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3. Cereal alkylresorcinols elevate [gamma]-tocopherol levels in rats and inhibit [gamma]-tocopherol metabolism in vitro

Author

Ross, Alastair B., Chen, Yan, Frank, Jan, Swanson, Joy E., Parker, Robert S., Kozubek, Arkadiusz, Lundh, Torbjorn, Vessby, Bengt, Aman, Per, and Kamal-Eldin, Afaf

Subjects
Food/cooking/nutrition
Abstract

Alkylresorcinols (AR) are a class of amphiphilic phenolic lipids present in high amounts in wheat and rye bran. They have been reported to be both growth retarding and innocuous when fed to rats, and to have a broad range of bioactivities in vitro, suggested to be related to their ability to bind to proteins and modify membranes. This study was designed to test the effects of AR (purified from rye bran) on growth, tocopherol levels, and cholesterol levels in rats. Rats were fed 1 of 4 different levels of AR for 4 wk: 0 (control), 1, 2, and 4 g/kg diet. AR did not affect final body, liver, or lung weights. The AR diets increased the levels of [gamma]-tocopherol in liver and lungs (P < 0.05). To investigate whether AR could have increased [gamma]-tocopherol levels via inhibition of tocopherol-[omega]-hydroxylase, HepG2 cells were incubated with AR and the metabolism of [gamma]-tocopherol measured. AR significantly inhibited the conversion of [gamma]-tocopherol to its water-soluble hydroxychroman metabolite in vitro, indicating that AR may increase [gamma]-tocopherol levels via inhibition of tocopherol metabolism in vivo. The 4 g AR/kg diet decreased liver cholesterol (P < 0.001), but did not affect plasma lipids. AR were detected in the perirenal adipose tissue samples of rats fed AR, indicating that they can accumulate in the fatty tissues of rats. High levels of dietary AR moderately affect [gamma]-tocopherol, possibly via inhibition of tocopherol metabolism, and decrease liver cholesterol in rats. KEY WORDS: * alkylresorcinols * cholesterol * cytochrome P450 * [gamma]-tocopherol * tocopherol-[omega]-hydroxylase

Published
2004

10. Contributors

Author

Alvarenga, Nelson, primary, Avato, Pinarosa, additional, Banaszek, Anna, additional, Benito, Paulina Bermejo, additional, Bessa, Ana Latourrette, additional, Bouzbouz, Samir, additional, Calixto, João B., additional, Capasso, Anna, additional, Cossy, Janine, additional, Cotelle, Philippe, additional, D'Ursi, Annamaria, additional, Ferreira, Juliano, additional, Ferro, Esteban A., additional, Filho, Valdir Cechinel, additional, Gu, Jian-Qiao, additional, Han, L-K., additional, Hasegawa, Takashi, additional, He, Rong-Qiao, additional, Kimura, Yoshiyuki, additional, Kinghorn, A. Douglas, additional, Kolak, Ufuk, additional, Kozubek, Arkadiusz, additional, Kumamoto, Shoichiro, additional, Li, Li, additional, Liaaen-Jensen, Synnøve, additional, Lutnaes, Bjart Frode, additional, Martínez, María Jose Abad, additional, Mcinnes, L. Alison, additional, Mlynarski, Jacek, additional, Nomoto, Kikuo, additional, Okuda, H., additional, Olmo, Luis Miguel Bedoya Del, additional, Qi, Shu-Ping, additional, Ruiz-Rubio, Manuel, additional, Tachibana, Yoji, additional, Topcu, Gulacti, additional, Tsuji, Masahiro, additional, Tyman, John H.P., additional, Ulubelen, Ayhan, additional, Wu, Jane, additional, Yoshikai, Yasunobu, additional, Yunes, Rosendo A., additional, and Zhao, Jing, additional

Published
2005
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12. Alkylresorcinols are abundant lipid components in different strains of Azotobacter chroococcum and Pseudomonas spp

Author

Kozubek, Arkadiusz, Pietr, Stanisxaw, and Czerwonka, Anna

Subjects
Resorcinols -- Research, Pseudomonas -- Physiological aspects, Biological sciences
Abstract

