Research Article

GABAergic phthalide dimers from Angelica sinensis (Oliv.) Diels

  1. Shixin Deng1,2,
  2. Shao-Nong Chen1,2,
  3. Jian Lu1,3,
  4. Zaijie Jim Wang1,3,
  5. Dejan Nikolic1,2,
  6. Richard B. van Breemen1,2,
  7. Bernard D. Santarsiero4,
  8. Andrew Mesecar4,
  9. Harry H.S. Fong1,2,
  10. Norman R. Farnsworth1,2,
  11. Guido F. Pauli1,2,*

Article first published online: 7 AUG 2006

DOI: 10.1002/pca.937

Issue

Phytochemical Analysis

Phytochemical Analysis

Volume 17, Issue 6, pages 398–405, November/December 2006

Additional Information

How to Cite

Deng, S., Chen, S.-N., Lu, J., Wang, Z. J., Nikolic, D., Breemen, R. B. v., Santarsiero, B. D., Mesecar, A., Fong, H. H., Farnsworth, N. R. and Pauli, G. F. (2006), GABAergic phthalide dimers from Angelica sinensis (Oliv.) Diels. Phytochemical Analysis, 17: 398–405. doi: 10.1002/pca.937

Author Information

  1. 1

    UIC/NIH Center for Botanical Dietary Supplements Research and Program for Collaborative Research in the Pharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, M/C 781, Chicago, IL 60612, USA

  2. 2

    Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, M/C 781, Chicago, IL 60612, USA

  3. 3

    Department of Biopharmaceutical Sciences, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, M/C 865, Chicago, IL 60612, USA

  4. 4

    Center for Pharmaceutical Biotechnology, College of Pharmacy, University of Illinois at Chicago, 900 South Ashland Avenve, M/C 780, Chicago, IL 60612, USA

*Department of Medicinal Chemistry and Pharmacognosy, College of Pharmacy, University of Illinois at Chicago, 833 South Wood Street, M/C 781, Chicago, IL, 60612, USA.

Publication History

  1. Issue published online: 18 OCT 2006
  2. Article first published online: 7 AUG 2006
  3. Manuscript Accepted: 21 JUN 2006
  4. Manuscript Revised: 20 JUN 2006
  5. Manuscript Received: 27 APR 2006

Funded by

  • NCCAM, ODS, NIGMS and ORWH. Grant Number: P50 AT00155, AT003476

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Keywords:

  • Angelica sinensis;
  • dimeric phthalides;
  • NMR;
  • GABAergic activity;
  • gelispirolide;
  • riligustilide

Abstract

The methanol extract of Angelica sinensis (Oliv.) Diels roots (Dang Gui) has been shown to exhibit competitive binding to the GABAa receptor, suggesting the presence of GABAergic ligands. Chromatographic fractionation of the methanol extract led to the isolation of two GABAergic dimeric phthalides 1 and 2. Gelispirolide (1) was elucidated as a new phthalide dimer composed of a Z-ligustilide and a Z-butylidenephthalide unit on the basis of spectroscopic approaches including one- and two-dimensional NMR, HRESIMS and HRESIMS-MS. Compound 2 was identified as the known dimeric phthalide, riligustilide, by comparison of its spectroscopic data with literature values. Its dimeric linkage and stereochemistry were ascertained by a single crystal X-ray diffraction experiment. Both dimers 1 and 2 were found to be active in an in vitro GABAa receptor-binding assay with IC50 values of 29 and 24 µm, respectively. Copyright © 2006 John Wiley & Sons, Ltd.

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