A naturally occurring nonaprenylsulfate (1) and its synthetic analogue (2) were synthesized from substituted phenolic precursors in three steps with an overall yield of 40-45%. Both compounds exhibited potent anti-inflammatory activity against 5-lipoxygenase, and potent brine shrimp lethality. They also showed moderate anti-oxidant activity in the super oxide radical scavenging model. Nonaprenylsulfate (1) showed moderate inhibition of paw edema in Freund's Complete Adjuvant (FCA) induced model of arthritis, thus confirming its anti-inflammatory activity.
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