1: Nat Prod Commun. 2009 Aug;4(8):1023/4.
A new sesquiterpenoid coumarin from Ferula assafoetida.
Ghosh A, Banerji A, Mandal S, Banerji J.
Centre of Advanced Studies on Natural Products including Organic Synthesis,
Department of Chemistry, Calcutta University, Kolkata, India.
The gum resin of Ferula assafoetida Linn. afforded one new sesquiterpene,
asimafoetida 1 and three known sesquiterpenoid coumarins. The structure has been
established from extensive 2D NMR spectral studies as
7'/[7/(1R,3S)/5/Hydroxy/6,6/dimethyl/2/methylene/cyclohexyl]/9/methyl/9/pentenyl]
oxy]/2H/1/benzopyran/2/one. The other three known compounds are ferulic acid,
farnesiferol A and farnesiferol C.
PMID: 19768976 [PubMed / in process]
2: Ethiop Med J. 2009 Jan;47(1):25/32.
Investigation of antibacterial activities of Albizia gummifera and Ferula
communis on Streptococcus pneumoniae and Streptoccus pyogenes.
Unasho A, Geyid A, Melaku A, Debela A, Mekasha A, Girma S, Kebede T, Fantaw S,
Asaminew N, Mamo K.
Dilla College of Health Sciences, Dilla.
BACKGROUND: Respiratory Tract infections continue to be a major cause of
morbidity and mortality world wide. There is a failure to treat respiratory
infections due to the emergence of antibiotic resistant strains among the most
common respiratory pathogens. OBJECTIVES: To evaluate the in vitro antibacterial
activities of two traditionally used plants: Albizia gummifera (Ambabesa/Muka,
Oromifa, Sessa/Amharic.) and Ferula communis (Doge/Oromifa, Dog/Amharic) against
clinical isolates of S. pyogenes and S. pneumoniae. METHODS: The study involving
the antibacterial susceptibility test of traditionally used plant species against
Gram/positive bacterial pathogens was conducted over a period of 5 months
(January / August, 2004) at the Ethiopian Health, and Nutrition Research
Institute. The in vitro antibacterial activities of 80% methanol crude extracts
prepared from the seeds of Ablizia gummifera and, roots of Ferula communis as
well as their respective hydro alcoholic solvent fractionates of both plant
species were tested for inhibitory activity against the clinical isolates of six
S. pneumonae and twenty two S. pyogenes using agar dilution method. RESULTS:
Eighty percent ethanol solubilized fractions of both plants were found to have
antibacterial effects to all assayed bacteria while aqueous solubilized fractions
did not exhibit any effect. Minimum inhibitory concentration (MIC) of the 80%
ethanol solubilized fractions was determined and the MIC of the fractions ranged
from 500 mg/ ml to 1000 mg/ml for both plants showing the extracts may contain
bioactive compounds of therapeutic interest. CONCLUSION: All extracts showed
antibacterial activities against clinical isolates of S. pyogenes and S.
pneumoniae. The extracts may contain compounds with potential therapeutic
activity. Further purification and identification are needed to be tested using
animal models.
PMID: 19743777 [PubMed / in process]
3: J Nat Prod. 2009 Sep;72(9):1568/72.
Influenza A (H(1)N(1)) Antiviral and Cytotoxic Agents from Ferula assa/foetida.
Lee CL, Chiang LC, Cheng LH, Liaw CC, Abd El/Razek MH, Chang FR, Wu YC.
Graduate Institute of Natural Products, College of Pharmacy, Kaohsiung Medical
University, Kaohsiung 807, Taiwan, Republic of China.
Two new sesquiterpene coumarins, designated 5'/acetoxy/8'/hydroxyumbelliprenin
(1) and 10'R/acetoxy/11'/hydroxyumbelliprenin (2), and a new diterpene,
15/hydroxy/6/en/dehydroabietic acid (3), along with 27 known compounds, were
isolated from a CHCl(3)/soluble extract of Ferula assa/foetida through
bioassay/guided fractionation. The structures of the new metabolites 1/3 were
identified by spectroscopic data interpretation and by the Mosher ester method.
Compounds 4 and 6/13 showed greater potency against influenza A virus (H(1)N(1))
(IC(50) 0.26/0.86 microg/mL) than amantadine (IC(50) 0.92 microg/mL), and 11
exhibited the best potency (IC(50) 0.51, 2.6, and 3.4 microg/mL) of these
compounds against the HepG2, Hep3B, and MCF/7 cancer cell lines, respectively.
PMID: 19691312 [PubMed / in process]
4: Z Naturforsch C. 2009 May/Jun;64(5/6):317/22.
Cytotoxicity of vincristine on the 5637 cell line is enhanced by combination with
conferone.
Neshati V, Matin MM, Iranshahi M, Bahrami AR, Behravan J, Mollazadeh S, Rassouli
FB.
Institute of Biotechnology, Ferdowsi University of Mashhad, Mashhad, Iran.
Bladder cancer is one of the most common cancers worldwide, with the highest
incidence in industrialized countries. There are three major histological
subtypes of bladder cancer: transitional cell carcinoma (TCC) (> 90%), squamous
cell carcinoma (< 10%) and adenocarcinoma (1/2%). The present study was carried
out to assess the effects of conferone, a sesquiterpene coumarin isolated from
Ferula badrakema, on a TCC subline, 5637 cells. In order to test the effects of
conferone, 5637 cells were treated with different concentrations (16, 32, 64, 128
microg/ml) of conferone. The results indicated that conferone did not have any
significant cytotoxic effect on these neoplastic cells. To determine the
combining effects, the cells were cultured in the presence of different
concentrations of conferone (16, 32, 64, 128 microg/ ml) and vincristine (30, 40,
50 microg/ml) in combination. The morphological changes were then observed and
cytotoxicity effects were studied using the MTT assay 24, 48 and 72 h following
drug administration. The cells were more rounded and granulated after treatments
with both drugs in comparison to vincristine only. The results of the MTT assay
confirmed the morphological observations. After 48 h of combined treatment with
40 microg/ml vincristine and 16 microg/ml conferone, the cytotoxicity of
vincristine was increased by 23.6%.
PMID: 19678531 [PubMed / indexed for MEDLINE]
5: Phytomedicine. 2009 Jul 2. [Epub ahead of print]
Cancer chemopreventive activity of diversin from Ferula diversivittata in vitro
and in vivo.
Iranshahi M, Sahebkar A, Hosseini ST, Takasaki M, Konoshima T, Tokuda H.
Department of Pharmacognosy, Biotechnology Research Center, School of Pharmacy,
Mashhad University of Medical Sciences, (MUMS), P.O. Box: 91775/1365, Mashhad,
Iran.
A prenylated coumarin (diversin, 1) together with four new sesquiterpene lactones
(diversolides A, D, F and G, 2/5) isolated from the roots of Ferula
diversivittata were studied for their possible inhibitory effects on Epstein/Barr
virus early antigen (EBV/EA) activation induced by
12/O/tetradecanoylphorbol/13/acetate (TPA). All of the tested compounds were
active against EBV/EA activation. Among these compounds diversin (IC(50): 7.7)
exhibited the strongest inhibitory effect and was selected to examine its effects
on in vivo two/stage mouse skin carcinogenesis induced by
7,12/dimethylbenz[a]anthracene (DMBA) as initiator and TPA as promoter. Treatment
with compound 1 (85nmol) along with DMBA/TPA inhibited papilloma formation up to
week 7 and the percentage of papilloma bearers was approximately 93.3% at week
20. The average number of papillomas formed per mouse was only 5.5 even at week
20. The results of the present investigation indicated that diversin might be
valuable as a potent cancer chemopreventive agent and its potency was comparable
with those of curcumin and quercetin, two well/known cancer chemopreventive
agents.
PMID: 19577457 [PubMed / as supplied by publisher]
6: Nat Prod Res. 2009;23(9):861/5.
New sulphide derivative from Ferula rutabensis.
Abdel/Sattar E, El/Mekkawy S.
Department of Natural Products and Alternative Medicine, Faculty of Pharmacy,
King Abdulaziz University, Jeddah, Kingdom of Saudi Arabia. abdelsattar@yahoo.com
Reinvestigation of CH(2)Cl(2) extract of roots and rhizomes of Ferula rutabensis
led to the isolation of a new trisulphide (1) and phthalic acid derivative (2).
Their characterisation was based on their spectral data, including MS, 1D/ and
2D/NMR.
PMID: 19488925 [PubMed / indexed for MEDLINE]
7: Phytother Res. 2009 May 14. [Epub ahead of print]
Auraptene from Ferula szowitsiana protects human peripheral lymphocytes against
oxidative stress.
Soltani F, Mosaffa F, Iranshahi M, Karimi G, Malekaneh M, Haghighi F, Behravan J.
Biotechnology Research Center, Mashhad University of Medical Sciences, Mashhad,
Iran.
The antigenotoxicity effects of auraptene on DNA damage in human peripheral
lymphocytes were studied using alkaline single cell gel electrophoresis.
