Retarding Effects of Cyclodextrins on the Decomposition of Organic Isothiocyanates in an Aqueous Solution

Ohta, Yoshio; Matsui, Yoshihisa; Osawa, Toshihiko; Kawakishi, Shunrô

doi:10.1271/bbb.68.671

Cited by 18 publications

(8 citation statements)

References 10 publications

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“…4). The peaks for AITC were observed at around 4.2, 5.3, and 5.9 ppm corresponding to the protons of AITC [34]. The stoichiometry of AITC and ␤-CD-IC in PVA/AITC/␤-CD-IC-NF was determined as 0.68:1.00 (AITC:␤-CD) by integrating the peak ratio of the characteristic chemical shifts of AITC (5.3 ppm) and ␤-CD (5.7 ppm).…”

Section: Aitc Content In Nanofibersmentioning

confidence: 99%

Release and antibacterial activity of allyl isothiocyanate/β-cyclodextrin complex encapsulated in electrospun nanofibers

Aytaç

Doğan

Tekinay

et al. 2014

Colloids and Surfaces B: Biointerfaces

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a b s t r a c tAllyl isothiocyanate (AITC) is known as an efficient antibacterial agent but it has a very high volatility. Herein, AITC and AITC/␤-cyclodextrin (CD)-inclusion complex (IC) incorporated in polyvinyl alcohol (PVA) nanofibers were produced via electrospinning. SEM images elucidated that incorporation of AITC and AITC/␤-CD-IC into polymer matrix did not affect the bead-free fiber morphology of PVA nanofibers. 1 H-NMR and headspace GC-MS analyses revealed that very low amount of AITC was remained in PVA/AITC-NF because of the rapid evaporation of AITC during the electrospinning process. Nevertheless, much higher amount of AITC was preserved in the PVA/AITC/␤-CD-IC-NF due to the CD inclusion complexation. The sustained release of AITC from nanofibers was evaluated at 30 • C, 50 • C and 75 • C via headspace GC-MS. When compared to PVA/AITC-NF, PVA/AITC/␤-CD-IC-NF has shown higher antibacterial activity against Escherichia coli and Staphylococcus aureus due to the presence of higher amount of AITC in this sample which was preserved by CD-IC.

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Section: Aitc Content In Nanofibersmentioning

confidence: 99%

Release and antibacterial activity of allyl isothiocyanate/β-cyclodextrin complex encapsulated in electrospun nanofibers

Aytaç

Doğan

Tekinay

et al. 2014

Colloids and Surfaces B: Biointerfaces

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“…Many physicochemical methods were applied to investigate the complexation reaction between CDs and guest molecule, including phase solubility measurements , UV–Vis , fluorescence , circular dichroism , and NMR spectroscopy. Furthermore, many separation‐based methods such as HPLC and CE were also used to study the host–guest interaction.…”

Section: Introductionmentioning

confidence: 99%

Structure selective complexation of cyclodextrins with five polyphenols investigated by capillary electrokinetic chromatography

Cheung

Shangguan

Zheng

2012

J of Separation Science

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The complexation of five polyphenols, namely trans-resveratrol, astilbin, taxifolin, ferulic acid, and syringic acid (guest molecules) with α-, β-, and γ-cyclodextrin (host molecules), was investigated by capillary electrokinetic chromatography. The binding constants were calculated based on the effective electrophoretic mobility change of guests with the addition of cyclodextrins into the background electrolyte. Because of cavity size, cyclodextrins showed structure-selective complexation property to different guest. The stability of the trans-resveratrol complexes was in the order of β- > α- > γ-cyclodextrin. The cavity size of α-cyclodextrin was too small for astilbin and taxifolin molecules, and thus they could not form complexes. The molecular size of syringic acid was too big for all cyclodextrins cavity, and no cyclodextrin could form complexes with it. Temperature studies showed that the binding constants decreased with the rise of temperature. Enthalpy and entropy values were calculated and the negative values of these parameters indicated that the complexation process was enthalpy-controlled. Van der Waals force and release of high-enthalpy water molecules from the cyclodextrins cavity played important roles in the process.

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“…aCD provided better stabilization of MTBI than did bCD and gCD. Ohta et al (32) have reported the isothiocyanate group of AITC is located close to the secondary hydrogen group, and the hydrophobic allyl group is located within the hydrophobic cavity of aCD. We speculate that MTBI forms a complex with aCD through interactions (Fig.…”

Section: Discussionmentioning

confidence: 99%

“…12), similar to what has been reported for AITC. (32) The reactive site of MTBI can be protected from nucleophilic attack of water by the steric hindrance of the aCD torus. In addition, by forming the inclusion complex with aCD, MTBI in MTBI-aCD could be stably stored for a long time.…”

Section: Discussionmentioning

confidence: 99%

Anti-obesity effects of α-cyclodextrin-stabilized 4-methylthio-3-butenyl isothiocyanate from daikon (<i>Raphanus sativus</i> var. <i>longipinnatus</i>) in mice

Okamoto

Ino

Nihei

et al. 2019

J. Clin. Biochem. Nutr.

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unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. 4 Methylthio 3 butenyl isothiocyanate (MTBI) is a pungent bio active constituent found in daikon. However, MTBI is immediately hydrolyzed to 3 hydroxy methylene 2 thioxopyrrolidine in grated daikon. In this study, we evaluated whether MTBI in grated daikon complexed with α cyclodextrin (αCD) has anti obesity effects in mice. C57BL/6J mice were fed a normal diet (normal group), high fat diet (HFD, control group), HFD with αCD (αCD group), or HFD with MTBI αCD (MTBI αCD group) for 16 weeks. The results showed that the final body weight, epididymal white adipose tissue weight, and plasma triglyceride and total cholesterol levels were significantly lower in the MTBI αCD group than in the control group. The cell size in epididymal adipose tissue was significantly smaller and the accumulation of lipids in the liver was significantly lower in the MTBI αCD group than in the control group. Furthermore, real time polymerase chain reaction showed that the mRNA expression level of tumor necrosis factor alpha was suppressed in the MTBI αCD group. We also observed low superoxide dismutase activity in the MTBI αCD group, possibly because MTBI αCD has the potential to resist HFD induced oxida tive injury. In conclusion, MTBI αCD exerted anti inflammation and antioxidant effects to suppress lipid accumulation in epididymal adipose tissue and the liver. These effects then prevented HFD induced obesity in mice.

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Retarding Effects of Cyclodextrins on the Decomposition of Organic Isothiocyanates in an Aqueous Solution

Cited by 18 publications

References 10 publications

Release and antibacterial activity of allyl isothiocyanate/β-cyclodextrin complex encapsulated in electrospun nanofibers

Release and antibacterial activity of allyl isothiocyanate/β-cyclodextrin complex encapsulated in electrospun nanofibers

Structure selective complexation of cyclodextrins with five polyphenols investigated by capillary electrokinetic chromatography

Anti-obesity effects of α-cyclodextrin-stabilized 4-methylthio-3-butenyl isothiocyanate from daikon (<i>Raphanus sativus</i> var. <i>longipinnatus</i>) in mice

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