odseki
departments
-1
Teoretični odsek Theory Department
Na Teoretičnem odseku pristopamo k problemom s področja kemije in sorodnih ved s simulacijskimi in računskimi tehnikami, ki jih tudi sami razvijamo.
Ključne dejavnosti
• računska encimologija, proučevanje izvora ka-talitične funkcije encimov, raziskave farmako-logije centralnega živčnega sistema, načrtova-nje protibakterijskih in protirakavih zdravilnih učinkovin (L01);
• razvoj metodologij strojnega učenja za razvoj zdravilnih učinkovin, ocenjevanja toksičnosti in optimizacije materialov (L03);
• razvoj računskih in spektroskopskih metod za študij molekularnih interakcij in mehaniz-mov (L14);
• večskalno modeliranje in simulacija mehke in biološke snovi, razvoj in uporaba metod za si-mulacijo odprtih molekularnih sistemov (L17).
Glavni dosežki v letu 2020
1. Pridobitev ERC projekta 'Multiscale modeling and simulation approaches for biomedical ultra-sonic applications', usmerjenega v raziskave in-terakcije ultrazvoka z mikromehurčki in podmi-kronskimi plinskimi vezikli v bioloških tekočinah.
Our Department uses
simulation and computational techniques, in part developed on our own, to address
problems in chemistry and related disciplines.
Topic areas
• Computational enzymology; studies of the driving force behind enzyme catalysis; pharma-cology of the central nervous system; design of antibacterial and anticancer drugs (L01).
• Development of machine learning methods for drug design, toxicity assessment and materi-als optimisation (L03).
• Development of computational and spectro-scopic methods for the study of molecular interactions and mechanisms (L14).
• Multiscale modelling and simulation of soft and biological matter; development and application of methods for simulation of open molecular systems (L17).
Important achievements in 2020
1. ERC project 'Multiscale modelling and simula-tion approaches for biomedical ultrasonic appli-cations' aims to design a novel virtual research environment to assist medical applications of ultrasound-guided drug and gene delivery and
D01
Projekt bo z novimi simulacijskimi modeli zago-tovil razumevanje in optimizacijo nadzora ultra-zvočne kontrole dostave zdravil ali aktivacije celic na ciljana mesta v tkivih ter razumevanje fizike pri teh procesih. Raziskave bodo pospešile napredek biomedicinskih ultrazvočnih aplikacij pri zdravlje-nju raka, vnetij, bolezni srca in ožilja ter drugih bolezni (L17).
2. Z večnivojskimi simulacijami smo pojasnili drugi katalitični korak spajanja (ligacija eksona) v spliceosomu, ki poteka preko asociativnega meha-nizma z dvema Mg2+ ionoma, ki ga izključno ka-talizira RNA, pri čemer cepitveni fosfat posreduje pri prenosu protona iz nukleofila do produkta (L03).
3. Odkrili in raziskali smo nove inhibitorje mo-lekulskega motorja človeške DNA topoizomeraze IIα iz razredov substituiranih bitiazolov ter oksa-diazolov, ki izkazujejo dober potencial za razvoj kemoterapevtikov z manj stranskimi učinki. Sode-lovali smo tudi pri identifikaciji prvih dualnih
inhi-imaging. The project will advance therapeutic applications of ultrasound-guided drug and gene delivery and imaging in the treatment of various diseases (L17).
2. Through multiscale simulations, we eluci-dated the second catalytic step of fusion (exon li-gation) in the spliceosome, which takes place via an associative mechanism with two Mg2+ ions, exclusively catalysed by RNA, where the scissile phosphate mediates proton transfer from the nucleophile to product (L03).
3. We discovered new catalytic inhibitors of the human DNA topoisomerase IIα molecular motor from the series of substituted bitiazoles and oxadiazoles. Both show good potential for development of chemotherapeutics with re-duced side effects. We also participated in the identification of dual inhibitors of antiapoptotic proteins Mcl-1 and Bfl-1 as a new paradigm of anticancer therapy (L01).
Vodja / Head:
prof. dr.
Matej Praprotnik
(vodja do 31.8.2020)
prof. dr. Janez Mavri
(vodja od 1.9.2020)
Slika 1: ERC projekt za uveljavljene raziskovalce z naslovom 'Multiscale modeling and simulation approaches for biomedical ultrasonic applica-tions' ali na kratko 'MULTraSonicA' bo usmerjen v raziskave interakcije ultrazvoka z mikromehurčki in pod-mikronskimi plinskimi vezikli v biolo-ških tekočinah.
