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Antibacterial activity of Ferula gummosa essential oil was studied against bacterial laboratory ATCC standards using the disk diffusion method. The results showed activity against Gram(+) bacteria and Escherichia coli. Little antibacterial activity was found against Pseudomonas aeruginosa.
Matrix metalloproteinases (MMPs) play a role in several physiologic and pathologic events. There is some evidence indicating the involvement of MMPs in tumor invasion and inflammatory diseases. Here we studied the chloroform extract of Ferula persica var. persica. The influence of these extracts vs. a reference drug, diclofenac sodium, on MMP production by the fibrosarcoma cell line was investigated using an in vitro cytotoxicity assay, sodium dodecyl sulfate-polyacrylamide, and gelatin zymography. The total extract of the roots was found to exhibit a selective inhibitory effect on tumor cell invasion. The bioactivity-guided fractionation of this extract led to the isolation of two compounds. These compounds showed highest MMP inhibitory effect at minimal toxic dose levels. Using conventional spectroscopy methods, the active fractions were identified as t-butyl 3-[(1-methylthiopropyl)dithio]-2-propenyl malonate (persicasulphide B) and umbelliprenin, previously isolated from F. persica var. latisecta. Since inhibition of MMP activity has been employed in modality therapy in diseases such as cancer, this compound might be promising in the preparation of anti-MMP therapeutic derivatives.
The influence of Ferula hermonis root extract on sexual behavior was studied in female rats. Sexual receptivity, proceptivity and paced mating behavior were evaluated in ovariectomized females primed with estradiol benzoate (EB) and progesterone (P) and then treated with F. hermonis extract acutely (30 and 60 mg/kg) or subchronically (1 and 10 mg/kg daily for 10 consecutive days). A significant reduction in lordosis responses was observed in rats after acute (60 mg/kg) or subchronic (1 and 10 mg/kg) administration of the plant extract. Similarly, a decrease in proceptive behaviors was exhibited by F. hermonis treated rats in comparison with EB+P controls. No difference was found in the patterns of paced mating behavior between control and treated animals. The present results demonstrate that the acute or repeated ingestion of F. hermonis specifically impairs the receptive and proceptive components of female sexual behavior. The effect could be the consequence of an antiestrogenic action of the extract in hormone-primed female rats.
In the present study, we evaluated the effects of single components of Ferula hermonis extract on female rat sexual behaviour. Ovariectomized rats hormonally primed with estradiol benzoate (1.5 or 10 microg/rat s.c.) and progesterone (500 microg/rat s.c.) were acutely treated by oral gavage with ferutinin, teferin and teferdin (2.5 mg/kg). Thereafter they were tested for: a) partner preference, b) receptivity, c) proceptivity, d) paced mating behaviour. In the partner preference test, the choice of the female for a sexually active male was not influenced by the different treatments. Similarly, during the paced mating test, the contact-return latencies as well as the percentage of exits from the male compartment were not different in control and treated rats. Therefore none of the three compounds showed the capacity to alter sexual motivation. On the other hand, ferutinin, but not teferin and teferdin, significantly inhibited female receptivity. These results suggest a primary role of ferutinin in the impairment of sexual behaviour elicited by F. hermonis extract in hormone primed-female rats.
Re-examination of the chemical constituents of the leaves of Ferula sinaica afforded a new eudesmanolide and a new carotane. The structures were elucidated by spectroscopic methods.
Two monoterpene coumarins, designated ferulagol A and B, as well as three known monoterpene coumarins and three sesquiterpene lactones were isolated from the chloroform extract of the roots of Ferula ferulago. The structures of ferulagol A and B were determined to be 7-[(E)-3'-hydroxy-3',7'-dimethyl-4',6'-octadienyloxy]coumarin and 7-[(3'Z,5'E)-7'-hydroxy-3',7'-dimethyl-3',5'-octadienyloxy]coumarin, respectively.
