Limits...
Chemical Constituents of Gymnopilus spectabilis and Their Antioxidant Activity.

Lee IK, Cho SM, Seok SJ, Yun BS - Mycobiology (2008)

Bottom Line: In an effort to identify chemical constituents of Korean native wild mushrooms, 4,6-decadiyne-1,3,8-triol (1), ergosta-4,6,8(14), 22-tetraen-3-one (2), bisnoryangonin (3), and hispidin (4) were isolated from the methanolic extract of the fruiting bodies of G. spectabilis.Their structures were assigned on the basis of various spectroscopic studies.Compounds 3 and 4 displayed significant scavenging activity against the ABTS radical cation, DPPH radical, and superoxide radical anion, while 1 and 2 exhibited no antioxidant activity.

View Article: PubMed Central - PubMed

Affiliation: Korea Research Institute of Bioscience and Biotechnology (KRIBB), 111 Gwahangno, Yuseong-gu, Daejeon 305-806, Korea.

ABSTRACT
Gymnopilus spectabilis, a hallucinogenic mushroom belonging to the family Cortinariaceae, is found growing in dense clusters on stumps and logs of hardwoods and conifers. It contains the hallucinogenic alkaloid psilocybin and its strongly bitter taste makes it undesirable as an edible. In an effort to identify chemical constituents of Korean native wild mushrooms, 4,6-decadiyne-1,3,8-triol (1), ergosta-4,6,8(14), 22-tetraen-3-one (2), bisnoryangonin (3), and hispidin (4) were isolated from the methanolic extract of the fruiting bodies of G. spectabilis. Their structures were assigned on the basis of various spectroscopic studies. Compounds 3 and 4 displayed significant scavenging activity against the ABTS radical cation, DPPH radical, and superoxide radical anion, while 1 and 2 exhibited no antioxidant activity.

No MeSH data available.


Related in: MedlinePlus

Isolation procedures of compounds 1~4.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
getmorefigures.php?uid=PMC3755253&req=5

Figure 2: Isolation procedures of compounds 1~4.

Mentions: The molecular weight of compound 1 was determined to be 182 by the ESI-mass measurements, which exhibit quasi-molecular ion peaks at m/z 205 [M+Na]+ and m/z 387 [2M+H]+ in the positive mode, and m/z 181 [M-H]- and m/z 363 [2M-H]- in the negative mode. The 1H NMR spectrum of 1 in mixture of CD3OD and CDCl3 exhibited signals due to a methyl protons at δ 0.98, two methylene protons at δ 1.67 and 1.87, an oxygenated methylene protons at δ 3.75, and two methine protons at δ 4.29 and 4.53 (Table 1). In the 13C NMR spectrum, one methyl carbon at δ 9.8, three methylene carbons at δ 31.7, 41.3, and 59.0, two oxygenated methine carbons at δ 60.2 and 64.3, and four quaternary carbons at δ 68.9, 69.1, 81.2, and 81.6 were evident. Unique chemical shift values of four quaternary carbons at δ 68.9, 69.1, 81.2, and 81.6 suggested the presence of diyne moiety in 1 (Table 1). The structure of 1 was determined on the basis of HMBC correlations, as summarized in Fig. 2. The HMBC correlations of H-1 to C-2 and C-3, H-2 to C-1, C-3, and C-4, H-3 to C-1, C-2, C-4, and C-5, H-8 to C-6, C-7, C-9, and C-10, H-9 to C-7, C-8, and C-10, and H-10 to C-8 and C-9 were observed. Therefore, the structure of 1 was unambiguously determined to be 4,6-decadiyne-1,3,8-triol. This compound was previously isolated from this mushroom by Kusano et al. (1986).


Chemical Constituents of Gymnopilus spectabilis and Their Antioxidant Activity.

Lee IK, Cho SM, Seok SJ, Yun BS - Mycobiology (2008)

Isolation procedures of compounds 1~4.
© Copyright Policy - open-access
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC3755253&req=5

Figure 2: Isolation procedures of compounds 1~4.
Mentions: The molecular weight of compound 1 was determined to be 182 by the ESI-mass measurements, which exhibit quasi-molecular ion peaks at m/z 205 [M+Na]+ and m/z 387 [2M+H]+ in the positive mode, and m/z 181 [M-H]- and m/z 363 [2M-H]- in the negative mode. The 1H NMR spectrum of 1 in mixture of CD3OD and CDCl3 exhibited signals due to a methyl protons at δ 0.98, two methylene protons at δ 1.67 and 1.87, an oxygenated methylene protons at δ 3.75, and two methine protons at δ 4.29 and 4.53 (Table 1). In the 13C NMR spectrum, one methyl carbon at δ 9.8, three methylene carbons at δ 31.7, 41.3, and 59.0, two oxygenated methine carbons at δ 60.2 and 64.3, and four quaternary carbons at δ 68.9, 69.1, 81.2, and 81.6 were evident. Unique chemical shift values of four quaternary carbons at δ 68.9, 69.1, 81.2, and 81.6 suggested the presence of diyne moiety in 1 (Table 1). The structure of 1 was determined on the basis of HMBC correlations, as summarized in Fig. 2. The HMBC correlations of H-1 to C-2 and C-3, H-2 to C-1, C-3, and C-4, H-3 to C-1, C-2, C-4, and C-5, H-8 to C-6, C-7, C-9, and C-10, H-9 to C-7, C-8, and C-10, and H-10 to C-8 and C-9 were observed. Therefore, the structure of 1 was unambiguously determined to be 4,6-decadiyne-1,3,8-triol. This compound was previously isolated from this mushroom by Kusano et al. (1986).

Bottom Line: In an effort to identify chemical constituents of Korean native wild mushrooms, 4,6-decadiyne-1,3,8-triol (1), ergosta-4,6,8(14), 22-tetraen-3-one (2), bisnoryangonin (3), and hispidin (4) were isolated from the methanolic extract of the fruiting bodies of G. spectabilis.Their structures were assigned on the basis of various spectroscopic studies.Compounds 3 and 4 displayed significant scavenging activity against the ABTS radical cation, DPPH radical, and superoxide radical anion, while 1 and 2 exhibited no antioxidant activity.

View Article: PubMed Central - PubMed

Affiliation: Korea Research Institute of Bioscience and Biotechnology (KRIBB), 111 Gwahangno, Yuseong-gu, Daejeon 305-806, Korea.

ABSTRACT
Gymnopilus spectabilis, a hallucinogenic mushroom belonging to the family Cortinariaceae, is found growing in dense clusters on stumps and logs of hardwoods and conifers. It contains the hallucinogenic alkaloid psilocybin and its strongly bitter taste makes it undesirable as an edible. In an effort to identify chemical constituents of Korean native wild mushrooms, 4,6-decadiyne-1,3,8-triol (1), ergosta-4,6,8(14), 22-tetraen-3-one (2), bisnoryangonin (3), and hispidin (4) were isolated from the methanolic extract of the fruiting bodies of G. spectabilis. Their structures were assigned on the basis of various spectroscopic studies. Compounds 3 and 4 displayed significant scavenging activity against the ABTS radical cation, DPPH radical, and superoxide radical anion, while 1 and 2 exhibited no antioxidant activity.

No MeSH data available.


Related in: MedlinePlus