Russuphelol, a novel optically active chlorohydroquinone tetramer from the mushroom Russula subnigricans

Naturally Occurring Organohalogen Compounds

“…WK-349, 11 and Streptomyces rugosporus has furnished the antibiotic pyrroindomycin B (8), which is active against both penicillin-resistant Staphylococcus aureus and vancomycinresistant Enterococci. 12 The glycopeptide antibiotic vancomycin (9), which is produced by Amycolatopsis orientalis, has been used for 40 yielded organohalogen metabolites, and one of the more interesting is the enediyne C-1027, the chromophore of which is shown in 10.…”

“…4-Chloroindole-3-acetic acid ( 11) is a natural plant growth hormone, and 3,5-dichlorohexanophenone, which is produced by Dictyostelum discoideum, is a signal molecule that triggers the transformation of undifferentiated cells of this slime mold into fruiting bodies. The chlorine atoms in the clinical antibiotic vancomycin (9) are crucial in enforcing the requisite conformation for receptor binding. The extraordinary bromo ester 75 found in human cerebrospinal fluid may play an important role in inducing the sleep phenomenon.…”

“…The fungal pathogen Periconia circinata , which causes “milo disease” of grain, produces periconin B ( 4 ) as one of four chlorinated metabolites . The mushroom Russula subnigricans contains a number of chlorohydroquinones (e.g., russuphelol ( 5 )), and the wood-rotting forest fungus Lepista nuda produces 14 organohalogens including several brominated phenols (e.g., 6 ) …”

Non-peptide secondary metabolites from poisonous mushrooms: overview of chemistry, bioactivity, and biosynthesis

“…106,107 Distinctively, this mushroom produces chlorinated phenyl ethers, russuphelins A-G (65-71), and a chlorohydroquinone tetramer russuphelol (72). [108][109][110] Compound 65 has been tested for its cytotoxicity against various tumor cells. It showed cytotoxic activities against the mouse lymphocytic leukemia cell line L1210 (IC 50 ¼ 2.47 mg mL À1 ), mouse colon adenocarcinoma cell line Colon 26 (IC 50 ¼ 10.16 mg mL À1 ), mouse leukemia cell line P388 (IC 50 ¼ 4.64 mg mL À1 ), mouse leukemia cell line P388/ADM (IC 50 ¼ 2.96 mg mL À1 ), human mouth epidermal carcinoma cell line KB (IC 50 ¼ 2.09 mg mL À1 ), non-small-cell lung carcinoma cell line A549 (IC 50 ¼ 0.49 mg mL À1 ), murine melanoma cell line B16 (IC 50 ¼ 6.28 mg mL À1 ), chronic myeloid leukemia cell line K562 (IC 50 ¼ 0.16 mg mL À1 ), human colorectal adenocarcinoma cell line DLD-1 (IC 50 ¼ 0.79 mg mL À1 ), and human acute lymphoblastic leukemia cell line CCRF-CEM (IC 50 ¼ 0.49 mg mL À1 ).…”

Total Synthesis of Russuphelol: A Case of Mistaken Chirality

“…2 In 1995, Nozoe and co-workers isolated russuphelol (1), a tetracyclic member of this family, from the mushroom Russula subnigricans. 3 We became interested in russuphelol because it was reported to be a chiral molecule, and we have recently investigated conformationally chiral diphenyl ether natural products. 4 Specifically, the natural russuphelol sample was optically active ([α] D = −3.2) and had reported Cotton effects in the CD spectrum.…”