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Bioactive steroidal saponins from Agave offoyana flowers

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URI: http://hdl.handle.net/10498/20275

DOI: 10.1016/j.phytochem.2013.06.020

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Author/s
J. Pérez, Andy; Calle, Juan M.; Simonet Morales, Ana MaríaAuthority UCA; O. Guerra, José; Stochmal, Anna; Macías Domínguez, Francisco AntonioAuthority UCA
Date
2013-07
Department
Química Orgánica
Source
Phytochemistry 95 (2013) 298–307
Abstract
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-2a,3b-diol-12-one 3-O-{b-D-xylopyranosyl-(1-3)-O-b-D-glucopyranosyl-(1-2)-O-[b-D-xylopyranosyl-(1-3)]-O-b-D-glucopyranosyl-( 1-4)-O-b-D-galactopyranoside} (1), (25R)-spirost-5-en-2a,3b-diol-12-one 3-O-{b-D-glucopyranosyl-(1-2)-O-[b-D-xylopyranosyl-(1-3)]-O-b-D-glucopyranosyl-(1-4)-O-b-D galactopyranoside} (2), (25R)-spirost-5-en-2a,3b,12b-triol 3-O-{b-D-glucopyranosyl-(1-2)-O-[b-D-xylopyranosyl-(1-3)]- O-b-D-glucopyranosyl-(1-4)-O-b-D-galactopyranoside} (3), (25R)-5a-spirostan-2a,3b-diol-12-one 3-O-{b-D-xylopyranosyl-(1-3)-O-b-D-glucopyranosyl-(1-2)-O-[b-D-xylopyranosyl-(1-3)]-O-b-D-glucopyranosyl-(1-4)-O-b-D-galactopyranoside} (4), and (25R)-5a-spirostan-2a,3b-diol-9(11)-en-12-one 3-O-{b-D-xylopyranosyl-(1-3)-O-b-D-glucopyranosyl-(1-2)-O-[b-D-xylopyranosyl-(1-3)]-O-b-D-glucopyranosyl-( 1-4)-O-b-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 dosedependent phytotoxicity and low dose stimulation were observed.
Subjects
Agave offoyana; Steroidal saponins; Structural elucidation; Phytotoxic activity; Structure–activity relationship
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  • Artículos Científicos INBIO [264]
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Attribution-NonCommercial-NoDerivatives 4.0 Internacional
This work is under a Creative Commons License Attribution-NonCommercial-NoDerivatives 4.0 Internacional

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