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PubMed2001

Pesticidal properties of parthenin (from Parthenium hysterophorus) and related compounds.

Eleven sesquiterpene lactone derivatives of parthenin (1), obtained from wild feverfew, Parthenium hysterophorus, were prepared by chemical and photochemical transformations. The compounds tested were a pyrazoline adduct (2) of parthenin, its cyclopropyl (3) and propenyl (4) derivatives, anhydroparthenin (5), a dihydro-deoxygenated product (6), a formate (7) and its corresponding alcohol (8) and acetate (9), a rearranged product (10), lactone (11) and hemiacetal (12). All these derivatives, along with parthenin, were tried for their antifeedant action against sixth-instar larvae of Spodoptera litura, for insecticidal activity against the adults of store grain pest Callosobruchus maculatus, for phytotoxic activity against Cassia tora, and for nematicidal activity against the juvenile stage-II (J2) of the root knot nematode Meloidogyne incognita. Antifeedent bioassay revealed that parthenin is moderately antifeedant. Among the derivatives, the saturated lactone (11) was found to be about 2.25 times more active than parthenin. The pyrazoline adduct (2) was found to be the most effective as an insecticide, with LC50 values after 24, 48 and 72 h of 96, 43 and 32 mg litre-1, respectively, which are comparable with neem extract. Compound 4 was found to be the most effective inhibitor of germination and seedling growth of C tora, with ID50 values for germination, plumule length and radicle length of 136, 326 and 172 compared with 364, 738 and 427 mg litre-1, respectively, for parthenin. Compound 10 was found to be the most effective in terms of nematicidal activity. The LC50 values for this compound were 273 and 104 mg litre-1, respectively, after 48 and 72 h compared with 862 and 512 mg litre-1 observed for parthenin after 48 and 72 h.

Animals↗

PubMed2003

Bioactive flavonoids of Tanacetum parthenium revisited.

Bio-guided fractionation of an extract from Tanacetum parthenium showing activity as mitotic blocker allowed the isolation and identification of santin 3, jaceidin 2 and centaureidin 1. The latter two closely related flavonols, which, to the best of our knowledge, are isolated here together for the first time, form a mixture difficult to resolve and which is probably the reason for the confusion in the literature regarding their occurrence. Centaureidin 1 had an IC50 of 1 microM while jaceidin 2 and santin 3 were 200 times less active.

Animals↗

PubMed2001

Assessment of mutagenicity in Parthenium hysterophorus L.

The mutagenic potential of a crude extract of Parthenium hysterophorus L. was assessed in the Salmonella/microsome (Ames) assay and the mouse bone marrow micronucleus test. Results in the bacterial mutagenicity assay were negative for the five strains employed, e.g. TA 1535, TA1537, TA 98, TA 100 and TA 102, while cytotoxicity was evident in all cases at 5000 microg per plate, the highest concentration assayed. A decrease in toxicity was observed with exogenous mammalian metabolic activation (S9) or glutathione (5 micromol per plate). When mutagenicity was monitored after column chromatography fractionation of the crude, fraction 1 was mutagenic in strain TA 98 (+S9). Besides, cytotoxicity was found in fraction 5, where parthenin was eluted. The micronucleus test was negative in mice upon oral administration, at doses up to 96 mg of crude per kg. Bone marrow toxicity was not observed. The crude extract exhibited some in vitro pro-oxidant activity. It also inhibited lipid peroxidation (IC(50)=4.1 microg/ml) but failed to act as .OH scavenger.

Animals↗

PubMed1999

Antinociceptive and anti-inflammatory effects of Tanacetum parthenium L. extract in mice and rats.

Oral administration of the feverfew (Tanacetum parthenium) extract led to significant antinociceptive and anti-inflammatory effects against acetic acid-induced writhing in mice and carrageenan-induced paw edema in rats, respectively. These responses were dose-dependent (10, 20, 40 mg/kg, p.o.). Parthenolide (1, 2 mg/kg i.p.), the active constituent of the extract also produced antinociceptive and anti-inflammatory effects. Naloxone (1 mg/kg i.p.), an opiate antagonist, failed to reverse feverfew extract and parthenolide-induced antinociception. Feverfew extract in higher doses (40, 60 mg/kg p.o.) neither altered the locomotor activity nor potentiated the pentobarbitone-induced sleep time in mice. It also did not change the rectal temperature in rats. Feverfew extract exerted antinociceptive and anti-inflammatory effects without altering the normal behaviour of the animals.

Acetic Acid↗

PubMed2000

The efficacy and safety of feverfew (Tanacetum parthenium L.): an update of a systematic review.

