Rhizoleucinoside, a Rhamnolipid–Amino Alcohol Hybrid from the Rhizobial Symbiont Bradyrhizobium sp. BTAi1

Rhizoleucinoside (1), a unique rhamnolipid–amino alcohol hybrid, was isolated from the rhizobial symbiont bacterium Bradyrhizobium sp. BTAi1. Compound 1 features a rare rhamnolipid core attached to an unprecedented leucinol moiety. Its structure and absolute configuration were determined by spectros...

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Veröffentlicht in:	Organic letters 2016-03, Vol.18 (6), p.1490-1493
Hauptverfasser:	Chen, Jianwei, Sun, Jiadong, Deering, Robert W, DaSilva, Nicholas, Seeram, Navindra P, Wang, Hong, Rowley, David C
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Bradyrhizobium - chemistry Cytotoxins - chemistry Cytotoxins - isolation & purification Cytotoxins - pharmacology Glycolipids - chemistry Glycolipids - isolation & purification Leucine - analogs & derivatives Leucine - chemistry Leucine - isolation & purification Mice Microglia - chemistry Molecular Structure Nuclear Magnetic Resonance, Biomolecular Rats
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Beschreibung
Zusammenfassung:	Rhizoleucinoside (1), a unique rhamnolipid–amino alcohol hybrid, was isolated from the rhizobial symbiont bacterium Bradyrhizobium sp. BTAi1. Compound 1 features a rare rhamnolipid core attached to an unprecedented leucinol moiety. Its structure and absolute configuration were determined by spectroscopic analysis, tandem mass spectrometry, chemical degradation, and application of the Marfey’s method. Compound 1 possesses moderate cytotoxicity to BV-2 murine microglia and highly aggressive proliferating immortalized (HAPI) rat microglia cells.
ISSN:	1523-7060 1523-7052
DOI:	10.1021/acs.orglett.6b00461