Steric Effects on Interaction of Tea Catechins with Lipid Bilayers

Kajiya, Katsuko; Kumazawa, Shigenori; Nakayama, Tsutomu

doi:10.1271/bbb.65.2638

Cited by 153 publications

(146 citation statements)

References 21 publications

Supporting

Mentioning

134

Contrasting

Order By: Relevance

“…In addition, we previously showed that not all EGCg added is incorporated into liposomes. [8] Therefore, the central signal is probably due to free, nonmembrane-bound [4-2 H]EGCg similar as in the case of liposome system. It is noted that that the fraction of unbound [4-2 H]EGCg is higher than the fraction, bound to liposomes.…”

Section: Resultsmentioning

confidence: 89%

“…[8] Further, EGCg can diffuse laterally and rearrange its molecular orientation about the bilayer normal as an unique axis by keeping the tilt angle to the bilayer normal constant. Thus, EGCg molecules bound to lipid bilayers exhibit an above mentioned dynamic behavior.…”

Section: Resultsmentioning

confidence: 99%

“…We found that the affinity of tea catechins to lipid bilayers is characterized by (i) the number of hydroxyl groups on the B-ring, (ii) the presence of the galloyl moiety, and (iii) the stereochemical structure of each catechin. [8] The salt concentration in an aqueous medium, the electric charges on the membrane, and the presence of other catechins, are also important factors affecting the affinity of tea catechins for lipid bilayers. [9] These experimental findings suggest that tea catechins interact with the phospholipid domains of membranes.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Solid‐state NMR analysis of the orientation and dynamics of epigallocatechin gallate, a green tea polyphenol, incorporated into lipid bilayers

Kajiya

Kumazawa

Naito

et al. 2007

Magnetic Reson in Chemistry

Self Cite

View full text Add to dashboard Cite

Catechins are the principle polyphenolic compounds in green tea; the four major compounds identified are epicatechin (EC), epigallocatechin (EGC), epicatechin gallate (ECg) and epigallocatechin gallate (EGCg). Tea catechins tend to attach externally to their targets, such as viral envelopes, cell membranes, or the surface of low-density lipoproteins. In order to further our understanding of the molecular mobility of these compounds in cells, we examined the interaction of tea catechins with lipid membranes using solid-state NMR techniques. Our previous work indicated that the EGCg molecule is incorporated into lipid bilayers in a unique orientation. However, the detailed configuration, orientation, and dynamics of EGCg in lipid bilayers have not been well-characterized. Here, we investigated the orientation and dynamics of EGCg incorporated into multi-lamellar vesicles (MLVs) and bicelles using solid-state NMR spectroscopy.

show abstract

Section: Resultsmentioning

confidence: 89%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Solid‐state NMR analysis of the orientation and dynamics of epigallocatechin gallate, a green tea polyphenol, incorporated into lipid bilayers

Kajiya

Kumazawa

Naito

et al. 2007

Magnetic Reson in Chemistry

Self Cite

View full text Add to dashboard Cite

show abstract

“…The D-ring hydroxyl groups of the flavonoid structure occupy the first coordination sphere around metal ion to form a diolate combination ring, while B-ring hydroxyl groups have weak interactions with metal ions [29]. As suggested by previous reports [30,31], the number of hydroxyl groups on the B-ring in many flavonoids structures, the presence of a galloyl moiety, and the steric characters on the D-ring could affect its affinity for the lipid bilayers. As a result of this, incorporation of the flavonoids into the lipid bilayers was enhanced, which could lead to the formation of another ion channels after complexing of flavonoids with metal ions, which is expected to induce structural variation and influence the effects of structurally different flavonoids in this respect.…”

Section: Discussionmentioning

confidence: 88%

Effects of Long-Term Use of Flavonoids on the Absorption and Tissue Distribution of Orally Administered Doses of Trace Elements in Rats

Jaccob¹,

Hussain²

2012

View full text Add to dashboard Cite

The risk of pharmacokinetic polyphenols-trace elements interaction may undesirable therapeutic outcomes. We evaluate the long-term use of silibinin, epigallocatechin (ECGC), quercetin and rutin on the absorption and tissue distribution of zinc, copper and iron after single oral doses in rats. Five groups of rats received either with olive oil as control or one of the polyphenols silibinin, EPGC, quercetin or rutin, administered orally as oily solutions for 30 days. At day 30, a solution contains sulphate salt of zinc, copper and iron was administered orally; 3 hrs later blood samples, tissues of brain, kidney and liver were obtained for evaluation of the elements levels. The results showed that the polyphenols increased both serum and tissue levels of these elements compared with controls. This effect was relatively varied according to the structural differences among flavonoids. In conclusion, long-term use of supraphysiological doses of flavonoids increase absorption of Zn, Cu and Fe and their tissue availability in brain, kidney and liver; this effect seems to be different with variations in structural features.

show abstract

“…The interaction between orange pigment and the phospholipid was measured following the previous method (Kajiya et al 2001) with some modifications. Phosphatidylcholine from egg yolk (egg PC) was obtained from Beilian Fine Chemicals (Tianjin, China).…”

Section: Methodsmentioning

confidence: 99%

Antibacterial characteristics of orange pigment extracted from Monascus pigments against Escherichia coli

Zhao¹,

Li²,

Yang³

et al. 2016

Czech J. Food Sci.

View full text Add to dashboard Cite

Zhao G.P., Li Y.Q., Yang J., Cui K.Y. (2015): Antibacterial characteristics of orange pigment extracted from Monascus pigments against Escherichia coli. Czech J. Food Sci.,.The antibacterial characteristics of orange pigment, which is one of the Monascus pigments, against Escherichia coli were investigated. Orange pigment exhibited strong antibacterial activity against E. coli evidenced by an increase in the diameter of inhibition zone with orange pigment treatment. The concentration of 2.5 mg/ml was the minimum inhibitory concentration of orange pigment against E. coli. Scanning electron microscopy revealed that orange pigment could damage bacterial cells, eventually resulting in cell death. The increase in the electric conductivity of bacterial cell suspensions suggested that the cytoplasmic membrane was broken by treatment with orange pigment. The result of orange pigment incorporation into egg PC further demonstrated the interaction between orange pigment and the phospholipid led to the disruption of bacterial membrane.

show abstract

Steric Effects on Interaction of Tea Catechins with Lipid Bilayers

Cited by 153 publications

References 21 publications

Solid‐state NMR analysis of the orientation and dynamics of epigallocatechin gallate, a green tea polyphenol, incorporated into lipid bilayers

Solid‐state NMR analysis of the orientation and dynamics of epigallocatechin gallate, a green tea polyphenol, incorporated into lipid bilayers

Effects of Long-Term Use of Flavonoids on the Absorption and Tissue Distribution of Orally Administered Doses of Trace Elements in Rats

Antibacterial characteristics of orange pigment extracted from Monascus pigments against Escherichia coli

Contact Info

Product

Resources

About