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At least 19 recordsLinked to original sources

PubMed1995

Effects of essential oil of Croton zehntneri, and of anethole and estragole on skeletal muscles.

Extracts of the essential oil of Croton zehntneri (CzEO) yield a mixture of substances in which the major components are anethole and estragole. The action of CzEO and of pure anethole and estragole (at 0.05-1.0 mg/ml) were studied in muscle preparations of the toad and rat. All three oils blocked twitches evoked by nerve stimulation. In the rat diaphragm direct stimulation resulted in enhanced twitches (CzEO), partially depressed twitches (estragole) and anethole did not induce a significant change. The response of toad rectus to acetylcholine was reduced by all three oils. Caffeine contractions of the rectus abdominis and sartorius muscles were enhanced by all oils. This enhancement in the case of the sartorius was blocked by procaine. Lowering the temperature to 4 degrees C in the presence of CzEO, anethole or estragole provoked a contraction which could be blocked by procaine. CzEO, anethole or estragole alone sometimes caused contractions. The occurrence of this response was increased by elevation of calcium (to 22 mM). Other divalent cations and La3+ were also effective, in order: La3+ > Ca2+ > Mn2+ > Ba2+ > Mg2+ except in the case of anethole where the order of Ca2+ and Mn2+ are interchanged. CzEO- and estragole-induced contractions were blocked by procaine. The data suggest that CzEO, anethole and estragole may have two sites of action on muscle fibers: the post junctional membrane, by blocking neuromuscular transmission, and on the sarcoplasmic reticulum (SR), by increasing myoplasmic calcium.

Allylbenzene Derivatives↗

PubMed1998

Immunochemical identification of hepatic protein adducts derived from estragole.

Hepatic protein adducts derived from the allylbenzene food flavor estragole, which is hepatocarcinogenic when given to rodents at high doses, have been identified using immunochemical approaches. Male Fischer 344 rats were given estragole orally and hepatic protein adducts were detected by immunoblotting, using antisera raised by immunizing rabbits with 4-methoxycinnamic acid-modified rabbit serum albumin. A major 155-kDa adduct was expressed in livers of animals that had been treated with estragole at 100, 300, or 500 mg/kg. Levels of expression of the adduct increased disproportionately with respect to dose, and other adducts (170, 100, 44, and 35 kDa) were detected also in the high-dose group. Rats given estragole for 5 days, at 300 mg/kg/day, expressed predominantly 155- and 44-kDa adducts. The 155-, 100-, 44-, and 35-kDa adducts were detected in greatest abundance in liver microsomal fractions, while the 170-kDa adduct was most abundant in the nuclear fraction. Interestingly, whereas the 170-, 155-, 100-, and 35-kDa adducts were detected in cytosolic fractions, relatively low levels of the 44-kDa adduct were detected in nuclear fractions but not in cytosolic fractions. The various adducts were solubilized when microsomal fractions were extracted with sodium carbonate and were digested by trypsin. This implies that the target proteins are peripheral membrane proteins bound to the outer surface of microsomal membranes. Experiments undertaken with isolated rat hepatocytes and with V79 cells transfected with human monoamine phenol sulfotransferase cDNA revealed that adduct formation required 1'-hydroxylation of estragole, followed by sulfation. The pattern of adducts expressed when the transfected V79 cells were incubated with 1'-hydroxyestragole was very similar to that expressed in livers of estragole-treated rats. These cells should constitute a valuable in vitro model system for investigation of toxicological consequences arising from estragole-induced protein adduct formation.

Allylbenzene Derivatives↗

PubMed2004

Effects of estragole on the compound action potential of the rat sciatic nerve.

