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PROCEEDINGS 47Th International Conference of the Slovak Society of Chemical Engineering Slovak Society of Chemical Engineering Institute of Chemical and Environmental Engineering Slovak University of Technology in Bratislava PROCEEDINGS 47th International Conference of the Slovak Society of Chemical Engineering Institute of Chemical and Environmental Engineering Bratislava, Slovakia May 18 - 19, 2021 Editors: Prof. Jozef Markoš, Dr. Mário Mihaľ ISBN: 978-80-8208-057-8, EAN: 9788082080578 Guzowska, M., Wawrzyniak, R., Wasiak, W., Buczkowska-Chmielewska, K.: Composition of volatile com- pounds in Calypogeia integristipula (Calypogeiaceae, Marchantiophyta), Editors: Markoš, J., Mihaľ, M., In 47th International Conference of the Slovak Society of Chemical Engineering, Bratislava, Slovakia, 2021. 47th International Conference of SSCHE - online conference May 18 - 19, 2021, Bratislava, Slovakia COMPOSITION OF VOLATILE COMPOUNDS IN CALYPOGEIA INTEGRISTIPULA (CALYPOGEIACEAE, MARCHANTIOPHYTA) , M. Guzowska1*, R. Wawrzyniak1W. Wasiak1, B. Jasiewicz1, P. Gonera2, A. Bączkiewicz2, K. Buczkowska2 1Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61-614 Poznań, Poland, e-mail: [email protected] 2Faculty of Biology, Adam Mickiewicz University in Poznań, Umultowska 89, 61-614 Poznań, Poland Keywords: liverworts, Calypogeia integristipula, HS-SPME, gas chromatography, mass spectrometry ABSTRACT Calypogeia is a genus of liverworts in the family Calypogeiaceae. It contains the following species of the genus occurring in Europe: Calypogeia azurea, Calypogeia fissa, Calypogeia muelleriana, Calypogeia integritipula. The subject of the research was Calypogeia integristipula. The plant material for analysis came from Tatry, Pieniny, Beskid Sądecki and Bieszczady Mts., from Wielkopolska and Lubusz provinces and from north-eastern Poland. In general, 23 samples determined as C. integristipula based on morphological characters and oil bodies were examined. The samples were determined genetically based on DNA sequences. The volatile compounds from biological materials were extracted by headspace solid-phase microextraction (HS-SPME) technique. The samples were then analysed on the GC/MS. 93 compounds were detected in total of which 38 compounds were identified. The remaining compounds are described using the MS fragmentation spectrum. In terms of quantity among the identified volatile compounds, compounds belonging to the group of sesquiterpenes (up to 61.53%) and sesquiterpenoids (up to 10.87%) prevail. A smaller amount are compounds belonging to aliphatic compounds (up to 1.58%) and aromatic compounds (up to 4.44%). Unfortunately, monoterpenes and monoterpenoids weren’t identified in the samples tested. The main aim of this study was to select characteristic compounds which enable to differentiate the liverwort species Calypogeia integristipula from the morphologically very similar species Calypogeia neesiana. By comparing the composition of the two species, it was found that they could be distinguished on the basis of their anastreptene content. Calypogeia integristipula contains 4-5 times more of it than Calypogeia neesiana. Acknowledgements: This work was partly supported by a grant National Science Centre no. 2017/27/B/NZ8/01091. We thank the Directors of the Tatra National Parks, Bieszczady National Parks and Pieniny National Parks for their support provided during the fieldwork and sampling of plant material for research.The work was supported by grant no. POWR.03.02.00-00-I020/17 co-financed by the European Union through the European Social Fund under the Operational Program Knowledge Education Development. 1 47th International Conference of SSCHE - online conference May 18 - 19, 2021, Bratislava, Slovakia COMPOSITION OF VOLATILE COMPOUNDS IN CALYPOGEIA INTEGRISTIPULA (CALYPOGEIACEAE, MARCHANTIOPHYTA) M. Guzowska1, R. Wawrzyniak1 , W. Wasiak1, B. Jasiewicz1, P. Gonera2, A. Bączkiewicz2, K. Buczkowska2 1Faculty of Chemistry, Adam Mickiewicz University in Poznań, Umultowska 89b, 61-614 Poznań, Poland, e-mail: [email protected] 2Faculty of Biology, Adam Mickiewicz University in Poznań, Umultowska 89, 61-614 Poznań, Poland Keywords: liverworts, Calypogeia integristipula, HS-SPME, gas chromatography, mass spectrometry ABSTRACT Calypogeia is a genus of liverworts in the family Calypogeiaceae. It contains the following species of the genus occurring in Europe: Calypogeia azurea, Calypogeia fissa, Calypogeia muelleriana, Calypogeia integritipula [1]. The subject of the research was Calypogeia integristipula. Samples of the liverwort Calypogeia integristipula for chemotaxonomic studies were collected from different geographical areas in Poland: Tatras Mts, Pieniny, Beskid Sądecki,The plant material for analysis came from Tatry, Pieniny, Beskid Sądecki and Bieszczady