Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium

Hidetoshi Ogawa, Arihiro Iwasaki, Shinpei Sumimoto, Yuki Kanamori, Osamu Ohno, Masato Iwatsuki, Aki Ishiyama, Rei Hokari, Kazuhiko Otoguro, Satoshi Omura, Kiyotake Suenaga

Research output: Contribution to journalArticle

14 Citations (Scopus)

Abstract

Janadolide, a new cyclic polyketide-peptide hybrid possessing a tert-butyl group, was isolated from an Okeania sp. marine cyanobacterium. The gross structure was elucidated by spectroscopic analyses, and the absolute configurations of the amino acid moieties were determined by acid hydrolysis and chiral-phase HPLC analyses. The absolute configuration of the two stereogenic centers in the polyketide moiety was elucidated based on a combination of degradation reactions and spectroscopic analyses including the phenyl-glycine methyl ester method. Janadolide showed potent antitrypanosomal activity with an IC50 value of 47 nM without cytotoxicity against human cells at 10 μM.

Original languageEnglish
Pages (from-to)1862-1866
Number of pages5
JournalJournal of Natural Products
Volume79
Issue number7
DOIs
Publication statusPublished - 2016 Jul 22

Fingerprint

Polyketides
Cyclic Peptides
Cyanobacteria
Cytotoxicity
Inhibitory Concentration 50
Hydrolysis
High Pressure Liquid Chromatography
Cells
Amino Acids
Degradation
Acids
glycine methyl ester

ASJC Scopus subject areas

  • Drug Discovery
  • Pharmacology
  • Pharmaceutical Science
  • Analytical Chemistry
  • Organic Chemistry
  • Molecular Medicine
  • Complementary and alternative medicine

Cite this

Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium. / Ogawa, Hidetoshi; Iwasaki, Arihiro; Sumimoto, Shinpei; Kanamori, Yuki; Ohno, Osamu; Iwatsuki, Masato; Ishiyama, Aki; Hokari, Rei; Otoguro, Kazuhiko; Omura, Satoshi; Suenaga, Kiyotake.

In: Journal of Natural Products, Vol. 79, No. 7, 22.07.2016, p. 1862-1866.

Research output: Contribution to journalArticle

Ogawa, H, Iwasaki, A, Sumimoto, S, Kanamori, Y, Ohno, O, Iwatsuki, M, Ishiyama, A, Hokari, R, Otoguro, K, Omura, S & Suenaga, K 2016, 'Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium', Journal of Natural Products, vol. 79, no. 7, pp. 1862-1866. https://doi.org/10.1021/acs.jnatprod.6b00171
Ogawa, Hidetoshi ; Iwasaki, Arihiro ; Sumimoto, Shinpei ; Kanamori, Yuki ; Ohno, Osamu ; Iwatsuki, Masato ; Ishiyama, Aki ; Hokari, Rei ; Otoguro, Kazuhiko ; Omura, Satoshi ; Suenaga, Kiyotake. / Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium. In: Journal of Natural Products. 2016 ; Vol. 79, No. 7. pp. 1862-1866.
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