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IZOLACIJA I KARAKTERIZACIJA BIOAKTIVNIH SEKUNDARNIH METABOLITA IZ ODABRANIH SOJEVA RODA Streptomyces

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IZOLACIJA I KARAKTERIZACIJA BIOAKTIVNIH SEKUNDARNIH METABOLITA IZ ODABRANIH SOJEVA RODA Streptomyces UNIVERZITET U BEOGRADU BIOLOŠKI FAKULTET Nada N. Stanković IZOLACIJA I KARAKTERIZACIJA BIOAKTIVNIH SEKUNDARNIH METABOLITA IZ ODABRANIH SOJEVA RODA Streptomyces Doktorska disertacija Beograd, 2012 UNIVERSITY OF BELGRADE FACULTY OF BIOLOGY Nada N. Stanković ISOLATION AND CHARACTERIZATION OF BIOACTIVE SECONDARY METABOLITES FROM SELECTED Streptomyces STRAINS Doctoral Dissertation Belgrade, 2012 MENTORI: dr Branka Vasiljević, naučni savetnik Institut za molekularnu genetiku i genetičko inženjerstvo, Univerzitet u Beogradu dr Đorđe Fira, vanredni profesor Biološki fakultet, Univerzitet u Beogradu ČLANOVI KOMISIJE: dr Branka Vasiljević, naučni savetnik Institut za molekularnu genetiku i genetičko inženjerstvo, Univerzitet u Beogradu dr Đorđe Fira, vanredni profesor Biološki fakultet, Univerzitet u Beogradu dr Jasmina Nikodinović-Runić, viši naučni saradnik Institut za molekularnu genetiku i genetičko inženjerstvo, Univerzitet u Beogradu DATUM ODBRANE: Ova teza urađena je u Laboratoriji za molekularnu genetiku i ekologiju mikroorganizama u perodu od 2006. – 2012. godine. U toku duge izrade ove teze skoro da nema kolega i zaposlenih u IMGGI koji nisu na neki način doprineli da eksperimntalni rad i laboratorijski život idu glatko i budu lakši. Ja im se na tome iskreno zahvaljujem. Zahvaljujem se dr Đorđu Firi što se (više puta) prihvatio mentorstva nad mojom tezom. Takođe mu se zahvaljujem na kritičkom čitanju i stručnoj oceni teze. Mojim dragim kolegama iz LMGEM, onima koji su ovde i onima koji su otišli negde dalje, posebno se zahvaljujem. Mojim „najstarijim“ koleginicama Tanji, Sandri, Ivani M. za dugogodišnje druženje i deljenje svega kroz šta smo u ovih 14 godina prošli, Lidiji, koleginici iz MBT lab dana, veselom triju Tanja/Lidija/Sanja, Saši, Vanjici, kao i Miloju i Ivani pionirima PKS problematike u ovoj laboratoriji, svima od srca hvala. „Šefici“, dr Branki Vasiljević zahvaljujem se na kolegijalnom i ljudskom odnosu koji ima prema članovima svoje laboratorije, na razumevanju, strpljenju kao i otvorenosti za nove predloge i ideje. Zahvaljujem joj se i na uloženom trudu u oceni ove teze. Jasmini se zahvaljujem jednostavno na svemu. Bez njenog entuzijazma, ideja, energije i truda koji je uložila, ova teza ne bi u ovom obliku ugledala svetlost dana. Mojim najdražima Vladi, Urošu i Irini posvećujem ovu tezu. Zbog njih je sve vredno truda. Oktobar 2012. Izolacija i karakterizacija bioaktivnih sekundarnih metabolita iz odabranih sojeva roda Streptomyces REZIME: Aktinomicete su Gram-pozitivne zemljišne bakterije poznate kao proizvođači bioaktivnih sekundarnih metabolita. U cilju pronalaženja novih bioaktivnih jedinjenja pretraživana je kolekcija aktinomiceta Laboratorije za molekularnu gentiku i ekologiju mikroorganizama Instituta za molekularnu gentiku i genetičko inženjerstvo Univerziteta u Beogradu po više kriterijuma – bioaktivnosti, prisustvu gena za poliketid sintaze (PKS), pigmentaciji i profilu apsorpcije ukupnih ekstrakata kultura u ultraljubičastom i vidljivom (UV/Vis) delu spektra. Na osnovu ovoga izdvojena su tri izolata NP10, JS520 i Streptomyces durmitorensis, od ranije poznati proizvođač didehidroroflamikoina (DDHR). Izolati NP10 i JS520 identifikovani su kao pripadnici roda Streptomyces. Streptomyces sp. NP10 akumulirao je masne kiseline račvastog niza, pre svega izopalmitinsku kiselinu, i ciklične dipeptide sastavljene od prolina u kombinaciji sa valinom, izoleucinom ili alaninom koji su imali stimulativno dejstvo na trofoblastne ćelije u kulturi u niskim koncentracijama (1 ng/ml i 1 µg/ml) i citotoksično dejstvo u visokim (1 mg/ml) koncentracijama. Pokazano je da Streptomyces sp. JS520 ima sposobnost proizvodnje velike količine pigmenta undecilprodigiozina (UP) sa antibakterijskim, antimikotičkim, antioksidativnim i UV protektivnim osobinama koji je imao citotoksično dejstvo na trofoblastne ćelije u kulturi u visokim koncentracijama (1 ng/ml). Citotoksičnost polienskog makrolidnog antibiotika DDHR iz S. durmitorensis je potvrđena, a pokazan je i njegov antimikotički efekat. PKS klaster zadužen za sintezu DDHR je subkloniran u kozmidnu biblioteku i delimično sekvenciran. Optimizacijom uslova gajenja količina proizvedenog UP povećana je 2,12 puta, a DDHR 1,1 puta. KLJUČNE REČI: bioaktivna jedinjenja, sekundarni metaboliti, Streptomyces, pigmenti, undecilprodigiozin, izoalkanske masne kiseline, biciklični peptidi, Streptomyces durmitorensis, PKS. NAUČNA OBLAST: Biologija UŽA NAUČNA OBLAST: Primenjena mkrobiologija UDK BROJ: [579.873.7 : 579.222] (043.3) DODATNA POSEBNA KLASIFIKACIONA OZNAKA ZA DATU OBLAST: Isolation and characterization of bioactive secondary metabolites from