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“Fitohemijska Analiza I Biološka Aktivnost Ferulago Macedonica UNIVERZITET U BEOGRADU BIOLOŠKI FAKULTET Ksenija S. Mileski “Fitohemijska analiza i biološka aktivnost Ferulago macedonica Micevski et Mayer, Echinophora sibthorpiana Guss., Laserpitium ochridanum Micevski, Heracleum orphanidis Boiss. i Angelica pancicii Vandas (Apiaceae)“ -Doktorska disertacija- Beograd, 2017 UNIVERSITY OF BELGRADE FACULTY OF BIOLOGY Ksenija S. Mileski “Phytochemical analysis and biological activity of Ferulago macedonica Micevski et Mayer, Echinophora sibthorpiana Guss., Laserpitium ochridanum Micevski, Heracleum orphanidis Boiss. and Angelica pancicii Vandas (Apiaceae)“ -Doctoral dissertation- Belgrade, 2017 Komisija za ocenu i odbranu doktorske disertacije: dr Ana Džamić, vanredni profesor, mentor Univerzitet u Beogradu - Biološki fakultet __________________________________ dr Petar Marin, redovni profesor, mentor Univerzitet u Beogradu - Biološki fakultet __________________________________ dr Snežana Trifunović, viši naučni saradnik Univerzitet u Beogradu - Hemijski fakultet __________________________________ dr Ana Ćirić, viši naučni saradnik Univerzitet u Beogradu - Institut za biološka istraživanja „Siniša Stanković“ __________________________________ akademik Vlado Matevski, redovni profesor Univerzitet „Sv. Kiril i Metodij“ - Prirodno-matematički fakultet __________________________________ Datum odbrane: ________________ Zahvalnica Ovim putem želim da se zahvalim svim osobama koje su na bilo koji način pomogle u izradi ove doktorske disertacije. Pre svega, zahvaljujem se mentorima; prof. dr Ani Džamić, koja me je uvela u svet lekovitih i aromatičnih biljaka, pomogla u izboru teme, radu i realizaciji njenih ciljeva i prof. dr Petru Marinu na ukazanom poverenju da učestvujem na projektu, kao i na pomoći pri koncipiranju i izradi teme. Takođe, zahvaljujem dr Ani Ćirić na pomoći i savetima pri određivanju antimikrobne i anti-quorum sensing aktivnosti biljaka u okviru ovog rada. Veliko hvala dr Snežani Trifunović na stručnoj pomoći oko hemijskih analiza ekstrakata koje su doprinele kvalitetu ove disertacije. Iskrenu zahvalnost dugujem i kolegama sa Prirodno matematičkog fakulteta u Skoplju na pomoći pri sakupljanju biljnog materijala, a naročito akademiku prof. dr Vladi Matevskom na toploj dobrodošlici i pomoći oko determinacije biljaka. Zahvaljujem se dr Mihailu Ristiću bez koga analiza hemijskog sastava etarskih ulja u ovom radu ne bi bila moguća. Mr. Željani Šakić hvala na pomoći u eksperimentalnom radu i pisanju dela teze o hemijskom sastavu ekstrakata i Prof. dr Veletu Teševiću što mi je omogućio rad na Hemijskom fakultetu na Katedri za organsku hemiju. Hvala i kolegama sa Katedre za morfologiju i sistematiku biljaka, naročito prof. dr Sonji Duletić-Laušević, dr Slavici Grujić, Jasmini Gradojević, dr Ani Alimpić i Ivoni Veličković. Zahvaljujem se Ministarstvu prosvete, nauke i tehnološkog razvoja Republike Srbije koje je finansiralo projekt br. 173029 u okviru kojeg je realizovana izrada ove disertacije. Deo istraživanja urađen je zahvaljujući projektima br. 172053 i 173021. Posebno veliku zahvalnost dugujem svoj porodici i prijateljima za neizmernu podršku i