Psoralen and other linear furocoumarins as phytoalexins in celery

Beier, Ross C.; Oertli, Ernest H.

doi:10.1016/0031-9422(83)80173-3

Cited by 139 publications

(68 citation statements)

References 17 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…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).…”

mentioning

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

View full text Add to dashboard Cite

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.

show abstract

mentioning

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

View full text Add to dashboard Cite

show abstract

“…For example, Chaudhary et al (1985) considered the linear furanocoumarins, psoralen (6), xanthotoxin and bergapten (7) to be phytoalexins of celery (Apium graveolens) by reporting that diseased celery infected with the fungus Sclerotinia sclerotiorum had greatly increased the levels of these compounds that are normally found in healthy celery (Beier and Oertli, 1983;Chaudhary et al, 1985;Ashwood-Smith et al, 1986;Trumble et al, 1990). Similarly, Al-Barwani (2002) in her survey of phytoalexins in a number of umbelliferous species found that the majority of the species studied produce high levels of furanocoumarins as a result of induction.…”

Section: Discussionmentioning

confidence: 99%

Xanthotoxin and Other Furanocoumarins as Phytoalexins in Pastinaca sativa L. roots

Al-Barwani

Eltayeb

2004

SQU Journal for Science

View full text Add to dashboard Cite

ABSTRACT:Our results confirm the presence of the furanocoumarins psoralen, xanthotoxin, isopimpinellin, angelicin and bergapten as normal constituents of Pastinaca sativa roots. However, the amounts of these compounds were increased in induced roots. The amount of increase in the induced roots varied depending on the inducing agent and time of incubation. In addition the results show for the first time the presence of pimpinellin and isobergapten as constitutive antifungal compounds in P. sativa roots.

show abstract

“…In most studies, bergapten has been found to occur in highest concentrations, followed by xanthotoxin, but psoralen is often observed only in trace quantities (Trumbe et al, 1990;Trumbe et al, 1992;Diawara et al, 1993). However, other studies have found that xanthotoxin (Beier et al, 1983) or psoralen (Diawara et al, 1993;Trumble et al, 1990) is most abundant (Stanley-Horn, 1999).…”

Section: Name Of Compoundmentioning

confidence: 99%

Analytical Methods for Isolation, Separation and Identification of Selected Furanocoumarins in Plant Material

Szewczyk¹,

Kocka²

2012

Phytochemicals - A Global Perspective of Their Role in Nutrition and Health

View full text Add to dashboard Cite

Psoralen and other linear furocoumarins as phytoalexins in celery

Cited by 139 publications

References 17 publications

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

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

Xanthotoxin and Other Furanocoumarins as Phytoalexins in Pastinaca sativa L. roots

Analytical Methods for Isolation, Separation and Identification of Selected Furanocoumarins in Plant Material

Contact Info

Product

Resources

About