Sterols from a soft coral, Dendronephthya gigantea as farnesoid X-activated receptor antagonists

Kyoungjin Shin; Jungwook Chin; Dongyup Hahn; Jaehwan Lee; Hoosang Hwang; Dong Hwan Won; Jungyeob Ham; Hyukjae Choi; Eunsoo Kang; Hiyoung Kim; Moon Kyeong Ju; Sang Jip Nam; Heonjoong Kang

doi:10.1016/j.steroids.2011.12.027

Sterols from a soft coral, Dendronephthya gigantea as farnesoid X-activated receptor antagonists

Kyoungjin Shin, Jungwook Chin, Dongyup Hahn, Jaehwan Lee, Hoosang Hwang, Dong Hwan Won, Jungyeob Ham, Hyukjae Choi, Eunsoo Kang, Hiyoung Kim, Moon Kyeong Ju, Sang Jip Nam, Heonjoong Kang

Chemistry & Nanoscience

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

21 Scopus citations

Abstract

Three new steroids 3-oxocholest-1,22-dien-12β-ol (1), 3-oxocholest-1,4-dien-20β-ol (2), 3-oxocholest-1,4-dien-12β-ol (3), and three known steroids (20S)-20-Hydroxyergosta-1,4,24(28)-trien-3-one (4) [7a], 5α,8α-Epidioxycholesta-6,22-dien-3β-ol (5) [10] and 5-cholestene-3β,12β-diol (6) [11] were isolated from a soft coral Dendronephthya gigantea. Their chemical structures and relative stereochemistry were elucidated by the analysis of HRMS and 2-D NMR spectroscopic data. The steroids 1 and 2 showed notable inhibitory activity against farnesoid X-activated receptor (FXR) with IC ₅₀'s 14 and 15 μM.

Original language	English
Pages (from-to)	355-359
Number of pages	5
Journal	Steroids
Volume	77
Issue number	5
DOIs	https://doi.org/10.1016/j.steroids.2011.12.027
State	Published - Apr 2012

Keywords

Cholestasis
Dendronephthya gigantea
Farnesoid X-activated receptor

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10.1016/j.steroids.2011.12.027

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@article{9e35be2b054e4e7a954a98016260e25f,

title = "Sterols from a soft coral, Dendronephthya gigantea as farnesoid X-activated receptor antagonists",

abstract = "Three new steroids 3-oxocholest-1,22-dien-12β-ol (1), 3-oxocholest-1,4-dien-20β-ol (2), 3-oxocholest-1,4-dien-12β-ol (3), and three known steroids (20S)-20-Hydroxyergosta-1,4,24(28)-trien-3-one (4) [7a], 5α,8α-Epidioxycholesta-6,22-dien-3β-ol (5) [10] and 5-cholestene-3β,12β-diol (6) [11] were isolated from a soft coral Dendronephthya gigantea. Their chemical structures and relative stereochemistry were elucidated by the analysis of HRMS and 2-D NMR spectroscopic data. The steroids 1 and 2 showed notable inhibitory activity against farnesoid X-activated receptor (FXR) with IC 50's 14 and 15 μM.",

keywords = "Cholestasis, Dendronephthya gigantea, Farnesoid X-activated receptor",

author = "Kyoungjin Shin and Jungwook Chin and Dongyup Hahn and Jaehwan Lee and Hoosang Hwang and Won, {Dong Hwan} and Jungyeob Ham and Hyukjae Choi and Eunsoo Kang and Hiyoung Kim and Ju, {Moon Kyeong} and Nam, {Sang Jip} and Heonjoong Kang",

note = "Funding Information: This work was supported by the Marine Biotechnology Program, Ministry of Land, Transport and Maritime Affairs. S-J. Nam, K. Shin, J. Chin, H. Hwang and H. Choi were in part supported by the BK21 program, Ministry of Education, Science and Technology, Korea. The authors thank K.N. Maloney for her help in preparing this article. ",

year = "2012",

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doi = "10.1016/j.steroids.2011.12.027",

language = "English",

volume = "77",

pages = "355--359",

journal = "Steroids",

issn = "0039-128X",

publisher = "Elsevier Inc.",

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T1 - Sterols from a soft coral, Dendronephthya gigantea as farnesoid X-activated receptor antagonists

AU - Shin, Kyoungjin

AU - Chin, Jungwook

AU - Hahn, Dongyup

AU - Lee, Jaehwan

AU - Hwang, Hoosang

AU - Won, Dong Hwan

AU - Ham, Jungyeob

AU - Choi, Hyukjae

AU - Kang, Eunsoo

AU - Kim, Hiyoung

AU - Ju, Moon Kyeong

AU - Nam, Sang Jip

AU - Kang, Heonjoong

N1 - Funding Information: This work was supported by the Marine Biotechnology Program, Ministry of Land, Transport and Maritime Affairs. S-J. Nam, K. Shin, J. Chin, H. Hwang and H. Choi were in part supported by the BK21 program, Ministry of Education, Science and Technology, Korea. The authors thank K.N. Maloney for her help in preparing this article.

PY - 2012/4

Y1 - 2012/4

N2 - Three new steroids 3-oxocholest-1,22-dien-12β-ol (1), 3-oxocholest-1,4-dien-20β-ol (2), 3-oxocholest-1,4-dien-12β-ol (3), and three known steroids (20S)-20-Hydroxyergosta-1,4,24(28)-trien-3-one (4) [7a], 5α,8α-Epidioxycholesta-6,22-dien-3β-ol (5) [10] and 5-cholestene-3β,12β-diol (6) [11] were isolated from a soft coral Dendronephthya gigantea. Their chemical structures and relative stereochemistry were elucidated by the analysis of HRMS and 2-D NMR spectroscopic data. The steroids 1 and 2 showed notable inhibitory activity against farnesoid X-activated receptor (FXR) with IC 50's 14 and 15 μM.

AB - Three new steroids 3-oxocholest-1,22-dien-12β-ol (1), 3-oxocholest-1,4-dien-20β-ol (2), 3-oxocholest-1,4-dien-12β-ol (3), and three known steroids (20S)-20-Hydroxyergosta-1,4,24(28)-trien-3-one (4) [7a], 5α,8α-Epidioxycholesta-6,22-dien-3β-ol (5) [10] and 5-cholestene-3β,12β-diol (6) [11] were isolated from a soft coral Dendronephthya gigantea. Their chemical structures and relative stereochemistry were elucidated by the analysis of HRMS and 2-D NMR spectroscopic data. The steroids 1 and 2 showed notable inhibitory activity against farnesoid X-activated receptor (FXR) with IC 50's 14 and 15 μM.

KW - Cholestasis

KW - Dendronephthya gigantea

KW - Farnesoid X-activated receptor

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IS - 5

ER -

Sterols from a soft coral, Dendronephthya gigantea as farnesoid X-activated receptor antagonists

Abstract

Keywords

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