The FEMA GRAS Assessment of trans-Anethole Used as a Flavouring Substance

Newberne, Paul M.; Smith, Robert L.; Doull, John; Goodman, Jay I.; Munro, I.C.; Portoghese, Philip S.; Wagner, Bernard M.; Weil, Carrol S.; Woods, L. A.; Adams, Timothy B.; Lucas, C.D; Ford, R.A.

doi:10.1016/s0278-6915(99)00037-x

Cited by 117 publications

(58 citation statements)

References 44 publications

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“…trans-Anethole (p-methoxy propenylbenzene), the major component present in the essential oils of anise, fennel, and star anise, is also a type of phenylpropanoid compound formed by terpene synthesis in plants (10). trans-Anethole is used commercially as a flavor substance in baked goods, candy, ice cream, chewing gum, and alcoholic beverages (21).…”

mentioning

confidence: 99%

Isolation of a Gene Responsible for the Oxidation of trans -Anethole to para -Anisaldehyde by Pseudomonas putida JYR-1 and Its Expression in Escherichia coli

Han

Ryu

Kanaly

et al. 2012

Appl Environ Microbiol

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A plasmid, pTA163, in Escherichia coli contained an approximately 34-kb gene fragment from Pseudomonas putida JYR-1 that included the genes responsible for the metabolism of trans-anethole to protocatechuic acid. Three Tn5-disrupted open reading frame 10 (ORF 10) mutants of plasmid pTA163 lost their abilities to catalyze trans-anethole. Heterologously expressed ORF 10 (1,047 nucleotides [nt]) under a T7 promoter in E. coli catalyzed oxidative cleavage of a propenyl group of trans-anethole to an aldehyde group, resulting in the production of para-anisaldehyde, and this gene was designated tao (trans-anethole oxygenase). The deduced amino acid sequence of TAO had the highest identity (34%) to a hypothetical protein of Agrobacterium vitis S4 and likely contained a flavin-binding site. Preferred incorporation of an oxygen molecule from water into p-anisaldehyde using 18 Olabeling experiments indicated stereo preference of TAO for hydrolysis of the epoxide group. Interestingly, unlike the narrow substrate range of isoeugenol monooxygenase from Pseudomonas putida IE27 and Pseudomonas nitroreducens Jin1, TAO from P. putida JYR-1 catalyzed isoeugenol, O-methyl isoeugenol, and isosafrole, all of which contain the 2-propenyl functional group on the aromatic ring structure. Addition of NAD(P)H to the ultrafiltered cell extracts of E. coli (pTA163) increased the activity of TAO. Due to the relaxed substrate range of TAO, it may be utilized for the production of various fragrance compounds from plant phenylpropanoids in the future. Bacterial metabolism as a means of producing value-added compounds from natural resources has been given much attention as an alternative method to replace conventional chemical syntheses (21,27). If natural resources can be continuously supplied as the starting materials, biotransformation employing bacterial systems may become practical from the points of view of sustainability and applicability. One of the major groups of natural compounds targeted for the production of value-added compounds includes the group of chemicals that occur in plant phenylpropanoid pathways, which are involved in the production of lignin, flavonoids, anthocyanins, etc. (5, 16-19). For example, isoeugenol, eugenol, and ferulic acid produced by the phenylpropanoid pathway have often been attempted as the starting materials to produce vanillin, one of the most extensively used aromatic flavor compounds (25-27, 32).trans-Anethole (p-methoxy propenylbenzene), the major component present in the essential oils of anise, fennel, and star anise, is also a type of phenylpropanoid compound formed by terpene synthesis in plants (10). trans-Anethole is used commercially as a flavor substance in baked goods, candy, ice cream, chewing gum, and alcoholic beverages (21). However, there have been few research reports regarding its metabolism (8,12,21,22,31). Indeed, to date, the only two bacterial strains isolated that are known to use trans-anethole as a sole carbon source are Arthrobacter sp. strain TA13 and Pseudomonas putida JYR-1 ...

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confidence: 99%

Isolation of a Gene Responsible for the Oxidation of trans -Anethole to para -Anisaldehyde by Pseudomonas putida JYR-1 and Its Expression in Escherichia coli

Han

Ryu

Kanaly

et al. 2012

Appl Environ Microbiol

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“…there is a shift towards oxygenated metabolites . Especially in female rats, the hepatotoxic metabolite anetholepoxide is predominantly produced at higher concentrations (Newberne et al, 1999). In humans, already after administration of 1 mg trans-anethole the oxidative metabolism is predominant, with the 4-methoxyhippuric acid as the main metabolite.…”

Section: Absorption Distribution Metabolism Excretionmentioning

confidence: 99%

“…However, the intake of trans-anethole as a flavouring substance was stated to be very low (estimated 54 µg/kg b.w./day), and at this level it is efficiently detoxicated in humans. For this reason the Expert Panel concludes that the neoplastic effects in female rats associated with dose dependent hepatotoxicity are not indicators of any significant risk to human health from the use of trans-anethole as a flavouring substance, and the compound was reaffirmed as GRAS (generally regarded as safe) (Newberne et al, 1999). However, clinical safety data do not exist.…”

Section: Efficacymentioning

confidence: 99%

Study on the assessment of plants/herbs, plant/herb extracts and their naturally or synthetically produced components as ‘additives’ for use in animal production

