Psoralen, an inhibitor in the seeds of Psoralea subacaulis (Leguminosae)

Baskin, Jerry M.; Ludlow, C. Joseph; Harris, Thomas M.; Wolf, Frederick A.

doi:10.1016/s0031-9422(00)86083-5

Cited by 65 publications

(28 citation statements)

References 7 publications

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“…Psoralen compounds such as xanthotoxin have been found in an array of plants (17,19,22,23) including the family Leguminosae (to date, these compounds have not been isolated from peas) (1 2The term "inducer" in this paper will refer to an agent which can cause an increase in extractable PAL and pisatin.…”

Section: Methodsmentioning

confidence: 99%

Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Hadwiger

1972

Plant Physiol.

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Section: Methodsmentioning

confidence: 99%

Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Hadwiger

1972

Plant Physiol.

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“…Apiaceae, Rutaceae, Fabaceae, and Moraceae) (5,6). They are allelochemicals that have been assigned ecological functions, such as the defense against phytopathogens, germination inhibition of competitor plants, or herbivore deterrence (7)(8)(9)(10). Their toxicity is based on their ability to create covalent adducts of double-stranded DNA, impeding DNA replication (9,11), as well as to inhibit cytochrome P450 enzymes (12)(13)(14).…”

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confidence: 99%

Isolation and Functional Characterization of CYP71AJ4 Encoding for the First P450 Monooxygenase of Angular Furanocoumarin Biosynthesis

Larbat¹,

Hehn²,

Hans

et al. 2009

Journal of Biological Chemistry

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The biosynthesis of linear and angular furanocoumarins is still poorly understood at the molecular level, with only psoralen synthase (CYP71AJ1) identified from Ammi majus. Using cDNA probes inferred from CYP71AJ1, three orthologs were isolated from Apium graveolens (CYP71AJ2) and Pastinaca sativa (CYP71AJ3 and -4) and functionally expressed in yeast cells. CYP71AJ2 and CYP71AJ3 displayed psoralen synthase activity, whereas CYP71AJ4 only catalyzed the conversion of (؉)-columbianetin to angelicin and negligible amounts of a hydroxylated columbianetin by-product. CYP71AJ4 thus constitutes the first fully characterized P450 monooxygenase specific for the angular furanocoumarin pathway. The angelicin synthase exhibited an apparent K m of 2.1 ؎ 0.4 M for (؉)-columbianetin and a k cat of 112 ؎ 14 min ؊1 . Moreover, the use of 3-deuterated (؉)-columbianetin as substrate led to an almost complete "metabolic switch," resulting in the synthesis of anti-3-hydroxy-3-deuterated(؉)-columbianetin. This confirms that angelicin synthase attacks columbianetin by syn-elimination of hydrogen from C-3. Sequence comparison between psoralen synthase (CYP71AJ3) and angelicin synthase (CYP71AJ4) showed 70% identity, whereas the identity dropped to 40% in those regions thought to provide the substrate recognition sites. Accordingly, CYP71AJ3 and CYP71AJ4 might be derived from a common ancestor of unknown functionality by gene duplication and subsequent molecular evolution.Furanocoumarins are natural plant metabolites characterized by a furane moiety fused to benzopyran-2-one. The position of the furane substitution distinguishes two large groups of compounds, the linear (psoralens) and the angular furanocoumarins (angelicin and derivatives) (Fig.

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“…The identity of the compounds involved in allelopathy of the invader remains unknown, but we can rule out the furanocoumarins. Furanocoumarins had previously been indicated as possible agents responsible for allelopathy (Baskin et al 1967;Macias et al 1993;Garcia et al 2002). Junttila (1976), who studied inhibitory effects of a seed extract of H. laciniatum, reported three bioactive fractions including furanocoumarins to suppress germination of assay species although other unknown compounds were also involved.…”

Section: Discussionmentioning

confidence: 99%

Searching for Heracleum mantegazzianum allelopathy in vitro and in a garden experiment

2014

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One theory concerning the invasiveness of exotic plants suggests that they exude phytotoxic compounds that are novel in areas being invaded. For most invasive plants, however, little is known about the effects of their bioactive chemicals and how novel they are in invaded areas. From a methodological point of view, it also remains largely untested whether phytotoxicity found in vitro translates into allelopathic effects in more complex ecological settings. In this study, we tested for allelopathic effects of root exudates of the invasive plant Heracleum mantegazzianum (giant hogweed), its native congener Heracleum sphondylium (common hogweed) and two less-related native species. We also performed chemical analyses of the invader's root exudates to identify bioactive compounds. We found that root exudates of H. mantegazzianum contain allelopathic compounds which are not likely to be furanocoumarins, but other as yet unidentified molecules. Allelopathy of the invader detected in vitro conditions and in our garden experiment did not, however, differ from the allelopathy of the native species tested. A meta-analysis of two independent garden experiments indicated significantly negative, though similar, phytotoxic effects of H. mantegazzianum, its native congener and Dactylis glomerata in the absence of activated carbon. Our study thus indicates that allelopathy by producing unique compounds, as predicted by the novel weapons hypothesis, is not a principal driver of the invasion success of H. mantegazzianum.

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Psoralen, an inhibitor in the seeds of Psoralea subacaulis (Leguminosae)

Cited by 65 publications

References 7 publications

Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Induction of Phenylalanine Ammonia Lyase and Pisatin by Photosensitive Psoralen Compounds

Isolation and Functional Characterization of CYP71AJ4 Encoding for the First P450 Monooxygenase of Angular Furanocoumarin Biosynthesis

Searching for Heracleum mantegazzianum allelopathy in vitro and in a garden experiment

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