The lipids extracted from Azotobacter chroococcum and Pseudomonas spp. contain different amounts of 5-n-alkylresorcinols. Both produce saturated alkyl resorcinol homologs with C13 to C27 side chains. The C19, C21, C23 side chain homologs are predominant in A. chroococcum; C15 in P. chlororapsis and P. fluorescens; and C17 in P. aureofaciens. 5-n-(2-ketoalkyl)resorcinol is produced by the cells of A. chroococcum Az5. Alkylresorcinols are the end products of the polyketide biosynthesis pathway. Their amounts produced depends on the bacteria and is the highest in A. chroococcum.

Published
1996

17. Anacardic acid enhances the anticancer activity of liposomal mitoxantrone towards melanoma cell lines – in vitro studies [Corrigendum]

Author

Legut,Mateusz, Lipka,Dominik, Filipczak,Nina, Gubernator,Jerzy, Piwoni,Adriana, Kozubek,Arkadiusz, Legut,Mateusz, Lipka,Dominik, Filipczak,Nina, Gubernator,Jerzy, Piwoni,Adriana, and Kozubek,Arkadiusz

Abstract

Anacardic acid enhances the anticancer activity of liposomal mitoxantrone towards melanoma cell lines – in vitro studies [Corrigendum]Legut M, Lipka D, Filipczak N, et al. Int J Nanomedicine. 2014;9:653–668.The authors advise the Acknowledgment on page 666 is missing the final sentence:This study was supported by: the WrocÅ‚aw Research Centre EIT+ under the Biotechnologies and Advanced Medical Technologies project; BioMed (POIG.01.01.02-02-003/08), financed by the European Regional Development Fund (Operational Programme Innovative Economy, 1.1.2) #8221.Read the original article

Published
2015

19. Anacardic acid enhances the anticancer activity of liposomal mitoxantrone towards melanoma cell lines – in vitro studies

Author

Legut,Mateusz, Lipka,Dominik, Filipczak,Nina, Piwoni,Adriana, Kozubek,Arkadiusz, Gubernator,Jerzy, Legut,Mateusz, Lipka,Dominik, Filipczak,Nina, Piwoni,Adriana, Kozubek,Arkadiusz, and Gubernator,Jerzy

Abstract

Mateusz Legut, Dominik Lipka, Nina Filipczak, Adriana Piwoni, Arkadiusz Kozubek, Jerzy GubernatorDepartment of Lipids and Liposomes, Faculty of Biotechnology, University of WrocÅ‚aw, WrocÅ‚aw, PolandAbstract: This paper describes a novel formulation of antineoplastic drug: mitoxantrone loaded into liposomal carriers enriched with encapsulated anacardic acid in the liposomal bilayer using a vitamin C gradient. Anacardic acid is a potent epigenetic agent with anticancer activity. This is the first liposomal formulation to combine an actively encapsulated drug and anacardic acid. The liposomes were characterized in terms of basic parameters, such as size, zeta potential, optimal drug-to-lipid ratio, loading time and temperature, and stability at 4°C and in human plasma in vitro. The formulation was found to be stable, and the loading process was rapid and efficient (drug-to-lipid ratio of up to 0.3 with over 90% efficiency in 5 minutes). The cytotoxicity of these formulations was assessed using the human melanoma cell lines A375 and Hs294T and the normal human dermal fibroblast line. The results showed that anacardic acid and to a smaller extent vitamin C significantly increased the cytotoxicity of the drug towards melanoma compared to ammonium sulfate liposomes. On the other hand, vitamin C and anacardic acid both protected normal cells from damage caused by the drug. The formulation combining anacardic acid, vitamin C, and mitoxantrone showed promising results in terms of cytotoxicity and cytoprotection. Therefore, it has potential for anticancer treatment.Keywords: anacardic acid, vitamin C, ascorbic acid, liposomes, mitoxantrone, melanomaCorrigendum for this paper has been published&nbsp

