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HYPERICUM THYMOPSIS BOISS. (HYPERICACEAE) ÜZERİNDE FİTOKİMYASAL VE BİYOAKTİVİTE ÇALIŞMALARI Yüksek Lisans Tezi Benan OKYAY Eskişehir 2020 HYPERICUM THYMOPSIS BOISS. (HYPERICACEAE) ÜZERİNDE FİTOKİMYASAL VE BİYOAKTİVİTE ÇALIŞMALARI Benan OKYAY YÜKSEK LİSANS TEZİ Farmakognozi Anabilim Dalı Danışman: Prof. Dr. Nilgün ÖZTÜRK Eskişehir Anadolu Üniversitesi Sağlık Bilimleri Enstitüsü Temmuz 2020 Bu tez çalışması BAP Komisyonunca kabul edilen 1705S340 no.lu proje kapsamında desteklenmiştir. ÖZET HYPERICUM THYMOPSIS BOISS. (HYPERICACEAE) ÜZERİNDE FİTOKİMYASAL VE BİYOAKTİVİTE ÇALIŞMALARI Benan OKYAY Farmakognozi Anabilim Dalı Anadolu Üniversitesi Sağlık Bilimleri Enstitüsü, Temmuz 2020 Danışman: Prof. Dr. Nilgün ÖZTÜRK Bu çalışmada, Sivas-Kangal-Gürün yakınından toplanan endemik Hypericum thymopsis Boiss’in (Hypericaeae) toprak üstü kısımlarından hazırlanan farklı polaritedeki ekstrelerin ve infüzyonun toplam fenolik madde ve toplam flavonoid içerikleri spektrofotometrik metotla, hiperisin, psödohiperisin ve ayrıca fenolik asitlerinin miktarları ters-faz YBSK- DAD ile belirlenmiştir. Ayrıca, ekstrelerin antioksidan aktivitesi DPPH• serbest radikal süpürücü etki, ABTS katyon radikali süpürücü etki, metal şelatlama ve redükleyici güç tayinleri ile, asetilkolinesteraz ve butirilkolinesteraz enzim inhibisyonu aktivite tayinleri ile, antimikrobiyal aktivite tayini broth dilüsyon yöntemi ile; sitotoksitite çalışmalar ise Caco-2 kolon kanseri ve 3T3 hücre hatlarında gerçekleştirilmiştir. Sonuçlar Hypericum perforatum L. sonuçları ile karşılaştırılmıştır. YBSK ile H. thymopsis’in, H. perforatum’a kıyasla daha az miktarda hiperisin ve psödohiperisin; GK-KS/AID tekniği ile başlıca α-pinen, β-pinen, limonen gibi monoterpenler içerdiği tespit edilmiştir. En yüksek toplam fenolik madde ve toplam flavonoid miktarına sahip etil asetat ekstreleri, çalışılan diğer ekstrelerle karşılaştırıldığında, yüksek AChE enzim inhibisyonu, etil asetat ve %70 metanol ekstresi yüksek metal şelatlayıcı; %70 etanollü ekstresi yüksek serbest radikal süpürücü etki; metanol ekstresi ve infüzyonu yüksek redükleyici güç; sulu ekstresi yüksek ABTS radikal katyon renksizleştirici etki gösterdiği görülmüştür. Ayrıca etil asetat ve metanol ekstreleri çalışılan tüm suşlara karşı diğer ekstrelerden daha iyi aktivite gösterirken kloramfenikole göre belirgin antibakteriyel, Candida suşlarına karşıda yine belirgin antifungal aktivite göstermiştir. Ülkemiz endemik türlerinden biri olan H. thymopsis’in psödohiperisin içeriği ile anti-alzheimer, sitotoksik, antifungal ve antibakteriyel aktiviteleri ilk kez bu çalışmada sunulmuştur. Anahtar sözcükler: Hypericum thymopsis Boiss., Antioksidan, Anti-alzheimer, Sitotoksisite, Naftadiantronlar. iii ABSTRACT PHYTOCHEMICAL AND BIOACTIVITY STUDIES ON HYPERICUM THYMOPSIS BOISS. (HYPERICACEAE) Benan OKYAY Department of Pharmacognosy Anadolu University, Graduate School of Health Sciences, July 2020 Supervisor: Prof. Dr. Nilgün ÖZTÜRK In this study, it was determined the amounts of hypericin, pseudohypericin and also phenolic acids by reversed- phase HPLC-DAD, the total phenolic and total flavonoid contents by the spectrophotometric method, of the different polarity extracts and infusions prepared from the aboveground parts of the endemic Hypericum thymopsis Boiss (Hypericaeae) collected near Sivas-Kangal-Gürün. In addition, it were carried out the antioxidant activity of extracts by DPPH• free radical scavenging effect, ABTS cation radical scavenging effect, metal chelation and reductive power determinations anti- alzheimer activities by acetylcholinesterase and butyrylcholinesterase enzyme inhibition activity determinations; antimicrobial activity by broth dilution method, cytotoxicity studies on Caco2 and 3T3 cell lines. The results were compared with Hypericum perforatum L. results. It has been determined that H. thymopsis contain less amount of hypericin and pseudohypericin compared to H. perforatum by the HPLC; volatile terpenes, α-pinene, β- pinene and limonene by the GC-MS/FID technique. Ethyl acetate extracts with the highest total phenolic substance and total flavonoid amount, compared to other extracts studied, while showing high AChE enzyme inhibition, ethyl acetate and %70 methanol extract; %70 ethanol extract high free radical scavenging effect; methanol extract and infusion high reduction power; the aqueous extract has been shown to have high ABTS radical cation decolorizing effect. In addition, while ethyl acetate and methanol extracts showed better activity against all strains studied than other extracts, it showed significant antibacterial activity compared to chloramphenicol and significant antifungal activity against Candida strains. Pseudohypericin content and anti-alzheimer, cytotoxic, antifungal and antibacterial activities of H. thymopsis, one