Highly Regioselective Preparation and Characterization of New 6-O-Substituted Dieckol Derivatives

Kim, Yong-Kyun; Shin, Jooseok; Kang, Su Kyung; Song, Jinyoung; Shin, Hyeon‐Cheol; Keum, Young‐Sam; Hwang, Hye Jeong; Park, Kwangyong

doi:10.1016/j.jiec.2020.08.012

Journal of Industrial and Engineering Chemistry

2020

DOI: 10.1016/j.jiec.2020.08.012

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Highly Regioselective Preparation and Characterization of New 6-O-Substituted Dieckol Derivatives

Yong-Kyun Kim

Jooseok Shin

Su Kyung Kang

et al.

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Cited by 4 publications

References 47 publications

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Regioselective syntheses and analyses of phlorofucofuroeckol‐A derivatives

Kim

Shin

et al. 2021

Bulletin Korean Chem Soc

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Phlorofucofuroeckol-A (PFF-A) is a phlorotannin extracted from various brown algae. PFF-A shows low toxicity when ingested and various biochemical effects, including antioxidant, anti-inflammatory, anti-cancer, and anti-allergy properties. In this study, various di-O-substituted PFF-A derivatives were synthesized by introducing alkyl or acyl groups at two specific hydroxyls out of the nine nearly equivalent phenolic OH groups present in PFF-A. The exact molecular structures of the synthesized derivatives were analyzed using two-dimensional nuclear magnetic resonance (2D NMR) spectroscopy, which confirmed that the substituents were regioselectively introduced at the 1 OH and 6 OH positions. Small amounts of three mono-O-substituted derivatives were generated as by-products in this reaction, and their structures and regioselectivity were determined using 2D NMR spectroscopy. This study can provide insights into understanding the mechanism of action of eckol-based compounds and developing new drug candidates.

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Regioselective syntheses and analyses of phlorofucofuroeckol‐A derivatives

Kim

Shin

et al. 2021

Bulletin Korean Chem Soc

Self Cite

View full text Add to dashboard Cite

show abstract

Facile synthesis of fluorescent mesoporous nanocarriers with pH-sensitive controlled release of naturally derived dieckol

Son

Kim

Lee

2023

Colloids and Surfaces A: Physicochemical and Engineering Aspect

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Phlorotannins: A review on biosynthesis, chemistry and bioactivity

2021

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Highly Regioselective Preparation and Characterization of New 6-O-Substituted Dieckol Derivatives

Cited by 4 publications

References 47 publications

Regioselective syntheses and analyses of phlorofucofuroeckol‐A derivatives

Regioselective syntheses and analyses of phlorofucofuroeckol‐A derivatives

Facile synthesis of fluorescent mesoporous nanocarriers with pH-sensitive controlled release of naturally derived dieckol

Phlorotannins: A review on biosynthesis, chemistry and bioactivity

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