Bioprospecting of Less-Polar Constituents from Endemic Brown Macroalga Fucus virsoides J. Agardh from the Adriatic Sea and Targeted Antioxidant Effects In Vitro and In Vivo (Zebrafish Model)

The endemic brown macroalga Fucus virsoides J. Agardh from the Adriatic Sea was in the focus of the present research. The volatiles of fresh (FrFv) and air-dried (DrFv) samples of F. virsoides obtained by headspace solid-phase microextraction (HS-SPME) and hydro...

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Main Authors:	Igor Jerković, Ana-Marija Cikoš, Sanja Babić, Lara Čižmek, Krunoslav Bojanić, Krunoslav Aladić, Nikolay V. Ul’yanovskii, Dmitry S. Kosyakov, Albert T. Lebedev, Rozelindra Čož-Rakovac, Polonca Trebše, Stela Jokić
Format:	Article
Language:	English
Published:	MDPI AG 2021-04-01
Series:	Marine Drugs
Subjects:	brown algae volatiles fatty acids pigments bioassays embryotoxicity
Online Access:	https://www.mdpi.com/1660-3397/19/5/235

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collection	DOAJ
language	English
format	Article
sources	DOAJ
author	Igor Jerković Ana-Marija Cikoš Sanja Babić Lara Čižmek Krunoslav Bojanić Krunoslav Aladić Nikolay V. Ul’yanovskii Dmitry S. Kosyakov Albert T. Lebedev Rozelindra Čož-Rakovac Polonca Trebše Stela Jokić
spellingShingle	Igor Jerković Ana-Marija Cikoš Sanja Babić Lara Čižmek Krunoslav Bojanić Krunoslav Aladić Nikolay V. Ul’yanovskii Dmitry S. Kosyakov Albert T. Lebedev Rozelindra Čož-Rakovac Polonca Trebše Stela Jokić Bioprospecting of Less-Polar Constituents from Endemic Brown Macroalga <i>Fucus virsoides</i> J. Agardh from the Adriatic Sea and Targeted Antioxidant Effects In Vitro and In Vivo (Zebrafish Model) Marine Drugs brown algae volatiles fatty acids pigments bioassays embryotoxicity
author_facet	Igor Jerković Ana-Marija Cikoš Sanja Babić Lara Čižmek Krunoslav Bojanić Krunoslav Aladić Nikolay V. Ul’yanovskii Dmitry S. Kosyakov Albert T. Lebedev Rozelindra Čož-Rakovac Polonca Trebše Stela Jokić
author_sort	Igor Jerković
title	Bioprospecting of Less-Polar Constituents from Endemic Brown Macroalga <i>Fucus virsoides</i> J. Agardh from the Adriatic Sea and Targeted Antioxidant Effects In Vitro and In Vivo (Zebrafish Model)
title_short	Bioprospecting of Less-Polar Constituents from Endemic Brown Macroalga <i>Fucus virsoides</i> J. Agardh from the Adriatic Sea and Targeted Antioxidant Effects In Vitro and In Vivo (Zebrafish Model)
title_full	Bioprospecting of Less-Polar Constituents from Endemic Brown Macroalga <i>Fucus virsoides</i> J. Agardh from the Adriatic Sea and Targeted Antioxidant Effects In Vitro and In Vivo (Zebrafish Model)
title_fullStr	Bioprospecting of Less-Polar Constituents from Endemic Brown Macroalga <i>Fucus virsoides</i> J. Agardh from the Adriatic Sea and Targeted Antioxidant Effects In Vitro and In Vivo (Zebrafish Model)
title_full_unstemmed	Bioprospecting of Less-Polar Constituents from Endemic Brown Macroalga <i>Fucus virsoides</i> J. Agardh from the Adriatic Sea and Targeted Antioxidant Effects In Vitro and In Vivo (Zebrafish Model)
title_sort	bioprospecting of less-polar constituents from endemic brown macroalga <i>fucus virsoides</i> j. agardh from the adriatic sea and targeted antioxidant effects in vitro and in vivo (zebrafish model)
publisher	MDPI AG
series	Marine Drugs
issn	1660-3397
publishDate	2021-04-01