Figure 1. The ERC Advanced Grant 2019 project entitled 'Multiscale modelling and simulation approach-es for biomedical ultrasonic applica-tions' with the acronym 'MULTraSon-icA' aims to design a virtual research environment to assist medical ap-plications of ultrasound-guided drug and gene delivery and imaging.
bitorjev antiapoptotičnih proteinov Mcl-1 in Bfl-1 kot novi paradigmi protirakave terapije (L01).
4. S simulacijami smo pojasnili mehanizem en-cimske reakcije, ki uravnava presnovo živčnega prenašalca serotonina. Raziskava je pomembna za načrtovanje učinkovin za zdravljenje nevropsi-hiatričnih motenj (L01).
5. S pomočjo homolognega modeliranja in mo-lekularnega sidranja ligandov v 3D strukturo človeškega P-glikoproteina (ABCB1) smo dobili vpogled v vezavo liganda in razpoznali ključne fak-torje v kompleksnem mehanizmu celičnega iztoka toksičnih in kemoterapevtskih spojin (L03).
6. Z NMR spektroskopijo smo ovrednotili vezav-ne interakcije rožmarinske kislivezav-ne in njenih
bioak-4. We elucidated the mechanism of enzymat-ic reaction governing metabolism of the neu-rotransmitter serotonin, which is important for the design of inhibitors used in the treatment of neuropsychiatric disorders (L01).
5. Homology modelling and molecular docking studies of ligands into solved 3D structure of the human P-glycoprotein (ABCB1) provided insights into ligand binding; we identified key factors in a complex mechanism of the cell efflux of either toxic or chemotherapeutic substances (L03).
6. Using NMR spectroscopy, we elucidated the interaction profile of rosmarinic acid and its bio-active substructures with serum albumin as well as the mechanism of transformation of
immuno-Slika 2: (A) Model na osnovi C* kompleksa spliceosoma iz glive Saccharomyces cerevisiae (pdb id: 5YLZ), ki vsebuje številne proteine, RNA fragmente in kovinske ione (Mg2+ ioni so predstavljeni kot rumene sfere). (B) Izsek katalitič-nega mesta s katalitičnimi Mg2+ ioni M1 in M2 in nukleinskih kislin, ki jih koordinirajo. (C) Shematski prikaz drugega koraka spajanja (Borišek et al., ACS Catal., 2020, 10, 9, 5328–5334).
Figure 2. (A) Spliceosome C* complex model built on the structure of the yeast Saccharomyces cerevisiae (pdb id:
5YLZ), comprising various proteins, RNA filaments and metal ions (Mg2+ ions are represented as yellow spheres). (B) Inset of the catalytic site featuring the catalytic Mg2+ ions M1 and M2 and nucleic acids coordinating the metals in the reactant. (C) Schematic representation of the second splicing step. (Borišek et al., ACS Catal. 2020, 10, 9, 5328–5334)
Slika 3: (A) Dinoforni model interakcij med substituiranim 4,5′-bitiazolom in tarčnim ATP vezavnim mestom na člo-veški DNA topoizomerazi IIα. Odkrita spojina ima potencial za nadaljnji predklinični razvoj do varnejših kemotera-pevtikov. (B) Izračunani vezavni konformaciji dualnih inhibitorjev antiapoptotičnih proteinov Mcl-1 in Bfl-1 v vezav-nem mestu Bfl-1 proteina.
Figure 3. (A) Dinophore model of interactions between substituted 4,5′-bitiazole and ATP binding site on the human DNA topoisomerase IIα. The discovered compound has the potential for further preclinical development towards safer chemotherapeutic agents. (B) Calculated binding conformations of two dual inhibitors of antiapoptotic pro-teins Mcl-1 and Bfl-1 in the Bfl-1 protein binding site.
Slika 4: Analiza interakcije 169 fuleren- skih derivatov (FD) z velikim nizom po-tencialnih bioloških tarč (1117 proteinov, ki so povezani z različnimi boleznimi) Figure 4: Analysis of interaction (binding activity) of 169 fullerene derivatives (FD) with large set of disease-related biologi-cal targets (1117 proteins)
genic peptides of myelin glycoprotein and evalu-ated product structure and activity (L14).
