Ten flavone glycosides have been isolated and identified in aerial parts of alfalfa. These included six tricin, one 3'-O-methyltricetin, and three chrysoeriol glycosides. Most of these compounds were acylated with ferulic, coumaric, or sinapic acids, and acylation occurred on the terminal glucuronic acid. Eight of these compounds, including 7-O-beta-D-glucuronopyranosyl-3'-O-methyltricetin, 7-O-beta-D-glucuronopyranosyl-4'-O-beta-D-glucuronopyranosidechrysoeriol, 7-O-[2'-O-feruloyl-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]chrysoeriol, 7-O-[2'-O-feruloyl-[beta-D-glucuronopyranosyl(1-->3)]-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]chrysoeriol, 7-O-[2'-O-sinapoyl-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]tricin, 7-O-[2'-O- feruloyl-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]tricin, 7-O-[2'-O-p-coumaroyl-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]tricin, and 7-O-[2'-O-feruloyl-[beta-D-glucuronopyranosyl(1-->3)]-O-beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]tricin, have not been reported previously in the plant kingdom. Two previously identified alfalfa flavones, 7-O-beta-D-glucuronopyranosidetricin and 7-O-[beta-D-glucuronopyranosyl(1-->2)-O-beta-D-glucuronopyranoside]tricin, were also isolated.

The structures of four new, naturally occurring bioactive spiroditerpenoids, (+)-breviones B, C, D, and E, potential allelopathic agents, have been determined from extracts of semisolid fermented Penicillium brevicompactum Dierckx. The structures display the novel breviane spiroditerpenoid skeleton. Structure elucidation was performed by chemical transformations and by homo- and heteronuclear 2D-NMR spectral data. On the basis of combined studies of the theoretical conformations and NOEDIFF data, their relative stereochemistry is proposed. A mixed biogenesis for this novel family of spiroditerpenoids is tendered. The levels of activity shown by breviones B, C, and E in the etiolated wheat coleoptiles bioassay, especially breviones E (100% inhibition) and C (80% inhibition) both at 10(-4) M, suggest them as lead compounds for new agrochemicals.

Bioguided studies of flowers of Agave offoyana allowed the isolation of five steroidal saponins never described previously, Magueyosides A-E (1-5), along with six known steroidal saponins (6-11). The structures of compounds were determined as (25R)-spirost-5-en-2α,3β-diol-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} (1), (25R)-spirost-5-en-2α,3β-diol-12-one 3-O-{β-d-glucopyranosyl-(1→2)-O-[β-d-xylopyranosyl-(1→3)]-O-β-d-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (2), (25R)-spirost-5-en-2α,3β,12β-triol 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)-5α-spirostan-2α,3β-diol-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} (4), and (25R)-5α-spirostan-2α,3β-diol-9(11)-en-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 bioactivities of the isolated compounds on the standard target species Lactuca sativa were evaluated. A dose-dependent phytotoxicity and low dose stimulation were observed.

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-glucopyranosyl-(1→4)-O-β-d-galactopyranoside} (2), (25R)-spirost-5-en-3β-ol-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} (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-glucopyranosyl-(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.

Natural products involved in plant-plant and plant-microorganism ecological interaction (Allelochemicals) are an important potential source for alternative agrochemicals and pharmaceuticals, in order to solve the many problems derived from inadequate culture practices and abuse of synthetic herbicides. Isolation, structural determination, bioassay techniques and applicability for these compounds in crop protection and pharmaceutical research are discussed, and future trends on Allelochemicals applications are examined. The new strategies for sustainable ecosystems controlled by allelochemicals offer a particular interest for the development of human bases in space, since these products can stimulate or inhibit plant germination and growth, and permit to develop crops with low residue amounts in water, facilitating wastewater treatment and recycling.

A phytochemical study of a Serjania marginata leaf extract with antiulcer activity afforded 15 compounds, including the new 3-O-α-l-arabinopyranosyl(1→3)-α-l-rhamnopyranosyl(1→2)[β-d-glucopyranosyl(1→4)]-α-l-arabinopyranosyloleanolic acid (1) and 7,5″-anhydroapigenin 8-C-α-(2,6-dideoxy-5-hydroxy-ribo-hexopyranosyl)-4'-O-β-d-glucopyranoside (4). The structures of the new compounds were determined by spectroscopic analysis, including 1D and 2D NMR techniques, mass spectrometry, and chemical methods. Compound 4 is a C-hexopyranosylapigenin with an unusual cyclic ether linkage between C-5″ and C-7 of apigenin. The isolated proanthocyanidins have high antioxidant activities, and these compounds are probably responsible for the gastroprotective effect of the extract.

A careful NMR analysis, especially 1D TOCSY and 1D ROESY, of two refined saponin fractions allowed us to determine the structures of four new saponins from a polar extract of the Agave brittoniana Trel. spp. Brachypus leaves. A full assignment of the 1H and 13C spectral data for these new saponins, agabrittonosides A-D (1-4), and one previously known saponin, karatavioside A (5) is reported. Their structures were established using a combination of 1D and 2D (1H, 1H-COSY, TOCSY, ROESY, g-HSQC, g-HMBC and g-HSQC-TOCSY) NMR techniques and ESI-MS. Moreover, the work represents a new approach to structural elucidation of saponins in refined fractions by NMR investigations.

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