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16 TH INTERNATIONAL SYMPOSIUM ON CAROTENOIDS to develop new systems for its efficient production from novel microalgae Scenedesmus protuberans and Oocystis sp. at industrial scale. For this purpose, the effect of extraction solvent, extraction time, extraction number, saponification time, biomass amount and temperature on lutein content were investigated. The experiments were performed using ultrasonic bath. All extraction and work-up procedures were conducted under yellow light to prevent photo-isomerization and degradation of carotenoids. Internal standard (β-apo-12’-carotenal) calibration method was applied for the determination of lutein content in samples. Analyses were performed by using HPLC-DAD at 446 nm with a flow rate of 1.0 mL/min. Separation was achieved on a YMC Carotenoid (5 μm 4.6×250 mm) column at 25.0°C with gradient elution of methanol, methyl tert-butyl ether and water, each containing 0.1% TEA. Additional identification was carried out comparing the spectral data obtained with diode array detector with the reported values. The results showed that THF:DCM extraction gives the highest lutein yield within 10 minutes. According to the experimental evidence both of the microalgae high lutein content. Therefore, it is concluded that Scenedesmus protuberans and Oocystis sp. have a great potential for large-scale extraction of lutein. In conclusion, the results of this study can be a reference for the extraction of lutein from other microalgae. 3.9. Carotenoids determination in raw eggs of bluefin tuna (Thunnus thynnus) and in their salted product "bottarga" Daniele Giuffrida 1 , Paola Dugo 2 , Manuela Garaffo 1 , Germana Torre 2 , Ioannis Nengas 3 , Robert Vassallo-Agius 4 , Giacomo Dugo 1 1Universita di Messina, Facolta di Scienze MM. FF. NN., Dipartimento di Scienze degli Alimenti e dell'Ambiente, Contrada Papardo, Salita Sperone 31, 98166 Messina, Italy, dgiuffrida@unime.it, dugog@unime.it, mgaraffo@gmail.com 2Universita di Messina, Facolta di Farmacia, Dipartimento farmaco-chimico, Viale Annunziata, 98168, Messina, Italy, pdugo@pharma.unime.it, gtorre@unime.it 3Hellenic Center for Marine Research, Institute of Acquaculture, Laboratory of Fish Nutrition and Pathology, Agios Kosmas, Hellinikon, 16777 Athens, Hellas, Greece, jnegas@ath.hcmr.gr 4Malta Centre for Fisheries Science, MCFS Aquaculture, Fort San Lucjan, Marsaxlokk BBG 1283, Malta, robert.j.vassallo@gov.mt This contribution presents the first investigation on the carotenoids composition in raw eggs and in their salted product, known as "bottarga" in Italian and "karasumi" in Japanese, of wild Atlantic bluefin tuna (ABT) Thunnus thynnus. Tuna eggs, roe from maturing ovaries, and bottarga are both considered a delicacy by the consumers and the study of their carotenoids composition become relevant considering the importance of these micronutrients in our diet and of a precise knowledge of the food composition and quality. Astaxanthin was the main carotenoid detected in the samples investigated with an average content of 7.4 μg/g, w/w; β-cryptoxanthin and β-carotene were also detected in small amounts. Astaxanthin was determined in "bottarga" at a concentration of 0.91 μg/g. Astaxanthin chiral isomers were also directly separated on a chiral column and a distribution of respectively (3S,3'S) 13.1%, (3R,3'S) 47.8%, (3R,3'R) 8.4% astaxanthin isomers in the eggs of wild tuna samples was determined for the first time. This study could also be useful in the formulation of technologically appropriate functional diets for the aquaculture of this species which is seriously endangered by global massive overfishing. 3.10. Determination of carotenoids and their esters in chilli red pepper (Capsicum annuum L.) by comprehensive (LC x LC) liquid chromatography Daniele Giuffrida1 , Paola Dugo2 , Germana Torre2 , Francesco Cacciola2 , Luigi Mondello2 1Università di Messina, Facoltà di Scienze MM. FF. NN., Dipartimento di Scienze degli Alimenti e dell'Ambiente, Contrada Papardo, Salita Sperone 31, 98166 Messina, Italy, dgiuffrida@unime.it 2Università di Messina, Facoltà di Farmacia, Dipartimento farmaco-chimico, Viale Annunziata, 98168, Messina, Italy, pdugo@pharma.unime.it, lmondello@unime.it, gtorre@unime.it The great difficulties that are found when analyzing complex carotenoid samples, due to the high natural variability of these compounds as well as to the presence of carotenoid esters are well documented. Due to the significant