Abstract
Two new compounds, 4-(hydroxymethyl)-5-hydroxy-2H-pyran-2-one (1) and (5-hydroxy-2-oxo-2H-pyran-4-yl) methyl acetate (2), have been isolated from a marine-derived fungus Aspergillus flavus. Their structures were determined by spectroscopic data. Compound 1 induced the production of cAMP on GPR12 transfected CHO and HEK293 cells in a dose-dependent manner, which indicated 1 might be a possible ligand for GPR12.
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McGlacken GP, Fairlamb IJS . 2-Pyrone natural products and mimetics: isolation, characterisation and biological activity. Nat Prod Rep 22: 369–385 ( 2005)
Kobayashi S, Tsuchiya K, Kurokawa T, Nakagawa T, Shimada N, Iitaka Y . Pironetin, a novel plant growth regulator produced by Streptomyces sp. NK10958. II. Structural elucidation. J Antibiot 47: 703–707 ( 1994)
Tsuchiya K, Kobayashi S, Nishikiori T, Nakagawa T, Tatsuta K . Epopromycins, novel cell wall synthesis inhibitors of plant protoplast produced by Streptomyces sp. NK04000. J Antibiot 50: 261–263 ( 1997)
Suzuki K, Kuwahara A, Yoshida H, Fujita S, Nishikiori T, Nishikiori T . NF00659A1, A2, A3, B1 and B2, novel antitumor antibiotics produced by Aspergillus sp. NF 00659. I. Taxonomy, fermentation, isolation and biological activities. J Antibiot 50: 314–317 ( 1997)
Kondoh M, Usui T, Kobayashi S, Tsuchiya K, Nishikawa K, Nishikiori T, Mayumi T, Osada H . Cell cycle arrest and antitumor activity of pironetin and its derivatives. Cancer Lett 126: 29–32 ( 1998)
Barrero AF, Oltra JE, Herrador MM, Cabrera E, Sanchez JF, Quílez JF, Rojas F, Reyes JF . Gibepyrones: α-pyrones from Gibberella fujikuroi. Tetrahedron 49: 141–150 ( 1993)
Parker SR, Culter HG, Jacyno JM, Hillf RA . Biological activity of 6-pentyl-2H-pyran-2-one and its analogs. J Agric Food Chem 45: 2774–2776 ( 1997)
Christensen CM . Influence of small differences in moisture content upon the invasion of hard red winter wheat by Aspergillus restrictus and A. repens. Cereal Chem 40: 385–390 ( 1963)
Nielsen P, Sørensen J . Multi-target and medium-independent fungal antagonism by hydrolytic enzymes in Paenibacillus polymyxa and Bacillus pumilus strains from barley rhizosphere. FEMS Microbiol Ecol 22: 183–192 ( 1997)
Hirota A, Nemoto A, Tsuchiya Y, Hojo H, Abe N . Isolation of a 2-pyrone compound as an antioxidant from a fungus and its new reaction product with 1,1-diphenyl-2-picrylhydrazyl radical. Biosci Biotechnol Biochem 63: 418–420 ( 1999)
Yasuyuki H . Isolation of 5-hydroxy-α-pyrone and its β-D-glucoside from Erigeron and their use as aging inhibitors for plants and glycosidase inhibitors. JP 04198177, July 17 ( 1992)
Uhlenbrock K, Gassenhuber H, Kostenis E . Sphingosine 1-phosphate is a ligand of the human GPR3, GPR6 and GPR12 family of constitutively active G protein-coupled receptors. Cell Signal 14: 941–953 ( 2002)
Mosmann T . Rapid colorimetric assay for cellular growth and survival: application to proliferation and cytotoxicity assays. J Immunol Methods 65: 55–63 ( 1983)
Drews J . Drug discovery: a historical perspective. Science 287: 1960–1964 ( 2000)
Bjursell M, Gerdin AK, Jōnsson M, Surve VV, Svensson L, Huang XF, Tōrnell J, Bohlooly -YM . G protein-coupled receptor 12 deficiency results in dyslipidemia and obesity in mice. Biochem Biophys Res Commun 348: 359–366 ( 2006)
Eidne KA, Zabavnik J, Peters T, Yoshida S, Anderson L, Taylor PL . Cloning, sequencing and tissue distribution of a candidate G protein-coupled receptor from rat pituitary gland. FEBS 292: 243–248 ( 1991)
Song ZH, Modi W, Bommer TI . Molecular cloning and chromosomal localization of human genes encoding three closely related G protein-coupled receptors. Genomics 28: 347–349 ( 1995)
Tanaka S, Ishii K, Kasai K, Yoon SO, Saeki Y . Neural expression of G protein-coupled receptors GPR3, GPR6, and GPR12 up-regulates cyclic AMP levels and promotes neurite outgrowth. J Biol Chem 282: 10506–10515 ( 2007)
Ignatov A, Lintzel J, Hermans-Borgmeyer I, Kreienkamp HJ, Joost P, Thomsen S, Methner A, Schaller HC . Role of the G-protein-coupled receptor GPR12 as high-affinity receptor for sphingosylphosphorylcholine and its expression and function in brain development. J Neurosci 23: 907–914 ( 2003)
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Lin, A., Lu, X., Fang, Y. et al. Two New 5-Hydroxy-2-pyrone Derivatives Isolated from a Marine-derived Fungus Aspergillus flavus. J Antibiot 61, 245–249 (2008). https://doi.org/10.1038/ja.2008.36
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DOI: https://doi.org/10.1038/ja.2008.36
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