OBJECTIVE: Feverfew (Tanacetum parthenium L.) is a popular herbal remedy often advocated for the prevention of migraine. The aims of this systematic review are to update the evidence from rigorous clinical trials for or against the efficacy of feverfew for migraine prevention and to provide a safety profile of this herbal remedy. DESIGN: Literature searches were performed using the following databases: Medline, Embase, Biosis, CISCOM and the Cochrane Library (all from their inception to December 1999). Only randomized, placebo-controlled, double-blind trials of feverfew mono-preparations for the prevention of migraine in human subjects were included. All articles were read by two independent reviewers. Data were extracted in a pre-defined, standardized fashion. The methodological quality of the trials was evaluated by the Jadad score. For the assessment of safety issues, major reference texts were also consulted. RESULTS: Six trials met the inclusion/exclusion criteria. The majority favour feverfew over placebo. Yet important caveats exist. The data also suggest that feverfew is associated with only mild and transient adverse effects and few other safety concerns. CONCLUSIONS: Feverfew is likely to be effective in the prevention of migraine. There are no major safety problems.

Humans↗

PubMed1999

Rapid extraction and high-performance liquid chromatographic determination of parthenolide in feverfew (Tanacetum parthenium).

A rapid and sensitive method for quantifying parthenolide in feverfew herb (Tanacetum parthenium) was developed that is significantly faster than those reported in the literature. The extraction system consisted of acetonitrile/water (90:10, v/v) in a bottle with stirring for 30 min. Both Soxhlet and bottle-stirring extractions were studied. Samples were analyzed using high-performance liquid chromatography with a Cosmosil C18-AR column (150 x 4.6 mm, 5 microm, 120 A). The mobile phase consisted of acetonitrile/water (55:45, v/v) with a flow rate of 1.5 mL/min and UV detection at 210 nm. Analysis time was 6 min, with a detection limit of 0.10 ng on column. The calibration curve was linear over a range of 0.160-850 microg/mL parthenolide with R(2) = 0.9999. Replicate tests indicated good reproducibility of the method with an RSD% = 0.88 (n = 10). Spike recovery of parthenolide was found to be 99.3% with an RSD% = 1.6 (n = 6).

Chromatography, High Pressure Liquid↗

PubMed2002

Do monoterpenes released from feverfew (Tanacetum parthenium) plants cause airborne Compositae dermatitis?

The Compositae plant feverfew (Tanacetum parthenium) is an important sensitizer in Europe and has been suspected of causing airborne Compositae dermatitis. A previous investigation of substances emitted from feverfew plants detected no sesquiterpene lactones, however, but mainly monoterpenes. The aims of this study were to test whether feverfew-allergic patients were also sensitive to some of the above-mentioned monoterpenes and, if so, to study associations between sensitization patterns, relevance of feverfew allergy and clinical features. 17 patients with + +/+ + + reactions to feverfew and parthenolide were tested with 15 selected monoterpenes and 2 sesquiterpenes. Of the 17 persons, 13 had positive and/or doubtful positive reactions to 1 or more monoterpenes. Only 1 person was allergic to several monoterpenes. Her history of gradually worsening Compositae dermatitis culminating in a probable airborne dermatitis, mimicking photosensitivity, and the disappearance of symptoms upon removal of feverfew plants suggest monoterpenes as a possible contributing factor. Similar associations between doubtful positive monoterpene reactions and clinical patterns, fragrance/colophonium allergy and relevance of feverfew allergy were not established with certainty. In conclusion, sensitization to the sesquiterpene lactones of feverfew is not invariably accompanied by sensitization to its volatile monoterpenes. The presence of monoterpene allergy, however, may contribute to airborne Compositae dermatitis.

Adult↗

PubMedDate not supplied

Azathioprine as a corticosteroid sparing agent for the treatment of dermatitis caused by the weed Parthenium.

Air-borne contact dermatitis caused by Parthenium hysterophorus is a serious problem in India. Patients with this condition have to use corticosteroids regularly in order to maintain clinical remissions, but prolonged usage causes serious side-effects. The weed cannot be eradicated. We have used 3 therapeutic regimens with azathioprine, which led to an effective control with minimal side-effects even when used for long periods. A total of 22 patients (group I) were given 50 mg azathioprine twice a day; 11 patients (group II) received 50 mg azathioprine per day and 300 mg azathioprine every 28 days, and 10 patients (group III) were given 50 mg azathioprine twice a day along with 300 mg azathioprine every 28 days. The duration of treatment varied from 6 months to 3 years. Twenty patients in group I and 9 patients each in groups II and III had complete remission. Nine, 7 and 6 patients in the respective groups needed additional oral betamethasone 1-2 mg per day for brief periods only during the peak season in order to maintain complete remission. One patient in each group had only partial relief. The need for oral betamethasone during the second and the third year was further reduced. One patient each in group I and group II could not continue azathioprine due to the side-effects of the drug.

