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Hemijska i farmakološka karakterizacija odabranih taksona roda Heracleum L. (Apiaceae), autohtonih za jugoistočnu Evropu

Chemical and pharmacological characterisation of selected taxa of the genus Heracleum L. (APiaceae), autochthonous for Southeastern Europe

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2019
Disertacija.pdf (9.145Mb)
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Authors
Ušjak, Ljuboš
Contributors
Petrović, Silvana
Drobac, Milica
Soković, Marina
Stanojković, Tatjana
Niketić, Marjan
Doctoral thesis (Published version)
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Abstract
Predmet istraņivanja doktorske disertacije je devet taksona roda Heracleum (Apiaceae): H. sphondylium, H. sibiricum, H. montanum, H. ternatum, H. pyrenaicum subsp. pollinianum, H. pyrenaicum subsp. orsinii i H. verticillatum iz grupe H. sphondylium, i H. orphanidis, svi iz (tipske) sect. Heracleum, kao i H. austriacum subsp. siifolium iz sect. Wendia.Gasnom hromatografijom sa FID i MS detekcijom analiziran je sastav etarskih ulja izolovanih destilacijom vodenom parom iz podzemnih organa, listova, cvasti i plodova. U uljima podzemnih organa dominirali su monoterpeni i/ili fenilpropani (taksoni grupe H. sphondylium), ili (Z)-falkarinol (H. orphanidis i H. austriacum); u uljima plodova alifatiĉni estri oktilacetat (sect. Heracleum) ili oktilheksanoat (H. austriacum), a u uljima listova i cvasti alifatiĉni estri (H. orphanidis) ili seskviterpeni i/ili fenilpropani. S obzirom da je u pojedinim uljima utvrĊeno prisustvo furanokumarina koji mogu delovati fototoksiĉno, definisan je bezbednosni... profil ulja, tj. utvrĊen njihov maksimalni dozvoljeni dnevni unos.U dihlormetanskim ekstraktima podzemnih organa i plodova svih taksona identifikovano je ukupno 12 furanokumarina (LC-MS metodom pomoću standardnih supstanci ili na osnovu UV, MS, 1H i ROESY NMR spektara), od kojih su dominantni bili pimpinelin, bergapten, biakangelikol, heraklenin i/ili imperatorin.Hemosistematski znaĉaj komponenti etarskih ulja (u sluĉaju podzemnih organa i plodova i komponenti njihovih headspace frakcija) i furanokumarina utvrĊen je multivarijantnom statistiĉkom analizom (PCA, nMDS i UPGMA).U uljastim supernatantima dihlormetanskih ekstrakata plodova gasnom hromatografijom (GC-FID i GC-MS) analizirane su masne kiseline (dominantna je bila petroselinska), steroli (najzastupljeniji je bio β-sitosterol) i triterpeni.Antimikrobna aktivnost etarskih ulja pokazana je mikrodilucionom metodom na po osam sojeva bakterija i mikromiceta (u nekim sluĉajevima MIK su bile niņe ili bliske 0,1 mg/mL); selektivna citotoksiĉnost MTT testom na tumorske HeLa, LS174 i A549 ćelije (u nekim sluĉajevima IC50 su bile niņe ili bliske 30 μg/mL; ulja uglavnom nisuinhibirala rast normalnih MRC-5 ćelija)...

