Marinopyrones A-D, α-pyrones from marine-derived actinomycetes of the family Nocardiopsaceae

Jihye Lee; Chulkyeong Han; Tae Gu Lee; Jungwook Chin; Hyukjae Choi; Wonjae Lee; Man Jeong Paik; Dong Hwan Won; Gyusang Jeong; Jaeyoung Ko; Yeo Joon Yoon; Sang Jip Nam; William Fenical; Heonjoong Kang

doi:10.1016/j.tetlet.2016.03.084

Marinopyrones A-D, α-pyrones from marine-derived actinomycetes of the family Nocardiopsaceae

Jihye Lee, Chulkyeong Han, Tae Gu Lee, Jungwook Chin, Hyukjae Choi, Wonjae Lee, Man Jeong Paik, Dong Hwan Won, Gyusang Jeong, Jaeyoung Ko, Yeo Joon Yoon, Sang Jip Nam, William Fenical, Heonjoong Kang

Department of Chemistry & Nanoscience

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

18 Scopus citations

Abstract

Two actinomycetes, a member of the rare halophilic genus Streptomonospora and a Nocardiopsis sp. (Nocardiopsaceae), strains CNQ-082 and CNQ-675, respectively, were isolated from marine sediments collected off shore near La Jolla, California. HPLC-UV guided fractionations of the extracts of these strains yielded marinopyrones A-D (1-4), the structures of which were elucidated by interpretation of 1D and 2D NMR and HRMS spectroscopic data. Oxidative ozonation, followed by conversion of the acid product to an α-naphthyl amide, provided the absolute configuration at the chiral center on the side-chain. Marinopyrones A-D were examined for the inhibitory activity on nitric oxide production in LPS-activated mouse macrophage cells (RAW 264.7); marinopyrone D (4) was inhibitory with an IC₅₀ value of 13 μM. To our knowledge, marinopyrones A-C are only the second reported natural products from the rare halophilic genus Streptomonospora.

Original language	English
Pages (from-to)	1997-2000
Number of pages	4
Journal	Tetrahedron Letters
Volume	57
Issue number	18
DOIs	https://doi.org/10.1016/j.tetlet.2016.03.084
State	Published - 4 May 2016

Bibliographical note

Publisher Copyright:
© 2016 Elsevier Ltd. All rights reserved.

Keywords

Anti-inflammatory activity
Nocardiopsis sp.
Streptomonospora sp.
α-Pyrone

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10.1016/j.tetlet.2016.03.084

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title = "Marinopyrones A-D, α-pyrones from marine-derived actinomycetes of the family Nocardiopsaceae",

abstract = "Two actinomycetes, a member of the rare halophilic genus Streptomonospora and a Nocardiopsis sp. (Nocardiopsaceae), strains CNQ-082 and CNQ-675, respectively, were isolated from marine sediments collected off shore near La Jolla, California. HPLC-UV guided fractionations of the extracts of these strains yielded marinopyrones A-D (1-4), the structures of which were elucidated by interpretation of 1D and 2D NMR and HRMS spectroscopic data. Oxidative ozonation, followed by conversion of the acid product to an α-naphthyl amide, provided the absolute configuration at the chiral center on the side-chain. Marinopyrones A-D were examined for the inhibitory activity on nitric oxide production in LPS-activated mouse macrophage cells (RAW 264.7); marinopyrone D (4) was inhibitory with an IC50 value of 13 μM. To our knowledge, marinopyrones A-C are only the second reported natural products from the rare halophilic genus Streptomonospora.",

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author = "Jihye Lee and Chulkyeong Han and Lee, {Tae Gu} and Jungwook Chin and Hyukjae Choi and Wonjae Lee and Paik, {Man Jeong} and Won, {Dong Hwan} and Gyusang Jeong and Jaeyoung Ko and Yoon, {Yeo Joon} and Nam, {Sang Jip} and William Fenical and Heonjoong Kang",

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doi = "10.1016/j.tetlet.2016.03.084",

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AU - Lee, Jihye

AU - Han, Chulkyeong

AU - Lee, Tae Gu

AU - Chin, Jungwook

AU - Choi, Hyukjae

AU - Lee, Wonjae

AU - Paik, Man Jeong

AU - Won, Dong Hwan

AU - Jeong, Gyusang

AU - Ko, Jaeyoung

AU - Yoon, Yeo Joon

AU - Nam, Sang Jip

AU - Fenical, William

AU - Kang, Heonjoong

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AB - Two actinomycetes, a member of the rare halophilic genus Streptomonospora and a Nocardiopsis sp. (Nocardiopsaceae), strains CNQ-082 and CNQ-675, respectively, were isolated from marine sediments collected off shore near La Jolla, California. HPLC-UV guided fractionations of the extracts of these strains yielded marinopyrones A-D (1-4), the structures of which were elucidated by interpretation of 1D and 2D NMR and HRMS spectroscopic data. Oxidative ozonation, followed by conversion of the acid product to an α-naphthyl amide, provided the absolute configuration at the chiral center on the side-chain. Marinopyrones A-D were examined for the inhibitory activity on nitric oxide production in LPS-activated mouse macrophage cells (RAW 264.7); marinopyrone D (4) was inhibitory with an IC50 value of 13 μM. To our knowledge, marinopyrones A-C are only the second reported natural products from the rare halophilic genus Streptomonospora.

KW - Anti-inflammatory activity

KW - Nocardiopsis sp.

KW - Streptomonospora sp.

KW - α-Pyrone

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ER -

Marinopyrones A-D, α-pyrones from marine-derived actinomycetes of the family Nocardiopsaceae

Abstract

Bibliographical note

Keywords

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