Izolovanje i identifikacija diarilheptanoida iz biljnih vrsta crna jova (Alnus gltinosa (L.) Gaertn.) i zelena jova (Alnus viridis (Chaix) DC. subsp. viridis) i njihova biološka aktivnost
Isolation and identification of diarylheptanoids from plant species black alder (Alnus gltinosa (L.) Gaertn.) and green alder (Alnus viridis (Chaix) DC. subsp. viridis) and their biological activity

2014
Authors
Novaković, MarkoContributors
Tešević, Vele
Trifunović, Snežana S.

Vajs, Vlatka
Todorović, Nina
Pešić, Milica

Doctoral thesis (Published version)
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Show full item recordAbstract
Rod Alnus Mill. (jove), sa više od 30 vrsta, pripada familiji Betulaceae. Alnusvrste koje rastu u Srbiji su A. glutinosa (crna jova), A. viridis subsp. viridis (zelena jova)i A. incana (siva jova). U ovom radu izolovani su i okarakterisani diarilheptanoidi izkore crne jove i zelene jove i određena je njihova biološka aktivnost.Biljke ovog roda su u tradicionalnoj medicini korišćene u brojne svrhe, kaoalterativi, astringenti, purgativi, emetici, antipiretici, hemostatici, antiparazitici iantihelmintici, za lečenje različitih bolesti, uključujući tumor. Jedinjenja izolovana izjova poseduju širok spektar bioloških aktivnosti, a najvažnija su citotoksična,antitumorska, antivirusna, anti-inflamatorna, antimikrobna i antiparazitska.Vrste roda Alnus su bogat izvor diarilheptanoida. Oni se u biljci prvenstvenonalaze u kori i lišću, kao prosti, glikozidi ili složeni - diarilheptanoid glikozidiesterifikovani različitim fenolnim kiselinama, najčešće cinamičnim. U okviru ovedisertacije iz kora zel...ene i crne jove izolovano je i okarakterisano 39 jedinjenja, odkojih je 19 novih prirodnih proizvoda. Iz zelene jove izolovano je 13 jedinjenja (1-13), aiz crne 28 (1, 5, 14-39), pri čemu su diarilheptanoidi platifilozid (1) i acerozid VII (5)izolovani iz obe biljne vrste. Od 13 jedinjenja izolovanih iz zelene jove, 11 pripadagrupi diarilheptanoida (1-11), od kojih je 6 novih prirodnih proizvoda (3, 7, 8, 9, 11 i13). Svih 28 jedinjenja izolovanih iz crne jove su diarilheptanoidi, a 13 (19, 27, 29-39)je novih. Strukturne karakteristike diarilheptanoida zelene jove su da isključivo imaju phidroksifenilgrupe kao aromatične sisteme i da se, pored prostih, sreću glikozidi koji sesastoje iz mono- i disaharida. Složeni diarilheptanoidi su retki, izolovan je samo jedansa galnom kiselinom (3). Za većinu diarilheptanoida crne jove karakteristično je daimaju bar jednu kateholsku grupu. Od glikozida su zastupljeni isključivo oni samonosaharidnom jedinicom, prvenstveno glukozidi i ksilozidi. Za crnu jovu sukarakteristični složeni diarilheptanoidi sa različitim cinamičnim kiselinama, pretežnoonim sa metoksi grupama...
The genus Alnus Mill. (Alder), with more than 30 species, belongs to theBetulaceae family. Alnus species growing in Serbia are A. glutinosa (black alder), A.viridis subsp. viridis (green alder) and A. incana (gray alder). In this work,diarylheptanoids from the bark of black alder and green alder were isolated andcharacterized, and their biological activity was determined.Plants of this genus have been traditionally used for numerous purposes, e.g. asan alterative, astringent, cathartic, emetic, febrifuge, hemostatic, parasiticide, vermifuge,in the treatment of various diseases, including tumors. Compounds isolated from theAlder species possess a wide spectrum of biological activities and the most importantare cytotoxic, antitumoral, antiviral, anti-inflammatory, antimicrobial and antiparasitic.Alnus species are a rich source of diarylheptanoids. These are predominantlyfound in the bark and leaves as simple diarylheptanoids, glycosides and complexdiarylheptanoids – diarylheptanoid glyco...sides esterified with some phenolic acid, mostcommonly with some cinnamic acid. In this work, 39 compounds were isolated andcharacterized from the barks of green and black alder, of which 19 are new naturalproducts. Thirteen compounds were isolated from green alder (1-13), and 28 from blackalder (1, 5, 14-39), of which diarylheptanoids platyphylloside (1) and aceroside VII (5)were isolated from both species. Of the 13 compounds isolated from green alder, 11belong to diarylheptanoids (1-11) from which 6 are new natural products (3, 7, 8, 9, 11,and 13). All 28 compounds isolated from black alder are diarylheptanoids and 13 (19,27, 29-39) are new. The structural characteristics of the diarylheptanoids isolated fromgreen alder are that they have only p-hydroxyphenyl groups as aromatic systems andthat besides simple diarylheptanoids, diarylheptanoid glycosides are found whichconsist of mono- and disaccharides. Complex diarylheptanoids are rare and only onewas isolated with gallic acid (3). For the most diarylheptanoids isolated from black alderthe presence of at least one catechol moiety as an aromatic component is characteristic...