Mts., from Wielkopolska and Lubusz provinces and from north-eastern Poland. In general, 23 samples determined as C. integristipula based on morphological characters and oil bodies were examined. The samples were determined genetically based on DNA sequences. The volatile compounds from biological materials were extracted by headspace solid-phase microextraction (HS-SPME) technique. The samples were then analyzed on the GC/MS. 88 compounds were detected in total of which 38 compounds were identified. The remaining compounds are described using the MS fragmentation spectrum. In terms of quantity among the identified volatile compounds, compounds belonging to the group of sesquiterpenes (up to 61.53%) and sesquiterpenoids (up to 10.87%) prevail. A smaller amount are compounds belonging to aliphatic compounds (up to 1.58%) and aromatic compounds (up to 4.44%). Unfortunately, monoterpenes and monoterpenoids weren’t identified in the samples tested . INTRODUCTION A serious problem in the taxonomy of liverworts, including Calypogeia species, which is considered one of the most difficult genera among liverworts, is the limited number of diagnostically good quality traits due to the low morphological complexity of the gametophyte, as well as the high phenotypic plasticity [1,2]. A unique feature of most liverworts is the presence of oil bodies. Their shape, distribution in leaf and sub leaf cells, and color are important taxonomic features of the genus Calypogeia. Oil bodies are intracellular organelles surrounded by a single unit membrane, in which a wide range of terpenoids and other aromatic compounds are synthesized and accumulated [3-6]. Analysis of the 2 47th International Conference of SSCHE - online conference May 18 - 19, 2021, Bratislava, Slovakia composition of secondary metabolites that fall under the scope of chemotaxonomy can be one of the methods to help identify taxonomically difficult species [7]. The genus Calypogeia (Raddi) comprise about 90 species and represents leafy liverworts from the suborder Jungermanniineae. C. intergristipula is one of 9 species of the genus Calypogeia occurring in Europe. Figure 1 shows the occurrence of liverworts of the genus Calypogeia, which are widespread across almost the entire globe. So far, 65 species belonging to this genus have been identified, seven of which can be found in Poland [8,9] These are Calypogeia azurea, Calypogeia fissa, Calypogeia neesiana, Calypogeia sphagnicola, Calypogeia suecica, Calypogeia muelleriana, and Calypogeia integristipula, the subject of this paper. They are most easily found in mountainous areas, and in lake-rich areas of Pomerania [10]. Fig.1. Locations of liverworts [11]. C. integristipula is a small liverwort that grows in mats or mixed with other bryophytes. Its shoots are at most 3 mm wide and 30 mm long. The leaves are oblong-oval, in two opposite ranks, and usually pale green and rather dull and opaque. The smaller under leaves which occur as a third row on the underside of the stem are almost round (Fig 2) [12]. Calypogeia integristipula morphologically strongly resembles another species close to it - Calypogeia neesiana. Therefore, for a very long time these species were mistakenly considered as one, and only a few years ago their distinctness was recognized [13]. Fig.2. Calypogeia integristipula [12] ANALYTICAL PART 3 47th International Conference of SSCHE - online conference May 18 - 19, 2021, Bratislava, Slovakia Plant material Samples of the liverwort Calypogeia integristipula for chemotaxonomic analysis were collected from different geographical areas in Poland. Table 1 shows the habitats from which the material for the study was collected. Table 1. List of studied samples of C. intergristipula Date of Place on Symbol Collection place sample the map collection CI-107 S Poland, Tatry Mts, Bialka Valley 2006 A CI-110 S Poland, Tatry Mts, Bialka Valley 2006 A CI-217 S Poland, Tatry Mts, The valley of Sucha Woda and Panszczycki Potok 2015 A CI-219 S Poland, Tatry Mts, The valley of Sucha Woda and Panszczycki Potok 2016 A S Poland, Tatry Mts - Dolina Kościeliska, Wąwóz Kraków, Smreczyński Staw, CI-306 2006 A Jaferowy Żleb CI-805 S Poland, Tatry Mts - Sichlanski Stream 2006 A CI-1002 S Poland, Tatry Mts - Capovski Forest 2006 A CI-1006 S Poland, Tatry Mts - Capovski Forest 2006 A CI-1301 S Poland, Tatry Mts - Zolta Turnia, Gąsienicowa Valley 2007 A CI-1401 S Poland, Tatry Mts - Psia Trawka 2010 A CI-1405 S Poland, Tatry Mts - Psia Trawka 2017 A CI-603 S Poland, Beskid Sądecki 2008 B CI-3102 S Poland, Beskid Sądecki - Right tributary of the Kotlovy Stream 2015 B CI-2702 SE Poland, Bieszczady Mts - Rozsypaniec Wołosacki 2008 C CI-2704 SE Poland, Bieszczady Mts - Rozsypaniec Wołosacki 2008 C CI-2801 W Poland, Lubuskie Province - Forestry of Nabłoto, section 84i
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