Ethyl acetate extracts of the air-dried fruits of Ferula kuhistanica afforded three daucane esters: kuhistanicaol H, I and J, together with nine other known compounds. Their structures were established on the basis of spectroscopic evidence. Isolated compounds in this paper and previously reported compounds from the roots and stems of F. kuhistanica were tested for antibacterial activity. Some of them were selectively toxic against Gram-positive bacteria, including methicillin-sensitive and methicillin-resistant Staphylococcus aureus (MSSA and MRSA).
From the chloroform extract of the roots of Ferula assa-foetida, two sesquiterpene coumarins designated assafoetidnol A and assafoetidnol B were isolated, in addition to six known compounds, gummosin, polyanthin, badrakemin, neveskone, samarcandin and galbanic acid. The structures of the sesquiterpenes new compounds were established by spectroscopic methods.
Two new sulfur containing derivatives, t-butyl 3-[(1-methylpropyl)dithio]-2-propenyl malonate (1), t-butyl 3-[(1-methylthiopropyl)thio]-2-propenyl malonate (2) were isolated from the roots of Ferula persica Willd. var. latisecta D. F. Chamberlain. Their structures were elucidated by spectral methods.
The anti-fertility, anti-implantation, and ovarian histological alterations of the ethanolic extract of Ferula hormonis have been investigated in female mice. The intragastric application of 3 mg/kg per day of such extract for 6 weeks resulted in a significant reduction in female mice fertility. Furthermore, it caused a decrease in the number of mated females, the total number of implantations, and the number of viable fetuses. These changes were also associated with ovarian atrophy and a concomitant increase in the connective tissue. The ova showed degeneration while most of the ovarian follicles suffered follicular atresia.
The effect of 600 mg/kg given by oral route to rats of Ferula hermonis roots extracts (petroleum ether, ethyl acetate, methanol and water) was evaluated on sexual behaviour of male rats. Petroleum ether and ethyl acetate extracts produced a significant decrease in both the mount rate (MR) and the intromission rate (IR), significant prolongation of intromission latency (IL) was observed when these extracts were compared with both controls and sildenafil. Methanolic extract produced a significant increase in MR while no effect has been observed on IR or IL in comparison with control. The effect of water extract was not significantly different from controls for the MR and IR, but there was a significant prolongation in the IL.
Activity-guided fractionation of methanol-chloroform (1:1) extract of Ferula gummosa was carried out to investigate the isolation of the active component(s) responsible for the alleviation of morphine withdrawal syndrome induced by naloxone. Dependence was induced using subcutaneous (s.c.) injections of morphine daily for three days. On day 4, morphine was injected 0.5 h before the interaperitoneal (i.p.) injections of fractions or diazepam (5 mg/kg, i.p.) as positive control. Naloxone was injected (5 mg/kg, s.c.) 2 h after the final dose of morphine. The number of episodes of jumping during 30 min after the injection of naloxone was considered as the intensity of the withdrawal syndrome. The methanol-chloroform (1:1) extract of the aerial parts of plant was prepared and partitioned between water and chloroform. The active chloroform layer was concentrated and partitioned between methanol-water (9:1) and n-hexane. Activity was observed in the hydroalcoholic layer. This layer was concentrated and partitioned further between methanol-water (3:2) and chloroform. The chloroform layer showed a dose-dependent and significant activity. For all fractions the activity was observed at 470 mg/kg. Further purification on silica gel column chromatography gave a pure compound, which was 10 times as effective as the crude extract. The results of this study indicated that the plant extract contained component(s) that could be useful for the alleviation of morphine withdrawal syndrome.
Ferula gummosa Boiss. (Apiaceae) which has been used as an antiepileptic remedy in Iranian traditional medicine was evaluated for anticonvulsant activity against experimental seizures. The seed acetone extract of F. gummosa protected mice against tonic convulsions induced by maximal electroshock (the median effective dose [ED(50)]=198.3 mg/kg) and especially by pentylenetetrazole (ED(50)=55 mg/kg). Neurotoxicity (sedation and motor impairment) of the extract was assessed by the rotarod test and the median toxic dose (TD(50)) value of 375.8 mg/kg was obtained. Preliminary phytochemical analysis showed the presence of terpenoids and alkaloids in the extract. The acceptable acute toxicity of the extract recommends further studies to determine the mechanism(s) and compound(s) involved in the anticonvulsant activity.