Auraptene at concentrations of 5, 10, 25, 50, 100, 200 and 400 microM was tested
under simultaneous treatment with 25 microM H(2)O(2). The data are expressed as %
tail DNA and compared with ascorbic acid at concentrations of 25, 50, 100, 200
and 400 microM. Auraptene significantly reduced the genotoxicity of H(2)O(2 )at
concentrations higher than 25 microM (p < 0.001). Interestingly, the
antigenotoxicity activity of auraptene was higher than ascorbic acid (p < 0.01),
however, at some concentrations (25, 50 and 200 microM) there was no significant
difference between auraptene and ascorbic acid (p > 0.05). It seems that the
significant antigenotoxicity effects of auraptene may be due to the prenyl moiety
and also the suppression of superoxide anion (O(2) (/)) generation. This study
suggests that the antigenotoxic property of auraptene is of great pharmacological
importance and might be beneficial for cancer prevention. Copyright (c) 2009 John
Wiley & Sons, Ltd.
PMID: 19444820 [PubMed / as supplied by publisher]
8: J Bone Miner Metab. 2009;27(5):538/45. Epub 2009 Mar 31.
Influence of ferutinin on bone metabolism in ovariectomized rats. I: role in
preventing osteoporosis.
Palumbo C, Ferretti M, Bertoni L, Cavani F, Resca E, Casolari B, Carnevale G,
Zavatti M, Montanari C, Benelli A, Zanoli P.
Section of Human Anatomy, Department of Anatomy and Histology, University of
Modena and Reggio Emilia, Via del Pozzo 71 (Area policlinico), 41100, Modena,
Italy. palumbo.carla@unimore.it
Phytoestrogens play a role in maintaining bone mass in the post/menopausal period
for their putative function as osteoprotective agents. The aim of the present
study was to investigate the influence of Ferutinin, a phytoestrogen found in the
plants of Ferula genus, on bone loss in ovariectomized rats. Such an animal model
can simulate the various clinical syndromes deriving from osteoporosis. The
effect of the daily oral administration of ferutinin to ovariectomized rats
(dosed at 2 mg/kg per day for 30 and 60 days) was compared to that of estradiol
benzoate (subcutaneously administered at the dose of 1.5 microg/rat twice a
week). After the sacrifice, histomorphometrical analyses were performed on
trabecular bone of L4/L5 vertebrae and distal femoral metaphysis, as well as on
cortical bone of femoral diaphysis; biochemical parameters (bone mineral
components and markers) were also evaluated from the rat serum. The
histomorphometrical analyses of trabecular and cortical bone from lumbar
vertebrae and femur showed that ferutinin has the same antiosteoporotic effect of
estradiol benzoate on bone mass, and in some cases is even stronger. This fact
suggests that it could prevent osteoporosis caused by severe estrogen deficiency
in ovariectomized rats. The possibility of using ferutinin as an alternative to
the commonly employed hormonal replacing therapy in post/menopausal women is
discussed.
PMID: 19333679 [PubMed / in process]
9: Inflamm Allergy Drug Targets. 2009 Mar;8(1):2/10.
A systematic review of the potential herbal sources of future drugs effective in
oxidant/related diseases.
Hasani/Ranjbar S, Larijani B, Abdollahi M.
Endocrinology and Metabolism Research Center, and Faculty of Medicine, Tehran
University of Medical Sciences, Tehran, Iran.
OBJECTIVE: This review focuses on the medicinal plants growing and having history
of folk medicine in Iran and found effective as anti free radical damage in
animal or human. DESIGN: Embase, Scopus, Pubmed, Web of Science, Google Scholar,
IranMedex, and SID databases were searched up to 2 February 2008. The search
terms were antioxidant or "lipid peroxidation" and "plant, medicinal plant, herb,
traditional, natural or herbal medicine" limited to Iran. Studies that assessed
effects on cell lines or isolated organs, fetal toxicity, and reviews or letters
were excluded. Antioxidative effect and lipid peroxidation inhibition were the
key outcomes. RESULTS: Forty/six animal studies on the efficacy of medicinal
plants were reviewed. Lipid peroxidation was reduced in different clinical
circumstances by Ferula szovitsiana, Nigella sativa, Rosa damascene petal,
Phlomis anisodonta, Rosemary, Zataria multiflora Boiss, Saffron, Amirkabiria
odorastissima mozaffarian, Ficus carica Linn., Ziziphora clinopoides, Carica
papaya, Chichorium intybus, Turmer, Eugenol, Curcumin, and Pistacia vera L. Human
studies showed that Cinnamomum zeylanicum and Echium amoenum Fisch & C.A. Mey
reduce lipid peroxidation and improve total antioxidant power in healthy
subjects. Improvement of blood lipid profile was shown by Silybum marianum,
garlic, and wheat germ. CONCLUSION: Amongst these useful herbs, some like
Cinnamon, Silybum marianum, Garlic, Nigella, and Echium seem potential targets of
future effective drugs for diseases in which free radical damage play a
pathogenical role.
PMID: 19275687 [PubMed / in process]
10: J Exp Bot. 2009;60(3):715/7.
Symbolism of plants: examples from European/Mediterranean culture presented with
biology and history of art.
Kandeler R, Ullrich WR.
Institute of Botany, University of Natural Resources and Applied Life Sciences,
Gregor Mendelstr. 33, 1180 Wien, Austria.
PMID: 19269995 [PubMed / indexed for MEDLINE]
11: Mol Ecol. 2009 Jan 29. [Epub ahead of print]
The phylogeographical history of the Iberian steppe plant Ferula loscosii
(Apiaceae): a test of the abundant/centre hypothesis.
Pérez/Collazos E, SΑnchez/Gómez P, Jiménez JF, Catalán P.
Departamento de Agricultura y Economía Agraria, Escuela Politécnica Superior de
Huesca, Universidad de Zaragoza, C/Carretera de Cuarte s/n E/22071 Huesca, Spain.
Abstract The geology and climate of the western Mediterranean area were strongly
modified during the Late Tertiary and the Quaternary. These geological and
climatic events are thought to have induced changes in the population histories
of plants in the Iberian Peninsula. However, fine/scale genetic spatial
architecture across western Mediterranean steppe plant refugia has rarely been
investigated. A population genetic analysis of amplified fragment length
polymorphism variation was conducted on present/day, relict populations of Ferula
loscosii (Apiaceae). This species exhibits high individual/population numbers in
the middle Ebro river valley and, according to the hypothesis of an
abundant/centre distribution, these northern populations might represent a
long/standing/ancestral distribution centre. However, our results suggest that
the decimated southern and central Iberian populations are more variable and
structured than the northeastern ones, representing the likely vestiges of an
ancestral distribution centre of the species. Phylogeographical analysis suggests
that F. loscosii likely originated in southern Spain and then migrated towards
the central and northeastern ranges, further supporting a Late Miocene
southern/bound Mediterranean migratory way for its oriental steppe ancestors. In
addition, different glacial/induced conditions affected the southern and northern
steppe Iberian refugia during the Quaternary. The contrasting genetic homogeneity
of the Ebro valley range populations compared to the southern Iberian ones
possibly reflects more severe bottlenecks and subsequent genetic drift
experienced by populations of the northern Iberia refugium during the
Pleistocene, followed by successful postglacial expansion from only a few founder
plants.
PMID: 19207254 [PubMed / as supplied by publisher]
12: J Agric Food Chem. 2009 Feb 25;57(4):1433/9.
Novel key aroma components of galbanum oil.
Miyazawa N, Nakanishi A, Tomita N, Ohkubo Y, Maeda T, Fujita A.
Technical Research Center, T. Hasegawa Co., Ltd., 335 Kariyado, Nakahara/ku,
Kawasaki/shi 211/0022, Japan. norio_miyazawa@t/hasegawa.co.jp
Galbanum oil is composed of monoterpenes in large amounts and pyrazines in small
amounts. Although the monoterpenes are the main components of galbanum oil, they
hardly contribute to the distinct galbanum aroma. The scanty amounts of
pyrazines, in contrast, contribute significantly to the aroma. Considering the
complexity and potency of the odor, the essential oil was assumed to contain so
far not identified compounds with high odor contribution. By the gas
chromatography/mass spectrometry/olfactometry (GC/MS/O) analysis of galbanum oil,
fruity/green/balsamic notes were detected at two different retention times. The
mass spectra (MS) of the newly discovered notes were elucidated by conducting
multidimensional (MD) GC/MS/O. By analyzing the MS data, six chemical structures
were proposed: (6E/Z,8E)/undeca/6,8,10/trien/2/one,
(6E/Z,8E)/undeca/6,8,10/trien/3/one, and (6E/Z,8E)/undeca/6,8,10/trien/4/one. The
compounds were then synthesized in an attempt to match the MS, retention indices
(RI), and odor qualities. The MD/GC/MS/O analyses of the candidate compounds led
to the identification of the novel key aroma compounds
(6Z,8E)/undeca/6,8,10/trien/3/one and (6Z,8E)/undeca/6,8,10/trien/4/one in
galbanum oil.
