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Phytotoxic activity in Flourensia campestris and isolation of [-] hamanasic acid A as its active principle compound

Colaborador(es): Silva, Mariana Paola | Piazza, Leonardo Alberto | López, Daniela | López Rivilli, Marisa J | Turco, Mauricio D | Cantero, Juan José | Tourn, Graciela Mónica | Scopel, Ana Leonor.
ISSN: 0031-9422.Tipo de material: Artículos y capítulos. Recurso electrónico.Tema(s): [-]-HAMANASIC ACID A | ALLELOPATHIC AGENT | ASTERACEAE | BISABOLANOIDS | ESSENTIAL OILS | FLOURENSIA CAMPESTRIS | PHYTOTOXIC ACTIVITY | SESQUITERPENOIDS | VOLATILES | 7 CARBOXY 8 HYDROXY 1[2],12[13] DIEN BISABOLENE | 7-CARBOXY-8-HYDROXY-1[2],12[13]-DIEN-BISABOLENE | SESQUITERPENE | CHEMISTRY | DRUG EFFECT | FRACTIONATION | GAS CHROMATOGRAPHY | GERMINATION | GROWTH, DEVELOPMENT AND AGING | ISOLATION AND PURIFICATION | LETTUCE | PLANT | PLANT ROOT | CHEMICAL FRACTIONATION | CHROMATOGRAPHY, GAS | PLANT ROOTS | PLANT SHOOTS | SESQUITERPENES | FLOURENSIA CAMPESTRIS | LACTUCA | LACTUCA SATIVA | Recursos en línea: Haga clic para acceso en línea | LINK AL EDITOR. En: Phytochemistry vol.77 (2012) p.140-148Resumen: An aqueous extract from Flourensia campestris [Asteraceae] dry aerial parts showed strong inhibition on the germination and growth of Lactuca sativa. Based on bio-guided chromatographic fractionation of aq. extracts from dry and fresh leaves and spectroscopic means, [-]-hamanasic acid A [7-carboxy-8-hydroxy-1[2], 12[13]-dien-bisabolene [1]] was isolated as the most inhibitory active principle on germination [ECg50 = 2.9 mM] and on root [ECr50 = 1.5 mM]/shoot [ECs50 = 2.0 mM] growth. As measured by GC, and correlated with a simple designed 2D-TLC, compound 1 was distributed throughout the plant, with a remarkably high concentration [1.6 percent] in the leaves and the inflorescences. At least a quarter of the amount of 1 was found in aqueous extracts suggesting that leaching would be a key route for its release into the environment. By contrast, leaf essential oils [HD] between 0.5 and 1.5 ul ml-1 did not show herbicidal effects and 1 was not found in them [TLC] nor among volatiles [HS-SPME]. Volatile compositions were assessed by GC-FID and GC-MS and led to the identification of 23 compounds [4 monoterpenes and 19 sesquiterpenes] with a wide seasonal [spring-summer percent] variation, represented principally by bicyclo-germacrene [37-6 percent], spathulenol [4-32 percent], globulol [20-0 percent], beta-caryophyllene [15-6 percent], caryophyllene oxide [1-13 percent] and bicycloelemene [10-1 percent], respectively. The high amount of 1 in F. campestris together with its feasibility of being extracted with water suggest that [-]-hamanasic acid A is an allelochemical in this species. Species-specific studies must be carried out to evaluate the potential of 1 as a natural herbicidal compound.
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An aqueous extract from Flourensia campestris [Asteraceae] dry aerial parts showed strong inhibition on the germination and growth of Lactuca sativa. Based on bio-guided chromatographic fractionation of aq. extracts from dry and fresh leaves and spectroscopic means, [-]-hamanasic acid A [7-carboxy-8-hydroxy-1[2], 12[13]-dien-bisabolene [1]] was isolated as the most inhibitory active principle on germination [ECg50 = 2.9 mM] and on root [ECr50 = 1.5 mM]/shoot [ECs50 = 2.0 mM] growth. As measured by GC, and correlated with a simple designed 2D-TLC, compound 1 was distributed throughout the plant, with a remarkably high concentration [1.6 percent] in the leaves and the inflorescences. At least a quarter of the amount of 1 was found in aqueous extracts suggesting that leaching would be a key route for its release into the environment. By contrast, leaf essential oils [HD] between 0.5 and 1.5 ul ml-1 did not show herbicidal effects and 1 was not found in them [TLC] nor among volatiles [HS-SPME]. Volatile compositions were assessed by GC-FID and GC-MS and led to the identification of 23 compounds [4 monoterpenes and 19 sesquiterpenes] with a wide seasonal [spring-summer percent] variation, represented principally by bicyclo-germacrene [37-6 percent], spathulenol [4-32 percent], globulol [20-0 percent], beta-caryophyllene [15-6 percent], caryophyllene oxide [1-13 percent] and bicycloelemene [10-1 percent], respectively. The high amount of 1 in F. campestris together with its feasibility of being extracted with water suggest that [-]-hamanasic acid A is an allelochemical in this species. Species-specific studies must be carried out to evaluate the potential of 1 as a natural herbicidal compound.

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