nesebičnu pomoć i razumevanje tokom svih ovih godina. Ksenija Mileski Institicije u kojima je rađena doktorska disertacija: ► Katedra za morfolofiju i sistematiku biljaka, Institut za botaniku i Botanička bašta „Jevremovac“, Biološki fakultet, Univerzitet u Beogradu ► Mikološka laboratorija, Odeljenje za fiziologiju biljaka, Institut za biološka istraživanja „Siniša Stanković“, Univerzitet u Beogradu ► Institut za proučavanje lekovitog bilja „Dr Josif Pančić“, Beograd ► Katedra za organsku hemiju, Hemijski fakultet, Univerzitet u Beogradu Fitohemijska analiza i biološka aktivnost Ferulago macedonica Micevski et Mayer, Echinophora sibthorpiana Guss., Laserpitium ochridanum Micevski, Heracleum orphanidis Boiss. i Angelica pancicii Vandas (Apiaceae) REZIME Osnovni cilj ove doktorske disertacije je karakterizacija hemijskog sastava etarskih ulja i ekstrakata retkih i endemičnih vrsta iz Republike Makedonije koje su delimično ili potpuno neistražene: Ferulago macedonica Micevski et Mayer, Echinophora sibthorpiana Guss., Laserpitium ochridanum Micevski, Heracleum orphanidis Boiss. i Angelica pancicii Vandas (Apiaceae). Drugi deo ovog istraživanja odnosi se na utvrđivanje in vitro biološkog potencijala etarskih ulja, metanolnih, etanolnih i vodenih ekstrakata navedenih vrsta i to njihovog antioksidativnog, antimikrobnog i anti-quorum sensing dejstva. U ovom radu su prvi put predstavljeni rezultati hemijske analize etarskih ulja vršnog i nadzemnog dela F. macedonica kao i metanolnih ekstrakata nadzemnog dela i korena vrsta H. orphanidis i A. pancicii. Do sada nije bilo ni literaturnih podataka o biološkim aktivnostima vrsta F. macedonica, H. orphanidis i A. pancicii. GC-FID i GC-MS analiza sastava etarskih ulja proučavanih vrsta pokazala je dominantno prisustvo monoterpenskih i seskviterpenskih ugljovodonika i njihovih oksidovanih formi. Ove analize su pokazale da su etarska ulja vršnog i nadzemnog dela F. macedonica bogata α-pinenom (43,10%; 22,78%) i sabinenom (26,73%; 15,46%). Za etarsko ulje E. sibthorpiana karakteristično je prisustvo velike koncentracije metil eugenola (60,40%), p-cimena (11,18%) i α-felandrena (10,23%), a za etarsko ulje L. ochridanum veliki sadržaj sabinena (22,8%), viridiflorola (14,7%) i α-pinena (11,4%). U etarskom ulju H. orphanidis kao glavna jedinjenja identifikovani su n-oktanol (39,57%), n-oktil heksanoat (17,62%) i n-oktil acetat (14,12%), dok su bornil acetat (8,08%), n-oktanol (5,82%), kesan (4,26%) i β-selinen (4,25%) najzastupljenije komponente etarskog ulja A. pancicii. Rezultati tentativne analize sastava metanolnih ekstrakata odabranih vrsta, dobijenih pomoću HPLC-DAD/ESI-ToF-MS sistema, prvi put su predstavljeni i opisani u ovoj disertaciji. Identifikacija sekundarnih metabolita ekstrakata urađena je na osnovu molekulske formule dobijene korišćenjem Mass Hunter Workstation softvera za prikupljanje i obradu podataka i na osnovu literaturnih podataka o hemijskom sastavu vrsta odgovarajućih rodova i predstavnika drugih rodova familije Apiaceae. U metanolnim ekstraktima F. macedonica, E. sibthorpiana i L. ochridanum identifikovan je mali broj komponenata ili identifikacija jedinjenja nije bila moguća zbog nedostatka literaturnih podataka. Preliminarnom analizom identifikovano