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

doi:10.1021/acs.jnatprod.6b00171

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

26 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 language	English
Pages (from-to)	1862-1866
Number of pages	5
Journal	Journal of Natural Products
Volume	79
Issue number	7
DOIs	https://doi.org/10.1021/acs.jnatprod.6b00171
Publication status	Published - 2016 Jul 22

ASJC Scopus subject areas

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

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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10.1021/acs.jnatprod.6b00171

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

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.",

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doi = "10.1021/acs.jnatprod.6b00171",

language = "English",

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T1 - Janadolide, a Cyclic Polyketide-Peptide Hybrid Possessing a tert-Butyl Group from an Okeania sp. Marine Cyanobacterium

AU - Ogawa, Hidetoshi

AU - Iwasaki, Arihiro

AU - Sumimoto, Shinpei

AU - Kanamori, Yuki

AU - Ohno, Osamu

AU - Iwatsuki, Masato

AU - Ishiyama, Aki

AU - Hokari, Rei

AU - Otoguro, Kazuhiko

AU - Omura, Satoshi

AU - Suenaga, Kiyotake

PY - 2016/7/22

Y1 - 2016/7/22

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AB - 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.

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

Abstract

ASJC Scopus subject areas

UN SDGs

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