Isolation of Toxic Metabolites of Phomopsis leptostromiformis Responsible for Lupinosis

Culvenor, C. C. J.; Beck, A.; Clarke, M; Cockrum, Peter A.; Edgar, J. A.; Frahn, J.L.; Jago, Marjorie V.; Lanigan, GW; Payne, A. L.; Peterson, James E.; Petterson, D. S.; Smith, L. W.; White, R

doi:10.1071/bi9770269

Cited by 65 publications

(24 citation statements)

References 9 publications

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“…Usually a gradient elution is obtained using methanol and o-phosphoric acid solution as eluents (Reinhard et al, 2006). UV detection was performed at 210 nm and 290 nm, since phomopsins exhibit typical UV absorption maxima in this range when methanol is used as a solvent medium (Culvenor et al, 1977, Reinhard et al 2006. Electrochemical detection was also proposed as an alternative to UV detection, by using an amperometric analytical cell operating in DC mode (cell potential 600 mV, gain range 100 nA) (Reinhard et al, 2006).…”

Section: Methodsmentioning

confidence: 99%

“…Phomopsins are a family of macrocyclic hexapeptide mycotoxins produced by the fungus Phomopsis leptostromiformis (Culvenor et al, 1977;Allen and Hancock, 1989). phomopsin, phomopsin C, has been partially identified but a full structure is not yet available (Edgar, 1991).…”

Section: Physico-chemical Characteristicsmentioning

confidence: 99%

“…This organism has been reported to cause stem blight in young lupins (Lupin luteus L.) (Ostazeki and Wells, 1960) and to produce phomopsins (Culvenor et al, 1977). These mycotoxins, a number of compounds capable of binding to tubulin (Tonsing et al, 1984), cause the animal liver disease known as lupinosis (Van Warmelo et al, 1970;Gardiner, 1975;.…”

Section: Introductionmentioning

confidence: 99%

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Scientific information on mycotoxins and natural plant toxicants

Battilani

Costa

Dossena

et al. 2009

EFSA Supporting Publications

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Section: Methodsmentioning

confidence: 99%

Section: Physico-chemical Characteristicsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Scientific information on mycotoxins and natural plant toxicants

Battilani

Costa

Dossena

et al. 2009

EFSA Supporting Publications

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“…leptostromiformis (Shivas et al 1991). Mycotoxins produced in lupin plants colonized by Diaporthe toxica (Culvenor et al 1977) may cause lupinosis in sheep and other grazing animals (Allen 1987;Van Warmelo et al 1970). Resistance to phomopsis stem blight reduces stem symptoms and stubble toxicity in narrow-leafed lupins (Lupinus angustifolius L.) (Cowling et al 1988).…”

mentioning

confidence: 99%

Histological observations of latent infection and tissue colonization by Diaporthe toxica in resistant and susceptible narrow-leafed lupins

Shankar¹,

Cowling²,

Sweetingham³

1998

Can. J. Bot.

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Latent infection and tissue colonization by Diaporthe toxica was examined by light, scanning, and transmission electron microscopy in stems, leaves, and petioles of resistant and susceptible narrow-leafed lupins (Lupinus angustifolius). Resistance was observed during the latent phase of the disease as an incompatible reaction between the host and pathogen that appeared to occur after penetration of the cuticle. Conidia were attached firmly to the cuticle by an extracellular substance presumably exuded from the conidia. Conidia penetrated the cuticle directly via an infection peg and formed subcuticular coralloid hyphae. The frequency of subcuticular coralloid hyphae was similar on stems, leaves, and petioles of each line. At 14 days after inoculation, resistant plants had a high frequency of small coralloid hyphae (10-80 µm length). The epidermal cells beneath these small coralloid hyphae appeared necrotic and collapsed with accumulation of polyphenolics and electron-dense substances and a loss of internal organisation in the cytoplasm. Necrosis was occasionally observed in small coralloid hyphae as well. Susceptible plants had a high frequency of large coralloid hyphae (80-400 µm length) in which intrahyphal hyphae were observed, and host epidermal cells beneath large coralloid hyphae appeared normal. Colonization of tissues below the cuticle began immediately after excision of stems from susceptible plants, but was delayed in resistant plants. At 8 days after excision, hyphae had invaded all stem tissues and initiated the formation of pycnidia in susceptible plants, but few hyphae were observed in stems of resistant plants.Résumé : À l'aide de la microscopie photonique et électronique par balayage et par transmission, les auteurs ont examiné l'infection latente et la colonisation des tissus par le Diaporthe toxica au niveau des tiges, des feuilles et des pétioles de lupins à feuilles étroites (Lupinus angustifolius) susceptibles et résistants. La résistance se manifeste au cours de la période latente de la maladie sous forme d'une réaction d'incompatibilité entre l'hôte et le pathogène, laquelle semble survenir après la pénétration de la cuticule. Les conidies sont fermement attachées à la cuticule par une substance extracellulaire présumément exsudée par la conidie. Les conidies pénètrent la cuticule directement par une cheville d'infection et forment des hyphes coralloïdes sous la cuticule. La fréquence des hyphes sous-cuticulaires est semblable sur les tiges, les feuilles et les pétioles de chaque lignée. Quatorze jours après l'inoculation, les plantes résistantes montrent une grande fréquence de petits hyphes coralloïdes (10-80 µm de longueur). Les cellules épidermiques sous ces petits hyphes coralloïdes apparaissent nécrosées et affaissées avec accumulation de substances polyphénoliques denses aux électrons et désorganisation du cytoplasme. On observe également une nécrose occasionnelle des petits hyphes coralloïdes. Les plantes susceptibles montrent une plus grande fréquence de gros hyphes coralloïdes (80...

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“…Various genera of Diaporthe/Phomopsis are pathogenic fungi in economically important crops worldwide with lupin representing the main host for D. toxica (EFSA, 2012). Phomopsin A (PHO-A), the most investigated PHO, has been shown to be a potent microtubule inhibitor (Tönsing, Steyn, Osborn, & Weber, 1984), which is considered as the cause of its acute liver toxicity in sheep, mice and rats (Battilani et al, 2011;Culvenor et al, 1977;Lacey, Edgar, & Culvenor, 1987;Peterson & Lanigan, 1976). PHO-A is a hexapeptide (Culvenor et al, 1977) containing a 13-membered ring and a lateral chain of three dehydroamino acids.…”

Section: Introductionmentioning

confidence: 99%