Estragole, a relatively nontoxic terpenoid ether, is an important constituent of many essential oils with widespread applications in folk medicine and aromatherapy and known to have potent local anesthetic activity. We investigated the effects of estragole on the compound action potential (CAP) of the rat sciatic nerve. The experiments were carried out on sciatic nerves dissected from Wistar rats. Nerves, mounted in a moist chamber, were stimulated at a frequency of 0.2 Hz, with electric pulses of 50-100-micros duration at 10-20 V, and evoked CAP were monitored on an oscilloscope and recorded on a computer. CAP control parameters were: peak-to-peak amplitude (PPA), 9.9 +/- 0.55 mV (N = 15), conduction velocity, 92.2 +/- 4.36 m/s (N = 15), chronaxy, 45.6 +/- 3.74 micros (N = 5), and rheobase, 3.9 +/- 0.78 V (N = 5). Estragole induced a dose-dependent blockade of the CAP. At 0.6 mM, estragole had no demonstrable effect. At 2.0 and 6.0 mM estragole, PPA was significantly reduced at the end of 180-min exposure of the nerve to the drug to 85.6 +/- 3.96 and 13.04 +/- 1.80% of control, respectively. At 4.0 mM, estragole significantly altered PPA, conduction velocity, chronaxy, and rheobase (P < or = 0.05, ANOVA; N = 5) to 49.3 +/- 6.21 and 77.7 +/- 3.84, 125.9 +/- 10.43 and 116.7 +/- 4.59%, of control, respectively. All of these effects developed slowly and were reversible upon a 300-min wash-out. The data show that estragole dose-dependently blocks nerve excitability.

Action Potentials↗

PubMed1994

The genotoxic potential in vitro and in vivo of the allyl benzene etheric oils estragole, basil oil and trans-anethole.

Estragole, trans-anethole and basil oil were tested for their ability to induce DNA repair in rat hepatocytes in vitro and in rat liver in an ex vivo test. There was a marked induction of UDS by estragole and basil oil in vitro (LOEC about 10(-5) mol/l). The basil oil we used contained about 88.2% estragole. It is evident from our results that the induction of UDS with basil oil could be directly related to its main constituent estragole. trans-Anethole was only slightly effective in the in vitro UDS test. The ex vivo UDS test led to clearly elevated DNA repair for estragole and basil oil in rats treated orally with doses up to 2 g/kg body weight. Estragole was not positive in a chromosomal aberration test with V79 cells either via direct treatment, with rat liver S9 mix or with rat hepatocytes as source of metabolism.

Allylbenzene Derivatives↗

PubMed2000

Biosynthesis of estragole and methyl-eugenol in sweet basil (Ocimum basilicum L). Developmental and chemotypic association of allylphenol O-methyltransferase activities.

Sweet basil (Ocimum basilicum L., Lamiaceae) is a common herb, used for culinary and medicinal purposes. The essential oils of different sweet basil chemotypes contain various proportions of the allyl phenol derivatives estragole (methyl chavicol), eugenol, and methyl eugenol, as well as the monoterpene alcohol linalool. To monitor the developmental regulation of estragole biosynthesis in sweet basil, an enzymatic assay for S-adenosyl-L-methionine (SAM):chavicol O-methyltransferase activity was developed. Young leaves display high levels of chavicol O-methyltransferase activity, but the activity was negligible in older leaves, indicating that the O-methylation of chavicol primarily occurs early during leaf development. The O-methyltransferase activities detected in different sweet basil genotypes differed in their substrate specificities towards the methyl acceptor substrate. In the high-estragole-containing chemotype R3, the O-methyltransferase activity was highly specific for chavicol, while eugenol was virtually not O-methylated. In contrast, chemotype 147/97, that contains equal levels of estragole and methyl eugenol, displayed O-methyltransferase activities that accepted both chavicol and eugenol as substrates, generating estragole and methyl eugenol, respectively. Chemotype SW that contains high levels of eugenol, but lacks both estragole and methyl eugenol, had apparently no allylphenol dependent O-methyltransferase activities. These results indicate the presence of at least two types of allylphenol-specific O-methyltransferase activities in sweet basil chemotypes, one highly specific for chavicol; and a different one that can accept eugenol as a substrate. The relative availability and substrate specificities of these O-methyltransferase activities biochemically rationalizes the variation in the composition of the essential oils of these chemotypes.