description	The endemic brown macroalga <i>Fucus virsoides</i> J. Agardh from the Adriatic Sea was in the focus of the present research. The volatiles of fresh (FrFv) and air-dried (DrFv) samples of <i>F. virsoides</i> obtained by headspace solid-phase microextraction (HS-SPME) and hydrodistillation (HD) were analyzed by gas chromatography equipped with flame ionization detector and mass spectrometry (GC-FID/MS). The major HS-FrFv compound was pentadecane (61.90–71.55%) followed by pentadec-1-ene (11.00–7.98%). In HS-DrFv, pentadec-1-ene was not present, and few lower aliphatic compounds appeared, as well as benzaldehyde and benzyl alcohol. In HD-FrFv, particularly abundant were alkenes (such as pentadec-1-ene (19.32%), or (<i>E</i>)-pentadec-7-ene (8.35%)). In HD-DrFv, more oxidation products were present (e.g., carbonyl compounds such as tridecanal (18.51%)). The fatty acids profile of freeze-dried sample (FdFv) after conversion to methyl esters was determined by GC-FID, and oleic acid was dominant (42.28%), followed by arachidonic acid (15.00%). High-performance liquid chromatography-high-resolution mass spectrometry with electrospray ionization (HPLC-ESI-HRMS) was used for the screening of less polar fractions (F3 and F4) of <i>F. virsoides</i>. Mono- and diglycerides of stearic, palmitic, oleic, and arachidonic acids were found. Terpenoids and steroids comprised the compounds C<sub>20</sub>H<sub>30(32)</sub>O<sub>2</sub> and C<sub>29</sub>H<sub>48</sub>O<sub>(2)</sub>. Among carotenoids, fucoxanthin was identified. Chlorophyll derivatives were also found (C<sub>55</sub>H<sub>74(72)</sub>N<sub>4</sub>O<sub>(5‑7)</sub>), dominated by pheophytin <i>a</i>. The antioxidant activity of the fractions was investigated by in vitro assays (oxygen radical absorbance capacity (ORAC), reduction of radical cation (ABTS•<sup>+</sup>), 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) assay, and ferric reducing antioxidant power (FRAP)) and by in vivo zebrafish model (along with fish embryotoxicity). In vitro experiments proved good radical scavenging abilities of F3 and F4 fractions, which were additionally supported by the protective effect against hydrogen peroxide-induced oxidative stress in zebrafish embryos.
topic	brown algae volatiles fatty acids pigments bioassays embryotoxicity
url	https://www.mdpi.com/1660-3397/19/5/235
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spelling	doaj-f5e926302b8647babd5a2bc827516ee62021-04-22T23:05:00ZengMDPI AGMarine Drugs1660-33972021-04-011923523510.3390/md19050235Bioprospecting of Less-Polar Constituents from Endemic Brown Macroalga <i>Fucus virsoides</i> J. Agardh from the Adriatic Sea and Targeted Antioxidant Effects In Vitro and In Vivo (Zebrafish Model)Igor Jerković0Ana-Marija Cikoš1Sanja Babić2Lara Čižmek3Krunoslav Bojanić4Krunoslav Aladić5Nikolay V. Ul’yanovskii6Dmitry S. Kosyakov7Albert T. Lebedev8Rozelindra Čož-Rakovac9Polonca Trebše10Stela Jokić11Department of Organic Chemistry, Faculty of Chemistry and Technology, University of Split, Ruđera Boškovića 35, 21000 Split, CroatiaDepartment of Process Engineering, Faculty of Food Technology, Josip Juraj Strossmayer University of Osijek, Franje Kuhača 18, 31000 Osijek, CroatiaLaboratory for Aquaculture Biotechnology, Division of Materials Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10 000 Zagreb, CroatiaLaboratory for Aquaculture Biotechnology, Division of Materials Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10 000 Zagreb, CroatiaLaboratory for Aquaculture Biotechnology, Division of Materials Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10 000 Zagreb, CroatiaDepartment of Process