Biosynthesis of pseudoisoeugenols in tissue cultures ofPimpinella anisum

Abstract

The genus Pimpinella contains pseudoisoeugenols, phenylpropanoids with a rare 2,5-dioxy substitution pattern on the phenyl ring. To study the biosynthesis of these compounds, we set up a leaf-differentiating tissue culture of Pimpinella anisum. These cultures mainly produce epoxy-pseudoisoeugenol-(2-methylbutyrate). To corroborate the biosynthetic pathway of epoxy-pseudoisoeugenol-(2-methylbutyrate) as proposed on the basis of investigations with 13C/14C-labelled precursors, the key steps of the pathway were investigated at an enzyme level. Experiments with cell-free homogenates clearly revealed that L-phenylalanine is converted to (E)-cinnamic acid by phenylalanine ammonia lyase and that (E)-cinnamic acid is converted to p-coumaric acid by cinnamic acid 4-hydroxylase. L-2-aminooxy-3-phenylpropionic acid, an analogue of L-phenylalanine, inhibited the incorporation of L-[3'-13C]phenylalanine into epoxy-pseudoisoeugenol-(2-methylbutyrate). Up to 2% of the precursor DL-[3'-13C]phenyllactate was incorporated into epoxy-pseudoisoeugenol-(2-methylbutyrate). Inhibition experiments with oxalacetic acid clearly showed that cinnamic acid is not formed by dehydration of phenyllactic acid in this leaf-differentiating tissue culture of P. anisum.

Antispasmodic and relaxant effects of the hidroalcoholic extract of Pimpinella anisum (Apiaceae) on rat anococcygeus smooth muscle

“…Chemical studies demonstrated that the Pimpinella anisum seed contain anethole (Chandler and Hawkes, 1984;Fujita and Nagasawa, 1960), estragole (Zargari, 1989), eugenol (Monod and Dortan, 1950), pseudoisoeugenol (Reichling et al, 1995), methylchavicol and anisaldehyde (Wagner et al, 1984), coumarins, scopoletin, umbelliferon, estrols (Burkhardt et al, 1986), terpene hydrocarbons (Kartnig et al, 1975), polyenes and polyacetylenes (Schulte et al, 1970) as the major compounds. Among these compounds, eugenol, estragole ) and anethole (Albuquerque et al, 1995) were described to exert relaxant effect.…”

Chemical composition of the essential oils from the roots, fruits, leaves and stems of Pimpinella cumbrae Link growing in the Canary Islands (Spain)

“…14,22,24 -26 They have been found so far in P. cumbrae (this paper), P. anisum L. 14 Pseudoisoeugenol esters have also been found, but only in Apiaceae in in vitro systems. 28,29 Our finding in the oil from the roots of P. cumbrae of pregeijerene, geijerene, 1,4-dimethyl-azulene, trinoranastreptene, two isomers of dihydro-1,4-dimethylazulene, pseudoisoeugenyl-2-methyl-butyrate (I), pseudoisoeugenyl-tiglate (II), pseudoisoeugenyl-2-methyl-butyrate epoxides (III) and epoxy-pseudoisoeugenyl-tiglate (IV) strongly support the proposal of Kubeczka et al 14 and Kubeczka 22 in that the knowledge of the chemical composition of the volatiles from Pimpinella spp. hold substantial promise for establishing taxonomic infrageneric relationships.…”

Emerging Biopharmaceuticals from Pimpinella Genus

“…According to the skeletal characteristics of the phenylpropanoids in Pimpinella , they could be divided into three groups: pseudoisoeugenol, pseudoisoeugenol derivatives, and simple phenylpropanoids. Pseudoisoeugenol, as a representative chemical marker of Pimpinella , possessed a peculiar skeleton of 1-hydroxy-2-propyl-4-methoxybenzene, which has been found exclusively in the genus Pimpinella so far [ 28 ]. Since the first pseudoisoeugenol was discovered from the P. anisum by G. T. Carter et al [ 29 ] in 1977, scientists have successively obtained 12 pseudoisoeugenol ( 1 – 12 ) from the Chinese herb P. thellungiana , and llungianin A ( 1 ) and llungianin B ( 2 ), which presented significant antihypertensive activity [ 30 , 31 , 32 , 33 , 34 , 35 , 36 , 37 ].…”