Hypoxia-inducible factor-1 and nuclear factor-κB inhibitory meroterpene analogues of bakuchiol, a constituent of the seeds of Psoralea corylifolia

Cheng Zhu Wu; Seong Su Hong; Xing Fu Cai; Nguyen Tien Dat; Ji Xing Nan; Bang Yeon Hwang; Jung Joon Lee; Dongho Lee

doi:10.1016/j.bmcl.2008.03.028

Hypoxia-inducible factor-1 and nuclear factor-κB inhibitory meroterpene analogues of bakuchiol, a constituent of the seeds of Psoralea corylifolia

Cheng Zhu Wu, Seong Su Hong, Xing Fu Cai, Nguyen Tien Dat, Ji Xing Nan, Bang Yeon Hwang, Jung Joon Lee, Dongho Lee

Department of Biosystems and Biotechnology

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

38 Citations (Scopus)

Abstract

Two new meroterpenoids, 12,13-dihydro-12,13-dihydroxybakuchiol (2) and (12′S)-bisbakuchiol C (3), were isolated from the seeds of Psoralea corylifolia L. (Fabaceae). The structures of 2 and 3 were elucidated by spectroscopic and chemical methods. Six meroterpenoids isolated from P. corylifolia and three semi-synthetic analogues were evaluated for HIF-1 and NF-κB inhibition, and O-methyl and O-ethylbakuchiols (6 and 7) inhibited HIF-1 and NF-κB activation without significantly decreasing the viability of the AGS and HeLa cells, respectively.

Original language	English
Pages (from-to)	2619-2623
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	18
Issue number	8
DOIs	https://doi.org/10.1016/j.bmcl.2008.03.028
Publication status	Published - 2008 Apr 15

Keywords

Fabaceae
Hypoxia-inducible factor-1
Meroterpenoids
Nuclear factor-κB
Psoralea corylifolia

ASJC Scopus subject areas

Biochemistry
Molecular Medicine
Molecular Biology
Pharmaceutical Science
Drug Discovery
Clinical Biochemistry
Organic Chemistry

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10.1016/j.bmcl.2008.03.028

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title = "Hypoxia-inducible factor-1 and nuclear factor-κB inhibitory meroterpene analogues of bakuchiol, a constituent of the seeds of Psoralea corylifolia",

abstract = "Two new meroterpenoids, 12,13-dihydro-12,13-dihydroxybakuchiol (2) and (12′S)-bisbakuchiol C (3), were isolated from the seeds of Psoralea corylifolia L. (Fabaceae). The structures of 2 and 3 were elucidated by spectroscopic and chemical methods. Six meroterpenoids isolated from P. corylifolia and three semi-synthetic analogues were evaluated for HIF-1 and NF-κB inhibition, and O-methyl and O-ethylbakuchiols (6 and 7) inhibited HIF-1 and NF-κB activation without significantly decreasing the viability of the AGS and HeLa cells, respectively.",

keywords = "Fabaceae, Hypoxia-inducible factor-1, Meroterpenoids, Nuclear factor-κB, Psoralea corylifolia",

author = "Wu, {Cheng Zhu} and Hong, {Seong Su} and Cai, {Xing Fu} and Dat, {Nguyen Tien} and Nan, {Ji Xing} and Hwang, {Bang Yeon} and Lee, {Jung Joon} and Dongho Lee",

note = "Funding Information: This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD, Basic Research Promotion Fund) (KRF-2006-311-E00588 to D. Lee) and by a research Grant (PF06204-00 to J.J. Lee) from Plant Diversity Research Center of 21st Frontier Research Program funded by the Korean Ministry of Science and Technology. We thank the Korea Basic Science Institute for providing certain instruments used in this study. ",

year = "2008",

month = apr,

day = "15",

doi = "10.1016/j.bmcl.2008.03.028",

language = "English",

volume = "18",

pages = "2619--2623",

journal = "Bioorganic and Medicinal Chemistry Letters",

issn = "0960-894X",

publisher = "Elsevier Limited",

number = "8",

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TY - JOUR

T1 - Hypoxia-inducible factor-1 and nuclear factor-κB inhibitory meroterpene analogues of bakuchiol, a constituent of the seeds of Psoralea corylifolia

AU - Wu, Cheng Zhu

AU - Hong, Seong Su

AU - Cai, Xing Fu

AU - Dat, Nguyen Tien

AU - Nan, Ji Xing

AU - Hwang, Bang Yeon

AU - Lee, Jung Joon

AU - Lee, Dongho

N1 - Funding Information: This work was supported by the Korea Research Foundation Grant funded by the Korean Government (MOEHRD, Basic Research Promotion Fund) (KRF-2006-311-E00588 to D. Lee) and by a research Grant (PF06204-00 to J.J. Lee) from Plant Diversity Research Center of 21st Frontier Research Program funded by the Korean Ministry of Science and Technology. We thank the Korea Basic Science Institute for providing certain instruments used in this study.

PY - 2008/4/15

Y1 - 2008/4/15

N2 - Two new meroterpenoids, 12,13-dihydro-12,13-dihydroxybakuchiol (2) and (12′S)-bisbakuchiol C (3), were isolated from the seeds of Psoralea corylifolia L. (Fabaceae). The structures of 2 and 3 were elucidated by spectroscopic and chemical methods. Six meroterpenoids isolated from P. corylifolia and three semi-synthetic analogues were evaluated for HIF-1 and NF-κB inhibition, and O-methyl and O-ethylbakuchiols (6 and 7) inhibited HIF-1 and NF-κB activation without significantly decreasing the viability of the AGS and HeLa cells, respectively.

AB - Two new meroterpenoids, 12,13-dihydro-12,13-dihydroxybakuchiol (2) and (12′S)-bisbakuchiol C (3), were isolated from the seeds of Psoralea corylifolia L. (Fabaceae). The structures of 2 and 3 were elucidated by spectroscopic and chemical methods. Six meroterpenoids isolated from P. corylifolia and three semi-synthetic analogues were evaluated for HIF-1 and NF-κB inhibition, and O-methyl and O-ethylbakuchiols (6 and 7) inhibited HIF-1 and NF-κB activation without significantly decreasing the viability of the AGS and HeLa cells, respectively.

KW - Fabaceae

KW - Hypoxia-inducible factor-1

KW - Meroterpenoids

KW - Nuclear factor-κB

KW - Psoralea corylifolia

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DO - 10.1016/j.bmcl.2008.03.028

M3 - Article

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AN - SCOPUS:41849092669

SN - 0960-894X

VL - 18

SP - 2619

EP - 2623

JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 8

ER -

Hypoxia-inducible factor-1 and nuclear factor-κB inhibitory meroterpene analogues of bakuchiol, a constituent of the seeds of Psoralea corylifolia

Abstract

Keywords

ASJC Scopus subject areas

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