Total synthesis of sporidesmin A

Kishi, Yoshito; Nakatsuka, Shin‐ichi; Fukuyama, Tohru; Havel, M.

doi:10.1021/ja00800a079

Cited by 103 publications

(21 citation statements)

References 2 publications

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“…Sporidesmin a can be converted chemically via reduction and methylation to the non-toxic sporidesmin d. Sporidesmins a, E and G appear to slowly interconvert during storage in solution , presumably by exchanging sulphur atoms. Kishi et al (1973) published a total synthesis.…”

Section: The Toxinmentioning

confidence: 99%

A history of facial eczema (pithomycotoxicosis) research

Menna

Smith²,

Miles

2009

New Zealand Journal of Agricultural Research

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Facial eczema (pithomycotoxicosis), a photosensitisation of ruminants grazing pasture, has been known in New Zealand for over 100 years, but its cause, a toxin produced by a largely saprophytic fungus, Pithomyces chartarum, growing on litter at the base of pasture and sporing profusely under warm moist conditions in late summer and autumn, was found only 50 years ago. As the fungus spores it produces the toxin sporidesmin which, when eaten by sheep, cattle, goats or deer, causes liver injury with inflammation and blockage of bile ducts. Phylloerythrin, a photodynamic breakdown product of chlorophyll, is no longer excreted but circulates in the blood, causing lesions of unpigmented skin when the affected animal is exposed to sunlight. Lesions do not appear until at least a week after sporidesmin has been ingested, and this lag period delayed discovery of the causative agent, first thought to have been an abnormal metabolite of rapidly growing ryegrass. However, before the role of P. chartarum was discovered, the pathology of the disease had been described, toxic extracts had been made from herbage mown from pastures A08061; Online publication date 21 October 2009 Received 8 October 2008 accepted 4 September 2009 associated with facial eczema outbreaks, and the weather conditions preceding outbreaks had been defined. When the causative agent was identified, cultures of P. chartarum on artificial media produced sporidesmin for chemical characterisation and animal dosing trials. Control of facial eczema in the field was first by avoiding toxic pasture, detected by P. chartarum spore counts on herbage, later by reducing P. chartarum pasture populations by spray application of substituted thiabendazole fungicides, and later still by protecting animals with oral doses of zinc at close to toxic levels. Sheep vary widely in their sensitivity to sporidesmin, either under field conditions in facial eczema outbreaks or when dosed orally with sporidesmin, and breeding resistant animals by selection after sporidesmin challenge is the best long-term control method at present. Whilst facial eczema outbreaks have been most severe in New Zealand, the disease has been reported from an increasing number of countries with warm temperate climates in which ruminants are intensively grazed on pasture. The great majority of New Zealand isolates of P. chartarum produce sporidesmin, but varying proportions of those in other countries do not.

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Section: The Toxinmentioning

confidence: 99%

A history of facial eczema (pithomycotoxicosis) research

Menna

Smith²,

Miles

2009

New Zealand Journal of Agricultural Research

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“…1 H NMR spectra were recorded on Varian VXR (300 MHz) SCHEME 6 spectrometer as solutions in DMSO-d 6 with TMS as a internal standard. IR spectra were recorded on Specord M80 in tablets KBr.…”

Section: Methodsmentioning

confidence: 99%

“…Disulfides are used as antiradiation preparations, nootropic psychostimulators, and as drugs for the treatment of the alcoholism. The compounds that have high biological activity (for exam- ple, gliotoxin and sporidesmin), which have antifungal, antibacterial, and antivirus activities, are represented among disulfides [1]. Some disulfides are widely used as accelerators of the rubbers' vulcanization [2].…”

Section: Introductionmentioning

confidence: 99%

Sulfur-containing derivatives of 1,4-naphthoquinone, part 1: Disulfide synthesis

et al. 2005

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“…A potentially biomimetic Pictet-Spengler reaction of tryptophan derivative 42 with thioaldehyde 41 as a masked isoprene equivalent gave the desired cis-tetrahydrocarboline (43) with marginal selectivity (Scheme 4.8). N-Bromosuccinimide (NBS)-mediated oxidative rearrangement proceeded via intermediate 44 to the oxindole was followed by deprotection of the carbamate to give amine 45.…”

Section: Nphthmentioning

confidence: 99%