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

20 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",

year = "2016",

month = may,

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

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journal = "Tetrahedron Letters",

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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

PY - 2016/5/4

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N2 - 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.

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

UR - https://www.scopus.com/pages/publications/84962124794

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DO - 10.1016/j.tetlet.2016.03.084

M3 - Article

AN - SCOPUS:84962124794

SN - 0040-4039

VL - 57

SP - 1997

EP - 2000

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 18

ER -

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

Abstract

Bibliographical note

Keywords

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