Naphthalene glycosides

Naphthalene glycosides Hernerocallis flowers SiO, Multicomponent eluents... 

N.A. Anthraquinone, beta-sitosterol, rhein, dianthrone glucosides, sennosides A, B, naphthalene glycosides, aloe-emodin, mucilage.99 100 510 511 Laxative, stimulant, anticancer, cathartic. 

Kuruiiziim A, Demirezer LO, Bergere I, Zeeck A (2001) Two New Chlorinated Naphthalene Glycosides from Rumex patientia. J Nat Prod 64 688... 

Roubal et al. (8) applied TLC to the separation and identification of metabolites of l c-iabeled naphthalene administered to coho salmon fingerlings via intraperitoneal injection. 1-Naphthol, a dihydrodiol, mercapturic acid, 1-naphthyl glucuronic acid and a glycoside/sulfate fraction were identified in brain, liver, gall bladder, and muscle 1-naphthol, a dihydrodiol, and 1-naphthyl glucuronic acid were the only metabolites found in heart. 

Collier et al. (10) demonstrated that HPLC was an effective technique for the separation of aromatic hydrocarbon metabolites in exposed marine organisms. Radioactive bioconversion products were studied in liver and gall bladder of coho salmon dosed with H-naphthalene. Quantitative identifications of glucuronide, sulphate, dihydrodiol, glycoside, and 1-naphthol derivatives were obtained. Three additional polar compounds of unknown structure were found. A typical HPLC profile is shown in Figure 2. 

Andrews and Larsen also carried out Lewis acid catalyzed glycosidations of naphthalene derivatives with anomeric acetates to gain access to the ring systems of the Angucycline antibiotics [156]. Suzuki has also published an account of his work on novel Lewis acid catalysts in organic synthesis [157]. 

A n.m.r. spectroscopic study of 1 1 complexes between cycloamyloses and azo dyes having a naphthalene nucleus has been reported.Almost all carbons of the guest molecules showed low field shifts on inclusion, consistent with n.m.r. spectroscopic results. The shift may be due not to a simple steric polarization but to hydrophobic interaction with the host molecule, whose cavity uniformly affects the guest molecule as if it is dissolved in a hydrophobic solvent. The host molecule was shown to be deformed by the bulky naphthalene nucleus at the glycosidic linkage rather than at the small diameter side of the cavity. 

Aldono-1,4-lactone iV-tosyl- or iV-naphthalene-2-sulfonylhydrazone derivatives such as 77 were prepared from the corresponding free sugars (e.g. 76), and shown to act as glycofuranosylidene carbene precursors on deprotonation and photolysis (Scheme 14). The carbenes could be trapped with alkenes to give adducts such as 78, or phenols to give glycosides e.g. 79. ... 

Styrol Glycosides, Dihydrostilbenes, Lignans, Quinones and Naphthalenes 16... 

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