Structures of Colletochlorin C, Colletorin A and Colletorin C from<i>Colletotrichum nicotianae</i>

Kosuge, Yoshiaki; Suzuki, Akira; Tamura, Saburo

doi:10.1080/00021369.1974.10861322

Cited by 20 publications

(11 citation statements)

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“…amorphous solid; [α] 25 D + 6.24 ( c 0.20) [lit . [α] 25 D +11.6 ( c 10.0)]; 1 H NMR spectrum was very similar to that previously described; , ESIMS (+) m / z 379 [M + Na] + , 357 [M + H] + .…”

Section: Methodssupporting

confidence: 66%

“…1 and 2 were isolated together with the other three well-known fungal metabolites, which were identified by comparing their physical (OR) and spectroscopic (IR, UV, and 1 H NMR spectra) data with those previously reported in the literature as colletochlorin A, 4-chloroorcinol, and colletopyrone ( 3 , 4 , and 5 , respectively; Figure ). − Their identification was confirmed from the data of their ESIMS spectra. Indeed, those of 3 and 5 showed the sodium cluster [M + Na] + and the pseudomolecular ion [M + H] + at m / z 379 and 357 and at m / z 315 and 293, respectively, whereas those of 4 exhibited the pseudomolecular ions [M + H] + and [M – H] − at m / z 159 and 157.…”

Section: Resultsmentioning

confidence: 87%

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Colletochlorins E and F, New Phytotoxic Tetrasubstituted Pyran-2-one and Dihydrobenzofuran, Isolated from Colletotrichum higginsianum with Potential Herbicidal Activity

Masi

Cimmino

Boari

et al. 2017

J. Agric. Food Chem.

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A new tetrasubstituted pyran-2-one and a new dihydrobenzofuran, named colletochlorins E and F (1 and 2, respectively), were isolated from the culture filtrates of the fungus Colletotrichum higginsianum together with the already known colletochlorin A, 4-chloroorcinol, and colletopyrone. Colletochlorin E, the main metabolite, and colletochlorin F were characterized by spectroscopic (NMR, HRESIMS) and chemical methods as 3-[7-chloro-4-hydroxy-2-(1-hydroxy-1-methylethyl)-6-methyl-2,3-dihydrobenzofuran-5-ylmethyl]-4-hydroxy-5,6-dimethylpyran-2-one and 7-chloro-2-(1-hydroxy-1-methylethyl)-6-methyl-2,3-dihydrobenzofuran-4-ol, respectively. The absolute configuration 2'S of 1 was deduced by X-ray diffractometric analysis, whereas 2S of 2 was deduced by comparison of its NMR and CD data with those of 1. When assayed by leaf puncture on Sonchus arvensis and tomato leaves, 2 caused quite large necrosis (>1 cm), whereas 4-chloroorcinol proved to be the most active compound. These results were confirmed by those obtained in assays on Lemna minor and Phelipanche ramosa seed germination. Furthermore 1, colletochlorin A and colletopyrone were less or modestly active in the latter assay, respectively. Interestingly, the phytotoxicity was not associated with an antibiotic activity, whereas only 4-chloroorcinol and colletochlorin F exhibited zootoxic activity.

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Section: Methodssupporting

confidence: 66%

Section: Resultsmentioning

confidence: 87%

Colletochlorins E and F, New Phytotoxic Tetrasubstituted Pyran-2-one and Dihydrobenzofuran, Isolated from Colletotrichum higginsianum with Potential Herbicidal Activity

Masi

Cimmino

Boari

et al. 2017

J. Agric. Food Chem.

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“…The application of the aforementioned method for AC assignment of diols was tested on the naturally occurring phytotoxin colletochlorin A [(+)- 1 ], a well-known 3-diprenyl orsellinaldehyde derivative isolated for the first time in 1973 from the culture filtrate of Colletotrichum nicotianae , a pathogenic fungus that induces tobacco anthracnose 42 and more recently from the culture filtrate of Colletotrichum higginsianum . 29 Compound 1 was subsequently isolated also as the main phytotoxin from the culture filtrates of C. gloeosporioides and proposed as potential bioherbicide for biocontrol of Ambrosia artemisiifolia , 43 a widespread invasive weed native to North America causing severe crop losses 44 and huge medical costs as a consequence of its highly allergenic pollen production.…”

Section: Results and Discussionmentioning

confidence: 99%

Absolute Configuration Assignment to Chiral Natural Products by Biphenyl Chiroptical Probes: The Case of the Phytotoxins Colletochlorin A and Agropyrenol

et al. 2020

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The application of flexible biphenyls as chiroptical probes for the absolute configuration assignment to chiral natural products is described. The method is straightforward and reliable and can be applied to conformationally mobile and ECD silent compounds, not treatable by computational analysis of chiroptical data. By this approach, the (6′ R ) absolute configuration of the phytotoxin colletochlorin A ( 1 ) was confirmed, while the absolute configuration of the phytotoxin agropyrenol ( 2 ), previously assigned by the NMR Mosher method, was revised and assigned as (3′ S ,4′ S ). Moreover, with the biphenyl method the configurational assignment can be obtained simply by the sign of a diagnostic Cotton effect at 250 nm in the ECD spectrum, thus allowing application without the need of advanced knowledge of chiroptical spectroscopy and computational protocols.

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“…From the biogenetical considerations on the formation of r-pyrones, the possible precursor of colletotrichins might be formulated as 4, because diprenyl orsellinaldehyde derivatives named colletorins A and C have been isolated from this fungus. 2 ) The biosynthesis of rpyrone is easily explained in the following way (1) and (2) FIG. 2.…”

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confidence: 99%

Structures of Colletotrichin and Colletotrichin B, Phytotoxic Metabolites fromColletotrichum nicotianae

Suzuki

Gohbara

Kosuge

et al. 1976

Agricultural and Biological Chemistry

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Structures of Colletochlorin C, Colletorin A and Colletorin C fromColletotrichum nicotianae

Cited by 20 publications

References 0 publications

Colletochlorins E and F, New Phytotoxic Tetrasubstituted Pyran-2-one and Dihydrobenzofuran, Isolated from Colletotrichum higginsianum with Potential Herbicidal Activity

Colletochlorins E and F, New Phytotoxic Tetrasubstituted Pyran-2-one and Dihydrobenzofuran, Isolated from Colletotrichum higginsianum with Potential Herbicidal Activity

Absolute Configuration Assignment to Chiral Natural Products by Biphenyl Chiroptical Probes: The Case of the Phytotoxins Colletochlorin A and Agropyrenol

Structures of Colletotrichin and Colletotrichin B, Phytotoxic Metabolites fromColletotrichum nicotianae

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