Two new metabolites from an unidentified nigrospora species

Evans, Roger; Ellestad, George A.; Kunstmann, M. P.

doi:10.1016/s0040-4039(01)88013-8

Cited by 44 publications

(17 citation statements)

References 4 publications

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“…Osmundalactone is the aglycone of osmundalin, a hydroxypentenolide glucoside, and the NMR spectra of these two compounds were compared to determine the chemical structure. Hollenbeak and Kuehne reported that 4,5‐substituted Δ 2 ‐pentenolides can be assigned by comparison with analogous pentenolides of trans ( J = 9.0 Hz) and cis ( J = 2–3 Hz) 4,5‐substituted structures. The coupling constant, J 4,5 = 3.5 Hz, of our compound indicates the cis configuration, which means that our compound is angiopteroside, not osmundalin.…”

Section: Resultsmentioning

confidence: 99%

Two‐dimensional NMR analysis of Angiopteris evecta rhizome and improved extraction method for angiopteroside

Kamitakahara

Okayama

Praptiwi

et al. 2018

Phytochemical Analysis

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Introduction The rhizome of Angiopteris evecta is of academic interest in Kalimantan, Indonesia, from an ethnobotanical perspective. Angiopteroside is a substance of pharmaceutical importance that is found in the rhizome of A. evecta. Objective The aims of this research are to improve the extraction method for angiopteroside from the rhizome, compared to that in a previous report, and to determine the yield of angiopteroside from the rhizome of A. evecta, as well as to obtain precise data for extractives from the rhizome of A. evecta by using two‐dimensional NMR spectroscopy and liquid chromatography–mass spectrometry (LC–MS). Methodology We investigated the chemical constituents of the whole rhizome by means of two‐dimensional NMR (heteronuclear single quantum coherence or HSQC) spectroscopy, neutral sugar analysis using the alditol acetate method, and lignin analysis using alkaline nitrobenzene oxidation and Klason lignin methods. LC–MS revealed the purity of the angiopteroside. Antimicrobial assays were also performed for the purified angiopteroside by using a broth microdilution method. Results Angiopteroside was isolated by Soxhlet extraction with aqueous acetone followed by preparative thin‐layer chromatography (eluent: 20% methanol/dichloromethane). LC–MS revealed that angiopteroside can be found in the rhizome of A. evecta in 9.9% yield, which is an extremely high yield for a plant extractive. Conclusion HSQC analysis is a powerful tool for surveying compounds in plant materials, such as the whole rhizome of A. evecta. Soxhlet extraction with aqueous acetone is an effective method for extracting glycosides from plant materials.

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Section: Resultsmentioning

confidence: 99%

Two‐dimensional NMR analysis of Angiopteris evecta rhizome and improved extraction method for angiopteroside

Kamitakahara

Okayama

Praptiwi

et al. 2018

Phytochemical Analysis

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“…When considering all these observations in activity of these compounds, the mechanism of action is likely not the same as that for pyrethroids thus making these compounds a potentially useful chemical class against resistant mosquitoes. [12], Phoma sp. [13] [14], and Xylaria species [15].…”

Section: Resultsmentioning

confidence: 99%

Phomalactone as the Active Constituent against Mosquitoes from <i>Nigrospora spherica</i>

Meepagala

Becnel²,

Estep³

2015

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The culture filtrate of a plant pathogenic fungus that infected Zinnia elegans and Hydrangea macrophylla was investigated for mosquitocidal constituents by bioassay guided isolation. The fungus responsible for the pathogenic effects on Zinnia elegans and Hydrangea macrophylla plants had been identified as Nigrospora spherica by molecular techniques. The mosquito adulticidal constituent in the culture filtrate was identified as phomalactone by spectroscopic techniques. Laboratory bioassays showed that phomalactone had larvicidal activity against permethrin susceptible and resistant Aedes aegypti larvae and topical adulticide activities on permethrin susceptible and resistant Aedes aegypti and Anopheles quadrimaculatus mosquitoes. Phomalactone was effective as a topical adulticide against the standard Orlando reference strain of Ae. aegypti with an LD50 of 0.64 µg/org. Activity against An. quadrimaculatus was 0.20 µg/org.

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“…13A. The following growth characteristics were observed after incubation at ambient temperature (23 to 2400) on various media for a period of 4 weeks.…”

Section: Resultsmentioning

confidence: 99%

“…These compounds, however, do appear to represent a new class of macrodiolide antibiotics in which the dilactone ring is made up of two unequal subunits. They are presumably derived from C6-and C8-hydroxy acids or their derivatives which are, at least in the C-case, known to be fungal metabolites (1,4). The mode of action of these compounds is under speculation at this time, but it would appear from the structures that they could act as potent Michael acceptors and thus inhibit reproduction of the microorganisms by interacting with various enzymes.…”

Section: Grahamimycins 157mentioning

confidence: 99%

Grahamimycins: antibiotics from Cytospora sp. Ehrenb. W.F.P.L. 13A

Gurusiddaiah¹,

Ronald²

1981

Antimicrob Agents Chemother

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Aerobic fermentation of cultures of Cytospora sp. Ehrenb. W.F.P.L. 13A produces a group of novel, broad-spectrum, dilactone, macrocyclic antibiotics. These compounds, named grahamimycins, were isolated from the culture medium by extraction with organic solvents and separated by chromatography. Three active components have been obtained in crystalline form and have been designated grahamimycins A, A1, and B. The most active of these, grahamimycin A, exhibited activity against 36 species of bacteria, 8 species of blue-green algae (cyanobacteria), and 2 species of green algae, and antifungal activity against 5 fungi. Studies on the growth of the Cytospora with respect to formation of antibiotic activity, and the isolation, characterization, and structure elucidation of the grahamimycins are described. These studies indicate that the grahamimycins are distinct from other known antibiotics and represent a new class of antibiotic structures.

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Two new metabolites from an unidentified nigrospora species

Cited by 44 publications

References 4 publications

Two‐dimensional NMR analysis of Angiopteris evecta rhizome and improved extraction method for angiopteroside

Two‐dimensional NMR analysis of Angiopteris evecta rhizome and improved extraction method for angiopteroside

Phomalactone as the Active Constituent against Mosquitoes from <i>Nigrospora spherica</i>

Grahamimycins: antibiotics from Cytospora sp. Ehrenb. W.F.P.L. 13A

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Two new metabolites from an unidentified nigrospora species

Cited by 44 publications

References 4 publications

Two‐dimensional NMR analysis of Angiopteris evecta rhizome and improved extraction method for angiopteroside

Two‐dimensional NMR analysis of Angiopteris evecta rhizome and improved extraction method for angiopteroside

Phomalactone as the Active Constituent against Mosquitoes from &lt;i&gt;Nigrospora spherica&lt;/i&gt;

Grahamimycins: antibiotics from Cytospora sp. Ehrenb. W.F.P.L. 13A

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Phomalactone as the Active Constituent against Mosquitoes from <i>Nigrospora spherica</i>