Regioselective Synthesis of the FXR Antagonist E-Guggulsterone from Three Natural Steroids

Jungwook Chin; Dongyup Hahn; Dong Hwan Won; Sung Jin Cho; Kyung Hee Kim; Jungyeob Ham; Heonjoong Kang

doi:10.1002/bkcs.11120

Regioselective Synthesis of the FXR Antagonist E-Guggulsterone from Three Natural Steroids

Jungwook Chin, Dongyup Hahn, Dong Hwan Won, Sung Jin Cho, Kyung Hee Kim, Jungyeob Ham, Heonjoong Kang

School of Food Science & Biotechnology

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

3 Scopus citations

Abstract

In our attempt to develop a method to synthesize E- and Z-guggulsterones [antagonists of farnesoid X receptor (FXR)], we have succeeded in synthesizing E-guggulsterone selectively from three steroids, viz, 4-androsten-3, 17-dione (2), 5-androsten-3β-ol-17-one (DHEA) (3), and testosterone (4), in 68, 86 and 62% overall yield, respectively. We also investigated the biological effects of the synthetic E- and Z-guggulsterones and found that E-guggulsterone was more potent than Z-guggulsterone in inhibiting FXR transactivation.

Original language	English
Pages (from-to)	525-529
Number of pages	5
Journal	Bulletin of the Korean Chemical Society
Volume	38
Issue number	5
DOIs	https://doi.org/10.1002/bkcs.11120
State	Published - 1 May 2017

Keywords

Farnesoid X receptor antagonist
Guggulsterone
Lipid disorders
Natural steroid
Regioselective synthesis

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10.1002/bkcs.11120

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title = "Regioselective Synthesis of the FXR Antagonist E-Guggulsterone from Three Natural Steroids",

abstract = "In our attempt to develop a method to synthesize E- and Z-guggulsterones [antagonists of farnesoid X receptor (FXR)], we have succeeded in synthesizing E-guggulsterone selectively from three steroids, viz, 4-androsten-3, 17-dione (2), 5-androsten-3β-ol-17-one (DHEA) (3), and testosterone (4), in 68, 86 and 62\% overall yield, respectively. We also investigated the biological effects of the synthetic E- and Z-guggulsterones and found that E-guggulsterone was more potent than Z-guggulsterone in inhibiting FXR transactivation.",

keywords = "Farnesoid X receptor antagonist, Guggulsterone, Lipid disorders, Natural steroid, Regioselective synthesis",

author = "Jungwook Chin and Dongyup Hahn and Won, \{Dong Hwan\} and Cho, \{Sung Jin\} and Kim, \{Kyung Hee\} and Jungyeob Ham and Heonjoong Kang",

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doi = "10.1002/bkcs.11120",

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T1 - Regioselective Synthesis of the FXR Antagonist E-Guggulsterone from Three Natural Steroids

AU - Chin, Jungwook

AU - Hahn, Dongyup

AU - Won, Dong Hwan

AU - Cho, Sung Jin

AU - Kim, Kyung Hee

AU - Ham, Jungyeob

AU - Kang, Heonjoong

PY - 2017/5/1

Y1 - 2017/5/1

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AB - In our attempt to develop a method to synthesize E- and Z-guggulsterones [antagonists of farnesoid X receptor (FXR)], we have succeeded in synthesizing E-guggulsterone selectively from three steroids, viz, 4-androsten-3, 17-dione (2), 5-androsten-3β-ol-17-one (DHEA) (3), and testosterone (4), in 68, 86 and 62% overall yield, respectively. We also investigated the biological effects of the synthetic E- and Z-guggulsterones and found that E-guggulsterone was more potent than Z-guggulsterone in inhibiting FXR transactivation.

KW - Farnesoid X receptor antagonist

KW - Guggulsterone

KW - Lipid disorders

KW - Natural steroid

KW - Regioselective synthesis

UR - https://www.scopus.com/pages/publications/85017462602

U2 - 10.1002/bkcs.11120

DO - 10.1002/bkcs.11120

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JO - Bulletin of the Korean Chemical Society

JF - Bulletin of the Korean Chemical Society

IS - 5

ER -

Regioselective Synthesis of the FXR Antagonist E-Guggulsterone from Three Natural Steroids

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Keywords

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