Russuphelins B, C, D, E and F, New Cytotoxic Substances from the Mushroom Russula subnigricans HONGO.

Chlorinated Hydroquinone Derivatives of Fruiting Body of Russula subnigricans

“…According to the above data, compound 4 was identified as russuphelin E (Takahashi et al, 1993). The present study reported the isolation of one fatty acid (1) and three chlorinated hydroquinones (2,3,4) from the fruiting body of R. subnigricans.…”

“…Nonadecanoic acid (1) has been known to be isolated from several sources such as fungi, marine sponges, plants and larvae (Yoo et al, 2002), and it was characterized for the first time from R. subnigricans. 2,6-dichloro-4-methoxyphenol (2) has been isolated from Rhodococcus chlorophenolicus (Haggblom et al, 1988), Phanerochaete chrysosporium (Reddy et al, 1998) and R. subnigricans (Takahashi et al, 1993). Russuphelin A (3) and russuphelin E (4) have only been found in R. subnigricans (Takahashi et al, 1993).…”

“…2,6-dichloro-4-methoxyphenol (2) has been isolated from Rhodococcus chlorophenolicus (Haggblom et al, 1988), Phanerochaete chrysosporium (Reddy et al, 1998) and R. subnigricans (Takahashi et al, 1993). Russuphelin A (3) and russuphelin E (4) have only been found in R. subnigricans (Takahashi et al, 1993). 2,6-dichloro-4-methoxyphenol (2), russuphelin A (3) and russuphelin E (4), based on chlorinated hydroquinone unit, can be important chemotaxonomic markers of R. subnigricans, suggesting that they could be potential toxins.…”

“…1. According to the combination of spectroscopic data and literature (Takahashi et al, 1992(Takahashi et al, , 1993Ohta et al, 1995), compound 3 was elucidated as russuphelin A (2,6-bis(2,6-dichloro-4-hydroxyphenyloxy)-1,4-dimethoxybenzene). Compound 4 was obtained as a brownish amorphous powder, and R f value was 0.65 (benzene-acetone (8 : 2, v/v)).…”

“…The potential toxicity of these mushrooms has been known in Japan since 1954, and chemical constituents have been previously isolated and identified several amino acids ((2S,3R)-(-)-3-hydroxybaikiain, (S)-(-)-baikiain, (S)-(-)-pipecolic acid) and sterol derivatives (ergosterol, ergosteryl peroxide, cerevisterol) (Kusano et al, 1987). Chlorinated hydroquinone derivatives, russuphelol, russuphelin A, B, C, D, E and F were identified as cytotoxic compounds (Takahashi et al, 1992(Takahashi et al, , 1993Ohta et al, 1995). Cycloprop-2-ene carboxylic acid is fairly well known to synthetic organic chemists but has never before been observed in a biological system (Kim et al, 2009).…”