Isogloiosiphone B, a novel acetal, and hydrophobic compounds as β-glucuronidase inhibitors derived from the red alga Neodilsea yendoana

Abstract A novel acetal named isogloiosiphone B was isolated from the red alga Neodilsea yendoana, along with three known hydrophobic compounds as β-glucuronidase inhibitors. The acetal was determined as a naturally occurring compound from the extraction experiments with several kinds of solvent. The acetal showed the highest inhibition against β-glucuronidase among the compounds examined.

[1]  Qurat-Ul-Ain,et al.  Biology-oriented drug synthesis (BIODS): In vitro β-glucuronidase inhibitory and in silico studies on 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl aryl carboxylate derivatives. , 2017, European journal of medicinal chemistry.

[2]  N. Ismail,et al.  Synthesis of benzimidazole derivatives as potent β-glucuronidase inhibitors. , 2015, Bioorganic chemistry.

[3]  J. N. Kumar,et al.  Catalytic Aerobic Oxidation of Alcohols using Recoverable IAPNO α‐Hydrogen Nitroxyl Radicals , 2015 .

[4]  M. Choudhary,et al.  Synthesis and β-glucuronidase inhibitory activity of 2-arylquinazolin-4(3H)-ones. , 2014, Bioorganic & medicinal chemistry.

[5]  J. Zachary,et al.  Lysosomal β-glucuronidase regulates Lyme and rheumatoid arthritis severity. , 2014, The Journal of clinical investigation.

[6]  S. Saeidnia,et al.  Sterols from the red algae, Gracilaria salicornia and Hypnea flagelliformis, from Persian Gulf , 2011, Pharmacognosy magazine.

[7]  H. Kurihara,et al.  β-Glucuronidase Inhibitory Activity of Bromophenols Purified from Grateloupia elliptica , 2008 .

[8]  M. Court,et al.  Effect of the β‐glucuronidase inhibitor saccharolactone on glucuronidation by human tissue microsomes and recombinant UDP‐glucuronosyltransferases , 2008, The Journal of pharmacy and pharmacology.

[9]  H. W. Scheeren,et al.  Beta-glucuronidase-mediated drug release. , 2002, Current pharmaceutical design.

[10]  J. Backman,et al.  The Role of β-Glucuronidase in Drug Disposition and Drug Targeting in Humans , 1997 .

[11]  Y. Matsuo,et al.  Yendolipin, a Novel Lipobetaine with an Inhibitory Activity Toward Morphogenesis in a Foliaceous Green Alga Monostroma oxyspermum. , 1997 .

[12]  Minoru Suzuki,et al.  An allelopathic polyunsaturated fatty acid from red algae , 1996 .

[13]  W. Gerwick,et al.  Gloiosiphones A and B, novel metabolites from the red marine alga Gloiosiphonia verticillaris , 1993 .

[14]  H. Ohta,et al.  Serum immunoreactive beta-glucuronidase determined by an enzyme-linked immunosorbent assay in patients with hepatic diseases. , 1992, Clinica chimica acta; international journal of clinical chemistry.

[15]  J. Clardy,et al.  Laurencione, a heterocycle from the red alga Laurencia spectabilis , 1992 .

[16]  V. Chapman,et al.  The egasyn gene affects the processing of oligosaccharides of lysosomal beta-glucuronidase in liver. , 1986, The Biochemical journal.

[17]  S. Hatanaka,et al.  Sulfur-containing Amino Acids in Nature , 1977 .

[18]  R. Jacox,et al.  Variations of beta glucuronidase concentration in abnormal human synovial fluid. , 1955, The Journal of clinical investigation.

[19]  G. A. Levvy,et al.  Glucuronide Decomposition in the Digestive Tract , 1952, Nature.

[20]  J. Backman,et al.  The role of beta-glucuronidase in drug disposition and drug targeting in humans. , 1997, Clinical pharmacokinetics.

[21]  I. Tannock,et al.  Lysosomes, lysosomal enzymes, and cancer. , 1993, Advances in cancer research.

[22]  J. Cabezas,et al.  Properties of two molecular forms of beta-glucuronidase from the mollusc Littorina littorea L. , 1979, European journal of biochemistry.

[23]  R. Cutler,et al.  Failure of urinary beta-glucuronidase activity to localize the site of urinary tract infection. , 1971, Applied microbiology.

[24]  M. Kuriyama.  NINHYDRIN REACTIVE SUBSTANCES IN MARINE ALGAE-III , 1961 .