PMID: 19173603 [PubMed / indexed for MEDLINE]
13: Mycol Res. 2009 Mar;113(Pt 3):381/7. Epub 2008 Dec 24.
Molecular characterization and enzymatic activity of laccases in two Pleurotus
spp. with different pathogenic behaviour.
Punelli F, Reverberi M, Porretta D, Nogarotto S, Fabbri AA, Fanelli C, Urbanelli
S.
Dipartimento di Biologia Vegetale, Università La Sapienza, Largo Cristina di
Svezia 24, 00165 Roma, Italy.
Pleurotus eryngii and P. ferulae, two species belonging to the P. eryngii
complex, synthesize laccases, ligninolytic enzymes that play a role in the
host/pathogen interaction in the first step of infection. Ecological studies have
shown that although both fungi have been recognized as saprophytes, P. eryngii
weakly pathogenic when colonizing the roots and stems of Eryngium campestre,
whereas P. ferulae is mostly pathogenic to Ferula communis. The paper describes
the genomic organization of four putative laccase genes (lac1, lac2, lac3, and
lac5/like gene; gene names were assigned on the basis of sequence homologies) of
P. eryngii and P. ferulae. The mRNA expression and enzymatic activity of the
laccases were analysed under culture conditions where a source of lignin (wheat
bran) or lyophilized roots of E. campestre or F. communis were present. These
experiments indicated that the four lac/like genes were differentially regulated
in the two mushrooms. Specifically, the addition of the lyophilized roots of the
respective host plant to the culture media induced an advance in the mRNA
expression of the four lac/like genes and a seven/fold higher total laccase
activity in P. ferulae than in P. eryngii. The results obtained are discussed in
relation to the possible role of laccases in the interaction of P. eryngii and P.
ferulae with their respective host.
PMID: 19116166 [PubMed / indexed for MEDLINE]
14: J Ethnopharmacol. 2009 Jan 30;121(3):400/4. Epub 2008 Nov 20.
Screening of antiplasmodial properties among some traditionally used Iranian
plants.
Esmaeili S, Naghibi F, Mosaddegh M, Sahranavard S, Ghafari S, Abdullah NR.
School of Pharmacy, Shaheed Beheshti University of Medical Sciences, Tehran,
Iran.
ETHNOPHARMACOLOGICAL RELEVANCE: An investigation of plants was undertaken through
interviews and literature surveys on plants used to treat malaria or cancer or
microbial diseases in Iran. AIM OF STUDY: In vitro and in vivo antiplasmodial
tests were carried out on selected plants traditionally used in Iran. MATERIALS
AND METHODS: Thirty/two plants were extracted with methanol and tested for their
in vitro (pLDH assay) activity against Plasmodium falciparum, in vivo activity
against Plasmodium berghei and assessed for any cytotoxicity against the human
cancer cell line MCF7 and the normal cell MDBK. RESULTS: Extracts from four
plants, Buxus hyrcana Pojark. (Buxaceae), Erodium oxyrrhnchum M. Bieb.
(Geraniaceae), Glycyrrhiza glabra L. (Fabaceae) and Ferula oopoda (Boiss and
Bushe) Boiss. (Apiaceae) were found to have significant antiplasmodial activity
(IC50 ranging from 4.7 to 26.6 microg/ml). These findings lend support to the use
of Buxus hyrcana and Glycyrrhiza glabra in traditional medicine. The chloroformic
fraction also was active against K1 and 3D7 strains. The chloroformic fraction
was studied at 10 mg per kg body weight mouse per day. This fraction reduced
parasitaemia by 86.1% compared to untreated control mice. CONCLUSION: Glycyrrhiza
glabra showed antiplasmodial activity and has selectivity for Plasmodium
falciparum and Plasmodium berghei when tested on mammalian cells. This is the
first report that mentioned in vitro and in vivo antiplasmodial activity of
Glycyrrhiza glabra.
PMID: 19059470 [PubMed / indexed for MEDLINE]
15: Biol Pharm Bull. 2008 Dec;31(12):2187/93.
Umbelliferone and esculetin: inhibitors or substrates for polyphenol oxidases?
Sollai F, Zucca P, Sanjust E, Steri D, Rescigno A.
Department of Biomedical Science and Technology, University of Cagliari, Italy.
Recently, an interesting debate arose about the nature (substrate versus
inhibitor) of esculetin, a coumarin derivative, for mushroom polyphenol oxidase
(PPO). The present study examined the behavior of PPOs preparations from fungal
and plant origin towards esculetin as a substrate. Both enzymes were able to
oxidize esculetin though at a slow rate. A higher sensitivity was reached when
the assay was performed in the presence of 3/methyl/2/benzothiazolinone hydrazone
(MBTH) even with a lower amount of PPO. These observations unambiguously
confirmed that esculetin has to be considered a substrate for mushroom polyphenol
oxidase. The oxidation of esculetin was also demonstrated for the first time by a
fungal laccase. This should be taken into account because some mushroom PPO
preparations could exert contaminant laccase activity. In addition, a PPO
preparation from Ferula communis was demonstrated to use esculetin as a
substrate. Umbelliferone, the monophenolic precursor of esculetin along the
phenylpropanoid pathway, behaved as a competitive inhibitor for the monophenolase
activity of mushroom PPO with a K(i) value=0.014 mM. This is worth a mention
because only a few couples of mono/ and corresponding o/diphenol show such
opposite behavior towards PPO. A possible role of PPO in the esculetin fate along
biosynthesis pathway of coumarin derivatives is also discussed.
PMID: 19043197 [PubMed / indexed for MEDLINE]
16: Planta Med. 2009 Jan;75(1):32/6. Epub 2008 Nov 21.
Antigenotoxic effects of the disulfide compound persicasulfide A (PSA) on rat
lymphocytes exposed to oxidative stress.
Noroozi S, Mosaffa F, Soltani F, Iranshahi M, Karimi G, Malekaneh M, Haghighi F,
Behravan J.
Biotechnology Research Center, Department of Pharmacognosy and Biotechnology,
School of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran.
The antigenotoxic effect of persicasulfide A (PSA) from Ferula persica on DNA
damage induced by hydrogen peroxide (H2O2) was evaluated using single cell gel
electrophoresis (SCGE). PSA was extracted from F. persica, characterized by NMR
and its antioxidant/antigenotoxic effects were investigated. The antigenotoxic
effect of solutions containing either PSA (1, 10, 50, 100, 200, 300, 400 and 500
microM) or ascorbic acid (250, 500, 750 and 1000 microM) alone, or in the
presence of H2O2 (25, 50, 100 and 200 microM) were tested on lymphocytes derived
from the blood of healthy male Wistar rats (250/300 g) by using the comet assay.
The degree of damage to DNA after exposure to different solutions was calculated
based on the amount of DNA present in the tail compared to the total amounts of
lymphocyte DNA. PSA did not show genotoxicity and caused a 50% reduction in DNA
damage induced by H2O (EC50:476.47+//67.46 microM). Compared to the EC50 for
ascorbic acid (1399.23+//205.21 microM), it was deduced that PSA was more
effective than ascorbic acid in the prevention of oxidative damage to DNA.
PMID: 19031361 [PubMed / indexed for MEDLINE]
17: Phytochemistry. 2008 Dec;69(17):2979/83. Epub 2008 Nov 5.
Activity of elaeochytrin A from Ferula elaeochytris on leukemia cell lines.
Alkhatib R, Hennebelle T, Joha S, Idziorek T, Preudhomme C, Quesnel B, Sahpaz S,
Bailleul F.
Laboratoire de Pharmacognosie, E.A., Faculté des Sciences Pharmaceutiques et
Biologiques, Université de Lille 2, Lille, France.
Phytochemical investigation of the roots of Ferula elaeochytris made it possible
to isolate two sesquiterpene esters, 6/anthraniloyljaeschkeanadiol (elaeochytrin
A) and 4beta/hydroxy/6alpha/(p/hydroxybenzoyloxy)dauc/9/ene (elaeochytrin B), as
well as eight known compounds: 6/angeloyljaeschkeanadiol, teferidin, ferutinin,
6/(p/hydroxybenzoyl)epoxyjaeschkeanadiol, 6/(p/hydroxybenzoyl)lancerotriol,
5/caffeoylquinic acid, 1,5/dicaffeoylquinic acid and sandrosaponin IX. The
cytotoxic activities of all compounds were investigated on K562R
(imatinib/resistant) human chronic myeloid leukaemia and DA1/3b/M2(BCR/ABL)
(dasatinib/resistant) mouse leukemia cell line. Elaeochytrin A was the most
active compound on both cell lines (IC(50)=12.4 and 7.8microM, respectively). It
was also tested on non/resistant human promyelocytic leukemia cells (HL60,
IC(50)=13.1microM) and was not toxic to normal peripheral blood mononuclear cells
up to 100microM.
PMID: 18992904 [PubMed / indexed for MEDLINE]
18: Fitoterapia. 2009 Jan;80(1):68/72. Epub 2008 Oct 15.
Chemical composition and antimicrobial activity of the essential oil from Ferula
glauca L. (F. communis L. subsp. glauca) growing in Marche (central Italy).