Keywords:
Alnus glutinosa / Alnus viridis / Betulaceae / Isolation / Identification / Antitumor activity / DNA protective activity / Antimicrobial activity / Diarylheptanoids / Alnus glutinosa / Alnus viridis / Betulaceae / Izolovanje / Diarilheptanoidi / Antitumorska aktivnost / DNK protektivna aktivnost / Antimikrobna aktivnost / IdentifikacijaSource:
Универзитет у Београду, 2014Publisher:
- Универзитет у Београду, Хемијски факултет
Funding / projects:
- Natural products of wild, cultivated and edible plants: structure and bioactivity determination (RS-172053)
URI
http://eteze.bg.ac.rs/application/showtheses?thesesId=3340https://fedorabg.bg.ac.rs/fedora/get/o:11811/bdef:Content/download
http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=47629583
http://nardus.mpn.gov.rs/123456789/6035
https://cherry.chem.bg.ac.rs/handle/123456789/2691
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Hemijski fakultet / Faculty of ChemistryTY - THES AU - Novaković, Marko PY - 2014 UR - http://eteze.bg.ac.rs/application/showtheses?thesesId=3340 UR - https://fedorabg.bg.ac.rs/fedora/get/o:11811/bdef:Content/download UR - http://vbs.rs/scripts/cobiss?command=DISPLAY&base=70036&RID=47629583 UR - http://nardus.mpn.gov.rs/123456789/6035 UR - https://cherry.chem.bg.ac.rs/handle/123456789/2691 AB - Rod Alnus Mill. (jove), sa više od 30 vrsta, pripada familiji Betulaceae. Alnusvrste koje rastu u Srbiji su A. glutinosa (crna jova), A. viridis subsp. viridis (zelena jova)i A. incana (siva jova). U ovom radu izolovani su i okarakterisani diarilheptanoidi izkore crne jove i zelene jove i određena je njihova biološka aktivnost.Biljke ovog roda su u tradicionalnoj medicini korišćene u brojne svrhe, kaoalterativi, astringenti, purgativi, emetici, antipiretici, hemostatici, antiparazitici iantihelmintici, za lečenje različitih bolesti, uključujući tumor. Jedinjenja izolovana izjova poseduju širok spektar bioloških aktivnosti, a najvažnija su citotoksična,antitumorska, antivirusna, anti-inflamatorna, antimikrobna i antiparazitska.Vrste roda Alnus su bogat izvor diarilheptanoida. Oni se u biljci prvenstvenonalaze u kori i lišću, kao prosti, glikozidi ili složeni - diarilheptanoid glikozidiesterifikovani različitim fenolnim kiselinama, najčešće cinamičnim. U okviru ovedisertacije iz kora zelene i crne jove izolovano je i okarakterisano 39 jedinjenja, odkojih je 19 novih prirodnih proizvoda. Iz zelene jove izolovano je 13 jedinjenja (1-13), aiz crne 28 (1, 5, 14-39), pri čemu su diarilheptanoidi platifilozid (1) i acerozid VII (5)izolovani iz obe biljne vrste. Od 13 jedinjenja izolovanih iz zelene jove, 11 pripadagrupi diarilheptanoida (1-11), od kojih je 6 novih prirodnih proizvoda (3, 7, 8, 9, 11 i13). Svih 28 jedinjenja izolovanih iz crne jove su diarilheptanoidi, a 13 (19, 27, 29-39)je novih. Strukturne karakteristike diarilheptanoida zelene jove su da isključivo imaju phidroksifenilgrupe kao aromatične sisteme i da se, pored prostih, sreću glikozidi koji sesastoje iz mono- i disaharida. Složeni diarilheptanoidi su retki, izolovan je samo jedansa galnom kiselinom (3). Za većinu diarilheptanoida crne jove karakteristično je daimaju bar jednu kateholsku grupu. Od glikozida su zastupljeni isključivo oni samonosaharidnom jedinicom, prvenstveno glukozidi i ksilozidi. Za crnu jovu sukarakteristični složeni diarilheptanoidi sa različitim cinamičnim kiselinama, pretežnoonim sa metoksi grupama... AB - The genus Alnus Mill. (Alder), with more than 30 species, belongs to theBetulaceae family. Alnus species growing in Serbia are A. glutinosa (black alder), A.viridis subsp. viridis (green alder) and A. incana (gray alder). In this work,diarylheptanoids from the bark of black alder and green alder were isolated andcharacterized, and their biological activity was determined.Plants of this genus have been traditionally used for numerous purposes, e.g. asan alterative, astringent, cathartic, emetic, febrifuge, hemostatic, parasiticide, vermifuge,in the