Abstract
A novel nucleoside, 9-β-d-ribopyranosylpurine (2), along with three known nucleosides, adenosine (1), uridine (3) and nebularine (4), were isolated from the edible mushroom, Tricholoma japonicum. The structure of 2 was determined as 9-β-d-ribopyranosylpurine by comparing the reported spectral data of 2 with that of a synthetic compound. Isolation of the glycoside, which contains the sugar ribopyranose, from natural resources is very unusual. There are reports on the synthesis of 9-β-d-ribopyranosylpurine (2), but this is the first report on the isolation from natural resources. The antiproliferative activity of compounds 1–4 was evaluated using human umbilical vein endothelial cells. Compound 4 showed the highest inhibitory activity.
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References
Ohkawa Y, Miki K, Suzuki T, Nishio K, Sugita T, Kinoshita K, Takahashi K, Koyama K (2010) Antiangiogenic metabolites from a marine-derived fungus, Hypocrea vinosa. J Nat Prod 73:579–582
Kaneko A, Tsukada M, Fukai M, Suzuki T, Nishio K, Miki K, Kinoshita K, Takahashi K, Koyama K (2010) KDR kinase inhibitor isolated from the mushroom Boletopsis leucomelas. J Nat Prod 73:1002–1004
Tsukada M, Fukai M, Miki K, Shiraishi T, Suzuki T, Nishio K, Sugita T, Ishino M, Kinoshita K, Takahashi K, Shiro M, Koyama K (2011) Chemical constituents of a marine fungus, Arthrinium sacchari. J Nat Prod 74:1645–1649
Fukai M, Tsukada M, Miki K, Suzuki T, Sugita T, Kinoshita K, Takahashi K, Shiro M, Koyama K (2012) Hypoxylonols C-F benzo [j] fluoranthenes from Hypoxylon truncatum. J Nat Prod 75:22–25
Shiozaki T, Fukai M, Hermawati E, Juliawaty LD, Syah YM, Hakim EH, Puthongking P, Suzuki T, Kinoshita K, Takahashi K, Koyama K (2013) Anti-angiogenic effect of α-mangostin. J Nat Med 67:202–206
Nagasawa I, Kaneko A, Suzuki T, Nishio K, Kinoshita K, Shiro M, Koyama K (2014) Potential anti-angiogenesis effects of p-terphenyl compounds from Polyozellus multiplex. J Nat Prod 77:963–968
Fukai M, Suzuki T, Ikuko N, Kinoshita K, Takahashi K, Koyama K (2014) Antiangiogenic activity of hypoxylonol C. J Nat Prod 77:1065–1068
Iwamura H, Hashizume T (1968) Synthesis in nucleoside antibiotics. II. Facile synthesis of nebularine and its analogs by a modified fusion procedure. J Org Chem 33:1796–1799
Biesele JJ, Slautterback CM, Margolis M (1955) Unsubstituted purine and its riboside as toxic antimetanolites in mouse tissue cultures. Cancer 8:87–96
Sokoloski JA, Lee CW, Handschumacher RE, Nigam A, Sartorelli AC (1991) Effects of uridine on the growth and differentiation of HL-60 leukemia cells. Leuk Res 15:1051–1058
Kozlowska M, Smolenski RT, Makarewicz W, Hoffmann C, Jasotrff B, Swierczynski J (1999) ATP depletion, purine riboside triphosphate accumulation and rat thymocyte death induced by purine riboside. Toxicol Lett 104:171–181
Swayze EE, Drach JC, Worting LL, Townsend LB (1997) Synthesis, antiproliferative and antiviral activity of imidazo [4,5-d] isothiazole nucleosides as 5:5 fused analogs of nebularine and 6-methylpurine ribonucleoside. J Med Chem 40:771–784
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Haraguchi, A., Kinoshita, K., Fukai, M. et al. A novel nucleoside from the edible mushroom, Tricholoma japonicum . J Nat Med 69, 584–588 (2015). https://doi.org/10.1007/s11418-015-0917-5
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DOI: https://doi.org/10.1007/s11418-015-0917-5