Cassiaside C

Description

Cassiaside C belongs to the class of organic compounds known as naphthopyranone glycosides. Naphthopyranone glycosides are compounds containing a carbohydrate moiety glycosidically linked to a naphthopyranone moiety. Cassiaside C has been detected, but not quantified in, several different foods, such as arabica coffees (Coffea arabica), coffee and coffee products, herbs and spices, pulses, and robusta coffees (Coffea canephora). This could make cassiaside C a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Cassiaside C.

Definition

ChEBI: Cassiaside C is a benzochromenone and a glycoside.

Synthesis

1.Add Ag2CO3 (414 mg, 1.50 mmol) to a stirring suspension of 2,3,4-tri-O-benzoyl-6-O-acetyl-D-glucopyranosyl bromide (6d, 596 mg, 1.00 mmol) in acetone (10 mL) and water (0.5 mL) portionwise.2.After stirring for 40 minutes at ambient temperature, filter the mixture through a pad of Celite.3.Wash the filtrate with acetone.4.Dry the filtrate.5.Concentrate the filtrate.6.Purify the residue by column chromatography (petroleum ether-EtOAc, 3:1).

in vitro

Cassiaside C is a naphthopyrone isolated from the seed of Cassia tora. It has inhibitory activity on advanced glycation end products (AGE) formation in vitro.