Encapsulation Efficiency and Functional Stability of Cinnamon Essential Oil in Modified β-cyclodextrins: In Vitro and In Silico Evidence

Abstract

Essential oils (EOs) have good natural antioxidant and antimicrobial properties; however, their volatility, intense aroma, poor aqueous solubility, and chemical instability limit their applications in the food industry. The encapsulation of EOs in β-cyclodextrins (β-CDs) is a widely accepted strategy for enhancing EO applications. The complexation of cinnamon essential oil (CEO) with five types of β-CDs, containing different substituent groups (β-CD with primary hydroxyl, Mal-β-CD with maltosyl, CM-β-CD with carboxymethyl, HP-β-CD with hydroxypropyl, and DM-β-CD with methyl), inclusion process behaviors, volatile components, and antioxidant and antibacterial activities of the solid complexes were studied. The CEOs complexed with Mal-β-CD, CM-β-CD, and β-CD were less soluble than those complexed with DM-β-CD and HP-β-CD. Molecular docking confirmed the insertion of the cinnamaldehyde benzene ring into various β-CD cavities via hydrophobic interactions and hydrogen bonds. GC-MS analysis revealed that HP-β-CD had the greatest adaptability to cinnamaldehyde. The CEO encapsulated in β-, Mal-β-, and CM-β-CD showed lower solubility but better control-release characteristics than those encapsulated in DM- and HP-β-CD, thereby increasing their antioxidant and antibacterial activities. This study demonstrated that β-, Mal-β-, and CM-β-CD were suitable alternatives for the encapsulation of CEO to preserve its antioxidant and antibacterial activities for long-time use.

Active and Intelligent Packaging: A Review of the Possible Application of Cyclodextrins in Food Storage and Safety Indicators

“…In general, reasonable control over its release was observed, increasing its antioxidant and antibacterial activity and presenting itself as an alternative for storage [98]. Encapsulation in modified CDs affects the solubility, stability, and bioactive properties of the packaged compounds in different ways, but in all the cases studied, the solubility of essential oils increased [98,113,114]. This demonstrates CD's protective role as an active container for essential oils through encapsulation, protecting their antioxidant and antimicrobial properties.…”

“…Wu et al made active packaging based on cinnamon essential oil (CEO) with five varieties of β-CD. In general, reasonable control over its release was observed, increasing its antioxidant and antibacterial activity and presenting itself as an alternative for storage [98]. Encapsulation in modified CDs affects the solubility, stability, and bioactive properties of the packaged compounds in different ways, but in all the cases studied, the solubility of essential oils increased [98,113,114].…”

“…There has been an unceasing interest for a long time in preventing food spoilage by increasing its shelf life and controlling spoilage reactions such as the action of polyphenol oxidase (PPO) and enzymatic browning reactions. This is why microbial inhibition mechanisms, among others, have been studied to increase the shelf life of food [70,[95][96][97][98]. Many of the food packaging commonly sold in stores contains compound polymers derived from the petrochemical industry (low-density polyethylene, polyethylene terephthalate, and polypropylene, among others) that have the possibility of migrating into the food, altering its quality.…”

Natural Polymers as Carriers for Encapsulation of Volatile Oils: Applications and Perspectives in Food Products

“…As a result, the application of volatile oils requires their processing into solid forms like capsules, films, or spheres; semi-liquid forms like gels or liposomes; and liquid forms like emulsions, micelles, and liquid solutions [ 38 ]. Gums, chitosan, maltodextrins, starches, and proteins are examples of coating materials that can be used to encapsulate volatile oils [ 39 ]. Proteins and polysaccharides are examples of biopolymers that can be utilized to make food-grade capsules [ 37 ].…”

Comparative study of a liposome and emulsion system with cinnamon essential oil on the quality and proteolysis of refrigerated minced pork

“…CEO is the main component of cinnamon, which has a wide range of biological properties, including antibacterial, antifungal, antioxidant, and immunoregulation activities (4). However, pure essential oils (EOs) are known to be unstable and sensitive to factors such as light, oxygen, and high temperature.…”