of the endemic species of our country, were presented for the first time in this study. Keywords: Hypericum thymopsis Boiss., Antioxidant, Anti-alzheimer, Cytotoxicity, Naftadiantrons. iv TEŞEKKÜR Tez çalışmam süresince büyük bir sabır ve anlayışla, desteğini benden hiç ̧ esirgemeyen, değerli bilgilerini bana aktaran, danışman hocam, Prof. Dr. Nilgün ÖZTÜRK’e Laboratuvar çalışmalarım sırasında büyük bir sabır ve anlayışla her zaman yanımda olan, bildiğim her şeyi öğreten Dr. Öğr. Hülya Tuba KIYAN hocama, Tez bitkimin teminini sağlayan Trakya Üniversitesi Eczacılık Fakültesi Farmasötik Botanik ABD öğretim üyesi Doç. Dr. Mehmet TEKİN’e Tezimin uçucu bileşenlerinin GK-KS/AID analizlerimi büyük bir özveriyle gerçekleştiren Prof. Dr. Gülmira ÖZEK hocama, Hücre kültürü çalışmalarımda bana laboratuvarını açan, bilgi ve tecrübeleri ile bana yol gösteren Farmakoloji ABD öğretim üyesiProf. Dr. Miriş DİKMEN hocama, Mikrobiyolojik Analizlerimde Bilgi ve tecrübeleri esirgemeyen Mikrobiyoloji ABD öğretim üyesi Doç. Dr. Zerrin CANTÜRK hocama, Her zaman desteğini hissettiğim sevgili anneme, babama ve kardeşim Zeynep’e teşekkürlerimi sunuyorum. Benan OKYAY v 24/07/2020 ETİK İLKE VE KURALLARA UYGUNLUK BEYANNAMESİ Bu tezin bana ait, özgün bir çalışma olduğunu; çalışmamın hazırlık, veri toplama, analiz ve bilgilerin sunumu olmak üzere tüm aşamalarında bilimsel etik ilke ve kurallara uygun davrandığımı; bu çalışma kapsamında elde edilen tüm veri ve bilgiler için kaynak gösterdiğimi ve bu kaynaklara kaynakçada yer verdiğimi; bu çalışmanın Anadolu Üniversitesi tarafından kullanılan “bilimsel intihal tespit programı”yla tarandığını ve hiçbir şekilde “intihal içermediğini” beyan ederim. Herhangi bir zamanda, çalışmamla ilgili yaptığım bu beyana aykırı bir durumun saptanması durumunda, ortaya çıkacak tüm ahlaki ve hukuki sonuçları kabul ettiğimi bildiririm. vi 24/07/2020 STATEMENT OF COMPLIANCE WITH ETHICAL PRINCIPLES AND RULES I hereby truthfully declare that this thesis is an original work prepared by me; that I have behaved in accordance with the scientific ethical principles and rules throughout the stages of preparation, data collection, analysis and presentation of my work; that I have cited the sources of all the data and information that could be obtained within the scope of this study, and included these sources in the references section; and that this study has been scanned for plagiarism with “scientific plagiarism detection program” used by Anadolu University, and that “it does not have any plagiarism” whatsoever. I also declare that, if a case contrary to my declaration is detected in my work at any time, I hereby express my consent to all the ethical and legal consequences that are involved. vii İÇİNDEKİLER Sayfa JÜRİ ENSTİTÜ ONAYI………………………………………………… i FINAL APPROVAL FOR THESIS…………………………………….. ii ÖZET……………………………………………………………………... iii ABSTRACT………………………………………………………………. iv TEŞEKKÜR ……………………………………………………………… v ETİK İLKE VE KURALLARA UYGUNLUK BEYANNAMESİ……. vi STATEMENT OF COMPLIANCE WITH ETHICAL PRINCIPLES vii AND RULES……………………………………………………………… İÇİNDEKİLER…………………………………………………………… viii ÇİZELGELER DİZİNİ………………………………………………….. xi GÖRSELLER DİZİNİ…………………………………………………… xii ŞEKİLLER DİZİNİ……………………………………………………… xiii SİMGELER ve KISALTMALAR DİZİNİ……………………………... xiv 1. GİRİŞ ve AMAÇ……………………………………………………... 1 2. GENEL BİLGİLER…………………………………………………. 5 2.1. Hypericum Türlerinin Genel Özellikleri……………………… 5 2.1.1. Hypericum thymopsis Boiss…………………………….. 6 2.2. Hypericum Türlerinin Fitokimyasal Özellikleri……………… 8 2.2.1. Naftodiantronlar………………………………………... 8 2.2.2. Floroglusinoller…………………………………………. 13 2.2.3. Flavonoidler……………………………………………... 20 2.2.4. Biflavonlar………………………………………………. 28 2.2.5. Proantosiyanidinler……………………………………... 28 2.2.6. Fenolik asitler…………………………………………… 29 2.2.7. Terpenler………………………………………………... 32 2.2.8. Uçucu yağlar…………………………………………….. 33 2.3. Hypericum Türlerinin Biyolojik Aktiviteleri…………………. 36 viii Sayfa 2.3.1. Antioksidan aktivite…………………………………... 36 2.3.2. AChE ve BChE enzim inhibisyonu aktiviteleri …….. 39 2.3.3. Antimikrobiyal aktivite……………………………….. 43 2.3.4. Sitotoksik aktivite……………………………………... 47 2.3.5. Antidepresan aktivite…………………………………. 55 3. YÖNTEM……………………………………………………………. 57 3.1. Bitki Materyali…………………………………………………. 57 3.2. Kimyasal Maddeler ve Cihazlar………………………………. 58 3.2.1. Kimyasal maddeler…………………………………….. 58 3.2.2. Cihazlar…………………………………………………. 59 3.3. Bitki Ekstrelerinin Hazırlanması……………………………... 60 3.4. Toplam Fenolik Madde Miktarı………………………………. 62 3.5. Toplam Flavonoid Miktarı……………………………………. 63 3.6. YBSK ile Fenolik Asitlerin Miktar Tayini…………………… 63 3.7. YBSK ile Hiperisin ve Psödohiperisin Miktar Tayini……….. 64 3.8. GK-KS/AID ile Uçucu Yağ Bileşimi Tayini………………….. 65 3.9. Antioksidan
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  • Toxicity Assessment of Hypericum Olympicum Subsp. Olympicum L. On

