Fucoxanthin Derivatives: Synthesis and their Chemical Properties

Komba, Shiro; Kotake-Nara, Eiichi; Machida, Sachiko

doi:10.5650/jos.ess15039

Cited by 4 publications

(4 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Fucoxanthin was purified from wakame ( Undaria pinnatifida ) (1.09 mg fucoxanthin/g dry wakame), as referenced in previous experiments [30]. The 1 H-NMR and 13 C-NMR spectra were identical to those previously reported.…”

Section: Resultsmentioning

confidence: 97%

See 1 more Smart Citation

Degradation of Fucoxanthin to Elucidate the Relationship between the Fucoxanthin Molecular Structure and Its Antiproliferative Effect on Caco-2 Cells

2018

Self Cite

View full text Add to dashboard Cite

Fucoxanthin has an antiproliferative effect on cancer cells, but its detailed structure–activity correlation has not yet been elucidated. To elucidate this correlation, fucoxanthin was degraded by ozonolysis. The degraded compounds of fucoxanthin obtained by ozonolysis were purified by HPLC and analyzed by NMR. The polyene chain of fucoxanthin was cleaved by ozonolysis, and the fucoxanthin was divided into two types of cyclohexyl derivatives, one with a β,γ-epoxy ketone group and the other with an allenic bond. In order to elucidate the structure–activity correlation, Caco-2 cells (human colorectal carcinoma) were treated with fucoxanthin degradation compounds. It was found that the entire structure of fucoxanthin is not essential for its antiproliferative effect and that even a partial structure exerts this effect.

show abstract

Section: Resultsmentioning

confidence: 97%

“…The extraction solvents and purification method have been referenced in previous experiments [30]. A mixed solvent (chloroform/methanol/water 5:4:1) was used for the extraction and subsequent purification of the residue on the silica gel (ethyl acetate/toluene 1:5) through chromatography, resulting in pure fucoxanthin (1.09 mg/g dry wakame).…”

Section: Methodsmentioning

confidence: 99%

Degradation of Fucoxanthin to Elucidate the Relationship between the Fucoxanthin Molecular Structure and Its Antiproliferative Effect on Caco-2 Cells

2018

Self Cite

View full text Add to dashboard Cite

show abstract

“…Vitamin D is metabolized into 1,25-di(OH)-vitamin D of an activated form through a two-step metabolism. Thus, in this study, the biological activity of activated form was predicted by PASS online software, as we have previously examined with another component [81]. The result was output in both Pa values (probability to be active) and Pi values (probability to be inactive).…”

Section: Estimation Of Biological Activity Of Vitamin D By Online Sofmentioning

confidence: 99%

“…To subject these vitamins D to any functional test, the vitamin D needs to be further converted into an activated form, but it was difficult for us to secure adequate amounts. Therefore, we estimated the biological activities of vitamin D by using Prediction of Activity Spectra for Substances (PASS) online software, as we have used in the past [81]. However, there is no intention here to regard activated vitamins D as drugs, but only to discuss the biological activities after ingestion as food components.…”

Section: Introductionmentioning

confidence: 99%

Uptake of Vitamins D2, D3, D4, D5, D6, and D7 Solubilized in Mixed Micelles by Human Intestinal Cells, Caco-2, an Enhancing Effect of Lysophosphatidylcholine on the Cellular Uptake, and Estimation of Vitamins D’ Biological Activities

2021

Self Cite

View full text Add to dashboard Cite

Vitamins D have various biological activities, as well as intestinal calcium absorption. There has been recent concern about insufficient vitamin D intake. In addition to vitamins D2 and D3, there are lesser-known vitamins D4–D7. We synthesized vitamins D5–D7, which are not commercially available, and then evaluated and compared the mixed micelles-solubilized vitamins D uptake by Caco-2 cells. Except for vitamin D5, the uptake amounts of vitamins D4–D7 by differentiated Caco-2 cells were similar to those of vitamins D2 and D3. The facilitative diffusion rate in the ezetimibe inhibited pathway was approximately 20% for each vitamin D type, suggesting that they would pass through the pathway at a similar rate. Lysophosphatidylcholine enhanced each vitamin D uptake by approximately 2.5-fold. Lysophosphatidylcholine showed an enhancing effect on vitamin D uptake by reducing the intercellular barrier formation of Caco-2 cells by reducing cellular cholesterol, suggesting that increasing the uptakes of vitamins D and/or co-ingesting them with lysophosphatidylcholine, would improve vitamin D insufficiency. The various biological activities in the activated form of vitamins D4–D7 were estimated by Prediction of Activity Spectra for Substances (PASS) online simulation. These may have some biological activities, supporting the potential as nutritional components.

show abstract

Fucoxanthin: From chemical properties and sources to novel anticancer mechanistic insights and synergistic therapeutic opportunities

Koch,

Kukula-Koch,

Wawruszak

et al. 2024

Current Research in Biotechnology

View full text Add to dashboard Cite

Fucoxanthin Derivatives: Synthesis and their Chemical Properties

Cited by 4 publications

References 45 publications

Degradation of Fucoxanthin to Elucidate the Relationship between the Fucoxanthin Molecular Structure and Its Antiproliferative Effect on Caco-2 Cells

Degradation of Fucoxanthin to Elucidate the Relationship between the Fucoxanthin Molecular Structure and Its Antiproliferative Effect on Caco-2 Cells

Uptake of Vitamins D2, D3, D4, D5, D6, and D7 Solubilized in Mixed Micelles by Human Intestinal Cells, Caco-2, an Enhancing Effect of Lysophosphatidylcholine on the Cellular Uptake, and Estimation of Vitamins D’ Biological Activities

Fucoxanthin: From chemical properties and sources to novel anticancer mechanistic insights and synergistic therapeutic opportunities

Contact Info

Product

Resources

About