je 18 jedinjenja u metanolnom ekstraktu nadzemnog dela H. orphanidis i 25 jedinjenja u korenu ove biljke, dok je u metanolnom ekstraktu nadzemnog dela A. pancicii identifikovano 52, a u korenu 53 metabolita. Kumarini su bili najzastupljenija klasa jedinjenja u analiziranim uzorcima. Iz korena vrste A. pancicii izolovano je 6 poznatih furanokumarina: tert-O-metil-oksipeucedanin hidrat, oksipeucedanin hidrat, oksipeucedanin, saksalin, ostrutol, izoimperatorin i prvi put je izolovan hromon acetilknidimol A. Spektrofotometrijskim metodama najveći ukupan sadržaj fenola izmeren je u etanolnom ekstraktu nadzemnog dela A. pancicii (143,990 mg GA/g suvog ekstrakta), a flavonoida u etanolnom ekstraktu L. ochridanum (67,690 mg QE/g suvog ekstrakta). U ovom radu se pokazalo da je vršni deo F. macedonica bio bogatiji fenolnim jedinjenja od nadzemnog dela biljke, dok je kod ostalih vrsta koncentracija ovih metabolita bila veća u nadzemnom delu u odnosu na koren biljke. Etarska ulja i ekstrakti proučavanih vrsta su primenom tri različita antioksidativna testa pokazali dozno zavisnu sposobnost u neutralisanju slobodnih radikala. Najefikasniji u neutralizaciji slobodnih radikala u DPPH testu bili su ekstrakti vrste L. ochridanum (0,115-0,127 mg/mL), slično pokazanoj aktivnosti sintetičkih antioksidanasa BHA i BHT. Pregled rezultata dobijenih korišćenjem ABTS testa pokazao je da je etarsko ulje E. sibthorpiana (c=0,1 mg/mL) posedovalo najjaču antioksidativnu aktivnost (2,021 mg vit. C/g etarskog ulja), dok je od svih ispitivanih ekstrakata (c=1 mg/mL) najefikasniji bio vodeni ekstrakt nadzemnog dela L. ochridanum (2,172 mg vit. C/g suvog ekstrakta), slično dejstvu standarda kvercetin hidrata. Kao najefektivniji antioksidativni agens u β-karoten/linolna kiselina testu pokazao se metanolni ekstrakt nadzemnog dela A. pancicii (IC50=2,453 mg/mL), dok je antioksidans BHA pokazao duplo jači efekat (IC50=1,216 mg/mL). Metodom mikrodilucije određene su antimikrobne aktivnosti testiranih uzoraka protiv 16 vrsta patogenih mikroorganizama i determinisane su MIK, MBK/MFK koncentracije etarskih ulja i ekstrakata odabranih vrsta. Testirani uzorci su ispoljili umerenu antibakterijsku aktivnost u poređenju sa antibiotikom streptomicinom, a etarska ulja su imala jače dejstvo u odnosu na ekstrakte. Metanolni i etanolni ekstrakti korena A. pancicii i etarsko ulje H. orphanidis imali su jako inhibitorno dejstvo na rast bakterija, slično aktivnosti streptomicina. Najosetljivije bakterije u ovom radu bile su B. cereus i S. aureus, dok su najrezistentnije bile M. flavus, P. aeruginosa, L. monocytogenes i E. coli. Uporedni pregled rezultata antifungalne aktivnosti implicirao je slabo do umereno dejstvo testiranih ektrakata i umerenu do jaku efikasnost etarskih ulja. Kao najjači antifungalni agensi izdvojili su se metanolni ekstrakti korena H. orphanidis i vršnog dela F. macedonica i etanolni ekstrakt korena A. pancicii, a među etarskim uljima je to bio uzorak ulja vrste L. ochridanum. Najsenzitivnije mikrogljive korišćene u ovom istraživanju bile su P. ochrocloron, A. versicolor i T. viride, a najotpornije A. niger i A. ochraceus. U okviru ovog istraživanja određena je i anti-quorum
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