105(P-62) Ion Transporting Activities and Conformations of Divalent Monensin Derivatives

• Tanaka Rie

  Graduate School of Pharmaceutical Sciences, Nagoya City University

• Nagatsu Akito

  Graduate School of Pharmaceutical Sciences, Nagoya City University

• Hatano Keiichiro

  Graduate School of Pharmaceutical Sciences, Nagoya City University

• Mizukami Hajime

  Graduate School of Pharmaceutical Sciences, Nagoya City University

• Ogihara Yukio

  Graduate School of Pharmaceutical Sciences, Nagoya City University

• Sakakibara Jinsaku

  Graduate School of Pharmaceutical Sciences, Nagoya City University

Bibliographic Information

Other Title

• 105(P-62) Monensin二価誘導体のイオン輸送能とコンフォメーションに関する研究(ポスター発表の部)

Abstract

Antibiotic monensin (1), isolated from Streptomyces cinnamonensis, selectively transports Na^+ ion across the lipophilic biological membrane. Since the diameter of Na^+ ion is close to that of Ca^<2+> ion, the modification of monensin (1) to the divalent molecules should lead to the Ca^<2+> ionophores. Thus, we prepared 25-carboxymonensin (2) with two carboxyl groups at both ends of the molecule and measured its Ca^<2+> ion transport activity by a CHCl_3 liquid membrane method setting pH of the ionic water phase at 6.0, 7.4 and 10.0. Compound 2 transported more Ca^<2+> ion at pH 10.0 than at pH 7.4, indicating that 25-carboxymonensin shows more Ca^<2+> ion transport activity in divalent form. We measured long range ^<13>C-^1H coupling constants (^3J_<CH>) of 25-carboxymonensin (2) and 7-O-benzyl-25-carboxymonensin (2a) by J-HMBC experiment and compared with those of monensin. The values of ^3J_<CH> of 2 and 2a were similar to that of monensin, suggesting that the conformations of 25-carboxymonensins in a solution are almost same as that of monensin. These results indicated that 25-carboxymonensins transported Ca^<2+> ion in the similar conformation to monensin. We also prepared another dicarboxylic monensin derivative, 27-carboxymonensin (3), which could adopt to dicarboxylic form (3a) and lactone form (3b) depending on pH. The dicarboxlic form showed higher Ca^<2+> ion transport activity than the lactone form.

Journal

• Symposium on the Chemistry of Natural Products, symposium papers

  Symposium on the Chemistry of Natural Products, symposium papers 43 (0), 623-628, 2001

  Symposium on the Chemistry of Natural Products Steering Committee

Details

• CRID: 1390282681055873536
• NII Article ID: 110006682150
• DOI: 10.24496/tennenyuki.43.0_623
• ISSN: 24331856
• Text Lang: ja
• Data Source:
  • JaLC
  • CiNii Articles
• Abstract License Flag: Disallowed