selected Streptomyces strains SUMARRY: Actinomycetes are Gram-positive soil bacteria known as producers of secondary bioactive metabolites. In the search for new bioactive compounds collection of actinomycetes from the Laboratory for Microbial Molecular Genetics and Ecology (Institute of Molecular Genetic and Genetic Engineering, University of Belgrade) was screened according to several criteria - bioactivity, the presence of the genes for polyketide synthase (PKS), pigmentation, and crude culture extracts absorption profile in ultraviolet and visible (UV/Vis) spectra. Based on these we have isolated three strains NP10, JS520, and Streptomyces durmitotensis, previously renewed for didehydroroflamicoin (DDHR) production. Isolates NP10 and JS520 were identified to belong to the genus Streptomyces. Streptomyces sp. NP10 accumulated branched chain fatty acids, predominately isopalmitic, and cyclic dipeptides consisting of proline in combination with valine, isoleucine or alanine, that have a stimulating effect on the trophoblast cell line in culture at low concentrations (1 ng/ml and 1 mg/ml) and cytotoxic effect at high concentrations (1 mg/ml). Streptomyces sp. JS520 was determined to be exceptionally good producer of pigment undecylprodigiosine (UP) with antibacterial, antifungal, antioxidant and UV protective activities showing cytotoxic effects on trophoblast cell line in culture at high concentrations (1 ng/ml). Cytotoxicity of polyene macrolide antibiotic DDHR from S. durmitotensis was confirmed and it’s antifungal effects were shown. PKS cluster responsible for DDHR synthesis was subcloned in the cosmid library and partially sequenced. Optimization of culture conditions resulted in 2.12 times increased production of UP, and 1.1 times increased production of DDHR. KEY WORDS: bioactive compounds, secondary metabolites, Streptomyces, pigments, undecylprodigiosine, iso-branched fatty acids, bicyclic peptides, Streptomyces durmitotensis, PKS. SCIENTIFIC FIELD: Biology SCIENTIFIC DISCIPLINE: Applied microbiology UDC NUMBER: [579.873.7 : 579.222] (043.3) Sadržaj 1. Uvod ......................................................................................................................... 1 1.1. Sekundarni metaboliti kao bioaktivna jedinjenja ........................................... 2 1.1.1. Kolekcije bakterija kao izvor novih bioaktivnih jedinjenja ........................... 3 1.1.2. Bakterijska taksonomija i izučavanje sekundarnih metabolita ...................... 5 1.1.3. Molekularna identifikcija bakterijskih izolata .............................................. 6 1.1.4. Novi eseji za detekciju bioaktivnih sekundarnih metabolita - Saccharomyces cerevisiae FAV20 ......................................................................................... 7 1.2. Rod Streptomyces ............................................................................................ 10 1.2.1. Životni ciklus streptomiceta ....................................................................... 11 1.2.2. Organizacija genoma streptomceta ............................................................. 12 1.2.3. Streptomicete kao proizvođači sekundarnih metabolita .............................. 13 1.2.4. Streptomyces durmitorensis MS405T ......................................................... 14 1.3. Sinteza sekundarnih metabolita ..................................................................... 17 1.3.1. Sinteza masnih kiselina i poliketida ........................................................... 17 1.3.1.1. Sinteza masnih kiselina ravnog lanca .................................................. 17 1.3.1.2. Sinteza masnih kiselina račvastog lanca .............................................. 19 1.3.1.3. Sinteza poliketida ................................................................................ 20 1.3.1.4. Poliketid sintaze tipa I (PKS I) ............................................................ 23 1.3.2. Sinteza neribozomalnih peptida (NRPS) .................................................... 27 1.3.3. Sinteza hibridnih sekundarnih metabolita (NRPS/PKS) ............................. 29 1.3.3.1. Red klaster za sintezu undecilprodigiozina .......................................... 31 1.3.4. Regulacija sekundarnog metabolizma kod streptomiceta ............................ 34 2. Cilj rada ................................................................................................................. 36 2.1. Specifični ciljevi rada ..................................................................................... 36 3. Materijal i metode ................................................................................................. 38 3.1. Pretraživanje kolekcije aktinomiceta ............................................................ 38 3.1.1. Medijumi za gajenje streptomiceta ............................................................
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