Paspalum staggers: isolation and identification of tremorgenic metabolites from sclerotia of Claviceps paspali

Cole, Richard; Dorner, Joe W.; Lansden, John A.; Cox, Richard H.; Pape, Countney; Cunfer, B. M.; Nicholson, Stephen S.; Bedell, David M.

doi:10.1021/jf60213a061

Cited by 111 publications

(63 citation statements)

References 5 publications

(5 reference statements)

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“…It contains an indole and a diketopyperazine moiety, and the whole structure has much in common with verruculogen, a similar mycotoxin described by Cole et al (3,4). Several indolic mycotoxins have been reported to have violent motor effects in mammals (5)(6)(7)(8), and it has been pointed out that these mycotoxins might be responsible for naturally occurring neurological disorders in domestic animals (9). As a common mode of action of these toxins, increase in neuro transmitter release in the central nervous system has been reported (10, 11).…”

Section: Fumitremorginmentioning

confidence: 93%

Pharmacological Effects of the Tremorgenic Mycotoxin Fumitremorgin A

Nishiyama

Kuga

1986

Japanese Journal of Pharmacology

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Section: Fumitremorginmentioning

confidence: 93%

Pharmacological Effects of the Tremorgenic Mycotoxin Fumitremorgin A

Nishiyama

Kuga

1986

Japanese Journal of Pharmacology

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“…1A). 66 The main indole-diterpenoid tremorgens in C. paspali are paspalinine and paspalitrems A-C. 17 This mycotoxicosis occurs in southern Brazil, 66 Uruguay, 56 Argentina, 36 the United States, 17 Australia, 39 New Zealand, 80 Europe, 5,44 and South Africa. 9,81 Several species of Paspalum can be infected by C. paspali, including Paspalum dilatatum Poiret, Paspalum notatum Flügge, Paspalum distichum L. (syn.…”

Section: Poisoning By Indole-diterpenoid Mycotoxinsmentioning

confidence: 99%

Mycotoxicoses of ruminants and horses

et al. 2013

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Abstract. In the current study, mycotoxicoses of ruminants and horses are reviewed, with an emphasis on the occurrence of these diseases in South America. The main mycotoxicoses observed in grazing cattle include intoxications by indole-diterpenoid mycotoxins (Paspalum spp. contaminated by Claviceps paspali, Lolium perenne infected by Neotyphodium lolii, Cynodon dactylon infected by Claviceps cynodontis, and Poa huecu), gangrenous ergotism and dysthermic syndrome (hyperthermia) caused by Festuca arundinacea (syn. Festuca elatior) infected by Neotyphodium coenophialum (syn. Acremonium coenophialum), and photosensitization in pastures contaminated by toxigenic Pithomyces chartarum. Other mycotoxicoses in grazing cattle include slaframine toxicity in clover pastures infected by Rhizoctonia leguminicola and diplodiosis in cattle grazing in corn stubbles. The mycotoxicoses caused by contaminated concentrated food or byproducts in cattle include poisoning by toxins of Aspergillus clavatus, which contaminate barley or sugar beetroot by-products, gangrenous ergotism or dysthermic syndrome caused by wheat bran or wheat screenings contaminated with Claviceps purpurea, and acute respiratory distress caused by damaged sweet potatoes (Ipomoea batatas). The main mycotoxicosis of horses is leukoencephalomalacia caused by the fumonisins B1 and B2 produced by Fusarium spp. Poisoning by C. purpurea and F. elatior infected by N. coenophialum has also been reported as a cause of agalactia and neonatal mortality in mares. Slaframine toxicosis caused by the ingestion of alfalfa hay contaminated by R. leguminicola has also been reported in horses.

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“…1). Lolitrems are members of a large, structurally diverse group of secondary metabolites known as indole-diterpenes that includes paspaline (Cole et al 1977) and paxilline (Springer et al 1975). These metabolites have a common structural core comprised of a cyclic diterpene skeleton derived from geranylgeranyl diphosphate (GGPP) and an indole moiety derived from anthranilic acid.…”

Section: Introductionmentioning

confidence: 99%

Molecular cloning and genetic analysis of a symbiosis-expressed gene cluster for lolitrem biosynthesis from a mutualistic endophyte of perennial ryegrass

et al. 2005

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Lolitrems are potent tremorgenic mycotoxins that are synthesised by clavicipitaceous fungal endophytes of the Epichloë/Neotyphodium group in association with grasses. These indole-diterpenes confer major ecological benefits on the grass-endophyte symbiotum. A molecular signature for diterpene biosynthesis is the presence of two geranylgeranyl diphosphate (GGPP) synthases. Using degenerate primers for conserved domains of fungal GGPP synthases, we cloned two such genes, ltmG and ggsA, from Neotyphodium lolii. Adjacent to ltmG are two genes, ltmM and ltmK, that are predicted to encode an FAD-dependent monooxygenase and a cytochrome P450 monooxygenase, respectively. The cluster of ltm genes is flanked by AT-rich retrotransposon DNA that appears to have undergone extensive repeat induced point (RIP) mutation. Epichloë festucae, the sexual ancestor of N. lolii, contains an identical ltm gene cluster, but lacks the retrotransposon "platform'' on the right flank. Associations established between perennial ryegrass and an E. festucae mutant deleted for ltmM lack detectable levels of lolitrems. A wild-type copy of ltmM complemented this phenotype, as did paxM from Penicillium paxilli. Northern hybridization and RT-PCR analysis showed that all three genes are weakly expressed in culture but strongly induced in planta. The relative endophyte biomass in these associations was estimated by real-time PCR to be between 0.3 and 1.9%. Taking this difference into account, the steady-state levels of the ltm transcripts are about 100-fold greater than the levels of the endogenous ryegrass beta-tubulin (beta -Tub1) and actin (Act1) RNAs. Based on these results we propose that ltmG, ltmM and ltmK are members of a set of genes required for lolitrem biosynthesis in E. festucae and N. lolii.

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Paspalum staggers: isolation and identification of tremorgenic metabolites from sclerotia of Claviceps paspali

Cited by 111 publications

References 5 publications

Pharmacological Effects of the Tremorgenic Mycotoxin Fumitremorgin A

Pharmacological Effects of the Tremorgenic Mycotoxin Fumitremorgin A

Mycotoxicoses of ruminants and horses

Molecular cloning and genetic analysis of a symbiosis-expressed gene cluster for lolitrem biosynthesis from a mutualistic endophyte of perennial ryegrass

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