Journal Article↗

PubMed1983

Structure-activity studies of the carcinogenicities in the mouse and rat of some naturally occurring and synthetic alkenylbenzene derivatives related to safrole and estragole.

Twenty-three naturally occurring and synthetic alkenylbenzene derivatives structurally related to the hepatocarcinogen safrole (1-allyl-3,4-methylenedioxybenzene) were assayed for their hepatocarcinogenicity in mice. Some of these compounds (safrole, estragole, eugenol, anethole, methyleugenol, myristicin, elemicin, and dill and parsley apiols) may be ingested in very small amounts by human as natural components of certain spices, essential oils, or vegetables. Estragole (1-allyl-4-methoxybenzene) and its proximate carcinogenic metabolite 1'-hydroxyestragole, previously shown to induce hepatic tumors when administered to male CD-1 mice only during the preweaning period, also induced hepatic tumors on administration for 12 months in the diet of female CD-1 mice. Eugenol (1-allyl-4-hydroxy-3-methoxybenzene) and anethole (trans-4-methoxy-1-propenylbenzene) were inactive in this assay; they were also inactive when administered i.p. during the preweaning period at total doses of up to 9.45 mumol/mouse to male CD-1 or C57BL/6 x C3H F1 (hereafter called B6C3F1) mice. Methyleugenol (1-ally-3,4-dimethoxybenzene) and its 1'-hydroxy metabolite had activities similar to those of estragole and its 1'-hydroxy metabolite for the induction of hepatic tumors in male B6C3F1 mice treated prior to weaning; 1-allyl-1'-hydroxy-4-methoxynaphthalene was somewhat less active. At the levels tested, myristicin (1-allyl-5-methoxy-3,4-methylenedioxybenzene), elemicin (1-allyl-3,4,5-trimethoxybenzene) and its 1'-hydroxy metabolite, dill apiol (1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene), parsley apiol (1-allyl-2,5-dimethoxy-3,4-methylenedioxybenzene), 1'-hydroxyallybenzene, 3'-hydroxyanethole, and benzyl and anisyl alcohols had no detectable activity for the initiation of hepatic tumors on administration to male mice prior to weaning. The acetylenic derivative 1'-hydroxy-2',3'-dehydroestragole was much more active than either 1'-hydroxysafrole or 1'-hydroxyestragole when administered to preweanling mice. The 2',3'-oxides of safrole, estragole, eugenol, and 1'-hydroxysafrole, which are metabolites of these alkenylbenzenes, had little or no activity in this test. The 2',3'-oxides of safrole and estragole and their 1'-hydroxy derivatives likewise had little or no activity for the induction of lung adenomas in female A/J mice or for the induction of tumors on repetitive injections s.c. in male Fischer rats. However, the 2',3'-oxides of safrole, estragole, eugenol, 1'-hydroxysafrole, and 1'-hydroxyestragole, when administered topically to female CD-1 mice at relatively high doses, initiated benign skin tumors that could be promoted with croton oil.

Administration, Oral↗

PubMed2004

Anti-Candida effects of estragole in combination with ketoconazole or amphotericin B.

The anti-Candida effects of estragole combined with amphotericin B or ketoconazole, commonly used antifungal drugs for treatment of candidasis, were evaluated in this study. The fractional inhibitory concentration (FIC) indices of both estragole combined with ketoconazole against C. albicans and C. utilis calculated from the checkerboard microtiter assay were 0.28 and 0.50 respectively, indicating significant synergism. These drug combinations exhibited additive effects against C. tropicalis, with FIC index of 0.75. Consistent for the most part with the results from the checkerboard titer tests, the time-kill curves of the tested samples also indicated significant synergism or additive effect between ketoconazole and estragole against the Candida species evaluated. In contrast, amphotericin B showed antagonism in combination with estragole in most experiments of this study. Thus, we have shown the synergistic combination effects between estragole and ketoconazole, which may be effective combinations for the treatment of Candida infections.