7. We elucidated the mechanism for the modi-fied structuring and dynamics of water around solutes (L14).
8. Using vibrational spectroscopy, we participat-ed in the development of new battery systems and synthetic polypeptide scaffolds (L14).
9. Review articles on domain decomposition methods in the field of multiscale modelling of soft materials and on the Adaptive Resolution Simula-tion method and its recent extensions (L17).
10. Causal Network of Diseases (CaNDis), a web server for the exploration of a human causal in-teraction network (L17).
tivnih substruktur s serum albuminom, pojasnili mehanizem transformacije imunogenih peptidov mielinskega glikoproteina ter določili strukturo in aktivnost produktov (L14).
7. Pojasnili smo mehanizem za spremenjeno strukturiranje in dinamiko vode, ki je v stiku s to-pljenci (L14).
8. Z vibracijsko spektroskopijo smo sodelovali pri razvoju novih baterijskih sistemov in sintetič-nih polipeptidsintetič-nih ogrodij (L14).
9. Pregledni članek o numeričnih pristopih za simulacijo kompleksnih tekočin ter o metodi pri-lagodljive ločljivosti AdResS (L17).
10. Spletni strežnik CaNDis za raziskovanje "hu-man causal interaction" mreže (L17).
Raziskovalci / Researchers:
prof. dr. Simona Golič Grdadolnik prof. dr. Marjana Novič
izr. prof. dr. Urban Bren izr. prof. dr. Janez Konc izr. prof. dr. Franci Merzel doc. dr. Andrej Perdih dr. Jure Borišek dr. Amaury Coste dr. Viktor Drgan dr. Natalja Fjodorova dr. Jože Grdadolnik dr. Nikola Minovski dr. Urban Novak dr. Francesca Paoletti dr. Tilen Potisk dr. Jurij Sablić dr. Jaka Sočan dr. Jernej Stare dr. Daniel Svenšek dr. Marjan Tušar dr. Katja Venko dr. Neli Vintar
dr. Marjan Vračko Grobelšek dr. Barbara Zupančič
Doktorski študenti / PhD Students:
Benjamin Bajželj Kaja Bergant Loboda Aljaž Draškovič-Bračun Luka Golob
Barbara Herlah Maja Kokot Anja Kolarič
Liadys Mora Lagares Nikolaos Ntarakas Iza Ogris
Petra Papež Alja Prah Eva Prašnikar Neli Sedej Marko Sever Ema Slejko Janja Sluga
Strokovni sodelavci in tehnično osebje/
Technical Staff:
Erik Kristian Janežič
Zaslužni raziskovalci/Researher Emeritus:
prof. dr. Jure Zupan
Bibliografija Bibliography
36 Izvirnih znanstvenih člankov Original Scientific Articles 1 Pregledni znanstveni članek Review Article
1 Kratki znanstveni prispevek Short Scientific Article 4 Samostojni znanstveni sestavki ali poglavja
v monografskih publikacijah
Independent Scientific Component Parts or Chapters in Monographs
1 Samostojni strokovni sestavek ali poglavje v monografski publikaciji
Independent Professional Component Part or a Chapter in a Monograph
3 Predgovori, spremne besede Prefaces, Afterwords
2 Intervjuja Interviews
2 Univerzitetni, visokošolski ali višješolski učbenik z recenzijo
Reviewed University, Higher Education or Higher Vocational Education Textbooks 1 Objavljeni znanstveni prispevek na konferenci Published Scientific Conference Contribution 1 Objavljeni povzetek znanstvenega prispevka
na konferenci (vabljeno predavanje)
Published Scientific Conference Contribution Abstract (Invited Lecture)
14 Objavljenih povzetkov znanstvenih prispevkov na konferencah
Published Scientific Conference Contribution Abstracts
1 Patentna prijava Patent Application
1 Predavanje na tuji univerzi Invited Lectures at Foreign University 1 Vabljeno predavanje na konferenci
brez natisa Unpublished Invited Conference Lecture
1 Končno poročilo o rezultatih raziskav Final Research Report
1 Elaborat, predštudija, študija Treatise, Preliminary Study, Study
1 Diploma Undergraduate Thesis
5 Magisterijev Master's Theses
1 Doktorat Doctoral Dissertation
15 Uredništev revij Journal Editorships
D04
Študije in razvoj novih
analiznih orodij ter pristopov za elementno (bio)oslikovanje, elektrokemijsko (bio)senzoriko in atmosferske raziskave.