This doctoral dissertation focuses on nineHeracleumtaxa (Apiaceae): H. sphondylium, H. sibiricum, H. montanum, H. ternatum, H. pyrenaicumsubsp. pollinianum, H. pyrenaicumsubsp. orsiniiandH. verticillatum, belonging togroupH. sphondylium, andH. orphanidis, all from the (type)sect. Heracleum, as well asH.austriacum subsp.siifoliumfromsect. Wendia. By GC-FID and GC-MS, the composition of essential oils isolated by hydrodistillation fromunderground parts, leaves, flowers and fruits was analysed. Underground parts oils were dominated bymonoterpenesand/orphenylpropanoids (H. sphondyliumgroup), or(Z)-falcarinol (H. orphanidisandH. austriacum); fruit oils byaliphatic estersoctylacetate(sect. Heracleum) oroctylhexanoate(H. austriacum), andleaf and flower oilsby aliphatic esters(H. orphanidis) or sesquiterpenesand/orphenylpropanoids. Considering that in some of these oils potentially phototoxic furanocoumarins were detect...ed, safety profileof the oils, i.e. their maximum daily intake wasestimated.In dichloromethane extracts of underground parts and fruits of investigated taxa,atotal of 12 furanocoumarins were identified(by LC-MS using standard compoundsorbased onUV, MS, 1H andROESY NMR spectra), among which pimpinellin, bergapten, byakangelicol, heraclenin and/orimperatorinwere dominant. Chemosystematicsignificance ofessential oil components(in the case ofunderground parts and fruits, of their headspacefractioncomponents as well) and furanocoumarinswas demonstrated usingmultivariatestatistics (PCA, nMDS andUPGMA).In oily supernatants of fruit dichloromethaneextracts, by GC-FID and GC-MS,fatty acids (petroselinic acid was dominant), sterols (β-sitosterolwas the most abundant) and triterpeneswere analysed. Antimicrobialactivity of the essential oilswas showedbymicrodilutionmethodoneightbacteria and eightfungi(in some cases MICs werelower or around0.1 mg/mL); selective cytotoxicityby MTT teston cancerHeLa, LS174 andA549 cells(in some cases IC50werelower or around 30 μg/mL; oils mostly did not inhibit growth ofnormalMRC-5 cells). Essential oils showed weakanti-DPPH potential. The composition of their active zones in TLC-DPPH test was analysed byGC-FID and GC-MS(oxygenated terpenes and phenylpropanoidswere dominant).

Keywords:
taksoni roda Heracleum / Heracleum taxa / etarska ulja / furanokumarini / masne kiseline i nesaponifikovane supstance / GC-FID i GC-MS / LC-MS / multivarijantna statistiĉka analiza / antimikrobna aktivnost / citotoksiĉna aktivnost / anti-DPPH potencijal / essential oils / furanocoumarins / fatty acids and unsaponifiable compounds / GC-FID and GC-MS / LC-MS / multivariate statistics / antimicrobial activity / cytotoxic activity / anti-DPPH potential
Source:
Универзитет у Београду, 2019
Publisher:
  • Универзитет у Београду, Фармацеутски факултет
Funding / projects:
  • Investigation on the medicinal plants: morphological, chemical and pharmacological characterisation (RS-173021)
  • Ispitivanje lekovitog potencijala biljaka: morfološka, hemijska i farmakološka karakterizacija (RS-143012)
[ Google Scholar ]
Handle
https://hdl.handle.net/21.15107/rcub_nardus_11249
URI
http://eteze.bg.ac.rs/application/showtheses?thesesId=6810
http://nardus.mpn.gov.rs/handle/123456789/11249
https://fedorabg.bg.ac.rs/fedora/get/o:19901/bdef:Content/download
http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=2048355682
https://farfar.pharmacy.bg.ac.rs/handle/123456789/3696
Collections
  • Doktorati
Institution/Community
Pharmacy
TY  - THES
AU  - Ušjak, Ljuboš
PY  - 2019
UR  - http://eteze.bg.ac.rs/application/showtheses?thesesId=6810
UR  - http://nardus.mpn.gov.rs/handle/123456789/11249
UR  - https://fedorabg.bg.ac.rs/fedora/get/o:19901/bdef:Content/download
UR  - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=2048355682
UR  - https://farfar.pharmacy.bg.ac.rs/handle/123456789/3696
