Isolation and identification of two new [11]cytochalasins from Phomopsis sojae

Cole, Richard; Wilson, David M.; Harper, James; Cox, Richard H.; Cochran, Teena W.; Cutler, Horace G.; Bell, D. K.

doi:10.1021/jf00110a021

Cited by 26 publications

(11 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…): 175.0(C1), 170.0(C29), 138.0(C14), 137.2(C31), 136.0(C20), 130.2(C24,28), 128.7(C25, 27), 127.6(C19), 127.1(C13), 125.5(C26), 76.0(C21), 74.1(C18), 62.9(C7), 57.0(C6), 53.8(C3), 53.7(C17), 53.5(C9), 51.1(C4), 45.7(C15), 45.0(C8), 43.1(C10), 36.6(C5), 30.1(C16), 28.6(C23), 26.4(C22), 20.6(C30), 19.5(C12), 13.0(C11). And they are in accordance with those reported by Cole (Cole et al (1982)). Refinement.…”

Section: Special Detailssupporting

confidence: 93%

“…The absolute configuration could not be determined from the X-ray analysis, owing to the absence of significant anomalous scatterers, and Friedel pairs were merged. However, when the title compound was orginally isolated by Cole (Cole et al (1982)), its absolute configuration was confirmed by comparison with a similar compound (Cytochalasin H) of which the absolute configuration was previously reported by Beno (Beno et al (1977)). Thus the absolute configuration of the title…”

Section: S3 Refinementsupporting

confidence: 68%

“…For the isolation and structure elucidation of the title compound, see: Cole et al (1982). For related structures, see: Buchi et al (1973); Beno et al (1977); Capasso et al (1988); Edwards & Maitland et al (1989); Chen et al (1993); Feng et al (2002); Evidente et al (2002Evidente et al ( , 2003; Rochfort et al (2008); Herath et al (2005); Ding et al (2006).…”

Section: Related Literaturementioning

confidence: 99%

“…compound was assigned by a comparison between the measured optical rotatory power ([α] 25 D =-91° (c=0.1, CHCl 3 )) and the value ([α] 30 D =-84.68° (c=0.33, CHCl 3 )) reported by Cole (Cole et al (1982)).…”

Section: S3 Refinementmentioning

confidence: 99%

See 3 more Smart Citations

Epoxycytochalasin H methanol solvate

Li¹,

Liu²,

Tai³

et al. 2010

Acta Cryst E

View full text Add to dashboard Cite

In the title solvate, C30H39NO5·CH4O {systematic name: 21-acetoxy-18,21-dihydroxy-5,6,16,18-tetramethyl-10-phenyl-6,7-epoxy-[11]cytochalasa-13,19-dien-1-one methanol solvate}, the organic molecule exhibits the tetracyclic terpenoid skeleton of cytochalasin, consisting of fused five-, six-, three- and 11-membered rings. The five-membered ring adopts an envelope conformation, while the six-membered ring is in a boat conformation. The epoxy O atom on the six-membered ring is pointing away from the five-membered ring. An interstitial methanol solvent molecule is hydrogen bonded to the cytochalasin molecules and intermolecular O—H⋯O and N—H⋯O hydrogen bonds connect the molecules into infinite chains along the (10) direction.

show abstract

Section: Special Detailssupporting

confidence: 93%

Section: S3 Refinementsupporting

confidence: 68%

Section: Related Literaturementioning

confidence: 99%

Section: S3 Refinementmentioning

confidence: 99%

See 2 more Smart Citations

Epoxycytochalasin H methanol solvate

Li¹,

Liu²,

Tai³

et al. 2010

Acta Cryst E

View full text Add to dashboard Cite

show abstract

“…They are not a problem in drier inland areas. P. phaseoli can cause liver damage in chickens due to unidentified toxins (Kung et al 1977) and the fungus is known to produce cytochalasins (Cole et al 1982). Australian P. longicolla isolates have also been shown to produce cytochalasins (Allen et al 1989).…”

Section: Phomopsis Mycotoxinsmentioning

confidence: 99%

Effective use in livestock feeds of mouldy and weather-damaged grain containing mycotoxins—case histories and economic assessments pertaining to pig and poultry industries of Queensland

Blaney¹,

Williams²

1991

Aust. J. Agric. Res.

View full text Add to dashboard Cite

Mould growth in field crops or stored grain reduces starch and lipid content, with consequent increases in fibre, and an overall reduction in digestible energy; palatability is often adversely affected. If these factors are allowed for, and mycotoxin concentrations are low, there are sound economic reasons for using this cheaper grain.Mycotoxins are common in stock feed but their effects on animal productivity are usually slight because either the concentration is too low or the animal is tolerant to the toxin. In Australia, aflatoxins occur in peanut by-products and in maize and sorghum if the grain is moist when stored. Zearalenone is found in maize and in sorghum and wheat in wetter regions. Nivalenol and deoxynivalenol are found in maize and wheat but at concentrations that rarely affect pigs, with chickens and cattle being even more tolerant. Other mycotoxins including cyclopiazonic acid, T-2 toxin, cytochalasins and tenuazonic acid are produced by Australian fungi in culture but are not found to be significant grain contaminants.Extremely mouldy sorghum containing Alternaria and Fusarium mycotoxins decreased feed conversion in pigs and chickens by up to 14%. However, E moniliforme-and Diplodia maydis-infected maize produced only slight reductions in feed intake by pigs and Ustilagoinfected barley produced no ill effects. Use of these grains would substantially increase profits if the grain can be purchased cheaply.

show abstract

A Novel Phytotoxic Nonenolide from Phomopsis sp. HCCB03520

Yang

Ge²,

Yu³

et al. 2012

Chemistry & Biodiversity

View full text Add to dashboard Cite

A novel phytotoxic nonenolide, (6S,7R,9R)-6,7-dihydroxy-9-propylnon-4-eno-9-lactone (1), was isolated from solid cultures of the endophytic fungus Phomopsis sp. HCCB03520, together with three known compounds, cytochalasin H (2), cytochalasin N (3), and epoxycytochalasin H (4). The structures of these compounds were elucidated through spectroscopic analysis, and the absolute configurations were determined by CD spectroscopy. Phytotoxic activities of compounds 1-4 were also investigated. Compound 1 showed phytotoxic activity on germination and radicle growth of Medicago sativa, Trifolium hybridum, and Buchloe dactyloides.

show abstract

Isolation and identification of two new [11]cytochalasins from Phomopsis sojae

Cited by 26 publications

References 6 publications

Epoxycytochalasin H methanol solvate

Epoxycytochalasin H methanol solvate

Effective use in livestock feeds of mouldy and weather-damaged grain containing mycotoxins—case histories and economic assessments pertaining to pig and poultry industries of Queensland

A Novel Phytotoxic Nonenolide from Phomopsis sp. HCCB03520

Contact Info

Product

Resources

About