Ključne dejavnosti
• Elektrokemijska senzorika:
Razvoj elektrokemijskih senzorjev in bio-senzorjev ter študije elektrodnih procesov v realnem času, na nano-skali.
• Elementno oslikovanje:
Razvoj 2D/3D elementnega oslikovanja z lasersko ablacijo-ICP-masno spektrometrijo (LA-ICP-MS) in in-situ single-particle (SP) analiznih metod v nano(bio)metalomiki, vključujoč štetje po velikostnih redih, z LA-SP-ICP-MS.
• Atmosferska kemija:
mehanistične in kinetične študije večfaznih kemijskih pretvorb atmosferskih onesnaževal s poudarkom na nastanku rjavega ogljika in staranju sekundarnih organskih aerosolov.
Glavni dosežki v letu 2020
PPredstavili smo tankoslojno bakrovo elektrodo (CuFE), kot občutljiv senzor za detekcijo sledov Ni(II). Senzor je bil pripravljen in-situ, med
me-Studies and development of novel analytical tools and approaches for elemental (bio)imaging, electrochemical (bio)sensing, and atmospheric research.
Topic areas
• Electrochemical Sensing:
Development of electrochemical sensors and biosensors, and study of electrode processes in real-time, at nanoscale.
• Elemental Imaging:
Development of 2D/3D elemental imaging using laser ablation-ICP-mass spectrometry (LA-ICP-MS) and in-situ single-particle (SP) analysis methods in nano(bio)metallomics, including sizing and counting, based on LA-SP-ICP-MS.
• Atmospheric Chemistry:
Mechanistic and kinetic studies of multiphase chemical transformations of atmospheric pollutants with emphasis on brown carbon for-mation and secondary organic aerosol aging.
Important achievements in 2020
We presented a copper film electrode (CuFE) as a sensitive sensor for detection of trace Ni(II). It was prepared directly in-situ on a carbon electrode in
Odsek za
analizno kemijo Department of
Analytical Chemistry
ritvijo, na ogljikovi elektrodi v amonij. pufru (pH 9.2) in v prisotnosti nioksima kot liganda za Ni(II).
Senzor je izkazal nizek LOD (0.2 μg/L) in bil upora-bljen za merjenje Ni(II) v realnem vzorcu morske vode (Sens. Actuators B Chem., 2020).
Razvili smo plinski senzor za fenol s pomočjo Na-poliakrilata (NaPA), ki smo ga nanesli na ti-skano ogljikovo elektrodo. NaPA je služil hkrati kot (i) gelski elektrolit, (ii) akumulacijski milje in (iii) derivatizacijski medij. Senzor je pokazal odlično občutljivost v spodnjem ppbv (μg/m3) območju in
ammon. buffer solution (pH 9.2), in the presence of nioxime as a ligand for Ni(II). Sensor exhibited low LOD of 0.2 μg/L, and was employed for mea-suring Ni(II) in a real sample of seawater (Sens.
Actuators B Chem., 2020).
We developed a phenol gas sensor using Na-polyacrylate (NaPA) deposited on a screen-printed carbon electrode. NaPA served as a (i) gel-like electrolyte, (ii) accumulation milieu, and (iii) de-rivatization medium. Sensor showed excellent sensitivity in the low ppbv (μg/m3) range and linear
Vodja / Head:
dr. Samo Hočevar
Slika 1. Prikaz elektrokemijskega plinskega senzorja in njegovega delovanja za voltametrično detekcijo nizkih kon-centracij plinastega fenola. Senzorska membrana iz Na-poliakrilata služi hkrati kot poltrd gelski elektrolit, akumu-lacijski milje in derivatizacijski medij.
Figure 1. Scheme of the electrochemical gas sensor and its operation for voltammetric detection of low concentra-tion levels of gaseous phenol. The sensing membrane made of Na-polyacrylate serves simultaneously as a semi-solid gel-like electrolyte, accumulation milieu, and derivatization medium.
linearen odziv v območju 0.1-1.0 ppmv pri 105 min akumulacije plinskega analita (ACS Sensors, 2020).
V laserski ablaciji sklopljeni z elementno masno spektrometrijo (LA-ICP-MS) se vse več uporabljajo sistemi z nizko-disperzijskim hitrim transportom aerosola, ki zahtevajo laserje z visoko frekvenco.