AB  - Predmet istraņivanja doktorske disertacije je devet taksona roda Heracleum (Apiaceae): H. sphondylium, H. sibiricum, H. montanum, H. ternatum, H. pyrenaicum subsp. pollinianum, H. pyrenaicum subsp. orsinii i H. verticillatum iz grupe H. sphondylium, i H. orphanidis, svi iz (tipske) sect. Heracleum, kao i H. austriacum subsp. siifolium iz sect. Wendia.Gasnom hromatografijom sa FID i MS detekcijom analiziran je sastav etarskih ulja izolovanih destilacijom vodenom parom iz podzemnih organa, listova, cvasti i plodova. U uljima podzemnih organa dominirali su monoterpeni i/ili fenilpropani (taksoni grupe H. sphondylium), ili (Z)-falkarinol (H. orphanidis i H. austriacum); u uljima plodova alifatiĉni estri oktilacetat (sect. Heracleum) ili oktilheksanoat (H. austriacum), a u uljima listova i cvasti alifatiĉni estri (H. orphanidis) ili seskviterpeni i/ili fenilpropani. S obzirom da je u pojedinim uljima utvrĊeno prisustvo furanokumarina koji mogu delovati fototoksiĉno, definisan je bezbednosni profil ulja, tj. utvrĊen njihov maksimalni dozvoljeni dnevni unos.U dihlormetanskim ekstraktima podzemnih organa i plodova svih taksona identifikovano je ukupno 12 furanokumarina (LC-MS metodom pomoću standardnih supstanci ili na osnovu UV, MS, 1H i ROESY NMR spektara), od kojih su dominantni bili pimpinelin, bergapten, biakangelikol, heraklenin i/ili imperatorin.Hemosistematski znaĉaj komponenti etarskih ulja (u sluĉaju podzemnih organa i plodova i komponenti njihovih headspace frakcija) i furanokumarina utvrĊen je multivarijantnom statistiĉkom analizom (PCA, nMDS i UPGMA).U uljastim supernatantima dihlormetanskih ekstrakata plodova gasnom hromatografijom (GC-FID i GC-MS) analizirane su masne kiseline (dominantna je bila petroselinska), steroli (najzastupljeniji je bio β-sitosterol) i triterpeni.Antimikrobna aktivnost etarskih ulja pokazana je mikrodilucionom metodom na po osam sojeva bakterija i mikromiceta (u nekim sluĉajevima MIK su bile niņe ili bliske 0,1 mg/mL); selektivna citotoksiĉnost MTT testom na tumorske HeLa, LS174 i A549 ćelije (u nekim sluĉajevima IC50 su bile niņe ili bliske 30 μg/mL; ulja uglavnom nisuinhibirala rast normalnih MRC-5 ćelija)...
AB  - This    doctoral    dissertation focuses    on    nineHeracleumtaxa (Apiaceae): H.  sphondylium, H. sibiricum, H. montanum, H. ternatum, H. pyrenaicumsubsp. pollinianum, H. pyrenaicumsubsp. orsiniiandH. verticillatum,  belonging  togroupH.  sphondylium, andH. orphanidis, all  from  the (type)sect. Heracleum, as  well  asH.austriacum subsp.siifoliumfromsect. Wendia. By   GC-FID   and   GC-MS,   the   composition   of   essential   oils isolated by hydrodistillation fromunderground  parts,  leaves,  flowers  and  fruits  was  analysed. Underground  parts  oils  were  dominated  bymonoterpenesand/orphenylpropanoids (H. sphondyliumgroup), or(Z)-falcarinol (H. orphanidisandH. austriacum); fruit oils byaliphatic  estersoctylacetate(sect. Heracleum) oroctylhexanoate(H.  austriacum), andleaf  and  flower  oilsby  aliphatic  esters(H.  orphanidis) or  sesquiterpenesand/orphenylpropanoids. Considering   that   in   some   of   these   oils   potentially   phototoxic furanocoumarins  were  detected, safety  profileof  the  oils,  i.e.  their  maximum  daily intake wasestimated.In dichloromethane extracts of underground parts and fruits of investigated taxa,atotal  of 12  furanocoumarins  were  identified(by LC-MS using standard  compoundsorbased onUV, MS, 1H andROESY NMR spectra), among which pimpinellin, bergapten, byakangelicol, heraclenin and/orimperatorinwere dominant. Chemosystematicsignificance   ofessential   oil   components(in   the   case   ofunderground  parts  and  fruits,  of  their headspacefractioncomponents as  well) and furanocoumarinswas demonstrated  usingmultivariatestatistics  (PCA,  nMDS  andUPGMA).In  oily  supernatants  of  fruit dichloromethaneextracts,  by GC-FID and  GC-MS,fatty acids (petroselinic acid was dominant), sterols (β-sitosterolwas the most abundant) and triterpeneswere analysed. Antimicrobialactivity of the essential oilswas showedbymicrodilutionmethodoneightbacteria and eightfungi(in some cases MICs werelower or around0.1 mg/mL); selective cytotoxicityby  MTT  teston cancerHeLa,  LS174 andA549 cells(in  some 
cases IC50werelower or around 30 μg/mL; oils mostly did not inhibit growth ofnormalMRC-5 cells). Essential  oils  showed  weakanti-DPPH  potential. The  composition  of their active zones in TLC-DPPH test was analysed byGC-FID and GC-MS(oxygenated terpenes and phenylpropanoidswere dominant).