treatment of various diseases, including tumors. Compounds isolated from theAlder species possess a wide spectrum of biological activities and the most importantare cytotoxic, antitumoral, antiviral, anti-inflammatory, antimicrobial and antiparasitic.Alnus species are a rich source of diarylheptanoids. These are predominantlyfound in the bark and leaves as simple diarylheptanoids, glycosides and complexdiarylheptanoids – diarylheptanoid glycosides esterified with some phenolic acid, mostcommonly with some cinnamic acid. In this work, 39 compounds were isolated andcharacterized from the barks of green and black alder, of which 19 are new naturalproducts. Thirteen compounds were isolated from green alder (1-13), and 28 from blackalder (1, 5, 14-39), of which diarylheptanoids platyphylloside (1) and aceroside VII (5)were isolated from both species. Of the 13 compounds isolated from green alder, 11belong to diarylheptanoids (1-11) from which 6 are new natural products (3, 7, 8, 9, 11,and 13). All 28 compounds isolated from black alder are diarylheptanoids and 13 (19,27, 29-39) are new. The structural characteristics of the diarylheptanoids isolated fromgreen alder are that they have only p-hydroxyphenyl groups as aromatic systems andthat besides simple diarylheptanoids, diarylheptanoid glycosides are found whichconsist of mono- and disaccharides. Complex diarylheptanoids are rare and only onewas isolated with gallic acid (3). For the most diarylheptanoids isolated from black alderthe presence of at least one catechol moiety as an aromatic component is characteristic... PB - Универзитет у Београду, Хемијски факултет T2 - Универзитет у Београду T1 - Izolovanje i identifikacija diarilheptanoida iz biljnih vrsta crna jova (Alnus gltinosa (L.) Gaertn.) i zelena jova (Alnus viridis (Chaix) DC. subsp. viridis) i njihova biološka aktivnost T1 - Isolation and identification of diarylheptanoids from plant species black alder (Alnus gltinosa (L.) Gaertn.) and green alder (Alnus viridis (Chaix) DC. subsp. viridis) and their biological activity UR - https://hdl.handle.net/21.15107/rcub_nardus_6035 ER -
@phdthesis{ author = "Novaković, Marko", year = "2014", abstract = "Rod Alnus Mill. (jove), sa više od 30 vrsta, pripada familiji Betulaceae. Alnusvrste koje rastu u Srbiji su A. glutinosa (crna jova), A. viridis subsp. viridis (zelena jova)i A. incana (siva jova). U ovom radu izolovani su i okarakterisani diarilheptanoidi izkore crne jove i zelene jove i određena je njihova biološka aktivnost.Biljke ovog roda su u tradicionalnoj medicini korišćene u brojne svrhe, kaoalterativi, astringenti, purgativi, emetici, antipiretici, hemostatici, antiparazitici iantihelmintici, za lečenje različitih bolesti, uključujući tumor. Jedinjenja izolovana izjova poseduju širok spektar bioloških aktivnosti, a najvažnija su citotoksična,antitumorska, antivirusna, anti-inflamatorna, antimikrobna i antiparazitska.Vrste roda Alnus su bogat izvor diarilheptanoida. Oni se u biljci prvenstvenonalaze u kori i lišću, kao prosti, glikozidi ili složeni - diarilheptanoid glikozidiesterifikovani različitim fenolnim kiselinama, najčešće cinamičnim. U okviru ovedisertacije iz kora zelene i crne jove izolovano je i okarakterisano 39 jedinjenja, odkojih je 19 novih prirodnih proizvoda. Iz zelene jove izolovano je 13 jedinjenja (1-13), aiz crne 28 (1, 5, 14-39), pri čemu su diarilheptanoidi platifilozid (1) i acerozid VII (5)izolovani iz obe biljne vrste. Od 13 jedinjenja izolovanih iz zelene jove, 11 pripadagrupi diarilheptanoida (1-11), od kojih je 6 novih prirodnih proizvoda (3, 7, 8, 9, 11 i13). Svih 28 jedinjenja izolovanih iz crne jove su diarilheptanoidi, a 13 (19, 27, 29-39)je novih. Strukturne karakteristike diarilheptanoida zelene jove su da isključivo imaju phidroksifenilgrupe kao aromatične sisteme i da se, pored prostih, sreću glikozidi koji sesastoje iz mono- i disaharida. Složeni diarilheptanoidi su retki, izolovan je samo jedansa galnom kiselinom (3). Za