Ferulenol a new coumarin derivative from ferula communis

Carboni, S.; Malaguzzi, V.; Marsili, A.

doi:10.1016/s0040-4039(00)71730-8

Cited by 28 publications

(15 citation statements)

References 4 publications

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“…Ferulenol ( 212 ) is a prenylated 4‐hydroxycoumarin that was first isolated from the plant Ferula communis and shows potent antimycobacterial activity . This compound, which is a potent inhibitor of the l ‐malate:quinone oxidoreductase (PfMQO) of the malaria parasite P .…”

Section: Progress In Chemical Scaffolds and Aox Inhibitor Developmentmentioning

confidence: 99%

“…A more polar analogue of 209 lacking the lipophilic side chain, 2-hydroxynaphthoquinone (211), had little effect (20% inhibition) at a 50 µM concentration (Figure 16). 162 Ferulenol (212) is a prenylated 4-hydroxycoumarin that was first isolated from the plant Ferula communis 165 and shows potent antimycobacterial activity. 166 This compound, which is a potent inhibitor of the L-malate:quinone oxidoreductase (PfMQO) of the malaria parasite P. falciparum, 167 (188) was the first natural isoprenoid antibiotic reported to inhibit TAO in the subnanomolar range.…”

Section: Ubiquinone Analoguesmentioning

confidence: 99%

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Alternative oxidase inhibitors: Mitochondrion‐targeting as a strategy for new drugs against pathogenic parasites and fungi

Ebiloma

Balogun

Cueto-Díaz

et al. 2019

Medicinal Research Reviews

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The alternative oxidase (AOX) is a ubiquitous terminal oxidase of plants and many fungi, catalyzing the four‐electron reduction of oxygen to water alongside the cytochrome‐based electron transfer chain. Unlike the classical electron transfer chain, however, the activity of AOX does not generate adenosine triphosphate but has functions such as thermogenesis and stress response. As it lacks a mammalian counterpart, it has been investigated intensely in pathogenic fungi. However, it is in African trypanosomes, which lack cytochrome‐based respiration in their infective stages, that trypanosome alternative oxidase (TAO) plays the central and essential role in their energy metabolism. TAO was validated as a drug target decades ago and among the first inhibitors to be identified was salicylhydroxamic acid (SHAM), which produced the expected trypanocidal effects, especially when potentiated by coadministration with glycerol to inhibit anaerobic energy metabolism as well. However, the efficacy of this combination was too low to be of practical clinical use. The antibiotic ascofuranone (AF) proved a much stronger TAO inhibitor and was able to cure Trypanosoma vivax infections in mice without glycerol and at much lower doses, providing an important proof of concept milestone. Systematic efforts to improve the SHAM and AF scaffolds, aided with the elucidation of the TAO crystal structure, provided detailed structure‐activity relationship information and reinvigorated the drug discovery effort. Recently, the coupling of mitochondrion‐targeting lipophilic cations to TAO inhibitors has dramatically improved drug targeting and trypanocidal activity while retaining target protein potency. These developments appear to have finally signposted the way to preclinical development of TAO inhibitors.

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Section: Progress In Chemical Scaffolds and Aox Inhibitor Developmentmentioning

confidence: 99%

Section: Ubiquinone Analoguesmentioning

confidence: 99%

Alternative oxidase inhibitors: Mitochondrion‐targeting as a strategy for new drugs against pathogenic parasites and fungi

Ebiloma

Balogun

Cueto-Díaz

et al. 2019

Medicinal Research Reviews

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“…Nineteen prenylated coumarins ferprenin (118), 1 4 1, 14 2 (E)-w-hydroxyferprenin (119), 1 41 ,1 4 2 (Z )-whydroxyferprenin (120), 1 41, 142 (E)-w-acetoxyferprenin (121), 141,142 (Z )-w-acetoxyferprenin (122), 141 ,14 2 (E)-w-oxoferprenin (123), 1 41 ,1 42 is oferprenin (124), 1 43 ferchromone (125), 14 4 ferchromonol (126), 14 4 fercoprenol (127), 144 fercoprolone (128), 14 4 ferulenol (129), 145 (E)-w-hydroxyferulenol (130), 1 46 (Z)-whydroxyferulenol (131), 1 47 (E)-w-acetoxyferulenol (132), 146 (Z)-w-acetoxyferulenol (133), 14 7 (E)-woxoferulenol (134), 141 e-hydroxyferulenol (135), 14 8 and ferulenoloxyferulenol (136) 1 48 were is olated mostly from F. communis (Table 4 and Figure 9), and their structures were established from MS, IR, and NMR spectral analysis. Figure 9.…”

Section: Prenylated Coumarinsmentioning

confidence: 99%

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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“…The location of the R group (at C-15) is the result of the greater stability of 263 compared to the tautomer that would condense to a 13-R adduct [192,193]. This "undersired" type of product was obtained also from 259, which gave rise to 265 [176,194,195]. The condensation of 258 with enol ethers of 1,3-cyclohexanedione gave an ABD intermediate that added maleic anhydride, giving in 77% yield a 17a-keto steroid that underwent decarboxylation in quinoline to the methyl ether of 18-nor-Dhomoequilenin [196].…”

Section: Organometallic Couplingmentioning

confidence: 99%

Ab + D → Abd → Abcd

1974

Organic Chemistry: A Series of Monographs

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Ferulenol a new coumarin derivative from ferula communis

Cited by 28 publications

References 4 publications

Alternative oxidase inhibitors: Mitochondrion‐targeting as a strategy for new drugs against pathogenic parasites and fungi

Alternative oxidase inhibitors: Mitochondrion‐targeting as a strategy for new drugs against pathogenic parasites and fungi

Terpenoid Coumarins of the Genus Ferula

Ab + D → Abd → Abcd

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