Vienna

Graz

Hohenheim

et al. 2007

EFS3

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A As ss se es ss sm me en nt t o of f p pl la an nt ts s/ /h he er rb bs s a an nd d e ex xt tr ra ac ct ts s I In nt tr ro od du uc ct ti io on n 5 5 M Mo on no og gr ra ap ph hs s o of f t th he e f fo ol ll lo ow wi in ng g s sp pe ec ci ie es s: : FOREWORDIn September 2003 the European Parliament and the Council of the European Union adopted the Regulation No. 1831/2003 on additives for use in animal nutrition. The purpose of this regulation is to establish a Community procedure for authorising the placing on the market and use of feed additives and to lay down rules for the supervision and labelling of feed additives and premixtures in order to provide the basis for the assurance of a high level of protection of human health, animal health and welfare, environment, and "users and consumers" interests in relation to feed additives, whilst ensuring the effective functioning of the internal market. Under the current regulation detailed guidelines for some family of products are completely missing, that it is the case of the plants/herbs, plant/herb extracts and their naturally or synthetically produced components. For this reason it is one of the priorities of the FEEDAP Panel to implement guidelines/guidance for these types of compounds.It has been observed that plant/herbs and their extracts are increasingly being used (and informally marketed) not only as sensory additives, but also for other purposes not covered by the legislation, notably better growth or feed conversion, improved meat quality, and for prophylactic purposes. There are strong indications that such use will further increase as replacement additives for the antibiotic growth promoters whose use will be prohibited by the end of 2005.Nowadays, a compiled list of these compounds or extracts does not exists although the European Federation of Animal Feed Additive Manufacturers (FEFANA) notes that some 280 plant extracts and a further 1700 chemically defined compounds have been used within Member States as sensory additives in animal feeds.The results of this study will be used by EFSA, in consultation with the European Commission, Member States and other stakeholders, to provide input for the development of guidance/guidelines documents for the authorisation of plants/herbs, plant/herb extracts and their naturally or synthetically produced components for use in animal nutrition. ASSESSMENT OF PLANTS/HERBS, PLANT/HERB EXTRACTS AND THEIR NATURALLY OR SYNTHETICALLY PRODUCED COMPONENTS AS "ADDITIVES" FOR USE INTRODUCTIONThe last two decades have seen a substantial increase in use of herbs/botanicals and their products not only as herbal medicinal products and for food supplements, but also in the field of animal nutrition. The use of herbal feed additives, which include essential oils and (exotic) herbal mixtures, is extensively promoted by the producers, but the scientific background underpinning their use often is limited. Consequently an adequate knowledge of quality control (content of active substance(s) stability), efficacy and safety is oft...

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“…[7] Likewise naturally occurring alkanylbenzenes trans anethole (1-methoxy-4 propenylbenzene) and eugenol (4-allyl-1-hydroxy-2 methoxy benzene) are two common food flavouring agents acknowledged for preventative effects. [8] Eugenol is the chief component of clove oil. It is also present in other spices such as cinnamon, basil and nutmeg.…”

Section: Introductionmentioning

confidence: 99%

“…[11] Anethole is volatile constituent of more than 20 spices. [8] It is a major component of sweet and bitter fennel and anise. Trans anethole is used in chewing gums, baked goods, candy and ice-creams.…”

Section: Introductionmentioning

confidence: 99%

Ameliorative Effect of Eugenol and Anethole on Arsenic Induced Oxidative Dna Damage in Cultured Human Peripheral Blood Lymphocytes

Bal

Yadav

Verma

et al. 2017

Int. J. Pharm. Sci. Drug Res.

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Arsenic contamination is one of the major health concerns all over the world and associated with various types of cancer and pathological effects. The production of reactive oxygen species (ROS) plays a crucial role in arsenic mediated toxicity. Several studies have shown that population constantly exposed to arsenic have substantial oxidative stress that, in turn, induces DNA damage. In the present work eugenol and anethole were investigated for their protective effect against arsenic mediated oxidative DNA damage in peripheral blood lymphocytes. Comet assay and lipid peroxidation was used as biomarker of genotoxicity and oxidative stress respectively. A dose dependent increase in tail moment and lipid peroxidation was observed when lymphocytes were treated with sodium arsenite. Treatment of arsenic (50µM) along with eugenol (20µM) and anethole (50µM) showed a significant decrease in the tail moment and lipid peroxidation in cultured peripheral blood lymphocytes. The decrease in the tail moment and lipid peroxidation was significantly higher in combined supplementation of eugenol and anethole as compared to individual administration. The results of the present study suggests ameliorative role of eugenol and anethole against arsenic induced genotoxic and oxidative damage in cultured human peripheral blood lymphocytes.

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The FEMA GRAS Assessment of trans-Anethole Used as a Flavouring Substance

Cited by 117 publications

References 44 publications

Isolation of a Gene Responsible for the Oxidation of trans -Anethole to para -Anisaldehyde by Pseudomonas putida JYR-1 and Its Expression in Escherichia coli

Isolation of a Gene Responsible for the Oxidation of trans -Anethole to para -Anisaldehyde by Pseudomonas putida JYR-1 and Its Expression in Escherichia coli

Study on the assessment of plants/herbs, plant/herb extracts and their naturally or synthetically produced components as ‘additives’ for use in animal production

Ameliorative Effect of Eugenol and Anethole on Arsenic Induced Oxidative Dna Damage in Cultured Human Peripheral Blood Lymphocytes

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