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

6 Scopus citations

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
State	Published - 1 Oct 2014

Keywords

Absolute stereochemistry
Dimerization
Idesia polycarpa
Spiro compound

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10.1016/j.tetlet.2014.08.010

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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.",

keywords = "Absolute stereochemistry, Dimerization, Idesia polycarpa, Spiro compound",

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}",

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

language = "English",

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T1 - Isolation and structure elucidation of (-)-idescarparide, a new spiro compound from Idesia polycarpa

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

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.

KW - Absolute stereochemistry

KW - Dimerization

KW - Idesia polycarpa

KW - Spiro compound

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U2 - 10.1016/j.tetlet.2014.08.010

DO - 10.1016/j.tetlet.2014.08.010

M3 - Article

AN - SCOPUS:84910052722

SN - 0040-4039

VL - 55

SP - 5447

EP - 5449

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 40

ER -

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

Abstract

Keywords

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