steroidal saponins (1–5) along with six known saponins (6–11). The compounds were identified as (25R)-spirost-5-en-2α,3β-diol-12-one 3-O-{α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside} (1), (25R)-spirost-5-en-3β-ol-12-one 3-O-{α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glu copyranosyl-(1→4)-O-β-D-galactopyranoside} (2), (25R)-spirost-5-en-3β-ol-12-one 3-O-{β-D-xylopyrano syl-(1→3)-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-O-β -D-galactopyranoside} (3), (25R)-26-O-β-D-glucopyranosylfurost-5-en-3β,22α,26-triol-12-one 3-O- {α-L-rhamnopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyrano syl-(1→4)-O-β-D-galactopyranoside} (4) and (25R)-26-O-β-D-glucopyranosylfurost-5-en-3β,22α,26-triol- 12-one 3-O-{β-D-xylopyranosyl-(1→3)-O-β-D-glucopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β- D-glucopyranosyl-(1→4)-O-β-D-galactopyranoside} (5) by comprehensive spectroscopic analysis, including one- and two-dimensional NMR techniques, mass spectrometry and chemical methods. The phytotoxicity of the isolated compounds on the standard target species Lactuca sativa was evaluated

Triterpenoid saponins from the aerial parts of Trifolium argutum Sol. and their phytotoxic evaluation

Four triterpenoid saponins (1–4) were isolated from the aerial parts of Trifolium argutum Sol. (sharptooth clover) and their structures were elucidated by comprehensive spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry and chemical methods. Two of them are new compounds, characterized as 3-O-[α-L-rhamnopyranosyl-(1→2)-β-D-galactopyranosyl-(1→2)-β-D-glucuronopyra- nosyl]-3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (1) and 3-O-[β-D-galactopyranosyl-(1→2)- β-D-glucuronopyranosyl]-3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (2). The occurrence of 3β,24-dihydroxyolean-12-ene-22-oxo-29-oic acid (melilotigenin) in its natural form is reported for the first time as a triterpenoid aglycone within Trifolium species. The phytotoxicity of compounds was evaluated on four STS at concentration 1 μM to 333 mM. Compound 1 was the most active, showing more than 60% inhibition on the root growth of L. sativa at the higher dose, with IC50 (254.1 μM) lower than that of Logran1 (492.6 μM), a commercial herbicide used as positive control. The structure–activity relationships indicated that both aglycones and glycosidic parts may influence the phytotoxicity of saponins

Sexual dimorphism of AMH, DMRT1 and RSPO1 localization in the developing gonads of six anuran species.

Supplementary Material (tables and figures) for this paper is available at: http://dx.doi.org/10.1387/ijdb.130192rpInternational audienceIn vertebrates, several genes which are differentially expressed in various species, have been implicated in sex determination and gonadal differentiation. We used immunolocalization to study the expression pattern of three proteins AMH, DMRT1, RSPO1 involved in the sexual differentiation of gonads. The pattern of AMH, DMRT1 and RSPO1 expression was analyzed in X. laevis and in five other divergent anuran species: Bombina bombina, Bufo viridis, Hyla arborea, Rana arvalis and Rana temporaria during gonadal development. The pattern of expression of AMH in the developing testes of six studied anuran species was similar to that described for other vertebrates. AMH was strongly expressed in differentiating Sertoli cells. Interestingly, in B. viridis, R. arvalis and R. temporaria, AMH was also expressed in ovaries. In all studied species, DMRT1 was highly expressed in the developing testes, in both the somatic and germ cells. It was also expressed at low level in ovaries in all studied species, with the exception of H. arborea. RSPO1 was expressed in the developing ovaries, especially in the somatic cells, and was almost undetectable in developing testes in all examined anurans. These developmental expression patterns strongly suggest an involvement of AMH and DMRT1 in the development of male gonads and of RSPO1 in the female gonads. The differences in the expression patterns of these proteins in the gonads of different species might reflect the diversity of gonadal development patterns in anurans resulting from long lasting and diverged paths of their evolution

Triterpene Saponins from the Aerial Parts of Trifolium medium L. var. sarosiense

Seven previously unreported triterpene glycosides (1−7) were isolated from methanol extract of the aerial parts of Trifolium medium var. sarosiense (zigzag clover). Their structures were established by the extensive use of 1D and 2D NMR experiments along with ESI-MS and HRMS analyses. Compounds 1−7 are oleanane derivatives characterized by the presence of a keto group at C-22 of an aglycone and a primary alcoholic function at C-24 and differing functions at C-30. Among these, compounds 1−3 and 6 showed a secondary alcoholic function at C-11, which is methoxylated in compounds 4 and 7. Compound 5 was shown to possess a known aglycone, wistariasapogenol A; however, it is described here for the first time as a saponin constituent of the Trifolium genus. Some aspects of taxonomic classification of zigzag clover are also discussed

Spermiogenesis and spermatozoa ultrastructure in the Serrasalminae (Ostariophysi: Characiformes) with further evidence on the relationships of the piranhas and pacus

A ultraestrutura dos espermatozoides e espermiogênese foram estudadas nas espécies Piaractus mesopotamicus, Mylossoma duriventre, Serrasalmus maculatus e Metynnis mola de Serrasalminae, sendo dois padrões distintos reconhecidos: um comum a Mylossoma, Serrasalmus e Metynnis, e o segundo característico de Piaractus. Este último é mais similar ao observado em Salminus e Brycon. Por outro lado, o espermatozoide dos serrasalmíneos compartilha algumas características com espécies da superfamília Anostomoidea. O significado filogenético destes caracteres é discutido.Spermatozoa and spermiogenesis ultrastructure were studied in the serrasalmine species Piaractus mesopotamicus, Mylossoma duriventre, Serrasalmus maculatus, and Metynnis mola and two distinct patterns may be recognized: the first common to Mylossoma, Serrasalmus and Metynnis, and the other, characteristic of Piaractus. The latter pattern is more similar to the conditions found in Salminus and Brycon. On the other hand, serrasalmine spermatozoa also share characteristics with the spermatozoa of species of the superfamily Anostomoidea. The phylogenetic significance of these characters is discussed