Synthesis of andrographolide derivative with reduced bitterness

Abstract

The synthesis or modification of the structural formula of andrographolide, which can be found in the herb known as "Fa thalaai joan", was carried out through esterification by using acid chloride to give the product derivatives of andrographolide diacetate, 8-chloro-andrographolide triacetate, andrographolide dibutyrate, andrographolide tributyrate, androgra pholide trihexanoate and 14-deoxy-11,12-didehydroandrographolide p-nitro monobenzoate. All this, the resulting derivative maintained the structural formula of original andrographolide. However, the bitter was decreased, which is considered to be beneficial in the treatment of diarrhea in baby pigs and the structure of the synthesized derivative was also studied through the use of spectroscopy. Furthermore, through the use of X-ray crystallography, the structures of andrographolide and its derivatives were confirmed. The relationships between the hydrogen bonds within the molecule of the substances can be used to explain the mechanism of bitterness taste of andrographolide