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Chemical Constituents of the Fruiting Bodies of Clitocybe nebularis and Their Antifungal Activity.

Kim YS, Lee IK, Seok SJ, Yun BS - Mycobiology (2008)

Bottom Line: During a continuing search for antimicrobial substances from Korean native wild mushroom extracts, we found that the methanolic extract of the fruiting body of Clitocybe nebularis exhibited mild antifungal activity against pathogenic fungi.Nebularine showed mild antifungal activity against Magnaphorthe grisea and Trichophyton mentagrophytes, and phenylacetic acid potently inhibited the growth of Pythium ultiumand displayed moderate antifungal activity against Magnaphorthe grisea, Botrytis cinerea, and Trichophyton mentagrophytes.The other isolated compounds showed no antimicrobial activity.

View Article: PubMed Central - PubMed

Affiliation: Korea Research Institute of Bioscience and Biotechnology, Yuseong, Daejeon 305-333, Korea.

ABSTRACT
During a continuing search for antimicrobial substances from Korean native wild mushroom extracts, we found that the methanolic extract of the fruiting body of Clitocybe nebularis exhibited mild antifungal activity against pathogenic fungi. Therefore we evaluated the antifungal substances and other chemical components of the fruiting body of Clitocybe nebularis, which led to the isolation of nebularine, phenylacetic acid, purine, uridine, adenine, uracil, benzoic acid, and mannitol. Nebularine showed mild antifungal activity against Magnaphorthe grisea and Trichophyton mentagrophytes, and phenylacetic acid potently inhibited the growth of Pythium ultiumand displayed moderate antifungal activity against Magnaphorthe grisea, Botrytis cinerea, and Trichophyton mentagrophytes. The other isolated compounds showed no antimicrobial activity.

No MeSH data available.


Procedures used to isolate compounds 1-8 from the fruiting bodies of Clitocybe nebularis.
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Figure 1: Procedures used to isolate compounds 1-8 from the fruiting bodies of Clitocybe nebularis.

Mentions: The fresh fruiting bodies (20 kg) of C. nebularis were cut into small pieces and extracted with 70% aqueous MeOH at room temperature for 2 days. Following removal of the methanol under reduced pressure, the resulting solution was partitioned between ethyl acetate and H2O and then butyl alcohol and H2O. The ethyl acetate-soluble portion was then concentrated in vacuo, after which the residue was subjected to chromatography using a silica gel column. The reside was then eluted using a gradient of increasing amounts of MeOH in CHCl3. A fraction eluted with CHCl3-MeOH (4 : 1~2 : 1, v/v) was then concentrated and subjected to Sephadex LH-20 column chromatography, after which it was eluted with MeOH. A yellow antibiotic fraction was then subjected to chromatography on an ODS sep-pak cartridge, after which it was eluted using a gradient of increasing amounts of MeOH (10~100%) in water to give two yellow fractions. One of the yellow fractions was then purified by chromatography on a Sephadex LH-20 column with 50% aqueous MeOH, followed by reversed-phase TLC with 40% aqueous MeOH to provide compound 1 (25 mg, Rf 0.62), compound 2 (13 mg, Rf 0.5), compound 3 (6 mg, Rf 0.8), compound 4 (1 mg, Rf 0.4), and compound 5 (2 mg, Rf 0.82). The other fraction was purified on a Sephadex LH-20 column and then eluted with 70% aqueous MeOH. Next, the sample was subjected to preparative reversed-phase TLC and then developed with 70% aqueous MeOH, followed by preparative HPLC (column: ODS (4.6 × 250 mm, solvent: 80% aqueous MeOH, flow rate: 1 ml/min) to afford compound 6 (2 mg) and compound 7 (2 mg). The BuOH-soluble portion was then concentrated in vacuo, after which the residue was subjected to chromatography on a column of silica gel and eluted with a gradient with increasing amounts of MeOH in CHCl3. Each fraction was incubated at room temperature for 2 days, after which compound 8 (44 mg) was obtained as a crystal (Fig. 1).


