Biosynthesis of furanocoumarins in Pimpinella magna (umbelliferae)

Floss, H. G.; Paikert, H

doi:10.1016/s0031-9422(00)85405-9

Cited by 18 publications

(11 citation statements)

References 12 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Very often, for example, this results from the addition of one or more branched C 5 units derived from isopentenyl pyrophosphate or y,7-dimethylallylpyrophosphate 16 · x 7 . Similar correlations have been made by other workers [19][20][21] . Thus osthenol (4), columbianetin (5), angelicin (7), archangelicin (6) and isobergapten (8) are a typical group of coumarins from the Umbelliferae.…”

Section: Higher Plants: Phenylpropanoid Compounds 189supporting

confidence: 90%

See 1 more Smart Citation

The Shikimate Pathway in Higher Plants: Phenylpropanoid Compounds and their Derivatives

Haslam

1974

The Shikimate Pathway

View full text Add to dashboard Cite

Section: Higher Plants: Phenylpropanoid Compounds 189supporting

confidence: 90%

“…Examples which typically illustrate the various modes of chemical combination are shown in the accom panying formulae (19)(20)(21)(22)(23)(24)(25)(26)(27). Here the majority are found in combination with sugars or related com pounds either as glycosides or esters.…”

Section: Phenolic Esters and Glycosidesmentioning

confidence: 99%

The Shikimate Pathway in Higher Plants: Phenylpropanoid Compounds and their Derivatives

Haslam

1974

The Shikimate Pathway

View full text Add to dashboard Cite

“…The biosynthesis of furanocoumarins has been elucidated on the basis of precursor studies [12,36,37]. Most likely, umbelliferone is formed from L-phenylalanine via cinnamic acid, 4-coumaric acid and umbelliferic acid.…”

Section: Discussionmentioning

confidence: 99%

Differential Response of Cultured Parsley Cells to Elicitors from Two Non-pathogenic Strains of Fungi. 2. Effects on Enzyme Activities

Tietjen

Matern

1983

Eur J Biochem

View full text Add to dashboard Cite

Parsley cell cultures produce linear furanocoumarins and the linear benzodipyrandione, graveolone, in response to treatment with an elicitor from either Plzj~phthora mc~gaspernia or Alfernaria curthami. Activities of enzymes involved in general phenylpropanoid metabolism, phenylalanine ammonia-lyase and 4-coumarate : CoA ligase, as well as of an enzyme involved specifically in furanocoumarin biosynthesis, dimethylallyl diphosphate : umbelliferone dimethylallyltransferase, were monitored over several days after treatment with A . carthami elicitor. In addition, the activities of chalcone synthase, an enzyme involved in flavonoid formation, and of glucose-6-phosphate: NADP 1 -oxidoreductase were also monitored. The lyase and the ligase activities increased steadily for 48 h and the dimethylallyltransferase activity for 54 h, while the synthase activity was not altered and the oxidoreductase activity decreased gradually. In some experiments, phenylalanine ammonia-lyase activity reached a maximum value of 250 pkat/kg, twice the inaximal activity observed previously in parsley cells after treatment with either ultraviolet light or an elicitor preparation from P. mrgaspwma. In crude extracts, phenylalanine ammonia-lyase activity was shown to be inhibited by unidentified small-molecular-weight compounds which were formed in proportion to the elicitor treatment.While phenylalanine ammonia-lyase and dimethylallyl diphosphate:umbelliferone dimethylallyltransferase are known to be required for furanocoumarin biosynthesis, the involvement of 4-coumarate: CoA ligase is as yet unclear. The concomitant increase and decrease of the ligase activity with the activities of the lyase and the dimethylallyltransferase, as well as its similar response to elicitor concentrations, suggest that CoA esters of cinnamic acids play a role in the biosynthesis of furanocoumarins.Fungal invasion of soybean [I -31, pea [4], bean [ 5 ] , tomato [6] and parsley [7] results in the activation of phenylpropanoid metabolism. The first reaction of phenylpropanoid biosynthesis is catalyzed by phenylalanine ammonia-lyase which converts 1.-phenylalanine to trans-cinnamic acid. This enzyme appears to be regulated by small-molecular-weight compounds [8,9] and may catalyze the rate-limiting step of general phenylpropanoid biosynthesis. Under different induction conditions, maximum lyase activity was reported 4-24 h after induction. Treatment of parsley cell cultures with elicitor preparations from Pl~ytoplztiior-a rnegasprt~ma f.sp. g/jJc.inea led to maximal activities of the enzymes of general phenylpropanoid metabolism, e.g. phenylalanine ammonialyase and 4-coumarate: CoA ligase, designated as group I [lo], 6-8 h after treatment. De novo synthesis of the lyase [7] and the ligase