većinu diarilheptanoida crne jove karakteristično je daimaju bar jednu kateholsku grupu. Od glikozida su zastupljeni isključivo oni samonosaharidnom jedinicom, prvenstveno glukozidi i ksilozidi. Za crnu jovu sukarakteristični složeni diarilheptanoidi sa različitim cinamičnim kiselinama, pretežnoonim sa metoksi grupama..., The genus Alnus Mill. (Alder), with more than 30 species, belongs to theBetulaceae family. Alnus species growing in Serbia are A. glutinosa (black alder), A.viridis subsp. viridis (green alder) and A. incana (gray alder). In this work,diarylheptanoids from the bark of black alder and green alder were isolated andcharacterized, and their biological activity was determined.Plants of this genus have been traditionally used for numerous purposes, e.g. asan alterative, astringent, cathartic, emetic, febrifuge, hemostatic, parasiticide, vermifuge,in the treatment of various diseases, including tumors. Compounds isolated from theAlder species possess a wide spectrum of biological activities and the most importantare cytotoxic, antitumoral, antiviral, anti-inflammatory, antimicrobial and antiparasitic.Alnus species are a rich source of diarylheptanoids. These are predominantlyfound in the bark and leaves as simple diarylheptanoids, glycosides and complexdiarylheptanoids – diarylheptanoid glycosides esterified with some phenolic acid, mostcommonly with some cinnamic acid. In this work, 39 compounds were isolated andcharacterized from the barks of green and black alder, of which 19 are new naturalproducts. Thirteen compounds were isolated from green alder (1-13), and 28 from blackalder (1, 5, 14-39), of which diarylheptanoids platyphylloside (1) and aceroside VII (5)were isolated from both species. Of the 13 compounds isolated from green alder, 11belong to diarylheptanoids (1-11) from which 6 are new natural products (3, 7, 8, 9, 11,and 13). All 28 compounds isolated from black alder are diarylheptanoids and 13 (19,27, 29-39) are new. The structural characteristics of the diarylheptanoids isolated fromgreen alder are that they have only p-hydroxyphenyl groups as aromatic systems andthat besides simple diarylheptanoids, diarylheptanoid glycosides are found whichconsist of mono- and disaccharides. Complex diarylheptanoids are rare and only onewas isolated with gallic acid (3). For the most diarylheptanoids isolated from black alderthe presence of at least one catechol moiety as an aromatic component is characteristic...", publisher = "Универзитет у Београду, Хемијски факултет", journal = "Универзитет у Београду", title = "Izolovanje i identifikacija diarilheptanoida iz biljnih vrsta crna jova (Alnus gltinosa (L.) Gaertn.) i zelena jova (Alnus viridis (Chaix) DC. subsp. viridis) i njihova biološka aktivnost, Isolation and identification of diarylheptanoids from plant species black alder (Alnus gltinosa (L.) Gaertn.) and green alder (Alnus viridis (Chaix) DC. subsp. viridis) and their biological activity", url = "https://hdl.handle.net/21.15107/rcub_nardus_6035" }
Novaković, M.. (2014). Izolovanje i identifikacija diarilheptanoida iz biljnih vrsta crna jova (Alnus gltinosa (L.) Gaertn.) i zelena jova (Alnus viridis (Chaix) DC. subsp. viridis) i njihova biološka aktivnost. in Универзитет у Београду Универзитет у Београду, Хемијски факултет.. https://hdl.handle.net/21.15107/rcub_nardus_6035
Novaković M. Izolovanje i identifikacija diarilheptanoida iz biljnih vrsta crna jova (Alnus gltinosa (L.) Gaertn.) i zelena jova (Alnus viridis (Chaix) DC. subsp. viridis) i njihova biološka aktivnost. in Универзитет у Београду. 2014;. https://hdl.handle.net/21.15107/rcub_nardus_6035 .
Novaković, Marko, "Izolovanje i identifikacija diarilheptanoida iz biljnih vrsta crna jova (Alnus gltinosa (L.) Gaertn.) i zelena jova (Alnus viridis (Chaix) DC. subsp. viridis) i njihova biološka aktivnost" in Универзитет у Београду (2014), https://hdl.handle.net/21.15107/rcub_nardus_6035 .
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