Biosynthesis of anethole in pimpinella anisum L.

✍ Scribed by Paolo Manitto; Diego Monti; Paola Gramatica

• Publisher: Elsevier Science
• Year: 1974
• Tongue: French
• Weight: 126 KB
• Volume: 15
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)82521-1

✦ Synopsis

Until recently,the most plausible route for the biosynthesis of both ally1 and propenylphenols seemed to be by a series of reductive steps from the corresponding cinnamic acids (Birch's hypothesis). '\However, our finding that eugenol (I), estragole (II) and chavicol (III) are formed jn O&mum basilicum L.(Labiatae) from L-phenylalanine via oxygenated cinnar&c acids with loss of the carboxy group and incorporation of an llextra** carbon atom into the side-chain 2 led to reject the above hypothesis for the origin of allylphenols, and, on reflection, raised 3 new doubts about the biosynthesis of the propenyl isomers, e.g. anethole (IV).

In this paper we report precursor-incorporation data which prove unequivocally that the phenylpropane skeleton of L-phenylalanine is incorporated in anethole (Iv)4 with retention of all carbon atoms, thus giving evidence for the jn vivo _occurrence of independent routes to ally1 and propenylphenols.