    Toxicity Assessment of Hypericum Olympicum Subsp. Olympicum L. On

    J Appl Biomed journal homepage: http://jab.zsf.jcu.cz DOI: 10.32725/jab.2020.002 Journal of Applied Biomedicine Original research article Toxicity assessment of Hypericum olympicum subsp. olympicum L. on human lymphocytes and breast cancer cell lines Necmiye Balikci 1, Mehmet Sarimahmut 1, Ferda Ari 1, Nazlihan Aztopal 1, 2, Mustafa Zafer Özel 3, Engin Ulukaya 1, 4, Serap Celikler 1 * 1 Uludag University, Faculty of Science and Arts, Department of Biology, Bursa, Turkey 2 Istinye University, Faculty of Science and Literature, Department of Molecular Biology and Genetics, Istanbul, Turkey 3 University of York, Department of Chemistry, Heslington, York, United Kingdom 4 Istinye University, Faculty of Medicine, Department of Medical Biochemistry, Istanbul, Turkey Abstract There is a limited number of studies about the constituents ofHypericum olympicum subsp. olympicum and its genotoxic and cytotoxic potency. We examined the possible antigenotoxic/genotoxic properties of methanolic extract of H. olympicum subsp. olympicum (HOE) on human lymphocytes by employing sister chromatid exchange, micronucleus and comet assay and analyzed its chemical composition by GCxGC-TOF/MS. The anti-growth activity against MCF-7 and MDA-MB-231 cell lines was assessed by using the ATP viability assay. Cell death mode was investigated with fluorescence staining and ELISA assays. The major components of the flower and trunk were determined as eicosane, heptacosane, 2-propen-1-ol, hexahydrofarnesyl acetone and α-muurolene. HOE caused significant DNA damage at selected doses (250–750 µg/ml) while chromosomal damage was observed at higher concentrations (500 and 750 µg/ml). HOE demonstrated anti-growth activity in a dose-dependent manner between 3.13–100 µg/ml.
  • Výměna Semen

