In course of a research devoted to the identifi cation of natural pesticides in the surface exudates [1] of aromatic plants, we considered Salvia adenophora Fernald [2], which previously showed herbicide activity [3]. In this work we focused on the more lipophylic part of the exudate in order to isolate cyclic metabolites of the polyunsaturated fatty acids. As a matter of fact, due to their great structural variety, oxylipins may have various biological roles as antimicrobial, anti-insecticidal and antifungal compounds [4, 5]; these compounds have also shown eff ects of inhibition of root elongation, alteration of seedling growth and photosynthetic activity [6].Methods e surface exudate (36 g), obtained by rinsing the plant material with CH2Cl2, and washed with n-hexane, was subjected to column chromatography on Sephadex LH-20 (CHCl3/CH3OH 7:3), and then on silica gel (CHCl3), aff ording compound 1, that was purifi ed by means of HPLC-MS followed by semi-preparative RP HPLC (CH3OH/ H2O 80:20, RT 9 min, 6.7 mg). Results and discussion/conclusions e compound 1 was identifi ed by 1H and 13C NMR, including TOCSY, COSY, HSQC, HMBC experiments, ESI-TRAPMS, MS2 and HR-MS analysis. e relative stereochemistry of 1 was inferred on the basis of the 1H and 13C NMR data of pentenil and cyclopentenil moieties, consistent with those published in the literature for 12-oxo-trans-10,15- phytodienoic acid (13-epi-12-oxo-PDA) [7, 8, 9] and for its methyl ester [10, 11].
A New Derivative of 12-oxo-Phytodienoic Acid from Salvia adenophora Fernald.
BISIO, ANGELA;DAMONTE, GIANLUCA;GIACOMELLI, EMANUELA;MELE, GIACOMO;CAFAGGI, SERGIO;ROMUSSI, GIOVANNI
2011-01-01
Abstract
In course of a research devoted to the identifi cation of natural pesticides in the surface exudates [1] of aromatic plants, we considered Salvia adenophora Fernald [2], which previously showed herbicide activity [3]. In this work we focused on the more lipophylic part of the exudate in order to isolate cyclic metabolites of the polyunsaturated fatty acids. As a matter of fact, due to their great structural variety, oxylipins may have various biological roles as antimicrobial, anti-insecticidal and antifungal compounds [4, 5]; these compounds have also shown eff ects of inhibition of root elongation, alteration of seedling growth and photosynthetic activity [6].Methods e surface exudate (36 g), obtained by rinsing the plant material with CH2Cl2, and washed with n-hexane, was subjected to column chromatography on Sephadex LH-20 (CHCl3/CH3OH 7:3), and then on silica gel (CHCl3), aff ording compound 1, that was purifi ed by means of HPLC-MS followed by semi-preparative RP HPLC (CH3OH/ H2O 80:20, RT 9 min, 6.7 mg). Results and discussion/conclusions e compound 1 was identifi ed by 1H and 13C NMR, including TOCSY, COSY, HSQC, HMBC experiments, ESI-TRAPMS, MS2 and HR-MS analysis. e relative stereochemistry of 1 was inferred on the basis of the 1H and 13C NMR data of pentenil and cyclopentenil moieties, consistent with those published in the literature for 12-oxo-trans-10,15- phytodienoic acid (13-epi-12-oxo-PDA) [7, 8, 9] and for its methyl ester [10, 11].
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