Notizen: A New Type of Phenylpropane from the Essential Fruit Oil of Pimpinella anisum L.

Kubeczka, Karl-Heinz; Massow, Friedrich von; Formáček, Viktor; Smith, M. A. R.

doi:10.1515/znb-1976-0233

Cited by 29 publications

(9 citation statements)

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“…As long as the co-occurrence of isoeugenol-derivates in umbelliferae and compositae is not proven with absolute certainty, these constituents cannot be used as a base for the discussion of chemotaxonomic relationship. The compounds described in this paper show, that the unusual basic molecule of pseudoisoeugenol, first described by > Kubeczka et al (9), is present in different Pimpinella species in a reasonable variety of structures. Therefore, we conclude that a biosynthetic pathway for their own should be formulated.…”

Section: Discussionsupporting

confidence: 55%

“…Kubeczka et al (9) have already isolated a phenylpropanoid from P. anisum with a substitution pattern at the phenyl ring differing from the isoeugenol type and not known before to be present in natural products. These authors also indicated that the biosynthesis of certain phenylpropanoids does not necessarily have to go through isoeugenol-like steps.…”

Section: Introductionmentioning

confidence: 99%

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Reinvestigation of the Phenylpropanoids from the Roots of Pimpinella Species

Martin¹,

Reichling²,

Becker³

1985

Planta Med

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Section: Discussionsupporting

confidence: 55%

Section: Introductionmentioning

confidence: 99%

Reinvestigation of the Phenylpropanoids from the Roots of Pimpinella Species

Martin¹,

Reichling²,

Becker³

1985

Planta Med

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“…Whereas L-2-aminooxy-3-phenylpropionic acid inhibits phenylalanine ammonia lyase [I [3][4][5][6][7][8][9][10][11][12][13][14][15][16], oxalacetic acid affects phenylalanine aminotransferase [23]. Whereas L-2-aminooxy-3-phenylpropionic acid inhibits phenylalanine ammonia lyase [I [3][4][5][6][7][8][9][10][11][12][13][14][15][16], oxalacetic acid affects phenylalanine aminotransferase [23].…”

Section: Inhibition Experiments With Oxalacetic Acid and L-2-aminooxymentioning

confidence: 99%

Biosynthesis of pseudoisoeugenols in tissue cultures ofPimpinella anisum

1995

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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.

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“…During the last few years phytochemical investigations of a variety of Pimpinella species (Apiaceae) has revealed the presence of rare phenylpropanoids with an unusual 2,5-dioxy-substitution pattern at the phenylring (Kubeczka et al 1976;Martin et al 1985). We named the 1-(E)-propenyl-2-hydroxy-5-methoxy benzene skeleton of these compounds pseudoiseugenol.…”

Section: Introductionmentioning

confidence: 99%

Biosynthesis of pseudoisoeugenol-derivatives in liquid tissue cultures ofPimpinella anisum

Reichling

Martin

Kemmerer

1995

Plant Cell Tiss Organ Cult

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The genus Pimpinella contains rare phenylpropanoids. The 1-(E)-propenyl-2-hydroxy-5-methoxy benzene skeleton of these compounds is called pseudoisoeugenol. To study the biosynthesis of these compounds, we set up a tissue culture of Pimpinella anisum (PAD) that selectively promoted the production of epoxy-pseudoisoeugenol-(2methylbutyrate), termed EPB. This compound served as the final molecule of the biosynthetic pathway in all labelling experiments conducted.The putative precursors were labelled with 13C or lac. The incorporation of the label was followed by 13C-NMR-spectroscopy and liquid scintillation, respectively. Based on our labelling experiments as well as on enzymic reactions in a cell homogenate we proposed a genaral biosynthetic pathway for EPB. The biosynthetic sequence found was L-phenylalanine, trans-cinnamic acid, p-coumaric acid, p-coumaric aldehyde, p-coumaric alcohol, anol and trans-anethol. The biosynthetic step leading from trans-anethol to pseudo-isoeugenol involves migration of the side chain during the introduction of the second OH-group in the molecule (NIH-shift). The final biosynthetic steps to form EPB must be acylation and epoxidation of the propenyl double bond of pseudoisoeugenol.Abbreviations: NMR -Nuclear Magnetic Resonance, NOE -Nuclear Overhauser Effect

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Notizen: A New Type of Phenylpropane from the Essential Fruit Oil of Pimpinella anisum L.

Abstract: Apiaceae, Pimpinella anisum, Essential oil, 13 C NMR From the essential oil of Pimpinella anisum fruits a hitherto unknown type of phenylpropane was isolated. The mass, infrared, and 13 C NMR spectra indicate, that the unknown is a 2-methyl-butyric acid ester of 2-hydroxy-5-methoxy-

Cited by 29 publications

References 0 publications

Reinvestigation of the Phenylpropanoids from the Roots of Pimpinella Species

Reinvestigation of the Phenylpropanoids from the Roots of Pimpinella Species

Biosynthesis of pseudoisoeugenols in tissue cultures ofPimpinella anisum

Biosynthesis of pseudoisoeugenol-derivatives in liquid tissue cultures ofPimpinella anisum

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