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Download (Accessed on 6 November 2020) biomolecules Review Cyclodextrins, Natural Compounds, and Plant Bioactives—A Nutritional Perspective Svenja Wüpper *, Kai Lüersen and Gerald Rimbach Institute of Human Nutrition and Food Science, University of Kiel, Hermann-Rodewald-Strasse 6, 24118 Kiel, Germany; [email protected] (K.L.); [email protected] (G.R.) * Correspondence: [email protected]; Tel.: +49-431-880-5334 Abstract: Cyclodextrins (CDs) are a group of cyclic oligosaccharides produced from starch or starch derivatives. They contain six (αCD), seven (βCD), eight (γCD), or more glucopyranose monomers linked via α-1,4-glycosidic bonds. CDs have a truncated cone shape with a hydrophilic outer wall and a less hydrophilic inner wall, the latter forming a more apolar internal cavity. Because of this special architecture, CDs are soluble in water and can simultaneously host lipophilic guest molecules. The major advantage of inclusion into CDs is increased aqueous solubility of such lipophilic substances. Accordingly, we present studies where the complexation of natural compounds such as propolis and dietary plant bioactives (e.g., tocotrienol, pentacyclic triterpenoids, curcumin) with γCD resulted in improved stability, bioavailability, and bioactivity in various laboratory model organisms and in humans. We also address safety aspects that may arise from increased bioavailability of plant extracts or natural compounds owing to CD complexation. When orally administered, α- and βCD—which are inert to intestinal digestion—are fermented by the human intestinal flora, while γCD is almost completely degraded to glucose units by α-amylase. Hence, recent reports indicate that empty γ CD supplementation exhibits metabolic activity on its own, which may provide opportunities for new applications. Citation: Wüpper, S.; Lüersen, K.; Rimbach, G. Cyclodextrins, Natural Keywords: cyclodextrins; gamma-cyclodextrin; complex; ursolic acid; oleanolic acid; betulinic acid; Compounds, and Plant Bioactives—A propolis; tocotrienol; curcumin Nutritional Perspective. Biomolecules 2021, 11, 401. https://doi.org/ 10.3390/biom11030401 1. Introduction Academic Editor: Anika Wagner Cyclodextrins (CDs), also known as cyclomaltoses, cycloamyloses, and Schardinger dextrins, are a group of cyclic oligosaccharides that are produced from starch or starch Received: 10 February 2021 derivatives by the bacterial enzyme cyclodextrin glycosyltransferase (CGTase) [1,2]. CDs Accepted: 4 March 2021 contain six or more glucopyranose monomers linked via α-1,4-glycosidic bonds. The Published: 9 March 2021 most prominent members of the CD family are α- (six glucopyranose units), β- (seven glucopyranose units), and γCD (eight glucopyranose units, Figure1)[ 1]. Through the Publisher’s Note: MDPI stays neutral specific steric arrangement of their glucose units, CDs are soluble in water and can function with regard to jurisdictional claims in as important complexation agents for a broad range of more lipophilic molecules, including published maps and institutional affil- natural compounds and plant bioactives, with increasing use in industrial and research iations. applications [1,3]. The major advantage of the inclusion of lipophilic substances into CDs is increased aqueous solubility with enhanced stability and bioavailability of these guest molecules. In addition, CDs can be used to prevent drug-drug and drug-excipient interactions, convert liquid drugs into microcrystalline powder, and reduce gastrointestinal Copyright: © 2021 by the authors. drug irritation [4]. Licensee MDPI, Basel, Switzerland. This review aims to provide a short historical overview as well as a summary of the This article is an open access article synthesis, properties, pharmacokinetics, and safety of CDs. Furthermore, the differences distributed under the terms and among the three main CD types are addressed with respect to their complex formation and conditions of the Creative Commons route of administration. The present state of knowledge regarding the stability, bioavail- Attribution (CC BY) license (https:// γ creativecommons.org/licenses/by/ ability, and bioactivity of CD complexes with selected natural compounds and dietary 4.0/). plant bioactives is described. Finally, the biological activity of empty γCD is also reviewed. Biomolecules 2021, 11, 401. https://doi.org/10.3390/biom11030401 https://www.mdpi.com/journal/biomolecules Biomolecules 2021, 11, x 2 of 21 and route of administration. The present state of knowledge regarding the stability, bioa- vailability, and bioactivity of γCD complexes with selected natural compounds and die- Biomolecules 2021, 11, 401 2 of 21 tary plant bioactives is described. Finally, the biological activity of empty γCD is also re- viewed. Figure 1.1. ChemicalChemical structuresstructures andand physicochemicalphysicochemical propertiesproperties ofof thethe threethree mainmain cyclodextrinscyclodextrins αα-,-, ββ-,-, andand γγ-cyclodextrin-cyclodextrin (from left to right αCD, βCD, and γCD). ID: Inner diameter; OD: Outer diameter. 