    Výměna Semen

    Příloha časopisu Klubu skalničkářů Praha VÝMĚNA SEMEN INDEX SEMINUM 2014–2015 Příloha časopisu Klubu skalničkářů Praha Klub skalničkářů Praha Vám předkládá Index seminum – seznam semen rostlin pro rok 2014 – 2015 (Index). Tento seznam obsahuje přehled semen, která nabízejí do výměny členové našeho klubu, včetně zahraničních členů. Děkujeme všem, kteří zaslali semena k výměně. Umožnili tak dalším skalničkářům rozšířit si tak sortiment pěstovaných rostlin. Jako každoročně jsme ověřili jména všech Vámi dodaných položek za pomoci dostupné literatury a internetu. Zřetelné zkomoleniny jsme opravili, neověřitelná jména jsme v Indexu ponechali bez úprav a označili znaménkem +. Znovu žádáme dárce, aby si zkontrolovali názvy rostlin, jejichž semena dávají do výměny, aby se chyby v příštích výměnách již neopakovaly. Bohužel i letos se opět vyskytly stejné chyby, nejen pravopisné, ale i věcné, jako v seznamech minulých! Chtěli bychom poděkovat všem, kteří zaslali čitelný seznam darovaných semen v abecedním pořadí. Ještě větší poděkování patří těm, kteří seznam poslali elektronicky. Tato – pro Vás jistě maličkost – nám velmi usnadnila zpracování tohoto seznamu na počítači. Počítačové zpracování také umožňuje doplňovat Index i z opožděných zásilek až do doby předání textu tiskárně k vlastnímu vytištění Indexu. Letošní Index obsahuje ty druhy rostlin, které došly do 20. listopadu, přestože uzávěrka byla do konce října. Pro příští rok bychom opět přivítali zasílání seznamů elektronicky, nejlépe v programu Excel. Řada z Vás tak činí již třetím rokem. Tato „drobnost“ značně ulehčila redakční práce při přípravě Indexu. Jména dárců, resp. jejich čísla podle pořadí jak došly zásilky, jsou již tradičně uvedena za latinským názvem rostliny. Podmínky výměny semen 1. Dárcem se stává ten, který zaslal minimálně 10 druhů semen.
  • LC-MS and LC-PDA Analysis of Hypericum Empetrifolium and Hypericum Sinaicum Feras Q

    LC-MS and LC-PDA Analysis of Hypericum Empetrifolium and Hypericum Sinaicum Feras Q

    LC-MS and LC-PDA Analysis of Hypericum empetrifolium and Hypericum sinaicum Feras Q. Alalia,*, Khaled Tawahab, and Mohammad Gharaibehc a Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Al Isra Private University, P. O. Box 22, 33, Amman 11622, Jordan. E-mail: [email protected] b Department of Pharmaceutical Sciences, Faculty of Pharmacy, University of Jordan, Amman 11942, Jordan c Department of Natural Resources and Environment, Faculty of Agriculture, Jordan University of Science and Technology, P. O. Box 3030, Irbid 22110, Jordan * Author for correspondence and reprint requests Z. Naturforsch. 64 c, 476 – 482 (2009); received February 25/March 26, 2009 Within the framework of our continuous efforts to explore Hypericum species from Jor- dan, we report the analysis of the major active metabolites, naphthodianthrones and phloro- glucinols, in the methanolic extracts of two under-explored Hypericum species; H. empetri- folium Willd. and H. sinaicum Hochst. & Steud. ex Boiss., using LC-(+,–)-ESI-MS (TIC and SIM) and LC-UV/Vis spectroscopy. Based on their LC-UV/Vis profi les, retention times and (+,–)-ESI-MS (TIC and SIM) spectral data, hypericin, protohypericin and pseudohypericin were identifi ed in both of the investigated species. In addition adhyperfi rin was only de- tected in H. empetrifolium, while hyperforin and protopseudohypericin were only detected in H. sinaicum. This is the fi rst report documenting the presence of hypericin, protohypericin, pseudohypericin, protopseudohypericin, and hyperforin in H. sinaicum, and adhyperfi rin in H. empetrifolium. Key words: Hypericum, Naphthodianthrones, Phloroglucinols Introduction species of Hypericum can be identifi ed by: (i) op- posite simple entire exstipulate leaves contain- Hypericum is a genus of about 450 species ing translucent and often black or red glandular of herbs or shrubs belonging to the family Clu- secretions; (ii) fl owers with a 5-merous perianth siaceae, formerly Hypericaceae.
  • Die Soinmerflora Des Antilibanon

