ω-Oxygenated prenylated coumarins from Ferula communis

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

doi:10.1016/0031-9422(88)80778-7

Cited by 53 publications

(32 citation statements)

References 7 publications

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“…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). The hemorrhagic symptoms of this disease resemble those caused by the ingestion of moldy sweet clover.…”

Section: Discussionmentioning

confidence: 98%

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: 98%

A novel 4-hydroxycoumarin biosynthetic pathway

et al. 2009

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“…The reported compounds are mainly coumarin derivatives and sesquiterpene alcohol esters, most of which are aromatic esters bearing the daucane skeleton [9][10][11].…”

mentioning

confidence: 99%

“…The major constituents of the oils from the aerial parts of F. stenocarpa and F. macrocolea were β-pinene (30.1 and 15.9%) and α-pinene(48.8 and 10.4%), respectively [9,10]. The oil from the aerial parts of F. flabelliloba contained δ-cadinene (13.2%), α-cadinol (12.0%) and cadina-4,1(10)-dien-8β-ol (10.9%), and α-pinene (10.0%), as the major components [11].…”

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confidence: 99%

Chemical composition and antimicrobial activity of the essential oils of Ferula latisecta and Mozaffariania insignis from Iran

et al. 2006

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The hydrodistilled oils from the aerial parts of Ferula latisecta and Mozaffariania insignis, which is endemic to Iran, were analyzed by GC and GC/MS. (Z)-Ocimenone (32.4%), (E)-ocimenone (20.3%), and cis-pinocarvone (11.4%) were the main components among the 22 constituents characterized in the oil of F. latisecta, representing 87.7% of the total components detected. Twenty-five compounds were identified in the oil of M. insignis, representing 99.0% of the total oil, with octyl acetate (41.1%), β-pinene (30.3%), and α-pinene (23.9%) as the main constituents. The essential oils were examined for their potential antimicrobial activities.

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“…Ferulenol (82) is a major constituent of the poisonous chemotype of F. communis (Valle et al 1987, Appendino et al 1988, Al-Yahya et al 1998) and the universal precursor of farnesylated 4-hydroxycoumarins. In the extract isolated from F. communis, two x-hydroxylated derivatives of ferulenol were found, i.e.…”

Section: Prenylated 4-hydroxycoumarinsmentioning

confidence: 99%

Sesquiterpene coumarins

Gliszczyńska

Brodelius

2011

Phytochem Rev

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Plants have a long history as therapeutic tools in the treatment of human diseases and have been used as a source of medicines for ages. In search of new biologically active natural products, many plants and herbs used in traditional medicine are screened for natural products with pharmacological activity. In this paper, we present a group of natural products, the sesquiterpene coumarins isolated from plants, and describe their wide range of biological activity. Sesquiterpene coumarins are found in some plants of the families Apiaceae (Umbelliferae), Asteraceae (Compositae) and Rutaceae. The coumarin moiety is often umbelliferone (7-hydroxycoumarin) but scopoletin (7-hydroxy-6-methoxycoumarin) and isofraxidin (7-hydroxy-6,8-dimethoxycoumarin) are also found. These coumarins are linked to a C 15 terpene moiety through an ether linkage. Another group of sesquiterpene coumarins is the prenylated 4-hydroxycoumarins where the link between the coumarin and the C 15 terpene moiety is a C-C-bond at carbon 3 of the coumarin moiety. Finally, the prenyl-furocoumarintype sesquiterpenoids are a separate group of sesquiterpene coumarins based on the suggested biosynthetic pathway. Our relatively limited knowledge on the biosynthesis of sesquiterpene coumarins is reviewed.

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ω-Oxygenated prenylated coumarins from Ferula communis

Cited by 53 publications

References 7 publications

A novel 4-hydroxycoumarin biosynthetic pathway

A novel 4-hydroxycoumarin biosynthetic pathway

Chemical composition and antimicrobial activity of the essential oils of Ferula latisecta and Mozaffariania insignis from Iran

Sesquiterpene coumarins

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