Adult↗

PubMed2005

Parthenolide is the component of tanacetum parthenium that inhibits nitroglycerin-induced Fos activation: studies in an animal model of migraine.

Tanacetum parthenium (TP) is a member of the Asteracee family long used empirically as a herbal remedy for migraine. So far, however, clinical trials have failed to prove consistently the effectiveness of TP extracts in preventing migraine attacks, probably as a consequence of the uncertainty as regards the active principle. In this study, the biological effects of different TP extracts and purified parthenolide were tested in an animal model of migraine based on the quantification of neuronal activation induced by nitroglycerin. The extract enriched in parthenolide significantly reduced nitroglycerin-induced Fos expression in the nucleus trigeminalis caudalis. Purified parthenolide inhibited nitroglycerin-induced neuronal activation in additional brain nuclei and, significantly, the activity of nuclear factor-kappaB. These findings strongly suggest that parthenolide is the component responsible for the biological activity of TP as regards its antimigraine effect and provide important information for future controlled clinical trials.

Animals↗

PubMed1977

The role of sesquiterpene lactones in contact hypersensitivity to some North and South American species of feverfew (Parthenium-Compositae).

Sixteen taxa of the genus Parthenium from North and South America and 20 sesquiterpene lactones derived from plants of the Compositae family were used for patch testing six volunteers who were known to be contact sensitive to plants and lactones of this family. The patterns of cross-sensitivity and structure-activity relationships of the allergenic lactones are evaluated and the clinical and ecological relevance is discussed.

Cross Reactions↗

PubMed2005

Antileishmanial activity of parthenolide, a sesquiterpene lactone isolated from Tanacetum parthenium.

The in vitro activity of parthenolide against Leishmania amazonensis was investigated. Parthenolide is a sesquiterpene lactone purified from the hydroalcoholic extract of aerial parts of Tanacetum parthenium. This isolated compound was identified through spectral analyses by UV, infrared, (1)H and (13)C nuclear magnetic resonance imaging, DEPT (distortionless enhancement by polarization transfer), COSY (correlated spectroscopy), HMQC (heteronuclear multiple-quantum coherence), and electron spray ionization-mass spectrometry. Parthenolide showed significant activity against the promastigote form of L. amazonensis, with 50% inhibition of cell growth at a concentration of 0.37 microg/ml. For the intracellular amastigote form, parthenolide reduced by 50% the survival index of parasites in macrophages when it was used at 0.81 microg/ml. The purified compound showed no cytotoxic effects against J774G8 macrophages in culture and did not cause lysis in sheep blood when it was used at higher concentrations that inhibited promastigote forms. Sodium dodecyl sulfate-polyacrylamide gel electrophoresis with gelatin as the substrate showed that the enzymatic activity of the enzyme cysteine protease increased following treatment of the promastigotes with the isolated compound. This finding was correlated with marked morphological changes induced by parthenolide, such as the appearance of structures similar to large lysosomes and intense exocytic activity in the region of the flagellar pocket, as seen by electron microscopy. These results provide new perspectives on the development of novel drugs with leishmanicidal activities obtained from natural products.

Animals↗

PubMedDate not supplied

Attempts of chemical standardizing of Chrysanthemum parthenium as a prospective antimigraine drug.

A quantitative analysis of biologically active sesquiterpene lactones in ethanol and aqueous extracts of Chrysanthemum parthenium and its form flosculosum was carried out. The sesquiterpene lactone contents in the extracts were comparable, although the contents of ethanol extracts (ca. 0.5%) were higher than of aqueous ones (ca. 0.3%). Parthenolide was found to be the main constituent of the lactones. The applied IR and TLC/FID methods for quantitative determination of the total sesquiterpene lactones and parthenolide, respectively, may be used for chemical standardizing of the raw material and its preparations.

Chromatography, Thin Layer↗

PubMed1983

Contact allergy to parthenolide in Tanacetum parthenium (L.) Schulz-Bip. (feverfew, Asteraceae) and cross-reactions to related sesquiterpene lactone containing Compositae species.

