Mariannamides A and B, new cyclic octapeptides isolated from Mariannaea elegans NBRC102301

Kan'ichiro Ishiuchi; Dai Hirose; Taishi Kondo; Kohei Watanabe; Kazuyoshi Terasaka; Toshiaki Makino

doi:10.1016/j.bmcl.2019.126946

Mariannamides A and B, new cyclic octapeptides isolated from Mariannaea elegans NBRC102301

Kan'ichiro Ishiuchi, Dai Hirose, Taishi Kondo, Kohei Watanabe, Kazuyoshi Terasaka, Toshiaki Makino

School of Pharmacy

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

6 Citations (Scopus)

Abstract

Two new cyclic octapeptides, mariannamides A (1) and B (2), have been isolated from Mariannaea elegans NBRC102301, a Pinus densiflora-derived filamentous fungus. Their structures were elucidated to be cyclo-(L-Leu¹-L-Pro¹-L-Pro²-L-Leu²-L-Ile¹-L-Pro³-L-Val¹-L-Ile²) and cyclo-(L-Leu¹-L-Pro¹-L-Pro²-L-Leu²-L-Ile¹-L-Pro³-L-Val¹-L-Val²) based on spectroscopic data and Marfey's method. Mariannamide A (1) promoted mRNA expression of sirtuin 1 (SIRT1) in C2C12 cells, a mouse skeletal muscle myoblast cell line, and showed the antimicrobial activity against Escherichia coli and Cryptococcus neoformans.

Original language	English
Article number	126946
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	30
Issue number	4
DOIs	https://doi.org/10.1016/j.bmcl.2019.126946
Publication status	Published - 15 Feb 2020

Keywords

Cyclic peptides
Mariannaea elegans NBRC102301
Mariannamides A-B
Sirtuin 1

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10.1016/j.bmcl.2019.126946

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title = "Mariannamides A and B, new cyclic octapeptides isolated from Mariannaea elegans NBRC102301",

abstract = "Two new cyclic octapeptides, mariannamides A (1) and B (2), have been isolated from Mariannaea elegans NBRC102301, a Pinus densiflora-derived filamentous fungus. Their structures were elucidated to be cyclo-(L-Leu1-L-Pro1-L-Pro2-L-Leu2-L-Ile1-L-Pro3-L-Val1-L-Ile2) and cyclo-(L-Leu1-L-Pro1-L-Pro2-L-Leu2-L-Ile1-L-Pro3-L-Val1-L-Val2) based on spectroscopic data and Marfey's method. Mariannamide A (1) promoted mRNA expression of sirtuin 1 (SIRT1) in C2C12 cells, a mouse skeletal muscle myoblast cell line, and showed the antimicrobial activity against Escherichia coli and Cryptococcus neoformans.",

keywords = "Cyclic peptides, Mariannaea elegans NBRC102301, Mariannamides A-B, Sirtuin 1",

author = "Kan'ichiro Ishiuchi and Dai Hirose and Taishi Kondo and Kohei Watanabe and Kazuyoshi Terasaka and Toshiaki Makino",

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year = "2020",

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doi = "10.1016/j.bmcl.2019.126946",

language = "English",

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T1 - Mariannamides A and B, new cyclic octapeptides isolated from Mariannaea elegans NBRC102301

AU - Ishiuchi, Kan'ichiro

AU - Hirose, Dai

AU - Kondo, Taishi

AU - Watanabe, Kohei

AU - Terasaka, Kazuyoshi

AU - Makino, Toshiaki

PY - 2020/2/15

Y1 - 2020/2/15

N2 - Two new cyclic octapeptides, mariannamides A (1) and B (2), have been isolated from Mariannaea elegans NBRC102301, a Pinus densiflora-derived filamentous fungus. Their structures were elucidated to be cyclo-(L-Leu1-L-Pro1-L-Pro2-L-Leu2-L-Ile1-L-Pro3-L-Val1-L-Ile2) and cyclo-(L-Leu1-L-Pro1-L-Pro2-L-Leu2-L-Ile1-L-Pro3-L-Val1-L-Val2) based on spectroscopic data and Marfey's method. Mariannamide A (1) promoted mRNA expression of sirtuin 1 (SIRT1) in C2C12 cells, a mouse skeletal muscle myoblast cell line, and showed the antimicrobial activity against Escherichia coli and Cryptococcus neoformans.

AB - Two new cyclic octapeptides, mariannamides A (1) and B (2), have been isolated from Mariannaea elegans NBRC102301, a Pinus densiflora-derived filamentous fungus. Their structures were elucidated to be cyclo-(L-Leu1-L-Pro1-L-Pro2-L-Leu2-L-Ile1-L-Pro3-L-Val1-L-Ile2) and cyclo-(L-Leu1-L-Pro1-L-Pro2-L-Leu2-L-Ile1-L-Pro3-L-Val1-L-Val2) based on spectroscopic data and Marfey's method. Mariannamide A (1) promoted mRNA expression of sirtuin 1 (SIRT1) in C2C12 cells, a mouse skeletal muscle myoblast cell line, and showed the antimicrobial activity against Escherichia coli and Cryptococcus neoformans.

KW - Cyclic peptides

KW - Mariannaea elegans NBRC102301

KW - Mariannamides A-B

KW - Sirtuin 1

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SN - 0960-894X

VL - 30

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 4

M1 - 126946

ER -

Mariannamides A and B, new cyclic octapeptides isolated from Mariannaea elegans NBRC102301

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Keywords

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