Prenylated coumarins and sesquiterpenoids from Ferula communis

Valle, Maria Grazia; Appendino, Giovanni; Nano, Gian Mario; Picci, Vincenzo

doi:10.1016/s0031-9422(00)81522-8

Cited by 93 publications

(46 citation statements)

References 10 publications

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“…4-Hydroxycoumarin has so far not been detected in S. aucuparia, however, some species of the Apiaceae and Asteraceae contain 4-hydroxycoumarin or its derivatives independent of the action of microorganisms (Späth et al 1936;Valle et al 1987;Appendino et al 1988a, b;Aliotta et al 1994). The best studied species is Ferula communis (Apiaceae) which accumulates C-3 prenylated compounds, such as ferulenol (Fig.…”

Section: Discussionmentioning

confidence: 99%

“…The best studied species is Ferula communis (Apiaceae) which accumulates C-3 prenylated compounds, such as ferulenol (Fig. 2), ferprenin and their x-oxygenated derivatives (Valle et al 1987;Appendino et al 1988a, b;Arnoldi et al 2004). Consumption of F. communis can cause an often lethal intoxication of livestock, known as ferulosis, which is widespread in Sardinia and Morocco (Appendino et al 1988b and references therein).…”

Section: Discussionmentioning

confidence: 99%

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A novel 4-hydroxycoumarin biosynthetic pathway

et al. 2009

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Coumarin forms in melilotoside (trans-ortho-coumaric acid glucoside)-containing plant species upon cell damage. In moldy melilotoside-containing plant material, trans-ortho-coumaric acid is converted by fungi to 4-hydroxycoumarin, two molecules of which spontaneously combine with formaldehyde to give dicoumarol. Dicoumarol causes internal bleeding in livestock and is the forerunner of the warfarin group of medicinal anticoagulants. Here, we report 4-hydroxycoumarin formation by biphenyl synthase (BIS). Two new BIS cDNAs were isolated from elicitor-treated Sorbus aucuparia cell cultures. The encoded isoenzymes preferred ortho-hydroxybenzoyl (salicoyl)-CoA as a starter substrate and catalyzed a single decarboxylative condensation with malonyl-CoA to give 4-hydroxycoumarin. When elicitor-treated S. aucuparia cell cultures were fed with the N-acetylcysteamine thioester of salicylic acid, 4-hydroxycoumarin accumulated in the culture medium. Incubation of the BIS isoenzymes with benzoyl-CoA and malonyl-CoA resulted in the formation of 3,5-dihydroxybiphenyl which is the precursor of the phytoalexins of the Maloideae.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

A novel 4-hydroxycoumarin biosynthetic pathway

et al. 2009

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“…These spectral data were similar to those of 4-oxgenated-3-prenyl coumarin derivatives. [7][8][9] This structure was common to compounds 1-4.…”

Section: )mentioning

confidence: 99%

Sesquiterpenoid Derivatives from Ferula ferulioides. V.

Kojima

Isaka

Purev

et al. 2001

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…The chemistry of this genus has been studied by many investigators and is well documented as a good source of biologically active compounds such as sesquiterpene derivatives (Ahmed et al, 2001;Ahmed, 1999;Valle et al, 1987;Iranshahi et al, 2004bIranshahi et al, , 2007Iranshahi et al, , 2008Shahverdi et al, 2006). Sesquiterpene derivatives, especially sesquiterpene coumarins, were stored in the roots of the plants; therefore the roots are a better source for isolating sesquiterpene coumarins than the aerial parts.…”

Section: Introductionmentioning

confidence: 99%