Maggi F, Cecchini C, Cresci A, Coman MM, Tirillini B, Sagratini G, Papa F.
Department of Environmental Sciences, Section of Botany and Ecology, University
of Camerino, Via Pontoni 5, I/62032 Camerino, Italy. filippo.maggi@unicam.it
The essential oil obtained from different parts of Ferula glauca L. (formerly
considered as a subspecies of F. communis) growing in Marche (central Italy), was
analyzed for the first time by GC/FID and GC/MS. The major volatiles were
(E)/caryophyllene and caryophyllene oxide in leaves, alpha/pinene, myrcene and
germacrene D in flowers, alpha/ and beta/pinene in fruits, (E)/beta/farnesene,
myristicin and elemicin in roots, respectively. The differences in composition
detected with respect to F. communis, made the volatile fraction a reliable
marker to distinguish between them, and confirm the botanical data at the base of
their discrimination. Furthermore, the oil was assayed for its antimicrobial
activity by the broth microdilution method. B. subtilis was found to be the most
sensitive microorganism, with the lowest MIC values.
PMID: 18951959 [PubMed / indexed for MEDLINE]
19: Phytother Res. 2009 Feb;23(2):172/7.
Kinetics of enzyme inhibition by active molluscicidal agents ferulic acid,
umbelliferone, eugenol and limonene in the nervous tissue of snail Lymnaea
acuminata.
Kumar P, Singh VK, Singh DK.
Department of Zoology, DDU Gorakhpur University, Gorakhpur 273009, UP India.
Ferulic acid, umbelliferone (Ferula asafoetida), eugenol (Syzygium aromaticum)
and limonene (Carum carvi) are active molluscicidal components that inhibited the
activity of alkaline phosphatase and acetylcholinesterase in in vivo and in vitro
exposure of Lymnaea acuminata. It was observed that ferulic acid, umbelliferone
and eugenol are competitive and limonene is a competitive/non/competitive
inhibitor of alkaline phosphatase. Ferulic acid and umbelliferone are
competitive, whereas eugenol and limonene are competitive/non/competitive and
uncompetitive inhibitors of acetylcholinesterase, respectively. Copyright (c)
2008 John Wiley & Sons, Ltd.
PMID: 18814203 [PubMed / indexed for MEDLINE]
20: Phytochemistry. 2008 Nov;69(15):2753/7. Epub 2008 Sep 18.
Erratum in:
Phytochemistry. 2009 Apr;70(6):822.
Diversolides A/G, guaianolides from the roots of Ferula diversivittata.
Iranshahi M, Hosseini ST, Shahverdi AR, Molazade K, Khan SS, Ahmad VU.
Department of Pharmacognosy and Biotechnology, Biotechnology Research Center,
Faculty of Pharmacy, Mashhad University of Medical Sciences, Vakilabad Boulevard,
Mashhad, Iran. iranshahim@mums.ac.ir
Seven sesquiterpene lactone derivatives, diversolides A/G (1/7), together with
two known compounds, diversin (8) and stigmasterol, were isolated from the roots
of Ferula diversivittata. The structures of these compounds were elucidated by
extensive spectroscopic methods including 1D/(1H and 13C) and 2D/NMR experiments
(DQF/COSY, HSQC, HMBC, and NOESY) as well as high/resolution EIMS. Compounds 1, 4
and 6/8 were tested for their in vitro antifungal and antibacterial activities.
Some of the tested compounds showed moderate antifungal and antibacterial
activities with minimum inhibitory concentration (MIC) values from 40 to
80microg/ml.
PMID: 18804823 [PubMed / indexed for MEDLINE]
21: J Nat Prod. 2008 Sep;71(9):1513/7. Epub 2008 Sep 9.
Potent inhibition of human phosphodiesterase/5 by icariin derivatives.
Dell'Agli M, Galli GV, Dal Cero E, Belluti F, Matera R, Zironi E, Pagliuca G,
Bosisio E.
Department of Pharmacological Sciences, University of Milan, Via Balzaretti 9,
20133, Milan, Italy. mario.dellagli@unimi.it
Plant extracts traditionally used for male impotence (Tribulus terrestris, Ferula
hermonis, Epimedium brevicornum, Cinnamomum cassia), and the individual compounds
cinnamaldehyde, ferutinin, and icariin, were screened against
phosphodiesterase/5A1 (PDE5A1) activity. Human recombinant PDE5A1 was used as the
enzyme source. Only E. brevicornum extract (80% inhibition at 50 microg/mL) and
its active principle icariin (1) (IC50 5.9 microM) were active. To improve its
inhibitory activity, 1 was subjected to various structural modifications. Thus,
3,7/bis(2/hydroxyethyl)icaritin (5), where both sugars in 1 were replaced with
hydroxyethyl residues, potently inhibited PDE5A1 with an IC50 very close to that
of sildenafil (IC50 75 vs 74 nM). Thus, 5 was 80 times more potent than 1, and
its selectivity versus phosphodiesterase/6 (PDE6) and cyclic adenosine
monophosphate/phosphodiesterase (cAMP/PDE) was much higher in comparison with
sildenafil. The improved pharmacodynamic profile and lack of cytotoxicity on
human fibroblasts make compound 5 a promising candidate for further development.
PMID: 18778098 [PubMed / indexed for MEDLINE]
22: Phytomedicine. 2009 Mar;16(2/3):181/7. Epub 2008 Aug 15.
Mogoltacin enhances vincristine cytotoxicity in human transitional cell carcinoma
(TCC) cell line.
Behnam Rassouli F, Matin MM, Iranshahi M, Bahrami AR, Neshati V, Mollazadeh S,
Neshati Z.
Institute of Biotechnology, Ferdowsi University of Mashhad, Mashhad, Iran.
Bladder cancer is the second common cancer of the genitourinary system throughout
the world and intravesical chemotherapy is usually used to reduce tumour
recurrence and progression. Human transitional cell carcinoma (TCC) is an
epithelial/like adherent cell line originally established from primary bladder
carcinoma. Here we report the effect of mogoltacin, a sesquiterpene coumarin from
Ferula badrakema on TCC cells. Mogoltacin was isolated from the fruits of F.
badrakema, using silica gel column chromatography and preparative thin layer
chromatography. Mogoltacin did not have any significant cytotoxicity effect on
neoplastic TCC cells at 16, 32, 64, 128, 200 and 600 microg ml(/1)
concentrations. In order to analyse its combination effect, TCC cells were
cultured in the presence of various combining concentrations of mogoltacin and
vincristine. Cells were then observed for morphological changes (by light
microscopy) and cytotoxicity using MTT assay. The effect of mogoltacin on
vincristine toxicity was studied after 24, 48 and 72 h of drug administration.
The results of MTT assay showed that mogoltacin can significantly enhance the
cytotoxicity of vincristine and confirmed the morphological observations. Results
revealed that combination of 40 microg ml(/1) vincristine with 16 microg ml(/1)
mogoltacin increased the cytotoxicity of vincristine after 48 h by 32.8%.
PMID: 18707855 [PubMed / indexed for MEDLINE]
23: J Asian Nat Prod Res. 2008 Jul/Aug;10(7/8):711/7.
Feruhermonins A/C: three daucane esters from the seeds of Ferula hermonis
(Apiaceae).
Auzi AA, Gray AI, Salem MM, Badwan AA, Sarker SD.
Phytochemistry Research Laboratory, Department of Pharmaceutical Sciences,
University of Strathclyde, Glasgow, UK.
Seventeen daucane esters have been isolated from the seeds of Ferula hermonis
Boiss (Apiaceae). Three of these sesquiterpenes,
4beta/hydroxy/6alpha/benzoyl/7/daucen/9/one (1), 4beta,
8beta/dihydroxy/6alpha/benzoyl/dauc/9/ene (2), and 4beta,
9alpha/dihydroxy/6alpha/benzoyl/dauc/7/ene (4), named feruhermonins A/C,
respectively, are novel natural products. The structures of these compounds were
elucidated unequivocally by a series of 1D and 2D NMR analyses. Although 4beta,
8beta/dihydroxy/6alpha/(4/hydroxy/3/methoxybenzoyl)/dauc/9/ene (3) was reported
previously, the complete spectroscopic data for this compound are presented here
for the first time.
PMID: 18696321 [PubMed / indexed for MEDLINE]
24: Bull Acad Natl Med. 2008 Jan;192(1):153/60.
[Silphium from Cyrenaica, an extinct medicinal plant]
[Article in ]
Haas C.
Académie nationale de médecine.
Silphium was both a spice and a medicinal plant. It was regarded as "one of the
most precious gifts of Nature to man" (Pliny), and was one of the main sources of
revenue contributing to Cyrenaica's wealth. It was so critical to the Cyrenian
economy that most of their coins bore a picture of the plant. But, by the time of
Nero, the plant had become extinct, probably as a result of overgrazing and
overcropping. The botanical identification of silphium is dificult, but the plant
was an Umbellifera and most closely resembled Ferula tingitana. Hippocrates,
Celsus, Galen and Oribasius recommended it for quartan fever, but it was also
said to be useful for many other diseases.