Chemical Constituents of the Fruiting Bodies of Clitocybe nebularis and Their Antifungal Activity.

Kim YS, Lee IK, Seok SJ, Yun BS - Mycobiology (2008)

Procedures used to isolate compounds 1-8 from the fruiting bodies of Clitocybe nebularis.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3755233&req=5

Figure 1: Procedures used to isolate compounds 1-8 from the fruiting bodies of Clitocybe nebularis.
Mentions: The fresh fruiting bodies (20 kg) of C. nebularis were cut into small pieces and extracted with 70% aqueous MeOH at room temperature for 2 days. Following removal of the methanol under reduced pressure, the resulting solution was partitioned between ethyl acetate and H2O and then butyl alcohol and H2O. The ethyl acetate-soluble portion was then concentrated in vacuo, after which the residue was subjected to chromatography using a silica gel column. The reside was then eluted using a gradient of increasing amounts of MeOH in CHCl3. A fraction eluted with CHCl3-MeOH (4 : 1~2 : 1, v/v) was then concentrated and subjected to Sephadex LH-20 column chromatography, after which it was eluted with MeOH. A yellow antibiotic fraction was then subjected to chromatography on an ODS sep-pak cartridge, after which it was eluted using a gradient of increasing amounts of MeOH (10~100%) in water to give two yellow fractions. One of the yellow fractions was then purified by chromatography on a Sephadex LH-20 column with 50% aqueous MeOH, followed by reversed-phase TLC with 40% aqueous MeOH to provide compound 1 (25 mg, Rf 0.62), compound 2 (13 mg, Rf 0.5), compound 3 (6 mg, Rf 0.8), compound 4 (1 mg, Rf 0.4), and compound 5 (2 mg, Rf 0.82). The other fraction was purified on a Sephadex LH-20 column and then eluted with 70% aqueous MeOH. Next, the sample was subjected to preparative reversed-phase TLC and then developed with 70% aqueous MeOH, followed by preparative HPLC (column: ODS (4.6 × 250 mm, solvent: 80% aqueous MeOH, flow rate: 1 ml/min) to afford compound 6 (2 mg) and compound 7 (2 mg). The BuOH-soluble portion was then concentrated in vacuo, after which the residue was subjected to chromatography on a column of silica gel and eluted with a gradient with increasing amounts of MeOH in CHCl3. Each fraction was incubated at room temperature for 2 days, after which compound 8 (44 mg) was obtained as a crystal (Fig. 1).

Bottom Line: During a continuing search for antimicrobial substances from Korean native wild mushroom extracts, we found that the methanolic extract of the fruiting body of Clitocybe nebularis exhibited mild antifungal activity against pathogenic fungi.Nebularine showed mild antifungal activity against Magnaphorthe grisea and Trichophyton mentagrophytes, and phenylacetic acid potently inhibited the growth of Pythium ultiumand displayed moderate antifungal activity against Magnaphorthe grisea, Botrytis cinerea, and Trichophyton mentagrophytes.The other isolated compounds showed no antimicrobial activity.

View Article: PubMed Central - PubMed

Affiliation: Korea Research Institute of Bioscience and Biotechnology, Yuseong, Daejeon 305-333, Korea.

ABSTRACT
During a continuing search for antimicrobial substances from Korean native wild mushroom extracts, we found that the methanolic extract of the fruiting body of Clitocybe nebularis exhibited mild antifungal activity against pathogenic fungi. Therefore we evaluated the antifungal substances and other chemical components of the fruiting body of Clitocybe nebularis, which led to the isolation of nebularine, phenylacetic acid, purine, uridine, adenine, uracil, benzoic acid, and mannitol. Nebularine showed mild antifungal activity against Magnaphorthe grisea and Trichophyton mentagrophytes, and phenylacetic acid potently inhibited the growth of Pythium ultiumand displayed moderate antifungal activity against Magnaphorthe grisea, Botrytis cinerea, and Trichophyton mentagrophytes. The other isolated compounds showed no antimicrobial activity.

No MeSH data available.