Published
2014

22. Efficient Human Breast Cancer Xenograft Regression after a Single Treatment with a Novel Liposomal Formulation of Epirubicin Prepared Using the EDTA Ion Gradient Method

Author

Gubernator, Jerzy, primary, Lipka, Dominik, additional, Korycińska, Mariola, additional, Kempińska, Katarzyna, additional, Milczarek, Magdalena, additional, Wietrzyk, Joanna, additional, Hrynyk, Rafał, additional, Barnert, Sabine, additional, Süss, Regine, additional, and Kozubek, Arkadiusz, additional

Published
2014
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26. Vitamin C-driven epirubicin loading into liposomes

Author

Lipka,Dominik, Gubernator,Jerzy, Filipczak,Nina, Barnert,Sabine, Süss,Regine, Legut,Mateusz, Kozubek,Arkadiusz, Lipka,Dominik, Gubernator,Jerzy, Filipczak,Nina, Barnert,Sabine, Süss,Regine, Legut,Mateusz, and Kozubek,Arkadiusz

Abstract

Dominik Lipka,1 Jerzy Gubernator,1 Nina Filipczak,1 Sabine Barnert,2 Regine Süss,2 Mateusz Legut,1 Arkadiusz Kozubek1 1Department of Lipids and Liposomes, University of Wroclaw, Wroclaw, Poland; 2Department of Pharmaceutical Technology, Albert Ludwigs University, Freiburg, Germany Abstract: The encapsulation of anticancer drugs in a liposome structure protects the drug during circulation and increases drug accumulation in the cancer tissue and antitumor activity while decreasing drug toxicity. This paper presents a new method of active drug loading based on a vitamin C pH/ion gradient. Formulations were characterized in terms of the following parameters: optimal external pH, time and drug-to-lipid ratio for the purpose of remote loading, and in vitro stability. In the case of the selected drug, epirubicin (EPI), its coencapsulation increases its anticancer activity through a possibly synergistic effect previously reported by other groups for a free nonencapsulated drug/vitamin C cocktail. The method also has another advantage over other remote-loading methods: it allows faster drug release through liposome destabilization at the tumor site, thanks to the very good solubility of the EPI vitamin C salt, as seen on cryogenic transmission electron microscopy images. This influences the drug-release process and increases the anticancer activity of the liposome formulation. The liposomes are characterized as stable, with very good pharmacokinetics (half-life 18.6 hours). The antitumor activity toward MCF-7 and 4T-1 breast cancer cells was higher in the case of EPI loaded via our gradient than via an ammonium sulfate gradient. Finally, the EPI liposomal formulation and the free drug were tested using the murine 4T-1 breast cancer model. The antitumor activity of the encapsulated drug was confirmed (tumor-growth inhibition over 40% from day 16 until the end of the experiment), and the free drug was shown to have no anticancer activity at the tested dose. Keywords

Published
2013

27. Resorcinolic lipids, the natural non-isoprenoid phenolic amphiphiles and their biological activity

Author

Kozubek, Arkadiusz and Tyman, John H.P.

Subjects
Resorcinols -- Analysis, Lipids -- Physiological aspects, Lipid metabolism -- Analysis, Chemistry
Abstract

The biological activities of phenolic lipids derived from resorcinols or higher homologues of orcinol have been studied. These lipids are found to occur naturally in 11 families of higher plants, five lower plant families and three families of bacteria. They are used in catalyzing the semi-synthesis of various compounds such as long-lasting hydrophobic antiinflammatory drugs or analogues of cannabinoids. They are also used in treating various conditions from desensitization to obesity.

Published
1999

48. The Oil of Adenanthera pavonina L. Seeds and its Emulsions

Author

Zarnowski, Robert, primary, Jaromin, Anna, additional, Certik, Milan, additional, Czabany, Tibor, additional, Fontaine, Joël, additional, Jakubik, Tibor, additional, Iqbal, Mohamed C. M., additional, Grandmougin-Ferjani, Anne, additional, Kozubek, Arkadiusz, additional, and Pietr, Stanislaw J., additional

Published
2004
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