Isolation of Jahanene and Jahanane, and Total Synthesis of the Jahanyne Family

Arihiro Iwasaki, Haruka Fujimura, Shinichiro Okamoto, Takafumi Kudo, Shizuka Hoshina, Shimpei Sumimoto, Toshiaki Teruya, Kiyotake Suenaga

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

Two new jahanyne analogues, jahanene and jahanane, highly N-methylated lipopeptides, were isolated from a marine cyanobacterium Okeania sp., and their structures were determined by NMR and MS. In addition, we achieved total syntheses of the jahanyne family and assessed their activities. The resulting growth-inhibitory activity of jahanyne was nearly one-tenth of the previously reported activity. Furthermore, we found that the degree of unsaturation at the terminus of the fatty acid moiety affected the growth-inhibitory activity against human cancer cells.

Original languageEnglish
Pages (from-to)9592-9603
Number of pages12
JournalJournal of Organic Chemistry
Volume83
Issue number17
DOIs
Publication statusPublished - 2018 Sep 7

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Lipopeptides
Fatty Acids
Cells
Nuclear magnetic resonance
jahanyne
Cyanobacteria

ASJC Scopus subject areas

  • Organic Chemistry

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Isolation of Jahanene and Jahanane, and Total Synthesis of the Jahanyne Family. / Iwasaki, Arihiro; Fujimura, Haruka; Okamoto, Shinichiro; Kudo, Takafumi; Hoshina, Shizuka; Sumimoto, Shimpei; Teruya, Toshiaki; Suenaga, Kiyotake.

In: Journal of Organic Chemistry, Vol. 83, No. 17, 07.09.2018, p. 9592-9603.

Research output: Contribution to journalArticle

Iwasaki, A, Fujimura, H, Okamoto, S, Kudo, T, Hoshina, S, Sumimoto, S, Teruya, T & Suenaga, K 2018, 'Isolation of Jahanene and Jahanane, and Total Synthesis of the Jahanyne Family', Journal of Organic Chemistry, vol. 83, no. 17, pp. 9592-9603. https://doi.org/10.1021/acs.joc.8b00310
Iwasaki, Arihiro ; Fujimura, Haruka ; Okamoto, Shinichiro ; Kudo, Takafumi ; Hoshina, Shizuka ; Sumimoto, Shimpei ; Teruya, Toshiaki ; Suenaga, Kiyotake. / Isolation of Jahanene and Jahanane, and Total Synthesis of the Jahanyne Family. In: Journal of Organic Chemistry. 2018 ; Vol. 83, No. 17. pp. 9592-9603.
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