A new shikimate derivative, methyl 5-lactyl shikimate lactone, from Penicillium sp.

Isogai, Akira; Washizu, Masayoshi; Murakoshi, S.; Suzuki, Akira

doi:10.1271/bbb1961.49.167

Cited by 5 publications

(5 citation statements)

References 1 publication

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“…In the same paper Alberg et al also described the preparation of the 3 R ,4a R ,8 R ,8a R diastereomer of 2 . As expected, the spectroscopic (IR, 1 H and 13 C NMR, and MS) data of phyllostin were similar to those described in literature for the natural – and synthetic diastereomers, but the physical (melting point and specific optical rotation) properties appeared to be quite different, as reported under Materials and Methods. Furthermore, the data of the crystalline cells are also quite different with respect to those reported of an unidentified diastereomer of 2 previously synthesized by Sprecher and Sprinson .…”

Section: Resultssupporting

confidence: 87%

“…Phyllostin appeared to be the diastereomer of the 5-lactyl shikimate lactone previously isolated from a Penicillium sp. , for which the absolute stereostructure 3 S ,4a R ,8 R ,8a R was established by two independent enantioselective synthesis , . In the same paper Alberg et al also described the preparation of the 3 R ,4a R ,8 R ,8a R diastereomer of 2 .…”

Section: Resultsmentioning

confidence: 99%

“…Phyllostin, which had no toxicity in any of the assays performed, is one of the possible 16 stereoisomers having the same structure. Another is a fungal metabolite , whereas the others are all synthetic compounds , .…”

Section: Resultsmentioning

confidence: 99%

“…crystalline solid; mp 138–142 °C; [α] 25 D −29.4° ( c 0.1, MeOH); IR ν max 3419, 1733, 1715, 1628, 1303, 1251 cm −1 [lit. , mp 133–135 °C, [α] D −188.75° ( c = 2.0 MeOH); IR (nujol) 3410 (OH), 1750 (CO), 1725 (CO); lit. ., R mp 160–165 °C; S mp 136–137 °C; lit.…”

Section: Methodsmentioning

confidence: 99%

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Phyllostoxin and Phyllostin, Bioactive Metabolites Produced by Phyllosticta cirsii, a Potential Mycoherbicide for Cirsium arvense Biocontrol

Evidente

Cimmino²,

Andolfi³

et al. 2008

J. Agric. Food Chem.

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Phyllosticta cirsii, a fungal pathogen isolated from diseased Cirsium arvense leaves and evaluated as a biocontrol agent of this noxious perennial weed, produces different phytotoxic metabolites with potential herbicidal activity when grown in liquid cultures. Phyllostictines A-D, four novel oxazatricycloalkenones, were recently isolated from this pathogen and chemically and biologically characterized. Further purification of the same organic extract provided two other metabolites, named phyllostoxin (1) and phyllostin (2), which were characterized by spectroscopic technique (essentially NMR and MS). Phyllostoxin and phyllostin proved to be a new pentasubstituted bicyclo-octatrienyl acetic acid ester and a new pentasubstituted hexahydrobenzodioxine carboxylic acid methyl ester, respectively. When tested on punctured C. arvense leaves, phyllostoxin proved to be highly phytotoxic, causing rapid and large necrosis, whereas phyllostin had no phytotoxicity in this bioassay. This is not surprising, considering the noteworthy structural differences between the two compounds, suggesting the presence of active functional groups in phyllostoxin not present in the other metabolite. These results further support the focused approach of finding novel metabolites with herbicidal properties by looking at the culture extracts of weed fungal pathogens.

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Section: Resultssupporting

confidence: 87%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Phyllostoxin and Phyllostin, Bioactive Metabolites Produced by Phyllosticta cirsii, a Potential Mycoherbicide for Cirsium arvense Biocontrol

Evidente

Cimmino²,

Andolfi³

et al. 2008

J. Agric. Food Chem.

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show abstract

“…Phyllostin, which proved to have no toxicity in any of the assays performed, is one of the possible 16 stereoisomers having the same structure. Only one of the stereoisomers is a fungal metabolite, 191 whereas others are all synthetic compounds. 185,187,192 X-Ray Crystallographic Analysis of Phyllostin (-)-Phyllostin, obtained as a crystalline solid, was recrystallized from toluene for X-ray analysis.…”

Section: Phyllostoxin and Phyllostinmentioning

confidence: 99%

Relationships between the stereochemistry and biological activity of fungal phytotoxins

2011

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Toxins produced by phytopathogenic fungi assume great importance because of their involvement in several plant diseases. Although such pathogens are known to have seriously damaged crops, forest, and environmental resources, they represent a very important tool to develop new environmentally friendly herbicides and fungicides. This review deals with the relationships between the biological activity of some phytotoxins produced by pathogenic fungi for major forest plants and for damaging weeds and their stereochemistry. In particular, the methods used to determine their relative and/or absolute configuration will be illustrated. These include the application of Mosher's and Murata's methods, X-ray diffractometric analysis, circular dichroism, and the use of computational methods to determine the theoretical optical rotatory power as well as the CD spectrum. The importance of determining the absolute configuration to achieve the total synthesis of some phytotoxins, interesting for their potential practical application, is also discussed.

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X-Ray Crystal Structure of Phyllostin, a Metabolite Produced by Phyllosticta cirsii, a Potential Mycoherbicide of Cirsium arvense

et al. 2009

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The X-ray crystal structure of phyllostin (8-hydroxy-3-methyl-2-oxo-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester) is reported. Phyllostin was recently and for the first time isolated, together with phytotoxin phyllostoxin and the phyllostictines A–D, from the culture filtrates of Phyllosticta cirsii, a fungal pathogen isolated from diseased Cirsium arvense leaves and evaluated as biocontrol agent of this noxious perennial weed. Phyllostin crystallizes in the monoclinic space group P21 with unit cell parameters: a = 8.371(2), b = 7.026(1), c = 9.918(1) Å, β = 92.013(8)°, Z = 2. The final refinement converged to R1 = 0.0530 for 1026 observed reflections having I > 2σ(I). In the molecule two trans joined six-membered rings are present. The cyclohexene ring adopts a half-chair conformation. The 2-oxo-1,4-dioxan ring adopts a distorted half-chair conformation. The relative stereochemistry of the four chiral centers turns out to be 3R,4aS,8R,8aS. In the crystal packing molecules form infinite chains through O–H···O intermolecular hydrogen bonds. Chains run along the crystallographic a axis forming layers of molecules stacking in the [0 1 0] direction. Graphical Abstract The X-ray crystal structure of phyllostin (8-hydroxy-3-methyl-2-oxo-2,3,4a,5,8,8a-hexahydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester) (I) is reported. In the molecule two trans joined six-membered rings are present. The relative stereochemistry of the four chiral centers turns out to be 3R,4aS,8R,8aS

show abstract

A new shikimate derivative, methyl 5-lactyl shikimate lactone, from Penicillium sp.

Cited by 5 publications

References 1 publication

Phyllostoxin and Phyllostin, Bioactive Metabolites Produced by Phyllosticta cirsii, a Potential Mycoherbicide for Cirsium arvense Biocontrol

Phyllostoxin and Phyllostin, Bioactive Metabolites Produced by Phyllosticta cirsii, a Potential Mycoherbicide for Cirsium arvense Biocontrol

Relationships between the stereochemistry and biological activity of fungal phytotoxins

X-Ray Crystal Structure of Phyllostin, a Metabolite Produced by Phyllosticta cirsii, a Potential Mycoherbicide of Cirsium arvense

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