higher separation power of comprehensive LC when compared to its 1D counterpart, the technique has experienced large interest in diverse fields, and the number of applications is continuously increasing. More recent trends are towards the implementation of UPLC methods for high efficiency and reduced analysis time, as well as miniaturization of the system to reach higher sensitivity and reduce solvent consumption. In this contribution, new developments in the comprehensive LC instrumentation will be presented, with applications to the analysis of natural products. A dedicated software was developed to directly transform raw LCxLC data into 2D and 3D chromatograms. Retention time values and spectroscopic data were available directly from the 2D chromatogram, making peak identification easier. In particular, UP-LCxLC has been applied to the separation of the native carotenoids present in chilli red peppers. Thirty-five compounds were detected and separated into ten different chemical classes in the 2D plane. The applicability of UP-LCxLC to the separation of xanthophylls bearing keto groups has been shown. The UP-LCxLC separations were used with two different set ups for the second dimension separation; the first set up having two serially connected columns showed a better resolving power compared to the set up having a single column in the second dimension, especially for the separation of mono-esters and free carotenoids. 3.11. Cryptocapsin epoxides, new carotenoids isolated from mamey (Pouteria sapota) SESSION 3 Gergely Gulyás-Fekete 1 , Enrique Murillo 2 , Tibor Kurtán 3 , Tamás Papp 3 , Tünde-Zita Illyés 3 , László Drahos 4 , Attila Agócs 1 , József Deli 1 1University of Pécs, Medical School, Department of Biochemistry and Medical Chemistry, Szigeti út 12, 7624, Pécs, Hungary, gergely.gulyas@aok.pte.hu, attila.agocs@aok.pte.hu, jozsef.deli@aok.pte.hu 2University of Panama, Biochemistry and Nutrition Laboratory, Panama City, Panama, emurillo29@hotmail.com 3University of Debrecen, Faculty of Sciences, Department of Organic Chemistry, Egyetem tér 1, 4032, Debrecen, Hungary, kurtan.tibor@science.unideb.hu, ptomicica@gmail.hu, illyestz@gmail.com 4Institute of Structural Chemistry, Chemical Research Center, Hungarian Academy of Sciences, Pusztaszeri út 59-67, 1025 Budapest, Hungary, drahos@chemres.hu The well known carotenoids containing κ-end group such as capsanthin, capsorubin and cryptocapsin occur mainly in red papri- 56 ACTA BIOLOGICA CRACOVIENSIA Series Botanica
CHEMISTRY, ANALYSIS, CHEMICAL SYNTHESIS, AND INDUSTRIAL PRODUCTION OF CAROTENOIDS ka (Capsicum annuum) (Deli and Molnár, 2002). Capsanthin has also been found in the pollen anthers of Lilium tigrinum and in the fruit of Berberis spp. and Asparagus officinalis. Capsorubin has also been isolated from the integument of Encephalartos altensteinil, the petals of Cajophora lateritia, and the fruits of A. officinalis (Deli et al., 2000). In this year, the isolation of β,κ-carotene-6'-one from a panamian fruit mamey (Pouteria sapota) was published (Murillo et al., 2011). The structure elucidation was performed by MS and NMR. It was also established that the mamey fruit contains some carotenoids with κ-end group and the main carotenoid is cryptocapsin. In this study, we describe the isolation and structure elucidation of natural cryptocapsin 5,6-epoxide, cryptocapsin 5,8epoxides and 3'-deoxy-capsanthin 5,6-epoxide, new carotenoids from the fruits of mamey. The cryptocapsin 5,6-epoxide was also prepared by the epoxidation of cryptocapsin. The structures of the natural and semisynthetic compounds were compared. This study was supported by the grant OTKA K 83898 (Hungarian Scientific Research Foundation). REFERENCES DELI J and MOLNÁR P. 2002. Paprika Carotenoids: Analysis, Isolation, Structure Elucidation. Curr. Org. Chem. 6: 1197-1219. DELI J, MATUS Z, TÓTH G. 2000. Carotenoid Composition in the Fruits of Asparagus officinalis. J. Agr. Food Chem. 48: 2793-2796. MURILLO E, MCLEAN L, BRITTO, G, AGÓCS A, NAGY V, DELI J. 2011. Sapotexanthin, an A-Provitamin Carotenoid Isolated from Mamey (Pouteria sapota). J. Nat. Prod. 74: 283-285. 