A sesquiterpene quinone, 5-Epi-smenospongine, promotes TNF-α production in LPS-stimulated RAW 264.7 cells

Taiko Oda; Weifang Wang; Kazuyo Ukai; Takahiro Nakazawa; Masataka Mochizuki

doi:10.3390/md504151

A sesquiterpene quinone, 5-Epi-smenospongine, promotes TNF-α production in LPS-stimulated RAW 264.7 cells

Taiko Oda, Weifang Wang, Kazuyo Ukai, Takahiro Nakazawa, Masataka Mochizuki

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

16 Citations (Scopus)

Abstract

Eight sesquiterpene quinones: ilimaquinone (1), smenospongidine (3), smenospongiarine (5), smenospongine (7), and their corresponding 5-epimers 2, 4, 6, and 8, isolated from the Palauan marine sponge Hippospongia sp., were examined regarding their effects on TNF-α production in LPS-stimulated RAW 264.7 cells. 5-Epi-smenospongine (8) promoted the production of TNF-α to a level three times greater than the control at 10 μM, but compounds 1-7 did not show apparent activity. The results suggest that the cis-decaline ring and a primary amine in the benzoquinone ring are necessary for activity. This is the first study to report the modulation of TNF-α production by a sesquiterpene quinone.

Original language	English
Pages (from-to)	151-156
Number of pages	6
Journal	Marine Drugs
Volume	5
Issue number	4
DOIs	https://doi.org/10.3390/md504151
Publication status	Published - 2007 Dec
Externally published	Yes

Keywords

Hippospongia sp.
Marine sponge
RAW 264.7 cells
Sesquiterpene quinone
TNF-α production

ASJC Scopus subject areas

Drug Discovery

UN SDGs

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

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10.3390/md504151

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title = "A sesquiterpene quinone, 5-Epi-smenospongine, promotes TNF-α production in LPS-stimulated RAW 264.7 cells",

abstract = "Eight sesquiterpene quinones: ilimaquinone (1), smenospongidine (3), smenospongiarine (5), smenospongine (7), and their corresponding 5-epimers 2, 4, 6, and 8, isolated from the Palauan marine sponge Hippospongia sp., were examined regarding their effects on TNF-α production in LPS-stimulated RAW 264.7 cells. 5-Epi-smenospongine (8) promoted the production of TNF-α to a level three times greater than the control at 10 μM, but compounds 1-7 did not show apparent activity. The results suggest that the cis-decaline ring and a primary amine in the benzoquinone ring are necessary for activity. This is the first study to report the modulation of TNF-α production by a sesquiterpene quinone.",

keywords = "Hippospongia sp., Marine sponge, RAW 264.7 cells, Sesquiterpene quinone, TNF-α production",

author = "Taiko Oda and Weifang Wang and Kazuyo Ukai and Takahiro Nakazawa and Masataka Mochizuki",

year = "2007",

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journal = "Marine Drugs",

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AU - Oda, Taiko

AU - Wang, Weifang

AU - Ukai, Kazuyo

AU - Nakazawa, Takahiro

AU - Mochizuki, Masataka

PY - 2007/12

Y1 - 2007/12

N2 - Eight sesquiterpene quinones: ilimaquinone (1), smenospongidine (3), smenospongiarine (5), smenospongine (7), and their corresponding 5-epimers 2, 4, 6, and 8, isolated from the Palauan marine sponge Hippospongia sp., were examined regarding their effects on TNF-α production in LPS-stimulated RAW 264.7 cells. 5-Epi-smenospongine (8) promoted the production of TNF-α to a level three times greater than the control at 10 μM, but compounds 1-7 did not show apparent activity. The results suggest that the cis-decaline ring and a primary amine in the benzoquinone ring are necessary for activity. This is the first study to report the modulation of TNF-α production by a sesquiterpene quinone.

AB - Eight sesquiterpene quinones: ilimaquinone (1), smenospongidine (3), smenospongiarine (5), smenospongine (7), and their corresponding 5-epimers 2, 4, 6, and 8, isolated from the Palauan marine sponge Hippospongia sp., were examined regarding their effects on TNF-α production in LPS-stimulated RAW 264.7 cells. 5-Epi-smenospongine (8) promoted the production of TNF-α to a level three times greater than the control at 10 μM, but compounds 1-7 did not show apparent activity. The results suggest that the cis-decaline ring and a primary amine in the benzoquinone ring are necessary for activity. This is the first study to report the modulation of TNF-α production by a sesquiterpene quinone.

KW - Hippospongia sp.

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KW - RAW 264.7 cells

KW - Sesquiterpene quinone

KW - TNF-α production

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A sesquiterpene quinone, 5-Epi-smenospongine, promotes TNF-α production in LPS-stimulated RAW 264.7 cells

Abstract

Keywords

ASJC Scopus subject areas

UN SDGs

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