    Die Soinmerflora Des Antilibanon

    © Zool.-Bot. Ges. Österreich, Austria; download unter www.biologiezentrum.at Die Soinmerflora des Antilibanon. Yon Dr. Theodor Kotschy. Vorgetragen in der Sitzung vom 6- November 1861. -L'as Land Syrien, von Nord nach Süd langgestreckt, im West vom Mittel- meer, im Ost von der einem Sandmeere gleichenden Wüste begrenzt, bildet ein natürliches Verbindungsglied zwischen dem Hochlande des Tauriisgebietes und dem Tieflande Egypten's. Drei Gebirgketten sind es, welche ihm wesentlich seine plastische Gestaltung geben: der Amanus, Libanon und Antilibanon. Ihre Berg- züge, Hochrücken, Gipfelreihen und Thalspalten folgen vorzugsweise der Längenachse des Landes. Der Jordan und Orontes sind Gegenströme und ihre Normalrichtung bezeichnet den Parallelismus der Hauptthäler Syrien's. Dieses Land, dessen folgenreiche Geschichte einen so entschiedenen Einfluss auf die ganze übrige Welt genommen hat, zeigt im Osten beider Hauptströme ein Binnenland mit einer Plateaufläche bei 1200—2000 Fuss mittlerer Höhe über dem Meer, von weit gegen Osten hin gleichförmiger Ausdehnung. Die Westgrenzen bildet ein Küstensaum, niedrig gelegen und mehr oder minder breit.' Zwischen beiden liegt als Mittelglied der aus den drei genannten Gruppen bestehende Gebirgszug, wechselnd an mannigfaltiger Gestaltung und. Erhebung bis zu der Höhe von 9500 Fuss. Durch die Verschiedenheit der geognostischen Unterlage unterscheiden sich diese drei Bergsysteme in ihrem Baue von einander. Der Amanus weicht-von den beiden südlichen Ketten, welche vor- herrschend aus Kalkstein bestehen, gänzlich ab, indem bei seiner Entste- hung grösstentheils plutonische Eruptionen thätig waren. Die Höhen sind theilweise abgerundet, theilweise mehr ausgezeichnet kantig, ja im nörd- lichen Theil kegelförmig und steigen sogar im Duldul nadelartig auf. Der südliche Theil hat einen trachytischen Charakter aus Aphauit, Serpentin, Euphotid im Hauptzug , der übrige Theil wechselt mit crystallinischen und massigen Gesteinen und den Gebilden aus der Kreidereihe ab.
  • NVEO 2019, Volume 6, Special Issue

    NVEO 2019, Volume 6, Special Issue

    NVEO 2019, Volume 6, Special Issue CONTENTS Wellcome address of the Presidents of the Local Organizing Committee......... 2 ISEO 2019 Committees....................................................................................... 3 ISEO Medal of Honour........................................................................................ 4 IFEAT - Young Scientists Fellowship.................................................................... 5 NVEO 2019 Editorial........................................................................................... 6 Scientific Programme......................................................................................... 8 List of Poster Presentations................................................................................ 12 Abstracts............................................................................................................. 18 Sponsors............................................................................................................. 186 50th International Symposium on Essential Oils (ISEO2019) Key of Abbreviations: WS workshop WL welcome lecture PL plenary lecture IS invited speaker OP oral presentation YS young scientist presentation PD panel discussion PP poster presentation YS PP young scientist poster presentation All abstracts are from the 50th International Symposium on Essential Oils (ISEO2019) Abstract Book By Editors: Johannes Novak & Iris Stappen are adapted to the NVEO –ISEO 2019 Special Issue e-ISSN: 2148-9637 Nat. Vol. & Essent. Oils, 2019, 6