Identification and Structure Elucidation of Epoxyjanthitrems from Lolium perenne Infected with the Endophytic Fungus Epichloë festucae var. lolii and Determination of the Tremorgenic and Anti-Insect Activity of Epoxyjanthitrem I

Finch, Sarah C.; Prinsep, Michèle R.; Popay, Alison J.; Wilkins, Alistair L.; Webb, Nicola G.; Bhattarai, Sweta; Jensen, Joanne G.; Hawkes, Allan D.; Babu, Jacob V.; Tapper, B.A.; Lane, Geoffrey A.

doi:10.3390/toxins12080526

Cited by 20 publications

(21 citation statements)

References 43 publications

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“…Four major classes of alkaloids are known to be produced by Epichloë strains. These include lolines (saturated 1-aminopyrrolizidines), indole diterpenes (lolitrems, epoxyjanthitrems), ergot alkaloids (main terminal product is ergovaline), and peramine (a pyrrolopyrazine alkaloid) [ 30 , 66 ]. Naturally occurring strains of Epichloë may produce from none to all four types of these known alkaloids.…”

Section: Epichloë Endophytesmentioning

confidence: 99%

“…Also impacting persistence were root aphid [ 259 ] and pasture mealy bug [ 271 ]. The AR37 endophyte was identified in the early 1990s and was shown to not produce any known problematic alkaloid compounds, but did produce a unique set of epoxyjanthitrem compounds [ 66 , 425 ]. These compounds have been linked to staggers in sheep, but they tend to be less frequent and less severe than those caused by lolitrem B [ 191 , 417 , 426 ].…”

Section: Delivering Epichloë Into Managed Pastomentioning

confidence: 99%

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Epichloë Fungal Endophytes—From a Biological Curiosity in Wild Grasses to an Essential Component of Resilient High Performing Ryegrass and Fescue Pastures

Caradus¹,

Johnson

2020

JoF

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The relationship between Epichloë endophytes found in a wide range of temperate grasses spans the continuum from antagonistic to mutualistic. The diversity of asexual mutualistic types can be characterised by the types of alkaloids they produce in planta. Some of these are responsible for detrimental health and welfare issues of ruminants when consumed, while others protect the host plant from insect pests and pathogens. In many temperate regions they are an essential component of high producing resilient tall fescue and ryegrass swards. This obligate mutualism between fungus and host is a seed-borne technology that has resulted in several commercial products being used with high uptake rates by end-user farmers, particularly in New Zealand and to a lesser extent Australia and USA. However, this has not happened by chance. It has been reliant on multi-disciplinary research teams undertaking excellent science to understand the taxonomic relationships of these endophytes, their life cycle, symbiosis regulation at both the cellular and molecular level, and the impact of secondary metabolites, including an understanding of their mammalian toxicity and bioactivity against insects and pathogens. Additionally, agronomic trials and seed biology studies of these microbes have all contributed to the delivery of robust and efficacious products. The supply chain from science, through seed companies and retailers to the end-user farmer needs to be well resourced providing convincing information on the efficacy and ensuring effective quality control to result in a strong uptake of these Epichloë endophyte technologies in pastoral agriculture.

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Section: Epichloë Endophytesmentioning

confidence: 99%

Section: Delivering Epichloë Into Managed Pastomentioning

confidence: 99%

Epichloë Fungal Endophytes—From a Biological Curiosity in Wild Grasses to an Essential Component of Resilient High Performing Ryegrass and Fescue Pastures

Caradus¹,

Johnson

2020

JoF

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“…The epoxy-janthitrem alkaloids have been very difficult to analyse due to instability issues. This has recently been overcome [ 82 ] but it is still a complex HPLC protocol requiring acetone extraction in the dark to prevent degradation. For full structural elucidation, nuclear magnetic resonance (NMR) assignments for the four epoxyjanthitrem (I–IV) compounds, and a new epoxyjanthitriol were required.…”

Section: Practical Methods For Epichloë -Infectmentioning

confidence: 99%

The Impact of Alkaloid-Producing Epichloë Endophyte on Forage Ryegrass Breeding: A New Zealand Perspective