Preučevali smo zmogljivost LA enote z eksperi-mentalno 500 Hz lasersko glavo. Sistem je bil pre-izkušen in validiran za elementno oslikovanje z vi-soko ločljivostjo, ki omogoča oslikovanje hitrejše od 1 MPixel/h (J. Anal. At. Spectrom. 2020).
Razvili smo spletno aplikacijo, ki ponazarja sto-hastične procese med analizo kovinskih nanodel-cev v biomatrici z lasersko ablacijo sklopljeno z elementno masno spektrometrijo nanodelcev (LA-Single Particle-ICP-MS). Napoved surove-ga signala, kot funkcijo karakteristik biomatrice, lastnosti inštrumenta in sprememb operacijskih nastavitev, zagotavlja optimalno analizo štetja nanodelcev in njihove velikostne porazdelitve (J.
Anal. At. Spectrom. 2020).
Znano je, da fenoli zlahka reagirajo z OH•. Štu-dirali smo kinetiko in mehanizem adicije OH• na aromatski obroč v vodni fazi. Pokazali smo, da položaj funkcionalnih skupin na obroču določa nasprotujoča si efekta aktivacijske energije in
en-operation in the range of 0.1-1.0 ppmv using 105 min accumulation time (Sensors, 2020).
Low dispersion fast aerosol transport technolo-gies used in laser ablation inductively coupled plasma mass spectrometry (LA-ICP-MS) need high-repetition rate lasers. We studied the analyti-cal performance of a LA unit with an experimen-tal 500 Hz laser head. The system was tested and validated as a high-resolution imaging tool, which allows elemental imaging faster than 1 MPixel/h (J.
Anal. At. Spectrom. 2020).
An online simulation app was developed to mimic the stochastic processes occurring during metal nanoparticle (NP) analysis in biomatrices by laser ablation-single particle-inductively coupled plasma mass spectrometry (LA-SP-ICP-MS). Prediction of the raw signal output as a function of the biomatrix characteristics, instrumental specifications, and variable operational settings warrants for optimal NP counting and sizing (J. Anal. At. Spectrom. 2020).
Substituted phenols are known to readily react with OH•. Kinetics of aqueous-phase reactions and the mechanism of OH• addition to the aromatic ring were investigated. We show that the position of substituents on the ring critically influences the interplay between the activation energy and
en-Slika 2. Naslovnica revije Journal of Analytical Atomic Spectrometry, ki povzema naš članek “Analytical perfor-mance of a high-repetition rate laser head (500 Hz) for HR LA-ICP-QMS imaging” (J. Anal. At. Spectrom., 2020).
Figure 2. Cover of the Journal of Analytical Atomic Spec-trometry featuring our article “Analytical performance of a high-repetition rate laser head (500 Hz) for HR LA-ICP-QMS imaging” (J. Anal. At. Spectrom., 2020).
Slika 3. Posnetek zaslona, ki ponazarja delovanje LA-SP-ICP-MS aplikacije za simulacijo na primeru analize ko-vinskih nanodelcev dveh velikosti in raztopljene/ionske frakcije: surov signal linijskega oslikovanja (levo) in histo-gram velikostne porazdelitve nanodelcev (desno).
Figure 3. Screenshots of the output of the on-line LA-SP-ICP-MS simulation app for analysis of two metal nanopar-ticle sizes and a dissolved/ionic metal background: raw line scan output (left) and associated histogram (right).
Slika 4. 3-metilkatehol (3MC) se v hidratiranih delcih ozračja pretvori v obarvane produkte, ki prispevajo k rjavemu ogljiku in s tem k podnebnim spremembam.
Figure 4. 3-methylcatechol (3MC) in atmospheric hydrated particles transforms into colored Brown Car-bon products and contributes to cli-mate change.
tropije pri tvorbi adukta [OH–phenol]•, kar lahko razložimo le z upoštevanjem solvatacije (Phys.
Chem. Chem. Phys, 2020).
Preučevali smo reakcije 3-metilkatehola (3MC) v vodni fazi v prisotnosti dušikove(III) kisline pri blago kislem pH. 3MC pod vplivom svetlobe raz-pada hitreje kot v temi, pri tem pa nastajajo pro-dukti druge generacije, ki absorbirajo svetlobo v vidnem delu spektra. Pokazali smo, da so atmos-ferske reakcije v vodni fazi lahko pomemben vir rjavega ogljika, ki prispeva k podnebnim spre-membam (Atmosphere, 2020).
tropy of transient [OH–phenol]• adduct formation, which can only be explained if solvation is consid-ered (Phys. Chem. Chem. Phys. 2020).