show abstract

“…+Marmesin has been recognized as the precursor of linear furanocoumarins (psoralens) in several species belonging to the families of Umbelliferae, Apiaceae, Rutaceae, Moraceae, and Leguminoseae (Brown 1978;Floss 1972;Floss and Mothes 1966;Floss and Paikert 1969;Hamerski and Matern 1988;Matern et al 1988;Steck et al 1969). The conversion of +marmesin to the respective linear furanocoumarins involves the oxidative cleavage of the isopropyl alcohol side chain and the introduction of a double bond to the five-member ring moiety (Brown 1978;Hamerski and Matern 1988;Matern et al 1988).…”

Section: Comparison Of +Marmesin Psoralens and Ga 3 Contribution Tomentioning

confidence: 99%

“…This study examines the potential of +marmesin as a phytoalexin and naturally occurring chemical agent for preventing postharvest decay in parsley. It is known that +marmesin is the precursor of psoralens (linear furanocoumarins) in species belonging to the families of Umbelliferae, Apiaceae, Rutaceae, Moraceae, and Leguminoseae (Brown 1978;Floss 1972;Floss and Mothes 1966;Floss and Paikert 1969;Hamerski and Matern 1988;Matern et al 1988;Steck et al 1969). Afek et al (1995a) reported that +marmesin was involved in celery resistance to pathogens during storage and that GA 3 affected celery resistance (Afek et al 1995b).…”

Section: Introductionmentioning

confidence: 99%

The involvement of marmesin and its interaction with GA₃and psoralens in parsley decay resistance

Afek

Orenstein

Aharoni

2002

Canadian Journal of Plant Pathology

View full text Add to dashboard Cite

In parsley (Petroselinum crispum (Mill.) Mansf.) with no decay prior to storage, the incidence rose to 12% after 1 month of storage at 1°C, and the concentration of +marmesin in leaves decreased from 32 to 4 µg g -1 fresh mass (FM). During that time, the concentration of psoralens increased from 8 to 41 µg g -1 FM. When parsley was treated with GA 3 prior to storage, incidence of decay following 1 month of storage at 1°C was 3%, and the concentration of +marmesin was 21 µg g -1 FM. Concentrations of psoralens (psoralen, bergapten, and xanthotoxin) during that time reached 15 µg g -1 FM. Bioassays showed that +marmesin has much greater antifungal activity in vitro than psoralens.Résumé : Après 1 mois d'entreposage à 1°C, l'incidence de la carie augmenta à 12% et la concentration de marmesine + dans les feuilles diminua de 32 à 4 µg g -1 de masse fraîche (MF) dans du persil (Petroselinum crispum (Mill.) Mansf.) sans carie avant l'entreposage. Durant cette période, la concentration de psoralènes augmenta de 8 à 41 µg g -1 MF. Lorsque le persil fut traité avec du GA 3 avant l'entreposage, la fréquence de la carie après 1 mois d'entreposage à 1°C fut de 3% et la concentration de marmesine + fut de 21 µg g -1 MF. Les concentrations de psoralènes (psoralène, bergaptène et xanthotoxine) durant cette période atteignirent 15 µg g -1 MF. Des bioessais montrèrent que la marmesine + possède une bien plus grande activité antifongique in vitro que les psoralènes.

show abstract

Biosynthesis of furanocoumarins in Pimpinella magna (umbelliferae)

Cited by 18 publications

References 12 publications

The Shikimate Pathway in Higher Plants: Phenylpropanoid Compounds and their Derivatives

The Shikimate Pathway in Higher Plants: Phenylpropanoid Compounds and their Derivatives

Differential Response of Cultured Parsley Cells to Elicitors from Two Non-pathogenic Strains of Fungi. 2. Effects on Enzyme Activities

The involvement of marmesin and its interaction with GA₃and psoralens in parsley decay resistance

Contact Info

Product

Resources

About

Biosynthesis of furanocoumarins in Pimpinella magna (umbelliferae)

Cited by 18 publications

References 12 publications

The Shikimate Pathway in Higher Plants: Phenylpropanoid Compounds and their Derivatives

The Shikimate Pathway in Higher Plants: Phenylpropanoid Compounds and their Derivatives

Differential Response of Cultured Parsley Cells to Elicitors from Two Non-pathogenic Strains of Fungi. 2. Effects on Enzyme Activities

The involvement of marmesin and its interaction with GA3and psoralens in parsley decay resistance

Contact Info

Product

Resources

About

The involvement of marmesin and its interaction with GA₃and psoralens in parsley decay resistance