Lingaoamide, a cyclic heptapeptide from a Chinese freshwater cyanobacterium Oscillatoria sp.

Arihiro Iwasaki, Naoaki Kurisawa, Tingting Wang, Xiaohui Li, Haixi Luo, Chengcong Zhu, Gaurav Patial, Xiaojun Yan, Shan He, Tal Luzzatto-Knaan, Fuli Tian, C. Benjamin Naman, Kiyotake Suenaga

Research output: Contribution to journalArticlepeer-review

Abstract

Lingaoamide (1), a new cyclic heptapeptide natural product, was isolated from a freshwater Oscillatoria cyanobacterium. The producing organism was collected in Chinese water spinach paddy farm fields in Lingao County, Hainan, China. The structure of 1 was determined by conventional mass spectrometry, NMR spectroscopy, and chemical degradation studies. Lingaoamide concentration-dependently up-regulates the biogenesis of pro-pathogenic melanin pigments (melanogenesis) in the rice blast fungus, Magnaporthe grisea, when tested in vitro. This molecule also exhibits weak in vitro inhibition (MIC 32 μg/mL) of Gram-negative Pseudomonas aeruginosa and Gram-positive Bacillus pumilus, and does not appear to impact plant growth or immune response in vivo using the model organism, Arabidopsis thaliana.

Original languageAmerican English
Article number153214
JournalTetrahedron Letters
Volume75
DOIs
StatePublished - 6 Jul 2021

Keywords

  • Cyanobacteria
  • Lingaoamide
  • Natural product
  • Oscillatoria
  • Rice blast fungus

All Science Journal Classification (ASJC) codes

  • Drug Discovery
  • Biochemistry
  • Organic Chemistry

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