Abstract

Methyl-3-orsellinate can be generated from methyl-3-orcinol through the nitration of aryl function to be then reduced to amine group. This last derivative could be the substrat of a diazotonization for the corresponding diazonium salt. After this, a cyanide group could be introduced by nucleophilic substitution using potassium cyanide and then, the carboxyl function could be produced after hydrolysis. Alternatively, methyl-3-orsellinate could be produced by alginate-immobilized, atranorin-producing lichen cells loaded with acetate and treated with sodium azide. Acetate is used by acetyl-CoA carboxylase and aromatic synthase (methyl transfer) to produce methyl-3-orsellinate and its oxidation to haematommoyl alcohol is inhibited by sodium azide.

Highlights

  • Lichens produce depsides, phenolics composed by two or three monocyclic units linked by an ester bond and derived from orsellinic acid

  • Methyl-3-orsellinate can be generated from methyl-3-orcinol through the nitration of aryl function to be reduced to amine group

  • This last derivative could be the substrat of a diazotonization for the corresponding diazonium salt

Read more

Summary

Introduction

Phenolics composed by two or three monocyclic units linked by an ester bond and derived from orsellinic acid. Labelling experiments have indicated that an additional C-1 unit must be added to the polyketide chain prior to cyclasation to produce β-methyl orsellinate, the basic unit of depsides of the β-orcinol series[2,3]. This additional C1 unit can be derivatized or oxidized to alcohol or aldehyde functions, such as occurs in atranorin. Since atranorin is an inhibitor of elastase[9], its use would arise great interest among the cosmetic industry Usnic acid, another lichen phenol, is used as preservative in cosmetic creams[10], and atranorin and other related compounds are potential sunscreen materials[11]. Since atranorin seems to be a key compound for pharmaceutical and cosmetic industries, a simple procedure to obtain methyl-3-orsellinate as a precursor of haematommic acid is required in order to an efficient production of the depside

Production of methyl-3-orsellinate by organic synthesis
Findings
Bioproduction of methyl-3-orsellinate by immobilized lichen cells
Full Text
Published version (Free)

Talk to us

Join us for a 30 min session where you can share your feedback and ask us any queries you have

Schedule a call