PMID: 18663988 [PubMed / indexed for MEDLINE]
25: Cell Biol Toxicol. 2009 Jun;25(3):291/6. Epub 2008 Jul 10.
Evaluation of antigenotoxicity effects of umbelliprenin on human peripheral
lymphocytes exposed to oxidative stress.
Soltani F, Mosaffa F, Iranshahi M, Karimi G, Malekaneh M, Haghighi F, Behravan J.
Biotechnology Research Center, Mashhad University of Medical Sciences, Mashhad,
Iran.
The protective properties of a prenylated coumarin, umbelliprenin (UMB), on the
human lymphocytes DNA lesions were tested. Lymphocytes were isolated from blood
samples taken from healthy volunteers. DNA breaks and resistance to
H(2)O(2)/induced damage were measured using a single/cell microgel
electrophoresis technique under alkaline conditions (comet assay). Human
lymphocytes were incubated in UMB (10, 25, 50, 100, 200, and 400 microM) alone or
a combination of different concentrations of UMB (10, 25, 50, 100, 200, and 400
microM) and 25 microM H(2)O(2). Untreated cells, ascorbic acid (AA; 25, 50, 100,
200, and 400 microM) and H(2)O(2) (25 microM) were considered as negative
control, positive control, and the standard antioxidant agent for our study,
respectively. Single cells were analyzed with "TriTek Cometscore version 1.5"
software. The DNA damage was expressed as percent tail DNA. UMB exhibited a
concentration/dependent increase in protection activity against DNA damage
induced by 25 microM H(2)O(2) (from 67.28% to 39.17%). The antigenotoxic activity
of AA, in the range 0/50 microM, was greater than that of UMB. However, no
significant difference (p > 0.05) in the protective activity was found between
UMB and AA at concentrations of approximately higher than 50 microM.
PMID: 18618275 [PubMed / indexed for MEDLINE]
26: Plant Biol (Stuttg). 2008 Jul;10(4):492/501.
Conservation genetics of the endangered Iberian steppe plant Ferula loscosii
(Apiaceae).
Pérez/Collazos E, Catalán P.
Departamento de Agricultura y Economía Agraria, Escuela Politécnica Superior de
Huesca, Universidad de Zaragoza, Huesca, Spain. ernextop@unizar.es
Ferula loscosii (Lange) Willk (Apiaceae) is a threatened endemic species native
to the Iberian Peninsula. The plant has a narrow and disjunct distribution in
three regions, NE, C and SE Spain. Genetic variability within and among 11
populations from its natural distribution was assessed using allozymes.
Intermediate levels of genetic diversity were detected in F. loscosii (P(99%) =
36.83; H(E) = 0.125; H(T) = 0.152). However, the highest genetic diversity (58%)
corresponded to the threatened populations from SE and C Spain (H(T) = 0.169)
rather than the more abundant and larger populations from NE Spain (Ebro valley)
(H(T) = 0.122). Low to moderate levels of genetic structure were found among
regional ranges (G(ST) = 0.134), and several statistical spatial correlation
analyses corroborated substantial genetic differentiation among the three main
regional ranges. However, no significant genetic differentiation was found among
the NE Spain populations, except for a northernmost population that is
geographically isolated. Outcrossing mating and other biological traits of the
species could account for the maintenance of the present values of genetic
diversity within populations. The existence of an ancestral late Tertiary wider
distribution of the species in SE and C Spain, followed by the maintenance of
different Quaternary refugia in these warmer areas, together with a more recent
and rapid post/glacial expansion towards NE Spain, are arguments that could
explain the low genetic variability and structure found in the Ebro valley and
the higher levels of diversity in the southern Iberian populations.
PMID: 18557909 [PubMed / indexed for MEDLINE]
27: J Ethnopharmacol. 2008 Jul 23;118(2):213/9. Epub 2008 Mar 29.
Ethnoveterinary practices for the treatment of parasitic diseases in livestock in
Cholistan desert (Pakistan).
Farooq Z, Iqbal Z, Mushtaq S, Muhammad G, Iqbal MZ, Arshad M.
Department of Zoology and Fisheries, University of Agriculture, Faisalabad 38040,
Pakistan. zafaruaf@yahoo.com
AIM OF THE STUDY: This study was conducted to document the ethnoveterinary
medicinal (EVM) practices for the treatment of different parasitic diseases of
livestock in Cholistan desert, Pakistan. MATERIALS AND METHODS: An initial
reconnaissance survey (rapid rural appraisal) among the local shepherds was
conducted to identify the traditional healers. Information was collected from the
traditional healers using a well/structured questionnaire through open/ended
interviews and guided dialogue technique. RESULTS: The parasitic diseases
reported in livestock were: tick and lice infestation, mange, myiasis and
helminthiasis. A total of 77 ethnoveterinary practices comprising of 49 based on
plant usage and 28 based on dairy products, chemicals and other organic matter
were documented. A total of 18 plant species representing 14 families were
documented to treat the parasitic diseases. The plants included: Aerva javanica
(Amaranthaceae), Aizoon carariense (Aizoaceae), Azadirachta indica (Meliaceae),
Brassica campestris (Cruciferae), Capparis decidua (Capparaceae), Capsicum annuum
(Solanaceae), Citrullus colocynthis (Cucurbitaceae), Cyperus rotundus
(Cyperaceae), Calligonum polygonoides (Polygonaceae), Eruca sativa (Cruciferae),
Ferula assafoetida (Umbelliferae), Haloxylon salicornicum (Chenopodiaceae),
Mallotus philippinensis (Euphorbiaceae), Nicotiana tabacum (Solanaceae), Pinus
roxburghii (Pinaceae), Salsola baryosma (Chenopodiaceae), Solanum surratens
(Solanaceae) and Zingiber officinale (Zingiberaceae). CONCLUSION: The EVM
practices documented in this study need to be validated using standard
parasitological procedures. Issues that should be addressed are efficacy
(vis/à/vis claims made by the respondents), quality, safety and standardization
of doses.
PMID: 18524514 [PubMed / indexed for MEDLINE]
28: Phytochemistry. 2008 Jun;69(9):1933/8. Epub 2008 May 14.
Sesquiterpenes from aerial parts of Ferula vesceritensis.
Oughlissi/Dehak K, Lawton P, Michalet S, Bayet C, Darbour N, Hadj/Mahammed M,
Badjah/Hadj/Ahmed YA, Dijoux/Franca MG, Guilet D.
Université de Lyon, UMR 5557 CNRS, Département de Pharmacognosie, Botanique et
Phytothérapie, Faculté de Pharmacie, 8 Avenue Rockefeller, 69373 Lyon Cedex 08,
France.
From the dichloromethane extract of aerial parts of Ferula vesceritensis
(Apiaceae), 11 sesquiterpene derivatives were isolated. Among them five were
compounds designated as 10/hydroxylancerodiol/6/anisate,
2,10/diacetyl/8/hydroxyferutriol/6/anisate, 10/hydroxylancerodiol/6/benzoate,
vesceritenone and epoxy/vesceritenol. The six known compounds were identified as
feselol, farnesiferol A, lapidol, 2/acetyl/jaeschkeanadiol/6/anisate,
lasidiol/10/anisate and 10/oxo/jaesckeanadiol/6/anisate. All the structures were
determined by extensive spectroscopic studies including 1D and 2D NMR experiments
and mass spectroscopy analysis. Two of the compounds, the sesquiterpene coumarins
farnesiferol A and feselol, bound to the model recombinant nucleotide/binding
site of an MDR/like efflux pump from the enteropathogenic protozoan
Cryptosporidium parvum.
PMID: 18485426 [PubMed / indexed for MEDLINE]
29: Zhongguo Zhong Yao Za Zhi. 2007 Nov;32(22):2382/4.
[Chemical constituents from roots of Ferula sinkiangensis]
[Article in ]
Yang JR, Jing S, Li ZH, Qin HL.
Institute of Materia Medica, Chinese Academy of Medical Sciences, Peking Union
Medical College, Beijing 100050, China.
OBJECTIVE: To study the chemical constituents of the roots of Ferula
sinkiangensis. METHOD: Compounds were isolated by repeated chromatography on
silica gel. Their structures were elucidated by chemical and spectroscopic
methods. RESULT: Seven compounds were identified as fekrynol (1), fekolone (2),
farnesiferol B (3), isosamarcandin (4), episamarcandin (5), farnesiferol C (6),
umbelliferone (7). CONCLUSION: All the compounds were obtained from this plant
for the first time.
PMID: 18257264 [PubMed / indexed for MEDLINE]
30: J Med Chem. 2008 Feb 28;51(4):842/51. Epub 2008 Feb 5.
Structure/based virtual screening for the discovery of natural inhibitors for
human rhinovirus coat protein.
Rollinger JM, Steindl TM, Schuster D, Kirchmair J, Anrain K, Ellmerer EP, Langer
T, Stuppner H, Wutzler P, Schmidtke M.