1 From [2]. 2 From [5]. 3 From [1]. (from left to right αCD, βCD, and γCD). ID: Inner diameter; OD: Outer diameter. 1 From [2]. 2 From [5]. 3 From [1]. 2. History of Cyclodextrins 2. Historyα- and of βCD Cyclodextrins were discovered in 1891 by the French pharmacist and chemist Antoine Villiersα- andas digestionβCD were products discovered of potato in 1891 starch by the obtained French pharmacistby using the and bacterium chemist AntoineBacillus Villiersamylobacter as digestion (Figure 2). products Villiers ofnamed potato the starch novel obtained carbohydrates by using “cellulosines” the bacterium α-Bacillus and β- dextrinamylobacter and (Figuredescribed2). them Villiers as crystalline named the and novel slightly carbohydrates sweet [6]. At “cellulosines” the beginningα of- and the 20thβ-dextrin century,and the described Austrian them microbiologist as crystalline Franz and Schardinger, slightly sweet later [known6]. At theas the beginning “found- ingof the father” 20th of century, CD chemistry, the Austrian isolated microbiologist CDs, which Franzhe termed Schardinger, “crystalline later dextrins”, known as from the “foundingseveral sources father” of ofstarch CD chemistry,following digestion isolated CDs, by Bacillus which hemacerans termed. Notably, “crystalline B. macerans dextrins”, is stillfrom the several most sourcescommonly of starch used followingbacterial species digestion for by theBacillus production macerans of .CGTase Notably, toB. form macerans CDs [2,6,7]is still. theIn the most 1940s, commonly the German used chemist bacterial Freudenberg species for and the productionhis coworkers of CGTasediscovered to formγCD andCDs subsequently [2,6,7]. In the solved 1940s, thethe Germancyclic oligosaccharide chemist Freudenberg structure and of hisCD coworkers molecules. discovered After dis- coveγCDring and the subsequently feasibility solvedof preparing the cyclic CD- oligosaccharideinclusion complexes, structure Freudenberg, of CD molecules. Cramer After, and Plieningerdiscovering obtained the feasibility the first of CD preparing-related patent CD-inclusion in 1953, complexes,which marks Freudenberg, the starting point Cramer, for and Plieninger obtained the first CD-related patent in 1953, which marks the starting point for the application of CDs in drug formulations [8], so that they were no longer just part of academic research, but also part of industrial applications. In 1957, the American chemist and biochemist Dexter French reported on two larger CDs, δ-dextrin and "-dextrin, with 9 and 10 glucose monomers, respectively [9,10]. However, compared to those of the Biomolecules 2021, 11, x 3 of 21 the application of CDs in drug formulations [8], so that they were no longer just part of academic research, but also part of industrial applications. In 1957, the American chemist and biochemist Dexter French reported on two larger CDs, δ-dextrin and ε-dextrin, with 9 and 10 glucose monomers, respectively [9,10]. However, compared to those of the smaller CDs, the physicochemical properties of these larger CDs were found to be less suitable for complex formation [8]. In 1980, Saenger found that the amylase CGTase is responsible for the conversion of starch or starch derivatives into CDs via a cyclization reaction. Most importantly, this discovery enabled the mass production of CDs [2,7]. Biomolecules 2021, 11, 401 Roughly, the history of CDs can be classified into two main research fields. On3 ofthe 21 one hand, a main focus is the complexation property of CDs and their role as host mole- cules to improve the properties of guest molecules. As mentioned above, this traditional research area started in the 1950s, has become well established and is still continuing. With thesmaller turn of CDs, the thenew physicochemical millennium, a new properties branch ofof theseCD research larger CDscame were to the found fore, toafter be lessthe realizationsuitable for that complex empty formationCDs exhibit [8 bioactivity]. In 1980, on Saenger their own found and that have the potential amylase health CGTase ben- is efits.responsible Hence, forCD themolecules conversion per ofse starchhave received or starch attention derivatives in research, into CDs and via athis cyclization topic is increasreaction.ingly Most recognized importantly, as important this discovery [6,11] enabled. the mass production of CDs [2,7]. FigureFigure 2. 2. MilestonesMilestones of cyclodextrin of cyclodextrin research research history history.. CD, cyclodextrin; CD, cyclodextrin;
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