Disease relevance of Chavicyl methyl ether

• 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 [1].
• 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 [2].
• 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 [3].
• 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 [3].
• Our results also have toxicogenetic significance, as UGT2B7 is polymorphic and could potentially result in genetic differences in glucuronidation of 1'-HE and, hence, toxicity of estragole [4].

Psychiatry related information on Chavicyl methyl ether

• 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 [5].

High impact information on Chavicyl methyl ether

• 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 [6].
• 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 [7].
• The metabolic activation and nucleic acid adducts of naturally-occurring carcinogens: recent results with ethyl carbamate and the spice flavors safrole and estragole [8].
• These results imply that concomitant chronic intake of therapeutic drugs and dietary components that are UGT2B7 and/or UGT1A9 substrates may interfere with estragole metabolism [4].
• The genotoxic potential in vitro and in vivo of the allyl benzene etheric oils estragole, basil oil and trans-anethole [3].

Chemical compound and disease context of Chavicyl methyl ether

• Mutagenicity of trans-anethole, estragole, eugenol, and safrole in the Ames Salmonella typhimurium assay [9].
• Various possibilities leading to deoxygenation of the latter were examined, including reduction of the side-chain double bond to form p-dihydrocoumaryl alcohol, followed by dehydration to afford chavicol, as well as formation of p-methoxycinnamyl alcohol, with further side-chain modification to afford methylchavicol [10].

Biological context of Chavicyl methyl ether

• Feeding experiments of [2-(2)H]- and [4'-(2)H]phenylalanine in Artemisia dracunculus validate the hypothesis that the marked difference in deuterium content at the natural abundance level between the aromatic carbons of estragole (1) is due to an NIH shift during the hydroxylation of the benzene ring [11].
• Effects of estragole on the compound action potential of the rat sciatic nerve [5].
• 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 [5].

Anatomical context of Chavicyl methyl ether

• Effects of essential oil of Croton zehntneri, and of anethole and estragole on skeletal muscles [12].
• 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 [12].
• The side-chain epoxidation and hydroxylation of the hepatocarcinogens safrole and estragole and some related compounds by rat and mouse liver microsomes [13].
• 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 [13].

Associations of Chavicyl methyl ether with other chemical compounds

• AGASTACHE FOENICULUM contains 0.1-0.3% essential oil and the main components are limonene, beta-caryophyllene, methylchavicol, and germacrene B (92% altogether) [14].
• We have demonstrated that allylic epoxides derived from allylbenzene and estragole are capable of forming covalent adducts with all four deoxyribonucleotides in vitro and, in the case of deoxyguanosine, form at least four different adducts [15].
• 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 [16].
• 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 [17].
• Although Boswellia serrata olibanum also exhibits this biomarker, the presence of methylchavicol, methyleugenol and an unidentified oxygenated sesquiterpene distinguishes B. serrata olibanum from the two other species [18].

Gene context of Chavicyl methyl ether

• In addition, antioxidant and 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging activities of tarragon oil were determined, and weak antioxidant and DPPH radical scavenging activities were found in comparison to butylated hydroxytoluene [19].
• In a filter paper diffusion test, estragole at 0.168 mg cm-2 caused 91% mortality to S oryzae adults within 1 day after treatment (DAT), whereas (+)-fenchone and (E)-anethole gave over 90% mortality at 2 and 4 DAT, respectively [20].

Analytical, diagnostic and therapeutic context of Chavicyl methyl ether

• The metabolic disposition of [methoxy-14C]-labelled trans-anethole, estragole and p-propylanisole in human volunteers [17].
• The data show that estragole dose-dependently blocks nerve excitability [5].

References