Aqueous-phase reactions of 3-methylcatechol (3MC) in the presence of nitrous acid at moderate pH were investigated. Under illumination, degrada-tion of 3MC is faster than in the dark, with second-generation products formed exhibiting absorption in the visible range. We showed that atmospheric aqueous-phase reactions may be a significant source of atmospheric brown carbon, which con-tributes to climate change (Atmosphere, 2020).
Raziskovalci / Researchers:
dr. Ahmed Samy Mohamed AbdElAal Kreta
dr. Irena Grgić dr. Ana Kroflič dr. Tea Romih dr. Martin Šala dr. Vid Simon Šelih dr. Johannes Van Elteren dr. Kristijan Vidović
Doktorski študenti / PhD Students:
Ivana Drventić Jelena Isailović Kristina Mervič Dino Metarapi Monika Ogrizek
Strokovni sodelavci in tehnično osebje / Technical Staff:
Breda Novak Iris Štucin Nina Valentič Lidija Živec
Zaslužni raziskovalci / Researher Emeritus:
dr. Božidar Ogorevc
Bibliografija Bibliography
13 izvirnih znanstvenih člankov Original Scientific Articles
1 strokovni članek Professional Article
1 objavljeni znanstveni prispevek na konferenci Published Scientific Conference Contribution 10 objavljenih povzetkov znanstvenih
prispevkov na konferencah
Published Scientific Conference Contribution Abstracts
1 predavanje na tuji univerzi Invited Lectures at Foreign University 1 prispevek na konferenci brez natisa Unpublished Conference Contribution 1 elaborat, predštudija, študija Treatise, Preliminary Study, Study
1 magisterij Master's Thesis
1 doktorat Doctoral Dissertation
3 uredništva revij Journal Editorships
Kako »dobra« je naša hrana?
Ključne dejavnosti
• razvoj novih prehranskih dopolnil in njihovo vrednotenje;
• razvoj in priprava novih oblik naravnih biološko aktivnih spojin, s katerimi se poveča njihova obstojnost in spremenijo nekatere druge last-nosti, ter karakterizacija teh novih materialov;
• razvoj validiranih analiznih metod, večinoma kromatografskih, za potrebe raziskovalnega dela in za naročnike iz industrije in drugih institucij;
• izolacija in identifikacija spojin iz rastlinskih materialov s kromatografskimi in spek-troskopskimi tehnikami;
• izvajanje analiz živil, prehranskih dopolnil, zdravil in bioloških vzorcev.
Glavni dosežki v letu 2020
• Z upoštevanjem osnovnih načel zelene kemije smo razvili trajnosten postopek estrenja ksan-tofilov. Z uporabo različnih kislinskih anhidridov smo z visokimi izkoristki in v čisti obliki pripravili 55 različnih estrov petih ksantofilov (lutein, zea-ksantin, β-kriptozea-ksantin, violaksantin in kapsan-tin). Razvita platforma omogoča, da kot vir ksan-tofilov uporabimo tudi obnovljive naravne vire (odpadni rastlinski materiali, zavržena hrana).
• Razvili in validirali smo metodo GC-FID za kvantitativno določevanje vsebnosti terpenov
How »good« is our food?
Topic areas
• Development of new food supplements and their evaluation;
• Development and preparation of new forms of natural biologically active compounds with en-hanced stability and other certain properties of these compounds, as well as characterisation of these new materials;
• Development of validated analytical methods, mainly chromatographic, for research as well as industry and other institutions;
• Isolation of compounds from plant materials, their identification by means of chromato-graphic and spectroscopic techniques;
• Analysis of foods, food supplements, medicines and biological samples.
Important achievements in 2020
• Following the basic principles of green chem-istry, we developed a sustainable platform for xanthophyll esterification. By using various acid anhydrides, 55 different esters of five xantho-phylls (lutein, zeaxanthin, β-cryptoxanthin, vio-laxanthin and capsanthin) were prepared with high yields and purity. Renewable natural re-sources (waste plant materials, discarded food) can readily be used as xanthophyll sources.