Eady¹

2021

Toxins

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For 30 years, forage ryegrass breeding has known that the germplasm may contain a maternally inherited symbiotic Epichloë endophyte. These endophytes produce a suite of secondary alkaloid compounds, dependent upon strain. Many produce ergot and other alkaloids, which are associated with both insect deterrence and livestock health issues. The levels of alkaloids and other endophyte characteristics are influenced by strain, host germplasm, and environmental conditions. Some strains in the right host germplasm can confer an advantage over biotic and abiotic stressors, thus acting as a maternally inherited desirable ‘trait’. Through seed production, these mutualistic endophytes do not transmit into 100% of the crop seed and are less vigorous than the grass seed itself. This causes stability and longevity issues for seed production and storage should the ‘trait’ be desired in the germplasm. This makes understanding the precise nature of the relationship vitally important to the plant breeder. These Epichloë endophytes cannot be ‘bred’ in the conventional sense, as they are asexual. Instead, the breeder may modulate endophyte characteristics through selection of host germplasm, a sort of breeding by proxy. This article explores, from a forage seed company perspective, the issues that endophyte characteristics and breeding them by proxy have on ryegrass breeding, and outlines the methods used to assess the ‘trait’, and the application of these through the breeding, production, and deployment processes. Finally, this article investigates opportunities for enhancing the utilisation of alkaloid-producing endophytes within pastures, with a focus on balancing alkaloid levels to further enhance pest deterrence and improving livestock outcomes.

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“…The deterrent effects of these endophytes have primarily been attributed to the alkaloid, peramine, as demonstrated in semi-synthetic diet experiments (Popay et al 1990;Rowan et al 1990;. AR37 produces epoxy-janthitrems (Finch et al 2020(Finch et al , 2010 but not peramine and has no negative effect on ASW adult feeding and egg laying but it strongly reduces larval feeding (Popay and Wyatt 1995).…”

Section: Introductionmentioning

confidence: 99%

Olfactory responses of Argentine stem weevil to herbivory and endophyte-colonisation in perennial ryegrass

et al. 2021

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Argentine stem weevil adults (ASW, Listronotus bonariensis) feed on the leaves of agricultural grasses and their larvae mine the pseudostem, causing extensive damage that can result in plant death. Plants emit volatiles that serve as signals to host-searching insects and these odours can be altered by both herbivory and fungal endophyte-infection. This study investigated whether ASW adults utilise olfaction to identify their host plants, perennial ryegrass (Lolium perenne), and if conspecific herbivory or the presence of Epichloë festucae var. lolii fungal endophytes (strain wild-type or AR1) influenced such responses. Results from olfactometer bioassays established that ASW adults were able to utilise their olfactory response to orient towards volatiles released by perennial ryegrass and further, the weevils displayed a preference for plants previously damaged by conspecific weevils. However, there was no evidence that weevils had the ability to distinguish between endophyte-infected and endophyte-free plants using olfaction alone. Using a push–pull extraction technique, thirteen volatile compounds were identified in the blend released by perennial ryegrass. Endophyte and herbivory were found to alter these volatile compounds and quantities emitted by this forage grass. This study suggests that despite observing differences in the plant volatile blend, ASW do not perceive endophyte (wild-type and AR1) using olfaction alone and must rely on other cues, e.g. contact chemoreception or post-ingestional malaise, to detect the presence of a bioactive endophyte in an otherwise acceptable host plant.

show abstract

Identification and Structure Elucidation of Epoxyjanthitrems from Lolium perenne Infected with the Endophytic Fungus Epichloë festucae var. lolii and Determination of the Tremorgenic and Anti-Insect Activity of Epoxyjanthitrem I

Cited by 20 publications

References 43 publications

Epichloë Fungal Endophytes—From a Biological Curiosity in Wild Grasses to an Essential Component of Resilient High Performing Ryegrass and Fescue Pastures

Epichloë Fungal Endophytes—From a Biological Curiosity in Wild Grasses to an Essential Component of Resilient High Performing Ryegrass and Fescue Pastures

The Impact of Alkaloid-Producing Epichloë Endophyte on Forage Ryegrass Breeding: A New Zealand Perspective

Olfactory responses of Argentine stem weevil to herbivory and endophyte-colonisation in perennial ryegrass

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