Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii

Shimpei Sumimoto; Arihiro Iwasaki; Osamu Ohno; Kosuke Sueyoshi; Toshiaki Teruya; Kiyotake Suenaga

doi:10.1021/acs.orglett.6b02364

Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii

Shimpei Sumimoto, Arihiro Iwasaki, Osamu Ohno, Kosuke Sueyoshi, Toshiaki Teruya, Kiyotake Suenaga

Department of Chemistry

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

23 Citations (Scopus)

Abstract

Kanamienamide, an enamide with an enol ether, was isolated from the marine cyanobacterium Moorea bouillonii. The gross structure was established by spectroscopic analyses, and the relative stereochemistry was elucidated on the basis of the analyses of NOESY correlations and ¹H-¹H coupling constants. The absolute configuration was determined on the basis of the chiral HPLC analysis of the N-Me-Leu derived from kanamienamide. This is the first report of a natural product that possesses an N-Me-enamide adjacent to an enol ether. Kanamienamide showed growth-inhibitory activity toward HeLa cells with an IC₅₀ value of 2.5 μM and induced apoptosis-like cell death.

Original language	English
Pages (from-to)	4884-4887
Number of pages	4
Journal	Organic Letters
Volume	18
Issue number	19
DOIs	https://doi.org/10.1021/acs.orglett.6b02364
Publication status	Published - 2016 Oct 7

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

UN SDGs

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

Access to Document

10.1021/acs.orglett.6b02364

Cite this

@article{bd25df36975c45d2808b9c5b563310d5,

title = "Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii",

abstract = "Kanamienamide, an enamide with an enol ether, was isolated from the marine cyanobacterium Moorea bouillonii. The gross structure was established by spectroscopic analyses, and the relative stereochemistry was elucidated on the basis of the analyses of NOESY correlations and 1H-1H coupling constants. The absolute configuration was determined on the basis of the chiral HPLC analysis of the N-Me-Leu derived from kanamienamide. This is the first report of a natural product that possesses an N-Me-enamide adjacent to an enol ether. Kanamienamide showed growth-inhibitory activity toward HeLa cells with an IC50 value of 2.5 μM and induced apoptosis-like cell death.",

author = "Shimpei Sumimoto and Arihiro Iwasaki and Osamu Ohno and Kosuke Sueyoshi and Toshiaki Teruya and Kiyotake Suenaga",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2016",

month = oct,

day = "7",

doi = "10.1021/acs.orglett.6b02364",

language = "English",

volume = "18",

pages = "4884--4887",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "19",

}

TY - JOUR

T1 - Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii

AU - Sumimoto, Shimpei

AU - Iwasaki, Arihiro

AU - Ohno, Osamu

AU - Sueyoshi, Kosuke

AU - Teruya, Toshiaki

AU - Suenaga, Kiyotake

PY - 2016/10/7

Y1 - 2016/10/7

N2 - Kanamienamide, an enamide with an enol ether, was isolated from the marine cyanobacterium Moorea bouillonii. The gross structure was established by spectroscopic analyses, and the relative stereochemistry was elucidated on the basis of the analyses of NOESY correlations and 1H-1H coupling constants. The absolute configuration was determined on the basis of the chiral HPLC analysis of the N-Me-Leu derived from kanamienamide. This is the first report of a natural product that possesses an N-Me-enamide adjacent to an enol ether. Kanamienamide showed growth-inhibitory activity toward HeLa cells with an IC50 value of 2.5 μM and induced apoptosis-like cell death.

AB - Kanamienamide, an enamide with an enol ether, was isolated from the marine cyanobacterium Moorea bouillonii. The gross structure was established by spectroscopic analyses, and the relative stereochemistry was elucidated on the basis of the analyses of NOESY correlations and 1H-1H coupling constants. The absolute configuration was determined on the basis of the chiral HPLC analysis of the N-Me-Leu derived from kanamienamide. This is the first report of a natural product that possesses an N-Me-enamide adjacent to an enol ether. Kanamienamide showed growth-inhibitory activity toward HeLa cells with an IC50 value of 2.5 μM and induced apoptosis-like cell death.

UR - http://www.scopus.com/inward/record.url?scp=84990966328&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=84990966328&partnerID=8YFLogxK

U2 - 10.1021/acs.orglett.6b02364

DO - 10.1021/acs.orglett.6b02364

M3 - Article

C2 - 27623268

AN - SCOPUS:84990966328

SN - 1523-7060

VL - 18

SP - 4884

EP - 4887

JO - Organic Letters

JF - Organic Letters

IS - 19

ER -

Kanamienamide, an Enamide with an Enol Ether from the Marine Cyanobacterium Moorea bouillonii

Abstract

ASJC Scopus subject areas

UN SDGs

Access to Document

Other files and links

Fingerprint

Cite this