Isolation and structure elucidation of (-)-idescarparide, a new spiro compound from Idesia polycarpa

Tae Bum Kim; Hyeon Woo Kim; Mina Lee; Hyang Hwa Lee; Seung Hyun Kim; Sung Kwon Kang; Sang Hyun Sung

doi:10.1016/j.tetlet.2014.08.010

Isolation and structure elucidation of (-)-idescarparide, a new spiro compound from Idesia polycarpa

Tae Bum Kim, Hyeon Woo Kim, Mina Lee, Hyang Hwa Lee, Seung Hyun Kim, Sung Kwon Kang, Sang Hyun Sung

Department of Pharmacy

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

4 Citations (Scopus)

Abstract

(-)-Idescarparide, a new spiro compound possessing a tetrahydrobenzodioxole structure from the fruit of Idesia polycarpa Maxim. was identified to be a dimer of (-)-idescarpin by spectroscopic analysis. The absolute configuration of (-)-idescarpin was firstly determined to be of S form by using single-crystal X-ray diffraction. The absolute configuration of (-)-idescarparide was confirmed by comparison with semi-synthetic (-)-idescarparide, achieved via triethylamine-catalyzed dimerization of (-)-idescarpin. (-)-Idescarparide significantly reduced lipid production in 3T3-L1 cells.

Original language	English
Pages (from-to)	5447-5449
Number of pages	3
Journal	Tetrahedron Letters
Volume	55
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2014.08.010
Publication status	Published - 2014 Oct 1

Bibliographical note

Funding Information:
This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning ( NRF-2013R1A2A2A01016296 ). We thank Sang Il Han (Medicinal Plant Garden, Seoul National University, Goyang, Korea) for kindly providing the I. polycarpa . We also thank Dr. Suckchang Hong and Dr. Hong Chan An (College of Pharmacy, Seoul National University) for helpful discussions on dimerization chemistry.

Publisher Copyright:
© 2014 Elsevier Ltd. All rights reserved.

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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title = "Isolation and structure elucidation of (-)-idescarparide, a new spiro compound from Idesia polycarpa",

abstract = "(-)-Idescarparide, a new spiro compound possessing a tetrahydrobenzodioxole structure from the fruit of Idesia polycarpa Maxim. was identified to be a dimer of (-)-idescarpin by spectroscopic analysis. The absolute configuration of (-)-idescarpin was firstly determined to be of S form by using single-crystal X-ray diffraction. The absolute configuration of (-)-idescarparide was confirmed by comparison with semi-synthetic (-)-idescarparide, achieved via triethylamine-catalyzed dimerization of (-)-idescarpin. (-)-Idescarparide significantly reduced lipid production in 3T3-L1 cells.",

author = "Kim, {Tae Bum} and Kim, {Hyeon Woo} and Mina Lee and Lee, {Hyang Hwa} and Kim, {Seung Hyun} and Kang, {Sung Kwon} and Sung, {Sang Hyun}",

note = "Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning ( NRF-2013R1A2A2A01016296 ). We thank Sang Il Han (Medicinal Plant Garden, Seoul National University, Goyang, Korea) for kindly providing the I. polycarpa . We also thank Dr. Suckchang Hong and Dr. Hong Chan An (College of Pharmacy, Seoul National University) for helpful discussions on dimerization chemistry. Publisher Copyright: {\textcopyright} 2014 Elsevier Ltd. All rights reserved.",

year = "2014",

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doi = "10.1016/j.tetlet.2014.08.010",

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AU - Kim, Tae Bum

AU - Kim, Hyeon Woo

AU - Lee, Mina

AU - Lee, Hyang Hwa

AU - Kim, Seung Hyun

AU - Kang, Sung Kwon

AU - Sung, Sang Hyun

N1 - Funding Information: This research was supported by the Basic Science Research Program through the National Research Foundation of Korea (NRF) funded by the Ministry of Science, ICT and Future Planning ( NRF-2013R1A2A2A01016296 ). We thank Sang Il Han (Medicinal Plant Garden, Seoul National University, Goyang, Korea) for kindly providing the I. polycarpa . We also thank Dr. Suckchang Hong and Dr. Hong Chan An (College of Pharmacy, Seoul National University) for helpful discussions on dimerization chemistry. Publisher Copyright: © 2014 Elsevier Ltd. All rights reserved.

PY - 2014/10/1

Y1 - 2014/10/1

N2 - (-)-Idescarparide, a new spiro compound possessing a tetrahydrobenzodioxole structure from the fruit of Idesia polycarpa Maxim. was identified to be a dimer of (-)-idescarpin by spectroscopic analysis. The absolute configuration of (-)-idescarpin was firstly determined to be of S form by using single-crystal X-ray diffraction. The absolute configuration of (-)-idescarparide was confirmed by comparison with semi-synthetic (-)-idescarparide, achieved via triethylamine-catalyzed dimerization of (-)-idescarpin. (-)-Idescarparide significantly reduced lipid production in 3T3-L1 cells.

AB - (-)-Idescarparide, a new spiro compound possessing a tetrahydrobenzodioxole structure from the fruit of Idesia polycarpa Maxim. was identified to be a dimer of (-)-idescarpin by spectroscopic analysis. The absolute configuration of (-)-idescarpin was firstly determined to be of S form by using single-crystal X-ray diffraction. The absolute configuration of (-)-idescarparide was confirmed by comparison with semi-synthetic (-)-idescarparide, achieved via triethylamine-catalyzed dimerization of (-)-idescarpin. (-)-Idescarparide significantly reduced lipid production in 3T3-L1 cells.

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Isolation and structure elucidation of (-)-idescarparide, a new spiro compound from Idesia polycarpa

Abstract

Bibliographical note

All Science Journal Classification (ASJC) codes

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