N6-(2-hydroxyethyl)adenosine, a biologically active compound from cultured mycelia of Cordyceps and Isaria species

Furuya, Tsutomu; Hirotani, Masao; Matsuzawa, Masayuki

doi:10.1016/0031-9422(83)80150-2

Cited by 100 publications

(73 citation statements)

References 10 publications

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“…Additionally, nucleosides, including adenosine, cordycepin and N 6 -(2-hydroxyethyl)-adenosine (HEA), represent the major active components in Cordyceps sensu lato (Gong et al 2004; Li et al 2006). HEA was the first calcium antagonist derived from biological sources, and can be used as an inotropic agent (Furuya et al 1983). Recent studies have revealed HEA has various biological activities.…”

Section: Introductionmentioning

confidence: 99%

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Beauveria bassiana: a new N⁶-(2-hydroxyethyl)-adenosine–producing fungus

Liu

Wang

et al. 2017

Mycology

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N6-(2-Hydroxyethyl)-adenosine (HEA), which was the first calcium antagonist derived from biological sources, has been intensively investigated because of its ability to inhibit tumour cell proliferation, restrain inflammation, protect kidneys and function as a sedative and insecticide. Up to now, the production of HEA has been detected only in a few species such as Cordyceps pruinosa, C. militaris and Isaria tenuipes. Here, we found a new HEA-producing fungus, which was identified as Beauveria bassiana based on morphological and phylogenetic characteristics. The HEA production was verified by reversed-phase high-performance liquid chromatography/mass spectrometry in this fungus. Moreover, HEA was also detected in the mycelia of two other B. bassiana strains from different origins, but not in the culture medium of all tested B. bassiana strains. The maximum production of HEA (0.8483 ± 0.0439 mg/g mycelia dry weight) was achieved on day 7. The fungal biomass and kinetics of HEA production exhibited similar trends over the duration of the culture period. This is the first report describing HEA production in B. bassiana, which suggests that this fungal strain may have new applications as a source of HEA.

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Section: Introductionmentioning

confidence: 99%

“…Furuya et al (1983) tested for the presence of Ca 2+ antagonists and inotropic agents in the water–ethanol extracts from mycelia of 17 Cordyceps species and 6 Isaria species using the left atrium of a guinea pig heart in an in vitro system. The mycelial extracts from two Cordyceps species (i.e.…”

Section: Introductionmentioning

confidence: 99%

Beauveria bassiana: a new N⁶-(2-hydroxyethyl)-adenosine–producing fungus

Liu

Wang

et al. 2017

Mycology

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“…Biological and pharmaceutical compounds such as cordycepin and N 6 -(2-hydroxyethyl) adenosine were reported in Cordyceps mushroom (Furuya et al, 1983;Hsu et al, 2002;Li et al, 2003). Artificial culture techniques have been first developed for the fruiting body production of Cordyceps mushroom (Dongchunghacho) using silkworm as a host in Korea (Ha et al, 2005).…”

Section: Introductionmentioning

confidence: 99%

Synnemata Production by Isaria tenuipes using Colored Cocoon Silkworm, Golden Silk

Hong¹,

Kang²,

Kim³

et al. 2011

International Journal of Industrial Entomology

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This study was conducted to test the use of colored cocoon silkworm, Golden Silk, as a host for the fruiting body production of Cordyceps mushroom. Golden Silk variety had a shorter larval period than Yangwonjam at 25.3 o C and 78.5% RH: The average larval period of the Golden Silk was 24 days and 7 hr, and that of the Yangwonjam was 24 days and 15 hr. In the infection test of I. tenuipes on silkworm, the larval period of normal silkworms was longer than the silkworms inoculated with I. tenuipes in both Golden Silk and Yangwonjam. The pupae survival percentage of Golden Silk was 94.4%, whereas it was 91.9% in Yangwonjam. Golden Silk had a higher pupation rate than Yangwonjam. The pupation rate of normal silkworms was about 5% higher than that of silkworms inoculated with I. tenuipes. Infection rate of I. tenuipes into larvae of 5th instar newly exuviated silkworm was 93.8% in Golden Silk, and 96.9% in Yangwonjam. Synnemata production of I. tenuipes was better in Yangwonjam with an incidence rate of 99.8% than Golden Silk with 98.6%. The average synnemata weight of Golden Silk was 1.12 g and that of Yangwonjam 1.29 g. Golden Silk had a lower synnemata weight than Yangwonjam. But no significant difference was observed in synnemata weight varieties. The synnemata of I. tenuipes produced on pupae were white or milky-white in color, and similar in shape and color to wild synnemata collected in Korea.

