Irijimasides A-E, Macrolide Glycosides from an Okeania sp. Marine Cyanobacterium

Aki Yamano; Noriyuki Natsume; Miki Yamada; Shimpei Sumimoto; Arihiro Iwasaki; Kiyotake Suenaga; Toshiaki Teruya

doi:10.1021/acs.jnatprod.0c00042

Irijimasides A-E, Macrolide Glycosides from an Okeania sp. Marine Cyanobacterium

Aki Yamano, Noriyuki Natsume, Miki Yamada, Shimpei Sumimoto, Arihiro Iwasaki, Kiyotake Suenaga, Toshiaki Teruya

Department of Chemistry

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

7 Citations (Scopus)

Abstract

Irijimasides A-E (1-5), a series of new 14-membered macrolide glycosides, were isolated from a marine cyanobacterium collected in Okinawa. The gross structures of 1-5 were established by spectroscopic analysis, including 2D NMR, while absolute stereostructures were determined based on NOESY spectra, chemical derivatization, and ECD data. All five macrolides suppressed receptor activator of nuclear factor-κB ligand (RANKL)-induced tartrate-resistant acid phosphatase (TRAP) activity in mouse RAW264 macrophage cells, indicating that these compounds inhibit osteoclast formation.

Original language	English
Pages (from-to)	1585-1591
Number of pages	7
Journal	Journal of Natural Products
Volume	83
Issue number	5
DOIs	https://doi.org/10.1021/acs.jnatprod.0c00042
Publication status	Published - 2020 May 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.0c00042

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title = "Irijimasides A-E, Macrolide Glycosides from an Okeania sp. Marine Cyanobacterium",

abstract = "Irijimasides A-E (1-5), a series of new 14-membered macrolide glycosides, were isolated from a marine cyanobacterium collected in Okinawa. The gross structures of 1-5 were established by spectroscopic analysis, including 2D NMR, while absolute stereostructures were determined based on NOESY spectra, chemical derivatization, and ECD data. All five macrolides suppressed receptor activator of nuclear factor-κB ligand (RANKL)-induced tartrate-resistant acid phosphatase (TRAP) activity in mouse RAW264 macrophage cells, indicating that these compounds inhibit osteoclast formation.",

author = "Aki Yamano and Noriyuki Natsume and Miki Yamada and Shimpei Sumimoto and Arihiro Iwasaki and Kiyotake Suenaga and Toshiaki Teruya",

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year = "2020",

month = may,

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doi = "10.1021/acs.jnatprod.0c00042",

language = "English",

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T1 - Irijimasides A-E, Macrolide Glycosides from an Okeania sp. Marine Cyanobacterium

AU - Yamano, Aki

AU - Natsume, Noriyuki

AU - Yamada, Miki

AU - Sumimoto, Shimpei

AU - Iwasaki, Arihiro

AU - Suenaga, Kiyotake

AU - Teruya, Toshiaki

N1 - Funding Information: This work was supported in part by a Grant-in-Aid for Young Scientists (B) (15K01803) from the Ministry of Education, Culture, Sports, Science and Technology, Japan, and a University of the Ryukyus Strategic Research Grant. Publisher Copyright: Copyright © 2020 American Chemical Society and American Society of Pharmacognosy.

PY - 2020/5/22

Y1 - 2020/5/22

N2 - Irijimasides A-E (1-5), a series of new 14-membered macrolide glycosides, were isolated from a marine cyanobacterium collected in Okinawa. The gross structures of 1-5 were established by spectroscopic analysis, including 2D NMR, while absolute stereostructures were determined based on NOESY spectra, chemical derivatization, and ECD data. All five macrolides suppressed receptor activator of nuclear factor-κB ligand (RANKL)-induced tartrate-resistant acid phosphatase (TRAP) activity in mouse RAW264 macrophage cells, indicating that these compounds inhibit osteoclast formation.

AB - Irijimasides A-E (1-5), a series of new 14-membered macrolide glycosides, were isolated from a marine cyanobacterium collected in Okinawa. The gross structures of 1-5 were established by spectroscopic analysis, including 2D NMR, while absolute stereostructures were determined based on NOESY spectra, chemical derivatization, and ECD data. All five macrolides suppressed receptor activator of nuclear factor-κB ligand (RANKL)-induced tartrate-resistant acid phosphatase (TRAP) activity in mouse RAW264 macrophage cells, indicating that these compounds inhibit osteoclast formation.

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Irijimasides A-E, Macrolide Glycosides from an Okeania sp. Marine Cyanobacterium

Abstract

ASJC Scopus subject areas

UN SDGs

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