A case of specific, delayed hypersensitivity induced by repeated contact with a wild form of feverfew (Tanacetum parthenium) is reported. In the flowers investigated the content of the responsible contact allergen parthenolide--a potent sesquiterpene lactone--appeared to be 10 times greater (0.6-0.9%) than in earlier years. Guinea pig experiments confirm the strong sensitizing potency of this Compositae species. Cross-reactions were elicited with 11 of 21 mostly Compositae plants containing chemically related sesquiterpene lactones. The strongest reactions were elicited by tansy, yarrow (milfoil), marguerite, aster, sunflower, laurel and Frullania. Structure elucidation by X-ray crystallographic analysis established the precise molecule configuration of parthenolide, although the lattice parameters of the isolated compound were not in accordance with those published in the literature.

Animals↗

PubMed1999

Depolarizing neuromuscular junctional blocking action of Parthenium hysterophorus leaf extracts in rat.

Electromyographic (EMG) and electrodiagnostic studies were made on sciatic nerve-anterior tibialis muscle in vivo in rats administered with a sublethal dose of Parthenium hysterophorus dry leaf powder 100 mg/100 g body weight of rat. Nerve-evoked and muscle-evoked compound muscle action potentials were recorded at different frequencies of stimulations and at different time intervals. The EMG studies revealed depolarizing neuromuscular junctional (NMJ) blocking effects of the leaf extract. The decrement-increment (D-I) phenomena and the EMG pattern in general showed a resemblance to an established anticholinesterase agent like neostigmine. The studies confirm that the leaf extract contains a proven and promising new depolarizing NMJ blocker.

Action Potentials↗

PubMed1977

Toxicity of Parthenium hysterophorus L. to cattle and buffaloes.

Parthenium hysterophorus L., when fed to buffalo bull calves and cross bred bull calves resulted in acute toxicity leading to death. The former animals developed severe dermatitis. Autopsy revealed ulceration of alimentary tract. Extensive pathological changes were noticed in liver, kidney and skin.

Animals↗

PubMed1977

Clinical and immunological studies on persons exposed to Parthenium hysterophorus L.

Studies on 300 persons subjected by occupational hazard to the allergenic weed, Parthenium hysterophorus L. for periods ranging from 3 to 12 months revealed that 4% of them developed contact dermatitis of the exposed parts of the body, while 56% of them got sensitized to the weed without apparently exhibiting any dermatitis. None of them suffered from allergic manifestations like rhinitis or bronchial asthma during the period of study which extended for 2 years.

Allergens↗

PubMedDate not supplied

Airborne Compositae dermatitis: monoterpenes and no parthenolide are released from flowering Tanacetum parthenium (feverfew) plants.

The air around intact feverfew (Tanacetum parthenium) plants was examined for the presence of airborne parthenolide and other potential allergens using a high-volume air sampler and a dynamic headspace technique. No particle-bound parthenolide was detected in the former. Among volatiles emitted from the aerial parts of feverfew plants and collected by the dynamic headspace technique a total of 41 compounds, mainly monoterpenes, were identified and quantified by GC and GC-MS. Alpha-Pinene, camphene, limonene, gamma-terpinene, (E)-beta-ocimene, linalool, p-cymene, (E)-chrysanthenol, camphor and (E)-chrysanthenyl acetate were the predominant monoterpenes accounting for nearly 88% of the total volatiles emitted. The average total yield of volatiles emitted over 24 h was 18,160 ng/g fresh weight of leaves and flowers, corresponding to the emission of approximately 8 mg volatiles per day from one full-grown feverfew plant. No parthenolide or other sesquiterpene lactones were detected. The present investigation does not support the theory of airborne sesquiterpene lactone-containing plant parts or of direct release of sesquiterpene lactones from living plants as the only explanations for airborne Compositae dermatitis. Potential allergens were found among the emitted monoterpenes and their importance in airborne Compositae dermatitis is discussed.

Air Pollutants↗

PubMed1995

A biologically active lipophilic flavonol from Tanacetum parthenium.

A new lipophilic flavonol, 6-hydroxykaempferol 3,7,4'-trimethyl ether, called tanetin, has been characterized in the leaf, flower and seed of feverfew, Tanacetum parthenium. It co-occurs with the known 6-hydroxykaempferol 3,7-dimethyl ether, quercetagetin 3,7-dimethyl ether and quercetagetin 3,7,3'-trimethyl ether. Pharmacological tests indicate that tanetin could contribute to the anti-inflammatory properties of feverfew by inhibiting the generation of pro-inflammatory eicosanoids, although it is unlikely to be the only biologically active compound within the plant. Water soluble flavone glycosides were detected in the leaves and identified as apigenin 7-glucuronide, luteolin 7-glucuronide, luteolin 7-glucoside and chrysoeriol 7-glucuronide.

Chromatography, High Pressure Liquid↗