Agastache↗

PubMed1981

The side-chain epoxidation and hydroxylation of the hepatocarcinogens safrole and estragole and some related compounds by rat and mouse liver microsomes.

Safrole, estragole, and their 2',3'-oxides were hydroxylated by hepatic microsomes from rats and mice at the 1'-carbon; trans-anethole was hydroxylated at the 3'-carbon; and safrole, estragole, and their 1'-hydroxy derivatives were epoxidized at the 2',3'-double bond. The 2',3'-epoxidation of eugenol was just detectable. The formation of these metabolites was dependent on an NADPH-generating system and on cytochrome P-450. In the absence of 3,3,3-trichloropropylene oxide little or no safrole-, estragole-, or eugenol-2',3'-oxide was recovered when these oxides were added to the incubations; recoveries of 50-70% were obtained in its presence. The recoveries of the 2',3'-oxides of 1'-hydroxy-safrole and of 1'-hydroxyestragole were 50-80% in the absence of trichloropropylene oxide and nearly quantitative in its presence. All incubations for analysis of epoxidation rates contained trichloropropylene oxide. The rates of metabolite formation ranged from about 0.4 nmol of eugenol-2',3'-oxide/mg protein/h by female rat liver microsomes to about 270 nmol of trans-3'-hydroxyanethole/mg protein/h for male rat liver microsomes. The rates of epoxidation and hydroxylation were greater for the estragole derivatives than for the safrole derivatives. The rates of epoxidation of safrole and estragole were greater than for their 1'-hydroxy derivatives.

Allylbenzene Derivatives↗

PubMed2002

Safety assessment of allylalkoxybenzene derivatives used as flavouring substances - methyl eugenol and estragole.

This publication is the seventh in a series of safety evaluations performed by the Expert Panel of the Flavor and Extract Manufacturers' Association (FEMA). In 1993, the Panel initiated a comprehensive program to re-evaluate the safety of more than 1700 GRAS flavouring substances under conditions of intended use. In this review, scientific data relevant to the safety evaluation of the allylalkoxybenzene derivatives methyl eugenol and estragole is critically evaluated by the FEMA Expert Panel. The hazard determination uses a mechanism-based approach in which production of the hepatotoxic sulfate conjugate of the 1'-hydroxy metabolite is used to interpret the pathological changes observed in different species of laboratory rodents in chronic and subchronic studies. In the risk evaluation, the effect of dose and metabolic activation on the production of the 1'-hydroxy metabolite in humans and laboratory animals is compared to assess the risk to humans from use of methyl eugenol and estragole as naturally occurring components of a traditional diet and as added flavouring substances. Both the qualitative and quantitative aspects of the molecular disposition of methyl eugenol and estragole and their associated toxicological sequelae have been relatively well defined from mammalian studies. Several studies have clearly established that the profiles of metabolism, metabolic activation, and covalent binding are dose dependent and that the relative importance diminishes markedly at low levels of exposure (i.e. these events are not linear with respect to dose). In particular, rodent studies show that these events are minimal probably in the dose range of 1-10 mg/kg body weight, which is approximately 100-1000 times the anticipated human exposure to these substances. For these reasons it is concluded that present exposure to methyl eugenol and estragole resulting from consumption of food, mainly spices and added as such, does not pose a significant cancer risk. Nevertheless, further studies are needed to define both the nature and implications of the dose-response curve in rats at low levels of exposure to methyl eugenol and estragole.

Animals↗

PubMed2004

[Fennel tea: risk assessment of the phytogenic monosubstance estragole in comparison to the natural multicomponent mixture].

