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Org Lett. 2018 Jan 19;20(2):417-420. doi: 10.1021/acs.orglett.7b03716. Epub 2017 Dec 29.

Isolation, Synthesis, and Radical-Scavenging Activity of Rhodomelin A, a Ureidobromophenol from the Marine Red Alga Rhodomela confervoides.

Author information

1
Key Laboratory of Experimental Marine Biology, Institute of Oceanology, Chinese Academy of Sciences, and Laboratory of Marine Biology and Biotechnology of Qingdao National Laboratory for Marine Science and Technology , Nanhai Road 7, Qingdao 266071, China.
2
Key Laboratory of Marine Drugs, Ministry of Education, School of Medicine and Pharmacy, Ocean University of China, and Laboratory for Marine Drugs and Bioproducts of Qingdao National Laboratory for Marine Science and Technology , Yushan Road 5, Qingdao 266003, China.
3
Department of Chemistry, University of Iowa , Iowa City, Iowa 52242, United States.

Abstract

A novel ureidobromophenol, rhodomelin A (1), was characterized from Rhodomela confervoides. Its structure was elucidated by spectroscopic analysis. Both enantiomers of 1 were synthesized using a convergent strategy starting from d/l-pyroglutamic acids, respectively, allowing assignment of the R-configuration for the naturally occurring isomer by chiral HPLC analysis. Rhodomelin A represents the first example of a naturally occurring ureidopyrrolidone alkaloid incorporating a γ-aminobutyric acid unit. The scavenging activity of 1 toward DPPH (1,1-diphenyl-2-picrylhydrazyl) and ABTS (2,2'-azinobis(3-ethylbenzothiazoline-6-sulfonate)) radicals was assayed.

PMID:
29285928
DOI:
10.1021/acs.orglett.7b03716
[Indexed for MEDLINE]

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