Structures of Colletotrichin and Colletotrichin B, Phytotoxic Metabolites from<i>Colletotrichum nicotianae</i>

Suzuki, Akira; Gohbara, Masatoshi; Kosuge, Yoshiaki; Tamura, Saburo; Ohashi, Yuji; Sasada, Yoshio

doi:10.1080/00021369.1976.10862438

Cited by 7 publications

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“…The results suggest that all these treatments act at the same site in the respiratory chain and are best interpreted in terms of stimulation of the 'Q cycle' (Mitchell, 1976). These conclusions were supported by the use of a novel inhibitor of the respiratory chain, colletotrichin, a phytotoxic metabolite of the fungus Colletotrichum nicotianae (Suzuki et al, 1976). In contrast with results of other workers (Siess & Wieland, 1978, 1979Titheradge & Haynes, 1979), no consistent effect of glucagon treatment on succinate dehydrogenase activity was observed.…”

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confidence: 51%

“…Firstly, inhibition of respiration by colletotrichin, a ubiquinone analogue (Foucher et al, 1974;Suzuki et al, 1976), is enhanced in mitochondria (intact or disrupted) from glucagon-treated animals (Fig. 6).…”

Section: Discussionmentioning

confidence: 98%

“…Further information about the site of action of glucagon within Complex III comes from studies with the inhibitor of the respiratory chain, colletotrichin. This is a phytotoxic metabolite of the fungus Colletotrichum nicotianae (Suzuki et al, 1976), whose structure has some resemblance to ubiquinone. Aceytl-collectotrichin, an acetylated derivative also occurring naturally, has been shown to inhibit the respiratory chain somewhere within Complex III at a site distinct from the antimycin site (Foucher et al, 1974).…”

Section: Effects Of Glucagon On the Inhibition Of The Respiratory Chamentioning

confidence: 99%

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The nature of the stimulation of the respiratory chain of rat liver mitochondria by glucagon pretreatment of animals

Halestrap¹

1982

Biochemical Journal

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1. Studies on the cytochrome spectra of liver mitochondria from control and glucagon-treated rats in State 4, State 3 and in the presence of uncoupler are reported. 2. The stimulation of electron flow between cytochromes c1 and c observed previously [Halestrap (1978) Biochem. J. 172, 399-405] was shown to be an artefact of Ca2+-induced swelling of mitochondria. 3. When precautions were taken to prevent such swelling, glucagon treatment was shown to enhance the reduction of cytochromes c, c1 and b558 in both State 3 and uncoupled conditions with either succinate or glutamate + malate as substrate. An increase in the reduction of cytochromes b562 and b566 was also seen in some, but not all, experiments. 4. In State 4 with succinate but not glutamate + malate as substrate, cytochromes c, c1, b558, b562 and b566 showed increased reduction. 5. Glucagon stimulated oxidation of duroquinol and palmitoylcarnitine by intact mitochondria and of NADH by disrupted mitochondria. 6. No effect of glucagon on succinate dehydrogenase activity or the temperature-dependence of succinate oxidation could be detected. 7. Glucagon enhanced the inhibition of the respiratory chain by colletotrichin, but not antimycin or 8-heptyl-4-hydroxyquinoline N-oxide. 8. These results are interpreted in terms of a primary stimulation by glucagon of the 'Q cycle' [Mitchell (1976) J. Theor. Biol. 62, 827-367] within Complex III (ubiquinol:cytochrome c oxidoreductase) and a secondary site of action involving stimulation of electron flow into Complex III from the ubiquinone pool. 9. Ageing of mitochondria, hyperosmotic treatment or addition of 20 mM-benzyl alcohol opposed the effects of glucagon treatment on cytochrome spectra and colletotrichin inhibition of respiration. 10. These results support the hypothesis that glucagon exerts its effects on the mitochondria by perturbing the membrane structure.

