title: Phytotoxic steroidal saponins from Agave offoyana leaves.
abstract: 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.
authors.affiliation: Grupo de Alelopatía, Departamento de Química Orgánica, Instituto de Biomoleculas (INBIO), Facultad de Ciencias, Universidad de Cádiz, C/República Saharaui s/n, Apdo. 40, 11510-Puerto Real (Cádiz), Spain; Department of Biochemistry, Institute of Soil Science and Plant Cultivation, State Research Institute, ul. Czartoryskich 8, 24-100 Puławy, Poland. Electronic address: aperez@iung.pulawy.pl.
authors.forename: Andy J
authors.initials: AJ
authors.lastname: Pérez
authors.affiliation: Grupo de Alelopatía, Departamento de Química Orgánica, Instituto de Biomoleculas (INBIO), Facultad de Ciencias, Universidad de Cádiz, C/República Saharaui s/n, Apdo. 40, 11510-Puerto Real (Cádiz), Spain.
authors.forename: Ana M
authors.initials: AM
authors.lastname: Simonet
authors.affiliation: Grupo de Alelopatía, Departamento de Química Orgánica, Instituto de Biomoleculas (INBIO), Facultad de Ciencias, Universidad de Cádiz, C/República Saharaui s/n, Apdo. 40, 11510-Puerto Real (Cádiz), Spain.
authors.forename: Juan M
authors.initials: JM
authors.lastname: Calle
authors.affiliation: Department of Biochemistry, Institute of Soil Science and Plant Cultivation, State Research Institute, ul. Czartoryskich 8, 24-100 Puławy, Poland.
authors.forename: Łukasz
authors.initials: Ł
authors.lastname: Pecio
authors.affiliation: Departamento de Licenciatura en Química, Facultad de Química y Farmacia, Universidad Central 'Marta Abreu' de Las Villas, Carretera a Camajuaní km 5.5, 54830 Santa Clara, Cuba.
authors.forename: José O
authors.initials: JO
authors.lastname: Guerra
authors.affiliation: Department of Biochemistry, Institute of Soil Science and Plant Cultivation, State Research Institute, ul. Czartoryskich 8, 24-100 Puławy, Poland.
authors.forename: Anna
authors.initials: A
authors.lastname: Stochmal
authors.affiliation: Grupo de Alelopatía, Departamento de Química Orgánica, Instituto de Biomoleculas (INBIO), Facultad de Ciencias, Universidad de Cádiz, C/República Saharaui s/n, Apdo. 40, 11510-Puerto Real (Cádiz), Spain.
authors.forename: Francisco A
authors.initials: FA
authors.lastname: Macías
mesh_terms: D027882:Agave / Q000737:chemistry*; D019906:Nuclear Magnetic Resonance, Biomolecular; D010840:Phytosterols / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D018515:Plant Leaves / Q000737:chemistry; D012503:Saponins / Q000737:chemistry / Q000302:isolation & purification* / Q000494:pharmacology*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
chemical_list: D010840:Phytosterols; D012503:Saponins
keywords: Agave offoyana; Furostane saponin; Phytotoxic activity; Spirostane saponin; Structural elucidation; Structure–activity relationship