Giant fennel (Ferula communis L.) from Sardinia is characterized by two chemotypes with different biological activities. One chemotype is poisonous, due to prenylcoumarins, and responsible for ferulosis, which mainly affects sheep and goats, cattle, and horses; the other chemotype is nonpoisonous and contains daucane esters. The two chemotypes cannot be distinguished botanically. High-performance liquid chromatography-diode array-ultraviolet detection-mass spectrometry (HPLC-DAD-UV-MS) analysis of the composition of the fractions containing the biologically active metabolites and of the volatile fractions, by gas chromatography-mass spectrometry (GC-MS), of both essential oil and headspace sampled by headspace solid-phase microextraction (HS-SPME) are here shown to be effective in discriminating the poisonous and nonpoisonous chemotypes. HS-SPME with CAR/PDMS/DVB in combination with GC-MS has also been found to be a successful, fully automated one-step method for rapid and unequivocal discrimination of the two chemotypes, using aristolene and allohedycaryol as markers of the poisonous and nonpoisonous chemotypes, respectively.
The roots of the nonpoisonous chemotype of giant fennel (Ferula communis) from Sardinia afforded a novel cadinanetriol (1), whose structure was established by spectroscopic data and confirmed by synthesis from the E,E-Delta (1(10),5) germacradiene allohedycariol. A number of known compounds were also identified. Despite the lack of morphological differences, a broad chemical diversity exists within giant fennel, underlying the contrasting data on its poisonous properties.
The roots of Ferula hermonis Boiss yielded two new daucane esters, 14-(4'-hydroxybenzoyloxy)dauc-4,8-diene (1) and 14-(4'-hydroxy-3'-methoxybenzoyloxy)dauc-4,8-diene (2), together with the four known sesquiterpenes jaeschkeanadiol p-hydroxybenzoate (3), jaeschkeanadiol benzoate (4), jaeschkeanadiol (5), and epoxyjaeschkeanadiol (6). The identities of the isolated compounds were ascertained primarily using NMR and MS data. Compounds 1 and 3 exhibited antimicrobial activity against Staphylococcus aureus with IC(50) 1.5 and 3.5 microg/mL, respectively, and against Methicillin-resistant S. aureus with IC(50) 2.0 and 4.0 microg/mL, respectively.
The ethyl acetate-soluble fraction from a methanol extract of Ferula foetida has afforded six new sulfide derivatives, (E)-3-methylsulfinyl-2-propenyl sec-butyl disulfide (foetisulfide A) (1), (Z)-3-methylsulfinyloxy-2-propenyl sec-butyl disulfide (foetisulfide B) (2), (E)-3-methylsulfinyloxy-2-propenyl sec-butyl disulfide (foetisulfide C) (3), bis(3-methylthio-2E-propenyl) disulfide (foetisulfide D) (4), 3,4,5-trimethyl-2-thiophenecarboxylic acid (foetithiophene A) (5), 3,4,5-trimethyl-2-(methylsulfinyloxymethyl)thiophene (foetithiophene B) (6), along with six known compounds. The structures of 1-6 were established on the basis of spectroscopic studies, with the elucidation of 5 confirmed by single-crystal X-ray crystallography.
The ethyl acetate soluble extract of the dried roots of Ferula penninervis gave 17 new sesquiterpenes [15 of the guaiane-type, ferupennins A-O (1-15), and two of the eudesmane-type, 1alpha-hydroxy-2-oxo-5alpha,7beta,11betaH-eudesm-3-en-6alpha,12-olide (16) and penninervin (17)] and nine known sesquiterpenes. The structures of the new compounds were elucidated on the basis of spectroscopic evidence and X-ray analysis. The absolute configuration of ferupennin A (1) was determined by a modified Mosher method.