Stefanović, Milutin

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Antioxidant activities of the constituents of Picris echoides

Milovanović, Mirjana; Pićurić-Jovanović, Ksenija; Djermanović, Vladan; Stefanović, Milutin

(Srpsko hemijsko društvo, Beograd, 2002)

TY  - JOUR
AU  - Milovanović, Mirjana
AU  - Pićurić-Jovanović, Ksenija
AU  - Djermanović, Vladan
AU  - Stefanović, Milutin
PY  - 2002
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/509
AB  - Some flavonoids with antioxidant properties from the aerial parts of the plant species Picris echoides (family Asteraceae) were identified. Upon chromatography, the ethyl acetate extract afforded flavonoids, such as flavone apigenin (1) and its glucoside, cosmosiin (2), as well as common plant constituents from this family, flavonol galetin (3 3,4’,5,6,7-pentahydroxyflavone) and 4,4’,6,7-tetrahydroxyaurone (4). The structure of the aurone 4 has not been described so far in the literature and presented a very rare type of aurone skeleton. The structures of the isolated compounds were determined by interpretation of their physical and spectral data. The antioxidant activities of different extracts from Picris echoides were measured by the Schaal oven test at 60 ºC and by the Rancimat method at 100 ºC.Water/ethanol extracts (2:8, v/v), in concentrations of 0.02 and 0.05 %, showed lower activity than commercial tocopherol (Tch). On the contrary, the purified ethyl acetate extracts showed a strong concentration-dependent antioxidant effect. The investigation demonstrated that galetin was the main flavonol from this origin. According to the results of the two methods, galetin (3) showed a two-fold better activity than didTch and a lower activity than did butylated hydroxyanisole (BHA). The aurone 4 exhibited significantly lower antioxidant activity than did galetin at the same concentration level. Thus, the plant species P. echoides is a new and favorable source of natural lipid antioxidants.
AB  - Ispitan je hemijski sastav vodeno/etanolnog ekstrakta domaće biqke Picris echoides (familija Asteraceae). Izolovana su i identifikovana četiri flavonoida: apigenin (1), njegov 7-O-glukozid (2), galetin (3 3,4’,5,6,7-pentahidroksi-flavon) i 4,4’,6,7-tetrahidroksi-auron (4). Skelet tipa aurona 4 vrlo retko je prisutan u biqkama i njegova struktura do sada nije opisana u literaturi. Određena je antioksidativna aktivnost različitih ekstrakata biqke, kao i čistih flavonoidnih supstanci u uslovima Schaal oven testa na 60 ºC i Rancimat metoda na 100 ºC. Vodeno/etanolni ekstrakti (2:8) u koncentracijama 0,02 i 0,05 % pokazali su slabu aktivnost u pore- đenju sa tokoferolom, dok su etilacetatni ekstrakti, u istim koncentracijama delovali kao efikasni antioksidanti. Dokazano je da galetin (3) pokazuje duplo veću aktivnost od tokoferola.
PB  - Srpsko hemijsko društvo, Beograd
T2  - JOURNAL OF THE SERBIAN CHEMICAL SOCIETY
T1  - Antioxidant activities of the constituents of Picris echoides
T1  - Sastav i antioksidativna aktivnost Picris echoides
EP  - 15
IS  - 1
SP  - 7
VL  - 67
DO  - 10.2298/JSC0201007M
ER  - 
@article{
author = "Milovanović, Mirjana and Pićurić-Jovanović, Ksenija and Djermanović, Vladan and Stefanović, Milutin",
year = "2002",