For centuries, fennel fruits have been used as traditional herbal medicine in Europe and China. For the treatment of infants and sucklings suffering from dyspeptic disorders, fennel tea is the drug of first choice. Its administration as a carminativum is practiced in infant care in private homes and in maternity clinics as well where it is highly appreciated for its mild flavor and good tolerance. The long standing positive experience is astonishingly contrasted by a recent statement of the German 'Bundesinstitut für gesundheitlichen Verbraucherschutz und Veterinärmedizin' (BgVV, May 11, 2001), where consumers are advised to reduce their intake of foods containing estragole and methyleugenol, e.g. tarragon, basil, anis, star anis, jamaica pepper, nutmeg, lemon grass as well as bitter and sweet fennel fruits for reasons of health. These warnings are based on experiments with rats and mice where estragole, a natural ingredient of fennel fruits, proved to be carcinogenic. Meanwhile, criticism arose amongst experts concerning the interpretation of these studies. The crucial points of criticism concern the transfer of data obtained in animal models to the human situation as well as the high doses of the applied monosubstance, which do not at all represent the amounts humans are exposed to as consumers of estragole-containing foods and phytopharmaceuticals. Furthermore, studies on estragole metabolism revealed at least quantitative differences between the estragole metabolism of mice and men. In addition, it has been shown that an agent when administered in its isolated form may have significantly different effects and side effects than the same agent applied as a constituent in naturally occurring multicomponent mixtures. Thus, a multicomponent mixture such as fennel tea contains various antioxidants known to be protective against cancer. These differences were not considered in the risk assessment. A well done risk assessment should be based on appropriate data collected in humans. Considering the long traditional use of fennel tea and the total lack of epidemiological and clinical studies indicating a well founded cancerogenic potential, the probability of a serious risk connected with the consumption of fennel tea seems to be negligibly small.

Allylbenzene Derivatives↗

PubMed1979

The mutagenicities of safrole, estragole, eugenol, trans-anethole, and some of their known or possible metabolites for Salmonella typhimurium mutants.

Safrole, estragole, anethole, and eugenol and some of their known or possible metabolites were tested for mutagenic activity for S. typhimurium TA1535, TA100, and TA98. Highly purified 1'-hydroxyestragole and 1'-hydroxysafrole were mutagenic (approximately 15 and 10 revertants/micromole, respectively) for strain TA100 in the absence of fortified liver microsomes; trans-anethole and estragole appeared to have very weak activity. 3'-Hydroxyanethole was too toxic for an adequate test. Supplementation with NADPH-fortified rat-liver microsomes and cytosol converted 3'-hydroxyanethole to a mutagen(s) and increased the mutagenic activities for strain TA100 of 1'-hydroxyestragole, 1'-hydroxysafrole, estragole, and anethole. No mutagenicity was detected for safrole or eugenol with or without added NADPH-fortified liver preparations. The electrophilic 2',3'-oxides of safrole, 1'-hydroxysafrole, 1'-acetoxysafrole, 1'-oxosafrole, estragole, 1'-hydroxyestragole, and eugenol showed dose-dependent mutagenic activities for strain TA1535 in the absence of fortified liver microsomes. These mutagenic activities ranged from about 330 revertants/micromole for 1'-oxosafrole-2',3'-oxide to about 7000 revertants/micromole for safrole-2',3'-oxide. The arylalkenes, their hydroxylated derivatives, or their epoxides did not show mutagenic activity for strain TA98, except for 1'-oxosafrole-2',3'-oxide, which had weak activity. Since the arylalkenes are hydroxylated and/or epoxidized by hepatic microsomes, hydroxy and epoxide derivatives appear to be proximate and ultimate mutagenic metabolites, respectively, of the arylalkenes.

Anisoles↗

PubMed1995

Metabolism of allylbenzene 2',3'-oxide and estragole 2',3'-oxide in the isolated perfused rat liver.

