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

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...

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Detalles Bibliográficos
Otros Autores: Silva, Mariana Paola, Piazza, Leonardo Alberto, López, Daniela, López Rivilli, Marisa J., Turco, Mauricio D., Cantero, Juan José, Tourn, Graciela Mónica, Scopel, Ana Leonor
Formato: Artículo
Lenguaje:Inglés
Materias:
[-]-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
LACTUCA
LACTUCA SATIVA
Acceso en línea:http://ri.agro.uba.ar/files/intranet/articulo/2012Silva.pdf
LINK AL EDITOR
Aporte de:Registro referencial: Solicitar el recurso aquí
Biblioteca Central (FAUBA) de Universidad de Buenos Aires
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245 1 0 |a Phytotoxic activity in Flourensia campestris and isolation of [-] hamanasic acid A as its active principle compound 
520 |a 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. 
653 0 |a [-]-HAMANASIC ACID A 
653 0 |a ALLELOPATHIC AGENT 
653 0 |a ASTERACEAE 
653 0 |a BISABOLANOIDS 
653 0 |a ESSENTIAL OILS 
653 0 |a FLOURENSIA CAMPESTRIS 
653 0 |a PHYTOTOXIC ACTIVITY 
653 0 |a SESQUITERPENOIDS 
653 0 |a VOLATILES 
653 0 |a 7 CARBOXY 8 HYDROXY 1[2],12[13] DIEN BISABOLENE 
653 0 |a 7-CARBOXY-8-HYDROXY-1[2],12[13]-DIEN-BISABOLENE 
653 0 |a SESQUITERPENE 
653 0 |a CHEMISTRY 
653 0 |a DRUG EFFECT 
653 0 |a FRACTIONATION 
653 0 |a GAS CHROMATOGRAPHY 
653 0 |a GERMINATION 
653 0 |a GROWTH, DEVELOPMENT AND AGING 
653 0 |a ISOLATION AND PURIFICATION 
653 0 |a LETTUCE 
653 0 |a PLANT 
653 0 |a PLANT ROOT 
653 0 |a CHEMICAL FRACTIONATION 
653 0 |a CHROMATOGRAPHY, GAS 
653 0 |a PLANT ROOTS 
653 0 |a PLANT SHOOTS 
653 0 |a SESQUITERPENES 
653 0 |a FLOURENSIA CAMPESTRIS 
653 0 |a LACTUCA 
653 0 |a LACTUCA SATIVA 
700 1 |a Silva, Mariana Paola  |9 67304 
700 1 |a Piazza, Leonardo Alberto  |9 58155 
700 1 |a López, Daniela  |9 66957 
700 1 |a López Rivilli, Marisa J.  |9 67728 
700 1 |a Turco, Mauricio D.  |9 71900 
700 1 |a Cantero, Juan José  |9 12909 
700 1 |a Tourn, Graciela Mónica  |9 21205 
700 1 |a Scopel, Ana Leonor  |9 711 
773 |t Phytochemistry  |g Vol.77 (2012), p.140-148 
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900 |a ^tPhytotoxic activity in Flourensia campestris and isolation of [-]-hamanasic acid A as its active principle compound 
900 |a ^aSilva^bM.P. 
900 |a ^aPiazza^bL.A. 
900 |a ^aLópez^bD. 
900 |a ^aLópez Rivilli^bM.J. 
900 |a ^aTurco^bM.D. 
900 |a ^aCantero^bJ.J. 
900 |a ^aTourn^bM.G. 
900 |a ^aScopel^bA.L. 
900 |a ^aSilva^bM. P. 
900 |a ^aPiazza^bL. A. 
900 |a ^aLópez^bD. 
900 |a ^aLópez Rivilli^bM. J. 
900 |a ^aTurco^bM. D. 
900 |a ^aCantero^bJ. J. 
900 |a ^aTourn^bM. G. 
900 |a ^aScopel^bA. L. 
900 |a ^aSilva^bM.P.^tEstación de Biología Sierras, Facultad de Agronomía-Sede Punilla, Universidad de Buenos Aires, Casilda S/N, Huerta Grande 5174, Córdoba, Argentina 
900 |a ^aPiazza^bL.A.^tLaboratorio de Química Fina y Productos Naturales, Subsecretaría C.E.P.R.O.COR, MinCyT, Sta. María de Punilla 5164, Córdoba, Argentina 
900 |a ^aLópez^bD.^tCátedra de Botánica Sistemática Agrícola, Facultad de Agronomía y Veterinaria, Universidad de Río Cuarto, Río Cuarto 5800, Córdoba, Argentina 
900 |a ^aLópez Rivilli^bM.J.^tConcejo Nacional de Investigaciones Científicas y Técnicas [CONICET], Argentina 
900 |a ^aTurco^bM.D. 
900 |a ^aCantero^bJ.J. 
900 |a ^aTourn^bM.G. 
900 |a ^aScopel^bA.L. 
900 |a ^tPhytochemistry^cPhytochemistry 
900 |a en 
900 |a 140 
900 |a ^i 
900 |a Vol. 77 
900 |a 148 
900 |a [-]-HAMANASIC ACID A 
900 |a ALLELOPATHIC AGENT 
900 |a ASTERACEAE 
900 |a BISABOLANOIDS 
900 |a ESSENTIAL OILS 
900 |a FLOURENSIA CAMPESTRIS 
900 |a PHYTOTOXIC ACTIVITY 
900 |a SESQUITERPENOIDS 
900 |a VOLATILES 
900 |a 7 CARBOXY 8 HYDROXY 1[2],12[13] DIEN BISABOLENE 
900 |a 7-CARBOXY-8-HYDROXY-1[2],12[13]-DIEN-BISABOLENE 
900 |a SESQUITERPENE 
900 |a CHEMISTRY 
900 |a DRUG EFFECT 
900 |a FRACTIONATION 
900 |a GAS CHROMATOGRAPHY 
900 |a GERMINATION 
900 |a GROWTH, DEVELOPMENT AND AGING 
900 |a ISOLATION AND PURIFICATION 
900 |a LETTUCE 
900 |a PLANT 
900 |a PLANT ROOT 
900 |a CHEMICAL FRACTIONATION 
900 |a CHROMATOGRAPHY, GAS 
900 |a PLANT ROOTS 
900 |a PLANT SHOOTS 
900 |a SESQUITERPENES 
900 |a FLOURENSIA CAMPESTRIS 
900 |a LACTUCA 
900 |a LACTUCA SATIVA 
900 |a 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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