Conferone — A new terpenoid coumarin from the fruit of Ferula conocaula

Vandyshev, V. V.; Sklyar, Yu. E.; Perel'son, M. E.; Moroz, M. D.; Пименов, М. Г.

doi:10.1007/bf00564345

Cited by 7 publications

(8 citation statements)

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“…7 7 Microlobin (110) is the hydroxy derivative of the known coumarin kamolone (108) to which it is chemically related. 135 The ketone from chromium trioxide oxidation of microlobiden (112) was found to be identical with that from dehydration of galbanic acid (34) with phosphorus pentoxide. 135 The ketone from chromium trioxide oxidation of microlobiden (112) was found to be identical with that from dehydration of galbanic acid (34) with phosphorus pentoxide.…”

Section: Ferulamentioning

confidence: 88%

“…Feshurin acetate, kokanidin (96), has been isolated from F. kokanica. 68 However, microlobiden (112), which occurs with micolobin (110) in F. microloba, possesses a new type of terpenoid skeleton. 68 However, microlobiden (112), which occurs with micolobin (110) in F. microloba, possesses a new type of terpenoid skeleton.…”

Section: Ferulamentioning

confidence: 99%

“…68 However, microlobiden (112), which occurs with micolobin (110) in F. microloba, possesses a new type of terpenoid skeleton. The circular dichroism spectra of 16 natural sesquiterpene umbelliferone ethers have been recorded and a new compound, kamolonol (111), which is the C-9 epimer of microlobin (110), has been isolated from the gum resin of F. assafoetida. The circular dichroism spectra of 16 natural sesquiterpene umbelliferone ethers have been recorded and a new compound, kamolonol (111), which is the C-9 epimer of microlobin (110), has been isolated from the gum resin of F. assafoetida.…”

Section: Ferulamentioning

confidence: 99%

“…Dehydrogenation of gummosin(49), badrakemin(51) and kamolol(107).Oxidation of the hydroxyl groups in terpenoid coumarins with chromium trioxide in acetone and pyridine solutions gives oxo derivatives48,79,82 and in acid solution leads to the cleavage of the ether bond and to the formation of keto acids. The oxidation of colladonin…”

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confidence: 99%

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Terpenoid Coumarins of the Genus Ferula

El‐Razek¹,

Ohta²,

Hirata³

2003

HETEROCYCLES

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Chemical studies on the plants of the genus Ferula (Apiaceae) show the presence of many compounds belonging mainly to the groups of monoterpene coumarins, sesquiterpene coumarins, sesquiterpenes, furanocoumarins and aromatic compounds. Biological studies reveal significant activities, such as an anti-HIV activity, inhibition of cytokine release and early events of carcinogenesis. Extracts of some species of Ferula have long been used in folk medicine for treating various diseases, possess an antimicrobial and estrogenic actions, and are natural plant growth inhibitors and stimulators.

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Section: Ferulamentioning

confidence: 88%

Section: Ferulamentioning

confidence: 99%

Section: Ferulamentioning

confidence: 99%

mentioning

confidence: 99%

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Terpenoid Coumarins of the Genus Ferula

El‐Razek¹,

Ohta²,

Hirata³

2003

HETEROCYCLES

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“…1). Sesquiterpene coumarins are quite rare in higher plants except for plants of the genus Ferula (Apiaceae) distributed from the Mediterranean Sea to Central Asia [11], [12], [13], [14], [15]. Conferone was first isolated from Ferula conocaula [15].…”

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confidence: 99%

Conferone from Ferula schtschurowskiana Enhances Vinblastine Cytotoxicity in MDCK-MDR1 Cells by Competitively Inhibiting P-Glycoprotein Transport

et al. 2006

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Overexpression of the protein transporter P-glycoprotein (Pgp, MDR1) at the cell surface is a major cause of multidrug resistance (MDR) and poor response to treatment in cancer chemotherapy and therapy for leishmaniasis. The present study shows that conferone, a sesquiterpene coumarin ether isolated for the first time from Ferula schtschurowskiana, endemic in Uzbekistan, enhances the cell toxicity of vinblastine (VBL) in MDR1-transfected Madin-Darby canine kidney (MDCK-MDR1) cells. Conferone presents the advantage to mediate this effect at safe concentrations. At 10 microM, it efficiently competes with the photoactivatable cyclosporin A analogue (SDZ 212 - 122) for the binding to Pgp and accumulates [3H]-VBL to a higher extent than cyclosporin A or cnidiadin. [3H]-VBL accumulation is dose-dependent and correlates with the inhibition of Pgp photolabeling affinity, supporting the hypothesis that conferone sensitizes MDCK-MDR1 cells to VBL by competitively inhibiting drug efflux. In MDCK-MDR1 cells, [3H]-VBL accumulation appears to be almost completely dependent on inhibition of Pgp transport. However, the strict specificity of conferone to this efflux pump has to be demonstrated in cell lines expressing other protein transporters. Collectively, our findings identify conferone as a powerful modulator of Pgp transport and a promising molecule for the treatment of MDR malignancies and leishmaniasis. Complementary in vitro and in vivo studies are, however, needed to assess the value of conferone as a reversal drug in human therapy. Considering its high affinity for Pgp, conferone may have an additional usefulness as a tool for the design or the (hemi)synthesis of agents probing Pgp. To our knowledge, this is the first report identifying sesquiterpene coumarins from Ferula as possible drug candidates for the reversion of MDR encoded by the MDR1 gene or the synthesis of agents probing Pgp.

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The Naturally Occurring Coumarins

Murray

2002

Fortschritte Der Chemie Organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products

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Conferone — A new terpenoid coumarin from the fruit of Ferula conocaula

Cited by 7 publications

References 0 publications

Terpenoid Coumarins of the Genus Ferula

Terpenoid Coumarins of the Genus Ferula

Conferone from Ferula schtschurowskiana Enhances Vinblastine Cytotoxicity in MDCK-MDR1 Cells by Competitively Inhibiting P-Glycoprotein Transport

The Naturally Occurring Coumarins

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