64(P31) Structures of Amamistatins A and B, Novel Bioactive Lipopeptides from an Actinomycete

DOI

Bibliographic Information

Other Title
  • 64(P31) 放線菌由来の生物活性リポペプチド、アマミスタチンA、Bの構造(ポスター発表の部)

Description

Amamistatins A (1) and B (2), novel bioactive lipopeptides, have been isolated from an actinomycete. Amamistatins A (1) and B (2) inhibited mast cell growth at 20ng/mL under the existence of SCF (stem cell factor). Since mast cells proliferate, differentiate, and are activated in allergic inflammatory tissues, they play a key role for allergic responses. A potent and selective inhibitor of mast cell growth could be a candidate for antiinflammatory drugs. Molecular formulas of 1 and 2 were determined to be C_<37>H_<55>N_5O_<11> and C_<36>H_<53>N_5O_<10> from high resolution FABMS spectra. The IR spectrum showed absorption bands at 1740, 1660, 1500 cm^<-1> that were assigned to ester, amide, and nitro groups. FeCl_3 test of 1 indicates the presence of enol structure. The 2D NMR (phase sensitive DQF COSY, HOHAHA, HSQC, HMBC) spectra suggested four partial structures (two lysine, 2,2-dimethyl-3-hydroxy acid, and trisubstituted benzene ring). The HMBC correlations shown in Figure 1 disclosed connectivties of partial structures. Since further evidence for the connectivities of the partial structures could not be obtained from NMR data, the degradation reactions of 1 were carried out. Amamistatin A (1) has two N-OH groups. Considering the molecular formula of 1, C26 must be bonded to the C30 and C30 is connected to C29. Thus, the gross structure of amamistatins A and B are shown as 1 and 2, respectively. The stereochemical assignment of amamistatins is in progress.

Journal

Details 詳細情報について

  • CRID
    1390282681056079104
  • NII Article ID
    110006679670
  • DOI
    10.24496/tennenyuki.40.0_377
  • ISSN
    24331856
  • Text Lang
    ja
  • Data Source
    • JaLC
    • CiNii Articles
  • Abstract License Flag
    Disallowed

Report a problem

Back to top