Institute of Pharmacy/Pharmacognosy, University of Innsbruck, Innrain 52, A/6020
Innsbruck, Austria. judith.rollinger@uibk.ac.at
Inhibitors of the human rhinovirus (HRV) coat protein are promising candidates to
treat and prevent a number of upper respiratory diseases. The aim of this study
was to find antiviral compounds from nature, focusing on the HRV coat protein.
Through computational structure/based screening of an in/house 3D database
containing 9676 individual plant metabolites from ancient herbal medicines,
combined with knowledge from traditional use, we selected sesquiterpene coumarins
from the gum resin asafetida as promising natural products. Chromatographic
separation steps resulted in the isolation of microlobidene (1), farnesiferol C
(2), farnesiferol B (3), and kellerin (4). Determination of the inhibition of the
HRV/induced cytopathic effect for serotypes 1A, 2, 14, and 16 revealed a
dose/dependent and selective antirhinoviral activity against serotype 2 for
asafetida (IC50 = 11.0 microg/mL) and its virtually predicted constituents 2
(IC50 = 2.5 microM) and 3 (IC50 = 2.6 microM). Modeling studies helped to
rationalize the retrieved results.
PMID: 18247552 [PubMed / indexed for MEDLINE]
31: Planta Med. 2008 Feb;74(2):147/50. Epub 2008 Jan 31.
Cancer chemopreventive activity of terpenoid coumarins from Ferula species.
Iranshahi M, Kalategi F, Rezaee R, Shahverdi AR, Ito C, Furukawa H, Tokuda H,
Itoigawa M.
Department of Pharmacognosy and Biotechnology, Biotechnology Research Center,
Faculty of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran.
Iranshahim@mums.ac.ir
Several natural products have been found to have anti/tumor promoting activity.
In the present study, we carried out a primary screening of ten terpenoid
coumarins isolated from plants of the Ferula species, examining their possible
inhibitory effects on Epstein/Barr virus early antigen (EBV/EA) activation
induced by 12/ O/tetradecanoylphorbol 13/acetate (TPA) in Raji cells. Auraptene
(7/geranyloxycoumarin, 1) and umbelliprenin (7/farnesyloxycoumarin, 2) were found
to significantly inhibit EBV/EA activation and preserved the high viability of
Raji cells, suggesting that they might be valuable anti/tumor/promoting agents
(IC (50) 8.3 and 9.1 nM, respectively). Our findings revealed that the presence
of a prenyl moiety in the terpenoid coumarins plays an important role in
anti/tumor promoting activity as previously reported for xanthones, coumarins,
flavonoids and phenylpropanoids.
PMID: 18240102 [PubMed / indexed for MEDLINE]
32: J Nat Prod. 2007 Dec;70(12):1915/8. Epub 2007 Dec 4.
Sesquiterpene lactones from the roots of Ferula varia and their cytotoxic
activity.
Suzuki K, Okasaka M, Kashiwada Y, Takaishi Y, Honda G, Ito M, Takeda Y,
Kodzhimatov OK, Ashurmetov O, Sekiya M, Ikeshiro Y.
Graduate School of Pharmaceutical Sciences, University of Tokushima, Tokushima,
Japan.
The ethyl acetate/soluble fraction from a MeOH extract of the roots of Ferula
varia gave six new sesquiterpene lactones (1/6) and five known sesquiterpenes
(7/11). Their structures were established on the basis of spectroscopic evidence.
The cytotoxic activities of 1/11 were evaluated against selected human cancer
cell lines. Compound 4 showed significant selective cytotoxicity against
multidrug/resistant cancer cells (KB/C2). The cytotoxicities of compounds 1, 3,
5, 8, and 11 against KB/C2 cells were enhanced in the presence of nontoxic
concentrations of colchicine.
PMID: 18052129 [PubMed / indexed for MEDLINE]
33: Biopharm Drug Dispos. 2008 Mar;29(2):83/9.
Ferutinin stability in human plasma and interaction with human serum albumin.
Greige/Gerges H, Diab Y, Farah J, Magdalou J, Haddad C, Ouaini N.
Holy Spirit University of Kaslik, Faculty of Sciences and Computer Engineering,
B.P. 446 Jounieh, Lebanon. helenegreige@usek.edu.lb
Ferutinin is a potent phytoestrogen extracted from plants of the genus Ferula.
The biological activity of this sesquiterpene is associated with the
esterification of p/hydroxybenzoic acid with the daucane alcohol,
jaeschkeanadiol. A HPLC method was developed to investigate the stability of
ferutinin in acidic and basic solutions (pH 1.5 and 9.0, respectively), in buffer
(pH 7.4) as well as in serial dilutions of albumin and in human plasma. The
degradation of ferutinin was relatively slow at physiological pH 7.4 compared
with low or high pH. Ferutinin was fully stable in human plasma as well as in
albumin solution and the stability increased with albumin concentration. The
binding of ferutinin to albumin was investigated by fluorescence spectroscopy.
Ferutinin decreased the fluorescence of HSA and that of the only tryptophan
residue located in domain IIA. As a result of the interaction between ferutinin
and albumin, the binding of bilirubin decreased. The stability of ferutinin in
plasma is attributable to ferutinin/albumin binding. Copyright (c) 2007 John
Wiley & Sons, Ltd.
PMID: 18050264 [PubMed / indexed for MEDLINE]
34: SAR QSAR Environ Res. 2007 Oct/Dec;18(7/8):663/73.
Molecular modelling and QSAR analysis of the estrogenic activity of terpenoids
isolated from Ferula plants.
Rasulev BF, Saidkhodzhaev AI, Nazrullaev SS, Akhmedkhodzhaeva KS, Khushbaktova
ZA, Leszczynski J.
Computational Center for Molecular Structure and Interactions, Jackson State
University, 1235 J.R. Lynch Street, Jackson, MS 39217/0510, USA. rasulev@ccmsi.us
The relationship between chemical structure and estrogenic activity in a series
of terpenoid esters with aromatic and aliphatic acid substituents isolated from
Ferula plants, was studied. The fragments of the terpenoid structure that are
potentially responsible for estrogenic activity were revealed. A quantitative
structure/estrogenic activity study has been carried out using the QSAR approach
with use of data derived from quantum/chemical calculations as well as data
generated from three/dimensional structures of terpenoids. A number of molecular
descriptors was obtained from the density functional theory (DFT) at the
B3LYP/6/31G(d, p) level of calculation. Comparative analysis of the
quantum/chemical computational data was also performed to confirm hypothesis
concerning importance of the distance between the oxygen of alcohol hydroxyl
group and the functional group in the para/position of the benzene ring (the
hydroxyl or methoxy group). Use of the Genetic Algorithm in the QSAR analysis
allowed the structural and physicochemical parameters of the terpenoids
responsible for estrogenic activity to be determined. A significant QSAR model
was obtained with an r(2) value of 0.892. The resulting model showed a reliable
dependence of estrogenic activity of the terpenoids on such parameters as
molecular shape, number of phenolic groups, surface polarity and the energy of
the highest occupied molecular orbital.
PMID: 18038366 [PubMed / indexed for MEDLINE]
35: Phytochemistry. 2008 Jan;69(2):473/8. Epub 2007 Sep 12.
Polar secondary metabolites of Ferula persica roots.
Iranshahi M, Mojarab M, Sadeghian H, Hanafi/Bojd MY, Schneider B.
Department of Pharmacognosy and Biotechnology, Biotechnology Research Center,
Faculty of Pharmacy, Mashhad University of Medical Sciences, Mashhad, Iran.
Iranshahim@mums.ac.ir
Phytochemical investigation of the methanolic extract of the dried roots of
Ferula persica resulted in four sesquiterpene coumarin glycosides, persicaosides
A/D, and two known phytosterol glucosides, sitosterol 3/O/beta/glucoside and
stigmasterol 3/O/beta/glucoside. The structures of these compounds were
elucidated by extensive spectroscopic methods including 1D/((1)H and (13)C) and
2D NMR experiments (DQF/COSY, HSQC, HMBC, and ROESY) as well as ESIMS and TOFMS
analyses.
PMID: 17854851 [PubMed / indexed for MEDLINE]
36: Biol Pharm Bull. 2007 Sep;30(9):1805/7.
Galbanic acid from Ferula szowitsiana enhanced the antibacterial activity of
penicillin G and cephalexin against Staphylococcus aureus.
Shahverdi AR, Fakhimi A, Zarrini G, Dehghan G, Iranshahi M.
Department of Pharmaceutical Biotechnology and Medicinal Plant Research Center,
Faculty of Pharmacy, Medical Sciences/University of Tehran, Tehran 1417614411,
Iran. shahverd@sina.tums.ac.ir
In this study the enhancement effect of Ferula szowitsiana roots' acetone extract
on the antibacterial activity of penicillin G and cephalexin was evaluated
against Staphylococcus aureus. Disk diffusion and broth dilution methods were
used to determine the antibacterial activity of these antibiotics in the absence
and presence of plant extract and its various fractions separated by TLC plate.
