Regioselective syntheses and analyses of phlorofucofuroeckol-A derivatives
- Authors
- Kim, Yongkyun; Shin, Jooseok; Shin, Hyeon-cheol; Park, Kwangyong
- Issue Date
- Dec-2021
- Publisher
- 대한화학회
- Keywords
- brown algae; phlorofucofuroeckol-A; phlorotannin; regioselective substitution
- Citation
- Bulletin of the Korean Chemical Society, v.42, no.12, pp 1624 - 1632
- Pages
- 9
- Journal Title
- Bulletin of the Korean Chemical Society
- Volume
- 42
- Number
- 12
- Start Page
- 1624
- End Page
- 1632
- URI
- https://scholarworks.bwise.kr/cau/handle/2019.sw.cau/51529
- DOI
- 10.1002/bkcs.12414
- ISSN
- 0253-2964
1229-5949
- Abstract
- 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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