PB  - Универзитет у Београду, Фармацеутски факултет
T2  - Универзитет у Београду
T1  - Hemijska i farmakološka karakterizacija odabranih taksona roda Heracleum L. (Apiaceae), autohtonih za jugoistočnu Evropu
UR  - https://hdl.handle.net/21.15107/rcub_nardus_11249
ER  - 
@phdthesis{
author = "Ušjak, Ljuboš",
year = "2019",
abstract = "Predmet istraņivanja doktorske disertacije je devet taksona roda Heracleum (Apiaceae): H. sphondylium, H. sibiricum, H. montanum, H. ternatum, H. pyrenaicum subsp. pollinianum, H. pyrenaicum subsp. orsinii i H. verticillatum iz grupe H. sphondylium, i H. orphanidis, svi iz (tipske) sect. Heracleum, kao i H. austriacum subsp. siifolium iz sect. Wendia.Gasnom hromatografijom sa FID i MS detekcijom analiziran je sastav etarskih ulja izolovanih destilacijom vodenom parom iz podzemnih organa, listova, cvasti i plodova. U uljima podzemnih organa dominirali su monoterpeni i/ili fenilpropani (taksoni grupe H. sphondylium), ili (Z)-falkarinol (H. orphanidis i H. austriacum); u uljima plodova alifatiĉni estri oktilacetat (sect. Heracleum) ili oktilheksanoat (H. austriacum), a u uljima listova i cvasti alifatiĉni estri (H. orphanidis) ili seskviterpeni i/ili fenilpropani. S obzirom da je u pojedinim uljima utvrĊeno prisustvo furanokumarina koji mogu delovati fototoksiĉno, definisan je bezbednosni profil ulja, tj. utvrĊen njihov maksimalni dozvoljeni dnevni unos.U dihlormetanskim ekstraktima podzemnih organa i plodova svih taksona identifikovano je ukupno 12 furanokumarina (LC-MS metodom pomoću standardnih supstanci ili na osnovu UV, MS, 1H i ROESY NMR spektara), od kojih su dominantni bili pimpinelin, bergapten, biakangelikol, heraklenin i/ili imperatorin.Hemosistematski znaĉaj komponenti etarskih ulja (u sluĉaju podzemnih organa i plodova i komponenti njihovih headspace frakcija) i furanokumarina utvrĊen je multivarijantnom statistiĉkom analizom (PCA, nMDS i UPGMA).U uljastim supernatantima dihlormetanskih ekstrakata plodova gasnom hromatografijom (GC-FID i GC-MS) analizirane su masne kiseline (dominantna je bila petroselinska), steroli (najzastupljeniji je bio β-sitosterol) i triterpeni.Antimikrobna aktivnost etarskih ulja pokazana je mikrodilucionom metodom na po osam sojeva bakterija i mikromiceta (u nekim sluĉajevima MIK su bile niņe ili bliske 0,1 mg/mL); selektivna citotoksiĉnost MTT testom na tumorske HeLa, LS174 i A549 ćelije (u nekim sluĉajevima IC50 su bile niņe ili bliske 30 μg/mL; ulja uglavnom nisuinhibirala rast normalnih MRC-5 ćelija)..., This    doctoral    dissertation focuses    on    nineHeracleumtaxa (Apiaceae): H.  sphondylium, H. sibiricum, H. montanum, H. ternatum, H. pyrenaicumsubsp. pollinianum, H. pyrenaicumsubsp. orsiniiandH. verticillatum,  belonging  togroupH.  