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confidence: 51%

Section: Discussionmentioning

confidence: 98%

Section: Effects Of Glucagon On the Inhibition Of The Respiratory Chamentioning

confidence: 99%

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The nature of the stimulation of the respiratory chain of rat liver mitochondria by glucagon pretreatment of animals

Halestrap¹

1982

Biochemical Journal

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“…In the present paper use is made of a novel inhibitor of the respiratory chain, colletotrichin (Foucher et al, 1974;Suzuki et al, 1976), in conjunction with other inhibitors of the respiratory chain, uncouplers and glucagon pretreatment of animals to provide further evidence for the validity of the 'Q cycle'. Furthermore, a scheme is proposed for -electron flow through Complex III which accounts for both the effects of glucagon on the cytochrome spectra and the behaviour of the b cytochromes towards energization and a variety of respiratory-chain inhibitors.…”

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confidence: 99%

The pathway of electron flow through ubiquinol:cytochrome c oxidoreductase in the respiratory chain. Evidence from inhibition studies for a modified ‘Q cycle’

Halestrap¹

1982

Biochemical Journal

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1. Cytochrome spectra of the liver and heart mitochondria incubated under various conditions are presented to compare the effects of antimycin, colletotrichin and 2-heptyl-4-hydroxyquinoline N-oxide (HQNO) additions. 2. Under aerobic conditions, in State 4, in the presence of uncoupler or in the presence of cyanide, all three inhibitors caused oxidation of cytochromes c and c1, but different changes in the spectra of the b cytochromes. Antimycin caused oxidation of a peak at 558 nm and reduction of peaks at 562 nm and 566 nm, whereas colletotrichin caused reduction of peaks at 558 nm and 566 nm and oxidation at 562 nm. HQNO had an effect on the spectra intermediate between those of the two other inhibitors. 3. Under aerobic conditions in the presence of 5 mM-succinate and 5 mM-fumarate, antimycin caused reduction of a peak at 566 nm and oxidation of a peak at 558 nm, whereas colletotrichin had the reverse effect and HQNO caused reduction of a peak at 562 nm. 4. Colletotrichin inhibition of the ADP-stimulated oxidation of glutamate + malate was enhanced by succinate addition and declined again with rotenone addition. Similar but smaller effects were seen with inhibition by antimycin and HQNO. 5. Cytochrome spectra are shown of the effects of ADP and uncoupler addition to stimulate respiration progressively. 6. The results are interpreted in terms of a modified 'Q cycle' [Mitchell (1976) J. Theor. Biol. 62, 327-367] in which the three inhibitors are postulated to displace ubiquinone and ubisemiquinone specifically bound to cytochromes b on both sides of the membrane. 7. It is suggested that cytochromes b558 and b566 are the same b cytochrome located on the outer surface of the membrane, but binding ubisemiquinone or colletotrichin and ubiquinone or antimycin respectively. Cytochrome b562 is postulated to be on the inner surface of the mitochondrial membrane and to bind either ubiquinone or ubisemiquinone, HQNO would bind to the reduced form of the cytochrome and colletotrichin to the oxidized form. 8. Sites for the locus of action of glucagon and the protonmotive force on electron flow are suggested.

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“…The six atoms of the pyrone ring (C) are planar within experimental error and form an angle of 60.4 ° with the plane of the methoxycarbonyl group. This explains the UV absorption, /[max = 260 nm (Suzuki, Gohbara, Kosuge, Tamura, Ohashi & Sasada, 1976). While this paper was being prepared, the molecular structure of the monoacetate of this compound was reported (Goddard, Hatton, Howard, MacMillan & Gilmore, 1976).…”

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Colletotrichin monohydrate methanol solvate

Gohbara¹,

Kosuge²,

Suzuki³

et al. 1977

Acta Crystallogr Sect B

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Structures of Colletotrichin and Colletotrichin B, Phytotoxic Metabolites fromColletotrichum nicotianae

Cited by 7 publications

References 1 publication

The nature of the stimulation of the respiratory chain of rat liver mitochondria by glucagon pretreatment of animals

The nature of the stimulation of the respiratory chain of rat liver mitochondria by glucagon pretreatment of animals

The pathway of electron flow through ubiquinol:cytochrome c oxidoreductase in the respiratory chain. Evidence from inhibition studies for a modified ‘Q cycle’

Colletotrichin monohydrate methanol solvate

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