Tuberatolides, potent FXR antagonists from the korean marine tunicate Botryllus tuberatus

Hyukjae Choi; Hoosang Hwang; Jungwook Chin; Euno Kim; Jaehwan Lee; Sang Jip Nam; Byoung Chan Lee; Boon Jo Rho; Heonjoong Kang

doi:10.1021/np100489u

Tuberatolides, potent FXR antagonists from the korean marine tunicate Botryllus tuberatus

Hyukjae Choi, Hoosang Hwang, Jungwook Chin, Euno Kim, Jaehwan Lee, Sang Jip Nam, Byoung Chan Lee, Boon Jo Rho, Heonjoong Kang

Department of Chemistry & Nanoscience

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

62 Scopus citations

Abstract

One isoprenoid, tuberatolide A (1), meroterpenoids tuberatolide B (2) and 2'-epi-tuberatolide B (3), and the known meroterpenoids yezoquinolide (4), (R)-sargachromenol (5), and (S)-sargachromenol (6) were isolated from the Korean marine tunicate Botryllus tuberatus. The structures of these compounds were elucidated by NMR, MS, and CD spectroscopic analyses. These terpenoids antagonized the chenodeoxycholic acid (CDCA)-activated human farnesoid X receptor (hFXR) in a cell-based co-transfection assay with IC₅₀ values as low as 1.5 μM without significant effect on steroid receptors. Furthermore, they released the co-activator peptide from the CDCA-bound hFXR ligand binding domain in cell-free surface plasmon resonance experiments.

Original language	English
Pages (from-to)	90-94
Number of pages	5
Journal	Journal of Natural Products
Volume	74
Issue number	1
DOIs	https://doi.org/10.1021/np100489u
State	Published - 28 Jan 2011

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title = "Tuberatolides, potent FXR antagonists from the korean marine tunicate Botryllus tuberatus",

abstract = "One isoprenoid, tuberatolide A (1), meroterpenoids tuberatolide B (2) and 2'-epi-tuberatolide B (3), and the known meroterpenoids yezoquinolide (4), (R)-sargachromenol (5), and (S)-sargachromenol (6) were isolated from the Korean marine tunicate Botryllus tuberatus. The structures of these compounds were elucidated by NMR, MS, and CD spectroscopic analyses. These terpenoids antagonized the chenodeoxycholic acid (CDCA)-activated human farnesoid X receptor (hFXR) in a cell-based co-transfection assay with IC50 values as low as 1.5 μM without significant effect on steroid receptors. Furthermore, they released the co-activator peptide from the CDCA-bound hFXR ligand binding domain in cell-free surface plasmon resonance experiments.",

author = "Hyukjae Choi and Hoosang Hwang and Jungwook Chin and Euno Kim and Jaehwan Lee and Nam, {Sang Jip} and Lee, {Byoung Chan} and Rho, {Boon Jo} and Heonjoong Kang",

year = "2011",

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doi = "10.1021/np100489u",

language = "English",

volume = "74",

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journal = "Journal of Natural Products",

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T1 - Tuberatolides, potent FXR antagonists from the korean marine tunicate Botryllus tuberatus

AU - Choi, Hyukjae

AU - Hwang, Hoosang

AU - Chin, Jungwook

AU - Kim, Euno

AU - Lee, Jaehwan

AU - Nam, Sang Jip

AU - Lee, Byoung Chan

AU - Rho, Boon Jo

AU - Kang, Heonjoong

PY - 2011/1/28

Y1 - 2011/1/28

N2 - One isoprenoid, tuberatolide A (1), meroterpenoids tuberatolide B (2) and 2'-epi-tuberatolide B (3), and the known meroterpenoids yezoquinolide (4), (R)-sargachromenol (5), and (S)-sargachromenol (6) were isolated from the Korean marine tunicate Botryllus tuberatus. The structures of these compounds were elucidated by NMR, MS, and CD spectroscopic analyses. These terpenoids antagonized the chenodeoxycholic acid (CDCA)-activated human farnesoid X receptor (hFXR) in a cell-based co-transfection assay with IC50 values as low as 1.5 μM without significant effect on steroid receptors. Furthermore, they released the co-activator peptide from the CDCA-bound hFXR ligand binding domain in cell-free surface plasmon resonance experiments.

AB - One isoprenoid, tuberatolide A (1), meroterpenoids tuberatolide B (2) and 2'-epi-tuberatolide B (3), and the known meroterpenoids yezoquinolide (4), (R)-sargachromenol (5), and (S)-sargachromenol (6) were isolated from the Korean marine tunicate Botryllus tuberatus. The structures of these compounds were elucidated by NMR, MS, and CD spectroscopic analyses. These terpenoids antagonized the chenodeoxycholic acid (CDCA)-activated human farnesoid X receptor (hFXR) in a cell-based co-transfection assay with IC50 values as low as 1.5 μM without significant effect on steroid receptors. Furthermore, they released the co-activator peptide from the CDCA-bound hFXR ligand binding domain in cell-free surface plasmon resonance experiments.

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JO - Journal of Natural Products

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IS - 1

ER -

Tuberatolides, potent FXR antagonists from the korean marine tunicate Botryllus tuberatus

Abstract

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