3.12. Synthesis of carotenoid dimers and trimers Magdolna Háda, Veronika Nagy, Gergely Gulyás-Fekete, József Deli, Attila Agócs Department of Biochemistry and Medical Chemistry, University of Pécs, Medical School, H-7624 Pécs, Szigeti út 12, Hungary, magdolna.hada@aok.pte.hu In the present poster we describe the synthesis of some carotenoid dimers, trimers and their precursors which can serve as a starting point for further studies with other hydroxycarotenoids and form a basis for the synthesis of carotenoid dendrimers. The apocarotenoids retinol and 8'-β-apocarotenol were chosen as model compound for other carotenoids, being not too expensive, easily accesible and bearing a reactive primary hydroxy group. These dentritic structures can have enchanced or altered biological activity and can be used in aggregation studies of carotenoids. Our first aim was to make dicarotenoid diesters of bivalent acids in which secondary interactions are possible between the two polyene chains. To achieve this, retinol and some other carotenoids were esterified with several bivalent acid anhydrides (maleic, succinic and phtalic). These intramolecular anhydrides were chosen after several unsuccessful trials with the corresponding acyl dichlorides [1,2]. This way dimers of retinol with other carotenoids (heterodimers) and dimers of the same carotenoids (homodimers) were synthetized with satisfactory yields [3]. Some podand-like structures bearing a central aromatic moiety were also synthesized from aromatic di- and triacids and hydroxycarotenoids with DCC coupling of the acids and the carotenoid alcohols [4]. Di- and tribenzylic alcohols were coupled by the same manner to carotenoid succinates to give dimers and trimers with acceptable yields. A synthesis of star-like carotenoid trimers with PEG spacers in the arms was elaborated as well to enchance water solubility of the products. Some of the new compounds were tested for their antioxidant activity on human liver cells and showed considerable improvement over native carotenoids. Vol. 53, suppl. 1, 2011 This study was supported by OTKA K 60121 and PD 77467 (Hungarian National Research Foundation). We also thank Carotenature for providing us isozeaxanthin and canthaxathin. REFERENCES FREY DA, KATAISTO EW, EKMANIS JL, O'MALLEY S, LOCKWOOD SF. 2004. Org. Proc. Res. Dev. 8: 796-801. NADOLSKI G, CARDONUEL AJ, ZWEIER JL, LOCKWOOD SF. 2006. Bioorg. Med. Chem. Letters 16: 775-781. HÁDA M, NAGY V, TAKÁTSY A, DELI J, AGÓCS A. 2008. Tetrahedron Lett. 49: 3524-26. HÁDA M, NAGY V, GULYAS-FEKETE G, DELI J, AGÓCS A. 2010. Helv. Chim. Acta 93: 1149-1155. 3.13. 17–22 July 2011, Krakow, Poland Investigation of carotenoid composition in flowers of Chelidonium majus L. with CLC and HPLC techniques Györgyi Horváth1 , Péter Molnár1 , Tímea Takács1 , Erika Turcsi2 , József Deli2 1 Department of Pharmacognosy, Medical School, University of Pécs, Rókus utca 2, H-7624, Pécs, Hungary, gyorgyi.horvath@aok.pte.hu, peter.molnar@aok.pte.hu, tinty@citromail.hu 2 Department of Biochemistry and Medical Chemistry, Medical School, University of Pécs, Szigeti út 12, H-7624, Pécs, Hungary, erika.turcsi@aok.pte.hu, jozsef.deli@aok.pte.hu Chelidonium majus L. (greater celandine) is a member of the family Papaveraceae. The flowers comprise four yellow petals and two sepals. The whole plant is toxic as it contains a range of isoquinoline alkaloids, but there are numerous therapeutic uses when applied at the correct dosage (Szabó, 2005). The current research project aimed at the carotenoid analysis of total extract of the flower of Chelidonium majus L. To the best of our knowledge, we report for the first time the carotenoid composition of this medicinal plant. The fresh flowers were extracted three times with MeOH and once with Et2O. The methanolic extracts were combined and transferred into the mixture of toluene and hexane in a separation funnel. After evaporation of this solution the residue was dissolved in Et2O. The ethereal solutions were combined and this total extract was saponified in heterogeneous phase (30% KOH/MeOH) overnight. The saponified extract was distributed between MeOH : H2O (9:1) and hexane (Schiedt and Liaaen-Jensen, 1995). The partition resulted in a hypophasic and an epiphasic fraction, which were analyzed separately by CLC and HPLC. The carotenoid content of the flowers: 1.1 mg/g wet plant material; 13.6 mg/g dry plant material. In the total extract the identified carotenoids were violaxanthin (13.2%), lutein-5,6-epoxide (69.7%), flavoxanthin + crysanthemaxanthin (5.9%), (9Z)-lutein-5,6-epoxide (6.9%), (13Z) + (13'Z)-lutein-5,6-epoxide (4.3%) and lutein (
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Index of Authors Abe K 44 Abramchik
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ROMEO JT. 1973. A chemotaxonomic st
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