• We developed and validated a GC-FID method for the quantitative determination of terpenes
Odsek za
prehrambeno kemijo Department of Food Chemistry
D06
Slika 1: TLC ločba estrov ksantofila violaksantina, sintetiziranih z novim trajnostnim postopkom esterifikacije, na C18 RP HPTLC plošči. Pripravili smo naslednje estre violaksantina: (1) diacetat, (2) dipropanoat, (3) ditrimetilacetat, (4) divalerat, (5) di(pent-4-enoat), (6) dibenzoat, (7) didekanoat, (8) dipalmitat, (9) dioleat, (10) dipentafloropropanoat in (11) diftalat.
Figure 1. TLC separation of xanthophyll violaxanthin esters synthesised by a new sustainable esterification proced-ure on a C18 RP HPTLC plate. The following violaxanthin esters were prepared: (1) diacetate, (2) dipropanoate, (3) ditrimethyl acetate, (4) divalerate, (5) di (pent-4-enoate), (6) dibenzoate, (7) didecanoate, (8) dipalmitate, (9) dioleate, (10) dipentafluoropropanoate and (11) diphthalate.
Vodja / Head:
dr. Irena Vovk
(v.d. vodje do 18.6.2020)
dr. Samo Hočevar
(v.d. vodje od 19.6.2020
in kanabinoidov v vzorcih navadne konoplje (Cannabis sativa L.). Optimizirali smo pogoje ekstrakcije teh spojin iz rastlinskega materiala.
• Razvili smo HPLC metodo za določanje fenolnih kislin in flavonoidov (aglikoni in glikozilirani) v ekstraktih socvetij kanadske in orjaške zlate rozge. Optimizirali smo tudi pogoje ekstrakcije.
Z analizami hidroliziranih ekstraktov smo po-trdili, da so glikozilirani flavonoidi v socvetjih obeh zlatih rozg glikozidi kvercetina, kaempfe-rola in izoramnetina. S HPTLC-MSn in LC-MSn smo identificirali več fenolnih kislin in flavono-idov, od katerih smo jih prvi identificirali 8 v ka-nadski in 9 v orjaški zlati rozgi.
and cannabinoids from hemp (Cannabis sativa L.). The extraction of cannabinoids from the plant material was also optimised.
• We developed an HPLC method for the deter-mination of phenolic acids and flavonoids (agly-cones and glycosylated) from the extracts of Canadian and giant goldenrod inflorescences.
Analysis of the hydrolysed extracts confirmed that the main aglycons in the inflorescences of the two goldenrods were quercetin, kaempferol and isorhamnetin. Using HPTLC-MSn and LC-MSn, we identified several phenolic acids and flavo-noids, from which 8 in Canadian and 9 in giant goldenrod were identified for the first time.
• V korenikah češkega in sahalinskega dresnika smo kot prvi identificirali naslednje B-tip pro-antocianidine: pentamer galate, heksamere, heksamer galate, nonamere in dekamere. S HPTLC denzitometrijo, analizo slik in masno spektrometrijo smo potrdili, da imajo korenike obeh dresnikov enak kemijski profil proantoci-anidinov glede na stopnjo polimerizacije.
• We were the first to identify the following B-type proanthocyanidins in the rhizomes of Bohemian and giant knotweed: pentamer gal-lates, hexamers, hexamer galgal-lates, nonamers and decamers. HPTLC densitometry, image analysis and mass spectrometry confirmed that rhizomes of both knotweeds have the same proanthocyanidin profile with respect to the degree of polymerisation.
Slika 2: HPTLC (A, B) in HPLC-UV-Vis (C, D) analize fenolnih kislin in flavonoidov v ekstraktih socvetij kanadske (A, C) ter orjaške (B, D) zlate rozge. Oznake vrhov: klorogenska kislina (1), rutin (2), hiperozid (3), izokvercitrin (4), kvercitrin (5).
Figure 2. HPTLC (A, B) and HPLC-UV-Vis (C, D) analyses of phenolic acids and flavonoids in Canadian (A, C) and giant (B, D) goldenrod inflorescences extracts. Peak annotation: chlorogenic acid (1), rutin (2), hyperoside (3), isoquercitrin (4), quercitrin (5).
Slika 3: HPTLC in HPTLC-MS analize B-tipa proantocianidinov rizomov češkega (A) in sahalinskega (B) dresnika.
Figure 3. HPTLC and HPTLC-MS analyses of B-type proanthocyanidins from rhizomes of Bohemian (A) and giant (B) knotweed.