The metabolism of allylbenzene 2',3'-oxide, estragole 2',3'-oxide, allylbenzene and estragole was studied in the isolated perfused rat liver. Formation of dihydrodiol and glutathione conjugate metabolites was detected for both epoxides and the presence of dihydrodiol metabolites after perfusion of allylbenzene or estragole indicated the formation of allylic epoxide intermediates in the intact liver. A comparison of elimination kinetics for parent compounds and epoxides indicated that epoxides were relatively rapidly detoxified and probably do not accumulate on formation in vivo. Acute toxicity of epoxides, measured as the release of alanine aminotransferase activity into the perfusate, or genetic toxicity, determined as covalent binding of radiolabeled epoxide to DNA, were not observed. It was concluded that both epoxide hydrolases and glutathione S-transferases can effectively detoxify the allylic epoxides derived from either allylbenzene or estragole and effectively prevent cellular or genetic toxicity of these reactive intermediates. Epoxide hydrolases appear to play the major role in the detoxication of these epoxides in vivo.

Allyl Compounds↗

PubMed1987

Metabolism of estragole in rat and mouse and influence of dose size on excretion of the proximate carcinogen 1'-hydroxyestragole.

The major metabolic pathways of estragole have been established in rats and mice, and in both species the relative importance of the different pathways has been shown to be dose related. At low doses, estragole mainly undergoes detoxication reactions, notably O-demethylation and side-chain cleavage, but as the dose is increased, the extent of O-demethylation falls and other pathways, notably l'-hydroxylation, come into prominence. The disproportionate relationship between dose size and the elimination of the proximate carcinogenic metabolite l'-hydroxyestragole may influence the relationship between dose size and tumour incidence. These findings may have important implications for the safety assessment of this food flavouring, since the dose levels used in carcinogenicity studies have been very much larger than the estimated human daily intake. Moreover the percentage of an administered dose of estragole eliminated as 1-hydroxyestragole glucuronide in human urine is much lower than that found with even the lowest doses examined in rats in this study.

Allylbenzene Derivatives↗

PubMed1976

Hepatocarcinogenicity of estragole (1-allyl-4-methoxybenzene) and 1'-hydroxyestragole in the mouse and mutagenicity of 1'-acetoxyestragole in bacteria.

Approximately 20% of a dose of estragole, a naturally occurring flavoring agent, was excreted in the urine of outbred male CD -1 mice as a conjuage (presumably the glucuronide) of 1'-hydroxyestragole, Estragole and its 1'-hydroxy metabolite caused significant increases in the incidences of hepatocellular carcinomas in male CD-1 mice that received the compounds by sc injection at 1-22 days of age. Estragole induced hepatocellular carcinomas by 15 months in 23 and 39% of the mice that received total doses of 4.4 and 5.2 mumoles, respectively, and lived to an age of 12 months or more. Of the 12-month survivors given a total dose of 4.4 mumoles of 1'-hydroxyestragole, 70% developed hepatocellular carcinomas; the incidence in mice that received only the vehicle (trioctanoin) was 12%. Multiple tumors ocurred in 5, 28, 64, and 0%, respectively, of the mice in each of these 4 groups. Of the mice given a total dose of 4.4 mumoles of 1'-hydroxysafrole, 59developed hepatocellular carcinomas; 39% of the mice bore multiple liver tumors. As previsously demonstrated for 1'-acetoxysafrole, 1'-acetoxyestragole and 1'-acetoxy-1-allyl-4-methoxynaphthalene reacted nonenzymatically with guanosine and inosine to form adducts. These electrophilic esters were strongly mutagenic for the Salmonella typhimurium missense mutant TA100. 1'-Acetoxyallybenzene had little or no activity in either of these tests. Attempts to demonstrate liver-mediated mutagenicty for 1'-hydroxysafrole and 1'-hydroxyestragole in the bacterial test system were unsuccessful.

Allylbenzene Derivatives↗

PubMed1987

The metabolic disposition of [methoxy-14C]-labelled trans-anethole, estragole and p-propylanisole in human volunteers.