The active component of plant extract involved in enhancement of penicillin G's
and cephalexin's activities had Rf=0.336 on a TLC plate. The spectral data
((1)H/, (13)C/NMR) of this compound revealed that this compound was
7/[6/(beta/carboxyethyl)/5/isopropylidene/1,2/dimethylcyclo/hexylmethoxy]coumarin
(galbanic acid), previously isolated from Ferula assa/foetida. In the presence of
sub/inhibitory concentration of galbanic acid (100 microg/ml) the MIC of
penicillin G for S. aureus decreased from 64 to 1 (a sixteen four/fold decrease)
and for cephalexin from 128 to 1 microg/ml (a one hundred twenty eight/fold
decrease). The highest fold decrease in MIC was observed for cephalexin in
combination of galbanic acid against test strain. These results signify that the
low concentration of galbanic acid (100 microg/ml) potentiates the antimicrobial
action of penicillin G and cephalexin suggesting a possible utilization of these
compounds in combination therapy against S. aureus.
PMID: 17827745 [PubMed / indexed for MEDLINE]
37: Pak J Biol Sci. 2007 Sep 1;10(17):3006/9.
The Pleurotus eryngii species/complex in Kurdistan region of Iran.
Abdollahzadeh J, Asef MR, Mirmahmoodi T.
Department of Plant Pathology, Faculty of Agriculture, Islamic Azad University,
Mahabad Branch, Iran.
Pleurotus eryngii species/complex are known to be well distributed in Kurdistan
region of Iran. During a survey in 2003/2005 fourteen wild populations of the
Pleurotus eryngii species/complex were collected from Sanandaj, Hane Gelan and
Saral areas. Echomorphological studies and pairing tests showed that all isolates
were belong to P. eryngii and located into two groups associated with three
Umbelliferous host plants including isolates associated with Prangos and
Pimpinella with smaller spores and Ferula haussknechtii with larger spores. In
this study we introduce Ferula haussknechtii as a new host species of P. eryngii
in the world.
PMID: 19090219 [PubMed / indexed for MEDLINE]
38: Biochim Biophys Acta. 2007 Oct;1770(10):1437/40. Epub 2007 Jul 12.
Characterization of anti/coagulant properties of prenylated coumarin ferulenol.
Monti M, Pinotti M, Appendino G, Dallocchio F, Bellini T, Antognoni F, Poli F,
Bernardi F.
Dipartimento di Biochimica e Biologia Molecolare, Università di Ferrara, Italy.
We investigated the mechanisms underlying severe bleeding occurring upon
consumption of Ferula communis. The prenylated coumarin ferulenol extracted from
this plant did not directly affect blood coagulation but showed hepatocyte
cytotoxicity and, at non/cytotoxic concentrations (<100 nM), impaired factor X
biosynthesis (40% reduction). Studies with ferulenol derivatives indicated the
prenyl residue as major determinant of ferulenol activity.
PMID: 17693024 [PubMed / indexed for MEDLINE]
39: Biosci Biotechnol Biochem. 2007 Sep;71(9):2300/3. Epub 2007 Aug 7.
A new ester isolated from Ferula assa/foetida L.
Abd El/Razek MH.
Department of Chemistry, National Taiwan University, Roosevelt Road Section 4,
Taipei, Taiwan 106, Republic of China. abdelrazek3@yahoo.com
A new caffeic acid cinnamyl ester (1) was isolated from the n/hexane/soluble
fraction of an MeOH extract of the gum resin of Ferula assa/foetida L. The
structure was determined to be (2E)/3,4/dimethoxycinnamyl/3/(3,4 diacetoxyphenyl)
acrylate on the basis of spectroscopic data including 1D/ and 2D/NMR. Compound 1
showed moderate activity for inhibiting LPS/induced nitric oxide production in
murine macrophage RAW264.7 cells, with an IC50 value of 54.9 microm.
PMID: 17690448 [PubMed / indexed for MEDLINE]
40: Phytomedicine. 2008 Jan;15(1/2):103/11. Epub 2007 Aug 8.
Umbelliprenin from Ferula szowitsiana inhibits the growth of human M4Beu
metastatic pigmented malignant melanoma cells through cell/cycle arrest in G1 and
induction of caspase/dependent apoptosis.
Barthomeuf C, Lim S, Iranshahi M, Chollet P.
University Clermont1, Laboratoire de Pharmacognosie/Biotechnologies, INSERM,
U484, Groupe de Recherche Clinique, UFR Pharmacie, Clermont/Fd F/63001, France.
Chantal.Barthomeuf@u/clermont1.fr <Chantal.Barthomeuf@u/clermont1.fr>
Metastatic malignant melanoma have a bad prognosis (median survival: 6/8 months)
mainly due to the development of lung, hepatic and brain metastases. In this
study we have used the resazurin reduction test and FACS analysis to assess the
cytostatic and cytotoxic effect of umbelliprenin from Ferula szowitsiana
(Apiaceae) on human solid cancer cells and human primary fibroblasts. We have
observed that the cell susceptibility to umbelliprenin decreases in the order
M4Beu (metastatic pigmented malignant melanoma)>A549 (nonsmall cell lung
carcinoma) approximately PC3 (androgen/resistant prostate carcinoma)>PA1 (ovary
teratocarcinoma)>human primary fibroblasts approximately MCF7 (breast
adenocarcinoma)>DLD1 (colon adenocarcinoma). M4Beu cell/proliferation is
inhibited through cell/cycle arrest in G1 and induction of caspase/dependent
apoptosis. The finding that the cytotoxic effect of umbelliprenin is markedly
more pronounced in M4Beu cells than in primary fibroblasts, suggests a
therapeutic margin. As M4Beu cell proliferation is more potently inhibited by
umbelliprenin (IC50 12.3 microM) than by the citrus coumarin auraptene
(7/geranyloxycoumarin, IC50 17.1 microM) previously reported capable of
inhibiting the prevalence of lung metastasis in mice bearing B16BL6 murine
melanoma, our data suggest that umbelliprenin orally administered and foods and
folk medicines containing this coumarin, may afford protection against the
development and early recurrence of malignant melanoma. In vivo investigations
are needed to test these hypotheses.
PMID: 17689942 [PubMed / indexed for MEDLINE]
41: Pak J Biol Sci. 2007 Jun 15;10(12):1977/83.
Ferula gummosa Boiss. Embryogenic culture and karyological changes.
Bernard F, Bazarnov HS, Khatab LJ, Darabi AS, Sheidai M.
Department of Biology, Faculty of Sciences, Plant Physiology and Biotechnology
Laboratory, Shahid Beheshti University, Tehran, Iran.
Ferula gummosa Boiss. a highly valuable medicinal plant which naturally
propagates in very limited areas of the Middle East with specific environmental
conditions. The production of Ferula gummosa somatic embryos and the karyological
analysis of somatic seedlings were the purpose of this study. High frequency
indirect embryogenesis was induced in callus derived from zygotic embryonic axes.
Embryogenesis was obtained when callus tissues were placed onto an agar induction
Murashige and Skoog medium with 1/naphthalene acetic acid and after the transfer
of the cultures in a thermoperiod regime of 16 h, 19 degrees C/8 h, 7 degrees C
under photoperiod of 16 h light/8h dark. Embryogenic callus tissues were
maintained by subculture on induction medium. Globular proliferation was achieved
with suspension culture in the Murashige and Skoog medium added with
1/naphthalene acetic acid or 2,4/dichlorophenoxyacetic acid for two weeks.
Maturation of embryos and development of plantlets arose on the induction agar
medium, but was better after transfer into the hormone free Murashige and Skoog
medium. However, the level of abnormal embryos was high. Direct embryogenesis was
obtained from somatic seedlings. The best results were obtained from hypocotyl
explants. Embryo induction was achieved by two week culture of the explants in
2,4/dichlorophenoxyacetic acid liquid medium; somatic embryo growth and
maturation was recovered on the hormone free medium. High level of abnormalities
was recorded in the culture. Karyological analysis showed a high incidence level
of cytochimerism in somatic seedlings with chromosome stickiness, polypoidy and
aneuploidy in metaphase cells of the same root tip. The frequency of these
karyological changes varied with the type of somatic embryos with regard to
morphological abnormalities. Normal and abnormal rooted somatic seedlings were
able to grow until production of the first leaf and then entered dormancy in the
same manner as zygotic plantlets.
PMID: 19093435 [PubMed / indexed for MEDLINE]
42: Biochem Biophys Res Commun. 2007 Mar 30;355(1):252/7. Epub 2007 Feb 2.
Ferulenol specifically inhibits succinate ubiquinone reductase at the level of
the ubiquinone cycle.
Lahouel M, Zini R, Zellagui A, Rhouati S, Carrupt PA, Morin D.
Département de pharmacologie et phytochimie, Université de Jijel, Algeria.
