Microsomal metabolism of the terpene 1,8-cineole in the common brushtail possum (<i>Trichosurus vulpecula</i>), koala (<i>Phascolarctos cinereus</i>), rat and human

Pass, Georgia J.; McLean, Stuart; Stupans, Ieva; Davies, Noel W.

doi:10.1080/00498250110043535

Cited by 63 publications

(56 citation statements)

References 37 publications

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“…The absolute costs of any one of the physiological avoidance or elimination strategies are likely to be small , but are hypothesised to vary with the nutrient intake, becoming excessive when nutrient intakes are below maintenance levels (Illius & Jessop, 1995). The fact that the cytochrome P450 system and the salivary tannin-binding proteins are inducible on exposure to the PSM stimulus (Mehansho et al 1983;Pass et al 2001) suggests that these systems are efficient, in that their maintenance carries at least some costs that are not borne unless they are necessary, i.e. when the diet contains PSM (Table 1).…”

Section: Diet Choicementioning

confidence: 99%

“…The salivary tannin-binding proteins tend to be present in browsing herbivores, but not in grazing herbivores (Austin et al 1989;Mole et al 1990). Specialist folivorous marsupials have greater liver microsomal metabolism of leaf monoterpenes (Pass et al 2001(Pass et al , 2002 and dietary specialist woodrats maintain lower plasma circulating levels of a-pinene than generalist woodrats (Sorensen & Dearing, 2003).…”

Section: Comparative Studies Of Plant Secondary Metabolite-mammal Intmentioning

confidence: 99%

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The role of plant secondary metabolites in mammalian herbivory: ecological perspectives

Iason¹

2005

Proc. Nutr. Soc.

126

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Plant secondary metabolites (PSM) have many ecological functions, but have long been considered as defences against pathogens or herbivores (vertebrate or invertebrate), reducing the likelihood and extent of attack. However, mammalian herbivores ingest many foods containing PSM and use both behavioural methods and physiological strategies to limit their negative effects. Most physiological counter-adaptations are inducible in response to ingested PSM, providing efficient protection against toxic effects. Possible positive effects of PSM include antioxidant and anthelminthic properties and complex formation between protein and condensed tannins that protects dietary protein from degradation by the symbiotic microflora of foregut fermenters, increasing its utilisation by the animal. This protein effect is probably only beneficial to animals under a narrow range of nutrient-rich conditions found mainly in agricultural systems. There are many examples of PSM causing food avoidance or reducing food intake, but there is as yet relatively little evidence for positive selection of them by herbivores. Although the feedback mechanisms relating the post-ingestive consequences of PSM to subsequent foraging behaviour are beginning to be understood, knowledge of the integration of behavioural and physiological strategies for regulating the effects of PSM is relatively poor. The opportunities for learned avoidance of PSM may be restricted in animals with complex diets that cannot associate a particular feedback signal with a given food type. A greater emphasis on the study of subclinical effects of PSM rather than acute effects, on pharmaco-kinetic studies in relation to behavioural studies and on the use of realistic experimental models is advocated. Plant secondary metabolites: Toxic effects: Counter-adaptation: Foraging behaviourThe evolution and ecology of plant secondary metabolites Plant secondary metabolites (PSM) have no known function in the primary metabolism of plants. They were formerly considered to be a means of depositing excess C fixed by photosynthesis, but the early suggestion that they mediate a range of specific ecological interactions between species (Fraenkel, 1959) sparked a wealth of subsequent research on these roles (see Rosenthal & Berenbaum, 1991; Appel, 1993). Given the enormous diversity of PSM and the way in which their structure determines their function, it is unsurprising that these specific effects can also combine to affect broader aspects of ecosystem function. Often the same chemical characteristics of PSM can influence and integrate different aspects of ecosystem function, such as the determination of plant-litter quality via plant-herbivore interactions and the degradation characteristics of that litter (McInnes et al. 1992;. There are clearly numerous reasons why the range of PSM as a whole could have evolved, but they are unlikely Abbreviation: PSM, plant secondary metabolites.

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Section: Diet Choicementioning

confidence: 99%

Section: Comparative Studies Of Plant Secondary Metabolite-mammal Intmentioning

confidence: 99%

The role of plant secondary metabolites in mammalian herbivory: ecological perspectives

Iason¹

2005

Proc. Nutr. Soc.