1. The metabolic fates of the naturally occurring food flavours trans-anethole and estragole, and their synthetic congener p-propylanisole, have been investigated in human volunteers using the [methoxy-14C]-labelled compounds. The doses used were close to those encountered in the diet, 1 mg, 100 micrograms and 100 micrograms respectively. 2. In each case, the major routes of elimination of 14C were in the urine and in the expired air as 14CO2. 3. Urinary metabolites were separated by solvent extraction, t.l.c. and h.p.l.c., and characterized by comparison of chromatographic mobilities with standards and by radioisotope dilution. Nine 14C urinary metabolites were found after trans-anethole administration, four after p-propylanisole and five after estragole. All were products of side chain oxidations. 4. The principal metabolites of p-propylanisole were 4-methoxyhippuric acid (12%) and 1-(4'-methoxyphenyl)propan-1-ol (2%) and -2-ol (8%). 5. The major metabolite of trans-anethole was 4-methoxyhippuric acid (56% of dose), accompanied by much smaller amounts of the two isomers of 1-(4'-methoxyphenyl)propane-1,2-diol (together 3%). 6. After estragole administration, the two volunteers eliminated 0.2 and 0.4% of the dose respectively as 1'-hydroxyestragole. 7. The human metabolic data is discussed with reference to the comparative metabolic disposition of these compounds in the mouse and rat, species commonly used in their safety assessment.

Adult↗

PubMed2005

[Effect of estragole on glucocorticoid induction of tyrosine aminotransferase and tryprophan oxygenase in the rat and mouse liver].

A single intraperitoneal injection of Estragole (300 mg/kg) to female ICR mice 19 hours prior to Dexamethasone induction decreased induced activities of tyrosine aminotransferase (TAT) and tryptophan oxygenase (TO) nearly to 50% of the control values. In these mice, activities of the marker enzymes of liver damage: alanine aminotransferase (ALAT) and aspartate aminotransferase (AAT) increased in the blood 1.7-2.3-fold as compared with the untreated controls. By contrast, carbon tetrachloride (100 mg/kg) increased the blood AIAT and AsAT activities 135- and 30-fold as compared with the control, but inhibited the TAT and TO induction much less than Estragole did. Estragole seems to inhibit the glucocorticoid induction of these hepatic enzymes not via the unspecific toxic damage of the liver.

Alanine Transaminase↗

PubMed2005

[Age- and sex-related differences in sensitivity to hepatotoxic action of estragole in mice].

As determined by blood activity of alanine- and aspartate aminotransferases, intraperitoneal injection of estragole in subcarcinogenic dose 300 mg/kg does not damage the liver of suckling off-spring of both sexes and of adult SWR/J males but drastically damages it in mature females of this strain. Castration only slightly decreases the resistance of males to hepatotoxic action of estragole but significantly increases it in females; exogenous administration of estradiole benzoate to castrated males decreases their resistance to the hepatotoxin, whereas administration of testosterone propionate to ovariectomyzed females does not elevate it. Morphologically, estragole damages the same number of liver cells in females and males, but in males it induces mostly hydropic degenerative, and in females--necrotic changes of hepatocytes.

Age Factors↗

PubMed2006

Estragole (4-allylanisole) is the primary compound in volatiles emitted from the male and female cones of Cycas revoluta.

The genus Cycas (Cycadaceae; gymnosperm) have circumstantially been considered to be wind-pollinated. The cones of Cycas revoluta Thunb., however, emit a strong unpleasant odor. The chemical profiles of floral scents often correlate with various pollination modes (pollinators). We collected and analyzed the volatiles emitted from male and female cones of C. revoluta native to Iriomote and Yonaguni Islands, Japan. The analyses indicated that estragole (4-allylanisole) dominated in the volatiles (67.0-92.7%), with small amounts of other benzenoids, e.g., anethole, methyl salicylate, methyl eugenol, and ethyl benzoate. Several fatty acid esters were also detected in the samples from Iriomote Island. The function of estragole in the reproductive biology of C. revoluta is discussed.

Allylbenzene Derivatives↗