Engineering, Faculty of Food Technology, Josip Juraj Strossmayer University of Osijek, Franje Kuhača 18, 31000 Osijek, CroatiaLaboratory of Environmental Analytical Chemistry, Core Facility Center “Arktika”, Northern (Arctic) Federal University, Nab. Severnoy Dviny 17, 163002 Arkhangelsk, RussiaLaboratory of Environmental Analytical Chemistry, Core Facility Center “Arktika”, Northern (Arctic) Federal University, Nab. Severnoy Dviny 17, 163002 Arkhangelsk, RussiaDepartment of Organic Chemistry, Lomonosov Moscow State University, 119991 Moscow, RussiaLaboratory for Aquaculture Biotechnology, Division of Materials Chemistry, Ruđer Bošković Institute, Bijenička cesta 54, 10 000 Zagreb, CroatiaFaculty of Health Sciences, University of Ljubljana, Zdravstvena Pot 5, 1000 Ljubljana, SloveniaDepartment of Process Engineering, Faculty of Food Technology, Josip Juraj Strossmayer University of Osijek, Franje Kuhača 18, 31000 Osijek, CroatiaThe endemic brown macroalga <i>Fucus virsoides</i> J. Agardh from the Adriatic Sea was in the focus of the present research. The volatiles of fresh (FrFv) and air-dried (DrFv) samples of <i>F. virsoides</i> obtained by headspace solid-phase microextraction (HS-SPME) and hydrodistillation (HD) were analyzed by gas chromatography equipped with flame ionization detector and mass spectrometry (GC-FID/MS). The major HS-FrFv compound was pentadecane (61.90–71.55%) followed by pentadec-1-ene (11.00–7.98%). In HS-DrFv, pentadec-1-ene was not present, and few lower aliphatic compounds appeared, as well as benzaldehyde and benzyl alcohol. In HD-FrFv, particularly abundant were alkenes (such as pentadec-1-ene (19.32%), or (<i>E</i>)-pentadec-7-ene (8.35%)). In HD-DrFv, more oxidation products were present (e.g., carbonyl compounds such as tridecanal (18.51%)). The fatty acids profile of freeze-dried sample (FdFv) after conversion to methyl esters was determined by GC-FID, and oleic acid was dominant (42.28%), followed by arachidonic acid (15.00%). High-performance liquid chromatography-high-resolution mass spectrometry with electrospray ionization (HPLC-ESI-HRMS) was used for the screening of less polar fractions (F3 and F4) of <i>F. virsoides</i>. Mono- and diglycerides of stearic, palmitic, oleic, and arachidonic acids were found. Terpenoids and steroids comprised the compounds C<sub>20</sub>H<sub>30(32)</sub>O<sub>2</sub> and C<sub>29</sub>H<sub>48</sub>O<sub>(2)</sub>. Among carotenoids, fucoxanthin was identified. Chlorophyll derivatives were also found (C<sub>55</sub>H<sub>74(72)</sub>N<sub>4</sub>O<sub>(5‑7)</sub>), dominated by pheophytin <i>a</i>. The antioxidant activity of the fractions was investigated by in vitro assays (oxygen radical absorbance capacity (ORAC), reduction of radical cation (ABTS•<sup>+</sup>), 2,2-diphenyl-1-picryl-hydrazyl-hydrate (DPPH) assay, and ferric reducing antioxidant power (FRAP)) and by in vivo zebrafish model (along with fish embryotoxicity). In vitro experiments proved good radical scavenging abilities of F3 and F4 fractions, which were additionally supported by the protective effect against hydrogen peroxide-induced oxidative stress in zebrafish embryos.https://www.mdpi.com/1660-3397/19/5/235brown algaevolatilesfatty acidspigmentsbioassaysembryotoxicity

Bioprospecting of Less-Polar Constituents from Endemic Brown Macroalga <i>Fucus virsoides</i> J. Agardh from the Adriatic Sea and Targeted Antioxidant Effects In Vitro and In Vivo (Zebrafish Model)

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