126

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“…2-Hydroxy-1,8-cineole was the major metabolite from pooled human liver microsomes, while 9-hydroxy-1,8-cineole was the minor metabolite. The authors concluded that in rats and humans, oxidation was preferred at the aliphatic ring carbons over methyl substituents (Pass et al, 2001). EFSA Journal 2011; 9(10):2398…”

Section: Iii3 Metabolismmentioning

confidence: 99%

Scientific Opinion on Flavouring Group Evaluation 23, Revision 3 (FGE.23Rev3): Aliphatic, alicyclic and aromatic ethers including anisole derivatives from chemical groups 15, 16, 22, 26 and 30

Flavourings¹

2011

EFSA Journal

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The Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids of the European Food Safety Authority was requested to evaluate 20 flavouring substances in the Flavouring Group Evaluation 23, Revision 3, using the Procedure in Commission Regulation (EC) No 1565/2000. None of the substances were considered to have genotoxic potential. The substances were evaluated through a stepwise approach (the Procedure) that integrates information on structure‐activity relationships, intake from current uses, toxicological threshold of concern, and available data on metabolism and toxicity. The Panel concluded that all 20 substances [FL‐no: 02.247, 02.248, 03.008, 03.011, 03.012, 03.015, 03.016, 03.020, 03.022, 03.024, 04.059, 04.067, 04.068, 04.069, 04.075, 04.079, 04.084, 08.127, 09.687 and 13.200] do not give rise to safety concerns at their levels of dietary intake, estimated on the basis of the MSDI approach. Besides the safety assessment of these flavouring substances, the specifications for the materials of commerce have also been considered. Specifications including complete purity criteria and identity for the materials of commerce have been provided for all 20 candidate substances.

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“…2-Hydroxy-1,8-cineole was the major metabolite from pooled human liver microsomes, while 9-hydroxy-1,8-cineole was the minor metabolite. The authors concluded that in rats and humans oxidation was preferred at the aliphatic ring carbons over methyl substituents (Pass et al, 2001). …”

Section: Iii22 Subgroup 2: Alicyclic Ethersmentioning

confidence: 99%

Opinion of the Scientific Panel on food additives, flavourings, processing aids and materials in contact with food (AFC) related to Flavouring Group Evaluation 23 (FGE.23): Aliphatic, alicyclic and aromatic ethers including anisole derivatives From chemical groups 15, 16 and 26 (Commission Regulation (EC) No 1565/2000 of 18 July 2000

Flavourings¹

2007

EFS2

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The present Flavouring Group Evaluation deals with 14 aliphatic, alicyclic and aromatic ethers including anisole derivatives belonging to EU chemical groups 15, 16 and 26. Two of the flavouring substances are aliphatic ethers, one is an alicyclic ether, one is an alicyclic hydrocarbon with an ether side chain, two are ethers containing a benzene moiety, seven are phenol ethers and one is a naphthol ether.One of the 14 flavouring substances possesses one chiral centre and one possesses three chiral centres. In both cases, the substances have been presented without any indication that the commercial flavouring substance has dominance of one or the other enantiomer.Two of the flavouring substances are classified into structural class I, six are classified into structural class II, and six are classified into structural class III.Ten of the flavouring substances in the present group have been reported to occur naturally in a wide range of food items.In its evaluation, the Scientific Panel as a default used the Maximised Survey-derived Daily Intakes (MSDIs) approach to estimate the per capita intakes of the flavouring substances in Europe. However, when the Scientific Panel examined the information provided by the European flavouring industry on the use levels in various foods, it appeared obvious that the MSDI approach in a number of cases would grossly underestimate the intake by regular consumers of products flavoured at the use level reported by the industry, especially in those cases where the annual production values were reported to be small. In consequence, the Scientific Panel had reservations about the data on use and use levels provided and the intake estimates obtained by the MSDI approach. In the absence of more precise information that would enable the Scientific Panel to make a more realistic estimate of the intakes of the flavouring substances, the Scientific Panel has decided also to perform an estimate of the daily intakes per person using a modified Theoretical Added Maximum Daily Intake (mTAMDI) approach based on the normal use levels reported by industry. In those cases where the mTAMDI approach indicated that the intake of a flavouring substance might exceed its corresponding threshold of concern, the Scientific Panel decided not to carry out a formal safety assessment using the Procedure. In these cases the Scientific Panel requires more precise data on use and use levels.According to the default MSDI approach, the 14 flavouring substances in this group have intakes in Europe from 0.012 to 4.1 microgram/capita/day which are below the threshold of concern value for structural class I (1800 microgram/person/day), structural class II (540 microgram/person/day) and structural class III (90 microgram/person/day) substances.On the basis of the data available on genotoxicity it is concluded that there is no indication that the 14 flavouring substances in the present flavouring group possess a genotoxic potential.No metabolism data are available on the flavouring substances in the present group, but ac...

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Microsomal metabolism of the terpene 1,8-cineole in the common brushtail possum (Trichosurus vulpecula), koala (Phascolarctos cinereus), rat and human

Cited by 63 publications

References 37 publications

The role of plant secondary metabolites in mammalian herbivory: ecological perspectives

The role of plant secondary metabolites in mammalian herbivory: ecological perspectives

Scientific Opinion on Flavouring Group Evaluation 23, Revision 3 (FGE.23Rev3): Aliphatic, alicyclic and aromatic ethers including anisole derivatives from chemical groups 15, 16, 22, 26 and 30

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