On the biosynthesis of furocoumarins in Pimpinella magna

Floss, H. G.; Mothes, U.

doi:10.1016/s0031-9422(00)85094-3

Cited by 38 publications

(11 citation statements)

References 18 publications

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“…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%

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

Haslam

1974

The Shikimate Pathway

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Section: Higher Plants: Phenylpropanoid Compounds 189supporting

confidence: 90%

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

Haslam

1974

The Shikimate Pathway

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“…Umbelliferone rather than coumarin is the parent compound of furanocoumarins, as was reported a long time ago (Floss and Mothes 1964). It is first prenylated in 6-(for linear furanocoumarins) or 8-position (for angular furanocoumarins) to yield demethylsuberosin and osthenol, respectively (Fig.…”

Section: Entry Of Umbelliferone Into the Furanocoumarin Pathwaymentioning

confidence: 85%

Biosynthesis of coumarins in plants: a major pathway still to be unravelled for cytochrome P450 enzymes

et al. 2006

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Coumarins (1,2-benzopyrones) are ubiquitously found in higher plants where they originate from the phenylpropanoid pathway. They contribute essentially to the persistence of plants being involved in processes such as defense against phytopathogens, response to abiotic stresses, regulation of oxidative stress, and probably hormonal regulation. Despite their importance, major details of their biosynthesis are still largely unknown and many P450-dependent enzymatic steps have remained unresolved. Ortho-hydroxylation of hydroxycinnamic acids is a pivotal step that has received insufficient attention in the literature. This hypothetical P450 reaction is critical for the course for the biosynthesis of simple coumarin, umbelliferone and other hydroxylated coumarins in plants. Multiple P450 enzymes are also involved in furanocoumarin synthesis, a major class of phytoalexins derived from umbelliferone. Several of them have been characterized at the biochemical level but no monooxygenase gene of the furanocoumarin pathway has been identified yet. This review highlights the major steps of the coumarin pathway with emphasis on the cytochrome P450 enzymes involved. Recent progress and the outcomes of novel strategies developed to uncover coumarin-committed CYPs are discussed.

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“…FLOSS a n d MOTHES [34] did indeed present evidence, from the feeding of Consideration of possible biosynthetic pathways to the furanocoumarins raises the question of how the fused furan ring is constructed, and the order in which the three rings are formed. The 'first question has not yet been fully answered, but the second was answered in early studies by FLOSS and MOTHES [3 31, who showed by 1 4 C tracer experiments that umbelliferone (7-hydroxycoumarin) is an efficient precursor of the fura- The specific incorporation of 14C from mevalonate into the furan ring suggests involvement of.…”

Section: Biosynthetic Routes To the Furanocoumarinsmentioning

confidence: 98%

Untitled

2009

Planta Med

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Abstract~oumarins, a group of naturally occurring phenylpropanoid lactones exerting a wide range of physiological effects, are elaborated by many plants and in a few microbial species. Early studies on the biosynthetic reactions leading to the simple coumarins in plants demonstrated derivation from the shikimic acid pathway via cinnamic acid and either ortho-or para-hydroxycinnamic acid. 'Radiotracer experiments later indicated that the furan ring of the furanocoumarins, found chiefly in the Rutaceae and Umbelliferae, is constructed on the coumarin nucleus following attachment of a mevalonate-derived sidechain to umbelliferone, and cyclization to dihydrofuranocoumarin intermediates. These findings have been substantiated and extended by the isolation and This document was downloaded for personal use only. Unauthorized distribution is strictly prohibited.

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On the biosynthesis of furocoumarins in Pimpinella magna

Cited by 38 publications

References 18 publications

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

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

Biosynthesis of coumarins in plants: a major pathway still to be unravelled for cytochrome P450 enzymes

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