Ferprenin, a prenylated coumarin from Ferula communis

Appendino, Giovanni; Tagliapietra, Silvia; Nano, Gian Mario; Picci, Vincenzo

doi:10.1016/0031-9422(88)84130-x

Cited by 51 publications

(26 citation statements)

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“…Different chemical investigations have reported the presence of daucane esters or drimane ethers, as main constituents in the "non-poisonous" chemotype, according to the geographic area and the presence of prenylated coumarins as main constituents in the "poisonous" chemotype (Appendino et al, 1987;Appendino et al, 2001;Fraigui et al, 2001;Miski and Mabry, 1985;Valle et al, 1987;Rubiolo et al, 2006). Among the prenylated coumarins of the toxic variety, both ferulenol, a 4hydroxycoumarin derivative, and ferprenin, a pyrane (3,2-c) coumarin derivative (Appendino et al, 1988;Carboni et al, 1964) (Figure 1) could affect blood clotting, as described for other 4-oxygenated coumarin derivatives such as dicoumarol or warfarin, the first developed antivitamin K molecules used in human medicine and as rodenticide for pest control.…”

Section: Introductionmentioning

confidence: 93%

Comparative inhibitory effect of prenylated coumarins, ferulenol and ferprenin, contained in the ‘poisonous chemotype’ of Ferula communis on mammal liver microsomal VKORC1 activity

et al. 2015

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Two distinguishable chemotypes of Ferula communis have been described: the 'nonpoisonous' chemotype, containing as main constituents the daucane esters; and the 'poisonous' chemotype containing prenylated coumarins, such as ferulenol and ferprenin. Ferulenol and ferprenin are 4-oxygenated molecules such as dicoumarol and warfarin, the first developed antivitamin K molecules. Antivitamin K molecules specifically inhibit VKORC1, an enzyme essential for recycling vitamin K. This latest is involved in the activation of clotting factors II, VII, IX, X. The inhibiting effect of ferulenol on VKORC1 was shown in rat, but not for species exposed to F. communis while in vivo studies suggest differences between animal susceptibility to ferulenol. The inhibiting effect of ferprenin on VKORC1 was never demonstrated. The aim of this study was to compare the inhibiting effect of both compounds on VKORC1 of different species exposed to F. communis. Vitamin K epoxide activity was evaluated for each species from liver microsomes and inhibiting effect of ferulenol and ferprenin was characterized. Ferulenol and ferprenin were shown to be able to inhibit VKORC1 from all analyzed species. Nevertheless, susceptibility to ferulenol and ferprenin presented differences between species, suggesting a different susceptibility to 'poisonous' chemotypes of F. communis.

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Section: Introductionmentioning

confidence: 93%

Comparative inhibitory effect of prenylated coumarins, ferulenol and ferprenin, contained in the ‘poisonous chemotype’ of Ferula communis on mammal liver microsomal VKORC1 activity

et al. 2015

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“…R" effect has recently been de~cribed.~ 13C NMR has proved to be a valuable tool in the structural elucidation of the increasing number of natural 3-prenylated (isoprenoid) coumarins such as those isolated from Gutenbergia and Bothriocline species," from Clausena anisatall and from Ferula communis.12- 16 This paper completes our contribution to the structural elucidation of new natural 3-prenylated coumarins, and represents one of the few I3C NMR spectroscopic studies of this type of c~m p o u n d .~* "~~~…”

Section: R"' R'mentioning

confidence: 99%

¹³C NMR of coumarins. V—3‐prenylated coumarins

Macı́as¹,

Hernández-Galán²,

Massanet³

et al. 1990

Magnetic Reson in Chemistry

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“…From some Ferula species, coumarins of sesquiterpene [3] [6] [7] and monoterpene type [8], and prenylated coumarins [9] [10] were previously isolated. Sesquiterpene coumarins, the most abundant class of secondary metabolites in Ferula species, are biologically active compounds, and so far they have demonstrated promising chemopreventive, antitumor, anti-inflammatory, and antileishmanial activities [11].…”

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confidence: 99%

Chloroform Extract of Underground Parts of Ferula heuffelii: Secondary Metabolites and Spasmolytic Activity

Pavlović

Krunić

Nikolić

et al. 2014

Chemistry & Biodiversity

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Plants from the genus Ferula L. (Apiaceae) were used for various purposes in traditional medicine of different nations throughout the history. Ferula heuffelii Griseb. ex Heuffel is a perennial species endemic for Balkan peninsula. Ten compounds which belong to classes of prenyl-furocoumarin-, prenyl-dihydrofurochromone-, prenyl-benzoyl- and prenyl-benzoylfuranone-type sesquiterpenoids, as well as sesquiterpene coumarins and phenylpropanoids, were, for the first time, isolated from the CHCl3 extract of the underground parts of this plant and identified. Furthermore, extract and three isolated compounds, i.e., latifolone (1), dshamirone (4), and (2S*,3R*)-2-[(3E)-4,8-dimethylnona-3,7-dien-1-yl]-2,3-dihydro-7-hydroxy-2,3-dimethylfuro[3,2-c]coumarin (6) were, for the first time, evaluated for their in vitro antispasmodic activities in three experimental models: spontaneous contraction, and ACh- and KCl-induced contraction of an isolated rat ileum. The extract (0.1-1.3 mg/ml) and compound 6 (1-10 μg/ml) exhibited dose-dependent effect in all three models. Compound 1 (1-6 μg/ml) affected spontaneous contractions and those induced by KCl, while compound 4 (8 μg/ml) displayed only moderate activity with ACh-induced contractions. It can be concluded that tested compounds contribute to exhibited antispasmodic activity of crude extract. Additionally, extract (0.1-1.3 mg/ml) was tested for in vitro relaxant activity on an isolated rat trachea, and relaxed the KCl-induced contractions in a dose-dependent manner.

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Ferprenin, a prenylated coumarin from Ferula communis

Cited by 51 publications

References 4 publications

Comparative inhibitory effect of prenylated coumarins, ferulenol and ferprenin, contained in the ‘poisonous chemotype’ of Ferula communis on mammal liver microsomal VKORC1 activity

Comparative inhibitory effect of prenylated coumarins, ferulenol and ferprenin, contained in the ‘poisonous chemotype’ of Ferula communis on mammal liver microsomal VKORC1 activity

¹³C NMR of coumarins. V—3‐prenylated coumarins

Chloroform Extract of Underground Parts of Ferula heuffelii: Secondary Metabolites and Spasmolytic Activity

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Ferprenin, a prenylated coumarin from Ferula communis

Cited by 51 publications

References 4 publications

Comparative inhibitory effect of prenylated coumarins, ferulenol and ferprenin, contained in the ‘poisonous chemotype’ of Ferula communis on mammal liver microsomal VKORC1 activity

Comparative inhibitory effect of prenylated coumarins, ferulenol and ferprenin, contained in the ‘poisonous chemotype’ of Ferula communis on mammal liver microsomal VKORC1 activity

13C NMR of coumarins. V—3‐prenylated coumarins

Chloroform Extract of Underground Parts of Ferula heuffelii: Secondary Metabolites and Spasmolytic Activity

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¹³C NMR of coumarins. V—3‐prenylated coumarins