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“…Some bioactive contents, for example, polysaccharides [1], galactomannan [2], cordycepin, adenosine [3], and ISP-1 (myriocin) [4] have been isolated from Cordyceps cicadae. Because the natural resource of Cordyceps cicadae is very scarce, it is important to research on the cultivation of fungi, pharmacological function and chemical contents of the cultivated mycelia of Cordyceps cicadae.…”

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confidence: 99%

“…Then, the syrup was suspended in water and extracted with CHCl 3 and BuOH orderly. The aqueous fraction after extraction by CHCl 3 and BuOH was concentrated to one liter. Then, this aqueous solution was subjected to column chromatography packed with MCI gel and eluted with MeOH : H 2 O (0 : 1ϳ4 : 6, step gradient) collecting 50 ml fractions to give Fractions B1ϳB5.…”

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Cyclopentenone and Furan Derivative from the Mycelia of Cordyceps cicadae

Zhang

Liu

2008

J Antibiot

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A new cyclopentenone derivative, named as 2-(3-carboxy-2-hydroxypropyl)-3-methyl-2-cyclopentenone, and a new furan derivative, named as 5-(2-hydroxyethyl)-2-furanacetic acid, were isolated from the cultivated Cordyceps cicadae mycelia. Their structures were determined by spectroscopic methods, including 2D NMR analyses.Keywords cyclopentenone derivative, furan derivative, structure elucidation, Cordyceps cicadae Cordyceps cicadae, belonging to the genus Cordyceps (family Clavicipitaceae, Ascomycotina), is a major parasitic fungus growing on the larvae of Cicada flammata, Platypleura kaempferi, Crytotympana pustulata, or Platylomia pieli. Some bioactive contents, for example, polysaccharides [1], galactomannan [2], cordycepin, adenosine [3], and ISP-1 (myriocin) [4] have been isolated from Cordyceps cicadae. Because the natural resource of Cordyceps cicadae is very scarce, it is important to research on the cultivation of fungi, pharmacological function and chemical contents of the cultivated mycelia of Cordyceps cicadae. Chen [5] found that Paecilomyces cicadae could grow on the wheat culture medium well and the cultivated mycelia show the same pharmacological function as the natural fungi. Jin [6] found that the cultivated mycelia of Cordyceps cicadae could prevent the progression of chronic renal failure (CRF) in the rat glomerulosclerosis model.In order to investigate the chemical contents of cultivated mycelia of Cordyceps cicadae, we isolated the extract of 70% aqueous ethanol. In the preceding paper, we have reported five new aromatic 4-O-methylglucosides from the cultivated mycelia of Cordyceps cicadae [7]. In this paper, we report the isolation and structure elucidation of a new cyclopentenone derivative and a new furan derivative, from the cultivated Cordyceps cicadae mycelia. They were characterized as 2-(3-carboxy-2-hydroxypropyl)-3-methyl-2-cyclopentenone (1) and 5-(2-hydroxyethyl)-2-furanacetic acid (2), respectively, by spectroscopic methods.The method of the cultivation of fungi was described in the preceding paper [5,7].The cultivated mycelia of Cordyceps cicadae (4.0 kg) were extracted three times with 24 liters 70% (v/v) aqueous EtOH at room temperature. The combined extracts were concentrated to give deep-brown syrup. Then, the syrup was suspended in water and extracted with CHCl 3 and BuOH orderly. The aqueous fraction after extraction by CHCl 3 and BuOH was concentrated to one liter. Then, this aqueous solution was subjected to column chromatography packed with MCI gel and eluted with MeOH : H 2 O (0 : 1ϳ4 : 6, step gradient) collecting 50 ml fractions to give Fractions B1ϳB5. Fraction B2 (eluted by 2 : 8 MeOH -H 2 O) was rechromatoraphed by column over MCI gel and eluted with 20% aqueous methanol collecting 10 ml fractions. Fractions 28ϳ43 afforded partially pure 1 and fractions 49ϳ60 afforded partially pure 2. Final purification was performed by HW-40F column chromatography eluted with H 2 O to provide purified samples of 1 (15 mg) and 2 (8.0 mg).

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N6-(2-hydroxyethyl)adenosine, a biologically active compound from cultured mycelia of Cordyceps and Isaria species

Cited by 100 publications

References 10 publications

Beauveria bassiana: a new N⁶-(2-hydroxyethyl)-adenosine–producing fungus

Beauveria bassiana: a new N⁶-(2-hydroxyethyl)-adenosine–producing fungus

Synnemata Production by Isaria tenuipes using Colored Cocoon Silkworm, Golden Silk

Cyclopentenone and Furan Derivative from the Mycelia of Cordyceps cicadae

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N6-(2-hydroxyethyl)adenosine, a biologically active compound from cultured mycelia of Cordyceps and Isaria species

Cited by 100 publications

References 10 publications

Beauveria bassiana: a new N6-(2-hydroxyethyl)-adenosine–producing fungus

Beauveria bassiana: a new N6-(2-hydroxyethyl)-adenosine–producing fungus

Synnemata Production by Isaria tenuipes using Colored Cocoon Silkworm, Golden Silk

Cyclopentenone and Furan Derivative from the Mycelia of Cordyceps cicadae

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Beauveria bassiana: a new N⁶-(2-hydroxyethyl)-adenosine–producing fungus

Beauveria bassiana: a new N⁶-(2-hydroxyethyl)-adenosine–producing fungus