sphondylium, andH. orphanidis, all  from  the (type)sect. Heracleum, as  well  asH.austriacum subsp.siifoliumfromsect. Wendia. By   GC-FID   and   GC-MS,   the   composition   of   essential   oils isolated by hydrodistillation fromunderground  parts,  leaves,  flowers  and  fruits  was  analysed. Underground  parts  oils  were  dominated  bymonoterpenesand/orphenylpropanoids (H. sphondyliumgroup), or(Z)-falcarinol (H. orphanidisandH. austriacum); fruit oils byaliphatic  estersoctylacetate(sect. Heracleum) oroctylhexanoate(H.  austriacum), andleaf  and  flower  oilsby  aliphatic  esters(H.  orphanidis) or  sesquiterpenesand/orphenylpropanoids. Considering   that   in   some   of   these   oils   potentially   phototoxic furanocoumarins  were  detected, safety  profileof  the  oils,  i.e.  their  maximum  daily intake wasestimated.In dichloromethane extracts of underground parts and fruits of investigated taxa,atotal  of 12  furanocoumarins  were  identified(by LC-MS using standard  compoundsorbased onUV, MS, 1H andROESY NMR spectra), among which pimpinellin, bergapten, byakangelicol, heraclenin and/orimperatorinwere dominant. Chemosystematicsignificance   ofessential   oil   components(in   the   case   ofunderground  parts  and  fruits,  of  their headspacefractioncomponents as  well) and furanocoumarinswas demonstrated  usingmultivariatestatistics  (PCA,  nMDS  andUPGMA).In  oily  supernatants  of  fruit dichloromethaneextracts,  by GC-FID and  GC-MS,fatty acids (petroselinic acid was dominant), sterols (β-sitosterolwas the most abundant) and triterpeneswere analysed. Antimicrobialactivity of the essential oilswas showedbymicrodilutionmethodoneightbacteria and eightfungi(in some cases MICs werelower or around0.1 mg/mL); selective cytotoxicityby  MTT  teston cancerHeLa,  LS174 andA549 cells(in  some 
cases IC50werelower or around 30 μg/mL; oils mostly did not inhibit growth ofnormalMRC-5 cells). Essential  oils  showed  weakanti-DPPH  potential. The  composition  of their active zones in TLC-DPPH test was analysed byGC-FID and GC-MS(oxygenated terpenes and phenylpropanoidswere dominant).",
publisher = "Универзитет у Београду, Фармацеутски факултет",
journal = "Универзитет у Београду",
title = "Hemijska i farmakološka karakterizacija odabranih taksona roda Heracleum L. (Apiaceae), autohtonih za jugoistočnu Evropu",
url = "https://hdl.handle.net/21.15107/rcub_nardus_11249"
}
Ušjak, L.. (2019). Hemijska i farmakološka karakterizacija odabranih taksona roda Heracleum L. (Apiaceae), autohtonih za jugoistočnu Evropu. in Универзитет у Београду
Универзитет у Београду, Фармацеутски факултет..
https://hdl.handle.net/21.15107/rcub_nardus_11249
Ušjak L. Hemijska i farmakološka karakterizacija odabranih taksona roda Heracleum L. (Apiaceae), autohtonih za jugoistočnu Evropu. in Универзитет у Београду. 2019;.
https://hdl.handle.net/21.15107/rcub_nardus_11249 .
Ušjak, Ljuboš, "Hemijska i farmakološka karakterizacija odabranih taksona roda Heracleum L. (Apiaceae), autohtonih za jugoistočnu Evropu" in Универзитет у Београду (2019),
https://hdl.handle.net/21.15107/rcub_nardus_11249 .

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