abstract = "Some flavonoids with antioxidant properties from the aerial parts of the plant species Picris echoides (family Asteraceae) were identified. Upon chromatography, the ethyl acetate extract afforded flavonoids, such as flavone apigenin (1) and its glucoside, cosmosiin (2), as well as common plant constituents from this family, flavonol galetin (3 3,4’,5,6,7-pentahydroxyflavone) and 4,4’,6,7-tetrahydroxyaurone (4). The structure of the aurone 4 has not been described so far in the literature and presented a very rare type of aurone skeleton. The structures of the isolated compounds were determined by interpretation of their physical and spectral data. The antioxidant activities of different extracts from Picris echoides were measured by the Schaal oven test at 60 ºC and by the Rancimat method at 100 ºC.Water/ethanol extracts (2:8, v/v), in concentrations of 0.02 and 0.05 %, showed lower activity than commercial tocopherol (Tch). On the contrary, the purified ethyl acetate extracts showed a strong concentration-dependent antioxidant effect. The investigation demonstrated that galetin was the main flavonol from this origin. According to the results of the two methods, galetin (3) showed a two-fold better activity than didTch and a lower activity than did butylated hydroxyanisole (BHA). The aurone 4 exhibited significantly lower antioxidant activity than did galetin at the same concentration level. Thus, the plant species P. echoides is a new and favorable source of natural lipid antioxidants., Ispitan je hemijski sastav vodeno/etanolnog ekstrakta domaće biqke Picris echoides (familija Asteraceae). Izolovana su i identifikovana četiri flavonoida: apigenin (1), njegov 7-O-glukozid (2), galetin (3 3,4’,5,6,7-pentahidroksi-flavon) i 4,4’,6,7-tetrahidroksi-auron (4). Skelet tipa aurona 4 vrlo retko je prisutan u biqkama i njegova struktura do sada nije opisana u literaturi. Određena je antioksidativna aktivnost različitih ekstrakata biqke, kao i čistih flavonoidnih supstanci u uslovima Schaal oven testa na 60 ºC i Rancimat metoda na 100 ºC. Vodeno/etanolni ekstrakti (2:8) u koncentracijama 0,02 i 0,05 % pokazali su slabu aktivnost u pore- đenju sa tokoferolom, dok su etilacetatni ekstrakti, u istim koncentracijama delovali kao efikasni antioksidanti. Dokazano je da galetin (3) pokazuje duplo veću aktivnost od tokoferola.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "JOURNAL OF THE SERBIAN CHEMICAL SOCIETY",
title = "Antioxidant activities of the constituents of Picris echoides, Sastav i antioksidativna aktivnost Picris echoides",
pages = "15-7",
number = "1",
volume = "67",
doi = "10.2298/JSC0201007M"
}
Milovanović, M., Pićurić-Jovanović, K., Djermanović, V.,& Stefanović, M.. (2002). Antioxidant activities of the constituents of Picris echoides. in JOURNAL OF THE SERBIAN CHEMICAL SOCIETY
Srpsko hemijsko društvo, Beograd., 67(1), 7-15.
https://doi.org/10.2298/JSC0201007M
Milovanović M, Pićurić-Jovanović K, Djermanović V, Stefanović M. Antioxidant activities of the constituents of Picris echoides. in JOURNAL OF THE SERBIAN CHEMICAL SOCIETY. 2002;67(1):7-15.
doi:10.2298/JSC0201007M .
Milovanović, Mirjana, Pićurić-Jovanović, Ksenija, Djermanović, Vladan, Stefanović, Milutin, "Antioxidant activities of the constituents of Picris echoides" in JOURNAL OF THE SERBIAN CHEMICAL SOCIETY, 67, no. 1 (2002):7-15,
https://doi.org/10.2298/JSC0201007M . .
9
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Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides

Milovanović, Mirjana; Pićurić-Jovanović, Ksenija; Djermanović, Miodrag; Djermanović, Vladan; Stefanović, Milutin

(Srpsko hemijsko društvo, Beograd, 2000)

TY  - JOUR
AU  - Milovanović, Mirjana
AU  - Pićurić-Jovanović, Ksenija
AU  - Djermanović, Miodrag
AU  - Djermanović, Vladan
AU  - Stefanović, Milutin
PY  - 2000
UR  - http://aspace.agrif.bg.ac.rs/handle/123456789/221
AB  - Investigation of the constituents of the aerial parts of domestic plant species Picris echoides afforded the sesquiterpene lactones, i.e., guaianolides jacquilenin (1), 11-epi-jacquilenin (2), achillin (3) and eudesmanolide telekin (4). The chemical indenti-fication of the two monoterpene glucosides (-)-cis-chrysanthenol-β-D-glucopyranoside (5) and its 6'-acetate 6 is also reported. The guaianolide achillin (3) and the two monoterpene glucosides 5 and 6 were isolated for the first time from this plant species. Isolation was achieved by column chromatography and the structures were established mainly by the interpretation of their physical and spectral data, which were in agreement with those in the literature.
AB  - Iz nadzemnog dela domaće biljne vrste Picris echoides (familija Asteraceae), korova poznatog pod imenom Grguša, izolovana su i identifikovana četiri seskviterpenska laktona, kao i dva monoterpenska glukozida. Identifikovani laktoni su gvajanolidi jakvilenin (1), ll-epi-jakvilenin (2) i ahilin (3) kao i eudesmanolid telekin (4). Monoterpenski glukozidi (-)-cis-krizantenol-β-D-glukopiranozid (5) i njegov 6'-acetat, 6 su takođe izolovani iz istog ekstrakta. Gvajanolid ahilin (3) i monoterpenski glukozidi (5,6) su po prvi put izolovani iz ove biljne vrste, dok su preostala tri laktona izolovana više puta iz evropske biljne vrste.
PB  - Srpsko hemijsko društvo, Beograd
T2  - Journal of the Serbian Chemical Society
T1  - Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides
T1  - Seskviterpenski laktoni i monoterpenski glukozidi biljne vrste Picris echoides L.
EP  - 767
IS  - 11
SP  - 763
VL  - 65
UR  - https://hdl.handle.net/21.15107/rcub_agrospace_221
ER  - 
@article{
author = "Milovanović, Mirjana and Pićurić-Jovanović, Ksenija and Djermanović, Miodrag and Djermanović, Vladan and Stefanović, Milutin",
year = "2000",
abstract = "Investigation of the constituents of the aerial parts of domestic plant species Picris echoides afforded the sesquiterpene lactones, i.e., guaianolides jacquilenin (1), 11-epi-jacquilenin (2), achillin (3) and eudesmanolide telekin (4). The chemical indenti-fication of the two monoterpene glucosides (-)-cis-chrysanthenol-β-D-glucopyranoside (5) and its 6'-acetate 6 is also reported. The guaianolide achillin (3) and the two monoterpene glucosides 5 and 6 were isolated for the first time from this plant species. Isolation was achieved by column chromatography and the structures were established mainly by the interpretation of their physical and spectral data, which were in agreement with those in the literature., Iz nadzemnog dela domaće biljne vrste Picris echoides (familija Asteraceae), korova poznatog pod imenom Grguša, izolovana su i identifikovana četiri seskviterpenska laktona, kao i dva monoterpenska glukozida. Identifikovani laktoni su gvajanolidi jakvilenin (1), ll-epi-jakvilenin (2) i ahilin (3) kao i eudesmanolid telekin (4). Monoterpenski glukozidi (-)-cis-krizantenol-β-D-glukopiranozid (5) i njegov 6'-acetat, 6 su takođe izolovani iz istog ekstrakta. Gvajanolid ahilin (3) i monoterpenski glukozidi (5,6) su po prvi put izolovani iz ove biljne vrste, dok su preostala tri laktona izolovana više puta iz evropske biljne vrste.",
publisher = "Srpsko hemijsko društvo, Beograd",
journal = "Journal of the Serbian Chemical Society",
title = "Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides, Seskviterpenski laktoni i monoterpenski glukozidi biljne vrste Picris echoides L.",
pages = "767-763",
number = "11",
volume = "65",
url = "https://hdl.handle.net/21.15107/rcub_agrospace_221"
}
Milovanović, M., Pićurić-Jovanović, K., Djermanović, M., Djermanović, V.,& Stefanović, M.. (2000). Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides. in Journal of the Serbian Chemical Society
Srpsko hemijsko društvo, Beograd., 65(11), 763-767.
https://hdl.handle.net/21.15107/rcub_agrospace_221
Milovanović M, Pićurić-Jovanović K, Djermanović M, Djermanović V, Stefanović M. Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides. in Journal of the Serbian Chemical Society. 2000;65(11):763-767.
https://hdl.handle.net/21.15107/rcub_agrospace_221 .
Milovanović, Mirjana, Pićurić-Jovanović, Ksenija, Djermanović, Miodrag, Djermanović, Vladan, Stefanović, Milutin, "Sesquiterpene lactones and monoterpene glucosides from plant species Picris echoides" in Journal of the Serbian Chemical Society, 65, no. 11 (2000):763-767,
https://hdl.handle.net/21.15107/rcub_agrospace_221 .