The natural compound ferulenol, a sesquiterpene prenylated coumarin derivative,
was purified from Ferula vesceritensis and its mitochondrial effects were
studied. Ferulenol caused inhibition of oxidative phoshorylation. At low
concentrations, ferulenol inhibited ATP synthesis by inhibition of the adenine
nucleotide translocase without limitation of mitochondrial respiration. At higher
concentrations, ferulenol inhibited oxygen consumption. Ferulenol caused specific
inhibition of succinate ubiquinone reductase without altering succinate
dehydrogenase activity of the complex II. This inhibition results from a
limitation of electron transfers initiated by the reduction of ubiquinone to
ubiquinol in the ubiquinone cycle. This original mechanism of action makes
ferulenol a useful tool to study the physiological role and the mechanism of
electron transfer in the complex II. In addition, these data provide an
additional mechanism by which ferulenol may alter cell function and demonstrate
that mitochondrial dysfunction is an important determinant in Ferula plant
toxicity.
PMID: 17292330 [PubMed / indexed for MEDLINE]
43: Bioorg Med Chem. 2007 Mar 15;15(6):2414/20. Epub 2007 Jan 17.
Synthesis and structure/activity relationships of novel warfarin derivatives.
Gebauer M.
Repatriation General Hospital, Pharmacy Department, Daws Rd., Daw Park, Adelaide,
SA 5041, Australia. markus59@adam.com.au
4/Hydroxycoumarins such as warfarin 1 have been the mainstay of oral
anticoagulation therapy for over 20 years. Yet little detail is known about the
molecular interactions between 4/hydroxycoumarins with vitamin K epoxide
reductase (VKER), inhibition of which produces a deficiency of vitamin K and
consequently a deficiency of vitamin K/dependent proteins involved in thrombus
formation. Using molecular probes, such as 4/sulfhydrylwarfarin 7 and
4/chlorowarfarin 10 it is shown in vitro that inhibition of VKER by warfarin is
dependent on deprotonation of the 4/hydroxycoumarin moiety. In addition, the
nature of the substituent on carbon 3 of the 4/hydroxycoumarin modulated
inhibition. More specifically, a linear isoprenyl side chain increased inhibition
of VKER when compared to cyclical substituents as present in warfarin. An example
of a 4/hydroxycoumarin with an isoprenyl side chain is the natural product
ferulenol 19 derived from Ferula communis. Ferulenol 19 confers approximately 22
times more potent inhibition than warfarin and is approximately 1.5 more potent
than the rodenticide brodifacoum in this in vitro assay. Based on these data it
is hypothesized that 4/hydroxycoumarins bind to the active site of VKER thereby
mimicking the transition state of the elimination of water from substrate
2/hydroxyvitamin K.
PMID: 17275317 [PubMed / indexed for MEDLINE]
44: Phytochemistry. 2007 Mar;68(5):680/6. Epub 2007 Jan 26.
Ferulsinaic acid, a sesquiterpene coumarin with a rare carbon skeleton from
Ferula species.
Ahmed AA, Hegazy ME, Zellagui A, Rhouati S, Mohamed TA, Sayed AA, Abdella MA,
Ohta S, Hirata T.
Department of Chemistry, El/Minia University, El/Minia 61519, Egypt.
Fractionation of methylene chloride extracts of the resin of Ferula vesceritensis
and F. sinaica afforded three sesquiterpene coumarins and a glucose derivative.
One of them was a sesquiterpene with a rare carbon skeleton. The structures of
these compounds were determined by extensive NMR studies, including DEPT, COSY,
NOE, HMQC, and HMBC.
PMID: 17258243 [PubMed / indexed for MEDLINE]
45: Phytochemistry. 2007 Feb;68(4):554/61. Epub 2006 Dec 29.
Sesquiterpene coumarins from Ferula szowitsiana and in vitro antileishmanial
activity of 7/prenyloxycoumarins against promastigotes.
Iranshahi M, Arfa P, Ramezani M, Jaafari MR, Sadeghian H, Bassarello C, Piacente
S, Pizza C.
Department of Pharmacognosy and Biotechnology, Faculty of Pharmacy, Mashhad,
Iran. Iransham@sina.tums.ac.ir
Two new sesquiterpene coumarins, named szowitsiacoumarin A (1) and
szowitsiacoumarin B (2), and a phenylpropanoid derivative, 2/epihelmanticine (3),
together with nine known compounds, auraptene (4), umbelliprenin (5), galbanic
acid (6), methyl galbanate (7), farnesiferol B (8), farnesiferol C (9),
persicasulfide A (10), beta/sitosterol and stigmasterol were isolated from the
roots of Ferula szowitsiana. The structures of these compounds were elucidated by
extensive spectroscopic methods including 1D/((1)H and (13)C) and 2D/NMR
experiments (DQF/COSY, HSQC, HMBC, and ROESY) as well as HR/MALDI/MS analysis.
Since the configuration of 2/epihelmanticine was previously only partly
determined, a relative configurational analysis of its four stereocenters was
carried out on the basis of the recently reported J/based method. The inhibiting
activity of prenylated coumarins, auraptene (4) and umbelliprenin (5), in
addition to galbanic acid (6), as major component, and of the Me(2)CO extract of
Ferula szowitsiana (Apiaceae) roots has been evaluated against promastigotes of
Leishmania major. Umbelliprenin and auraptene showed significant activity with
IC(50) values of 4.9microg/ml (13.3microM) and 5.1microg/ml (17.1microM) after
48h incubation, respectively.
PMID: 17196626 [PubMed / indexed for MEDLINE]
46: Chem Pharm Bull (Tokyo). 2006 Nov;54(11):1595/8.
Sesquiterpene coumarins from the roots of Ferula sinkiangensis and Ferula
teterrima.
Yang JR, An Z, Li ZH, Jing S, Qina HL.
Key Laboratory of Bioactive Substances and Resources Utilization of Chinese
Herbal Medicine (Peking Union Medical College), Ministry of Education, Beijing,
PR China.
Three new natural sesquiterpene coumarins, isofeterin (1), lehmannolol (3),
sinkianone (4), and one known compound, lehmannolone (2), were isolated from the
roots of Ferula teterrima and Ferula sinkiangensis. Their chemical structures
were established on the basis of spectroscopic analysis, including X/ray
crystallography and CD spectrum measurements for determining the absolute
configuration of compound 2.
PMID: 17077560 [PubMed / indexed for MEDLINE]
47: J Agric Food Chem. 2006 Oct 4;54(20):7556/63.
Analytical discrimination of poisonous and nonpoisonous chemotypes of giant
fennel (Ferula communis L.) through their biologically active and volatile
fractions.
Rubiolo P, Matteodo M, Riccio G, Ballero M, Christen P, Fleury/Souverain S,
Veuthey JL, Bicchi C.
Dipartimento di Scienza e Tecnologia del Farmaco, Università degli Studi di
Torino, via P. Giuria 9, I/10125 Torino, Italy. patrizia.rubiolo@unito.it
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.
PMID: 17002421 [PubMed / indexed for MEDLINE]
48: Physiol Behav. 2006 Dec 30;89(5):656/61. Epub 2006 Sep 12.
Role of ferutinin in the impairment of female sexual function induced by Ferula
hermonis.
Zavatti M, Montanari C, Zanoli P.
Department of Biomedical Sciences, Section of Pharmacology, and National
InterUniversity Consortium for the Study of Natural Active Principles (CINSPAN),
University of Modena and Reggio Emilia, Via Campi 287, 41100 Modena, Italy.
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.
PMID: 16970966 [PubMed / indexed for MEDLINE]
49: J Nat Prod. 2006 Jul;69(7):1101/4.
A meroterpenoid NF/kappaB inhibitor and drimane sesquiterpenoids from Asafetida.
Appendino G, Maxia L, Bascope M, Houghton PJ, Sanchez/Duffhues G, Muñoz E,
Sterner O.
Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche,
Università del Piemonte Orientale, Via Bovio 6, 28100 Novara, Italy.
appendino@pharm.unipmn.it
Investigation of an acetone extract from Asafetida afforded two drimane
sesquiterpene dienones (fetidones A and B, 1a,b) and several known sesquiterpene
coumarin ethers, one of which (8/acetoxy/5/hydroxyumbelliprenin, 2a) showed
potent and specific NF/kappaB/inhibiting properties. This, coupled to a
negligible cytotoxicity, qualifies 2a as a new anti/inflammatory chemotype, and
its occurrence in asafetida might rationalize the use of this gum resin to
alleviate and prevent colon inflammatory disturbances.
PMID: 16872156 [PubMed / indexed for MEDLINE]
50: Nat Prod Res. 2006 Aug;20(10):961/5.
Saradaferin, a new sesquiterpenoid coumarin from Ferula assafoetida.
Bandyopadhyay D, Basak B, Chatterjee A, Lai TK, Banerji A, Banerji J, Neuman A,
Prangé T.
Centre of Advanced Studies on Natural Products including Organic Synthesis,
Department of Chemistry, Calcutta University, 92, A. P. C. Road, Kolkata, 700
009, India.
Phytochemical investigation of the gum resin of Ferula assafoetida resulted in
the isolation and characterization of a new sesquiterpenoid coumarin, Saradaferin
(1) named as
[Decahydro/(3/alpha/hydroxy/4,4,10/trimethyl/8/methylene/9/naphthenyl)/alpha/hydr
oxymethyl] ether of umbelliferone.
PMID: 16854726 [PubMed / indexed for MEDLINE]
