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GABAergic phthalide dimers from Angelica sinensis (Oliv.) Diels.
Phytochem Anal. 2006 Nov-Dec; 17(6):398-405.PA

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 microM, respectively.

Authors+Show Affiliations

Deng S
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.
Chen SN
No affiliation info available
Lu J
No affiliation info available
Wang ZJ
No affiliation info available
Nikolic D
No affiliation info available
van Breemen RB
No affiliation info available
Santarsiero BD
No affiliation info available
Mesecar A
No affiliation info available
Fong HH
No affiliation info available
Farnsworth NR
No affiliation info available
Pauli GF
No affiliation info available

MeSH

Angelica sinensisBenzofuransGABA AgentsModels, MolecularMolecular StructurePlant RootsProtein BindingReceptors, GABA-A

Pub Type(s)

Journal Article
Research Support, N.I.H., Extramural

Language

eng

PubMed ID

17144247

Citation

Deng, Shixin, et al. "GABAergic Phthalide Dimers From Angelica Sinensis (Oliv.) Diels." Phytochemical Analysis : PCA, vol. 17, no. 6, 2006, pp. 398-405.
Deng S, Chen SN, Lu J, et al. GABAergic phthalide dimers from Angelica sinensis (Oliv.) Diels. Phytochem Anal. 2006;17(6):398-405.
Deng, S., Chen, S. N., Lu, J., Wang, Z. J., Nikolic, D., van Breemen, R. B., Santarsiero, B. D., Mesecar, A., Fong, H. H., Farnsworth, N. R., & Pauli, G. F. (2006). GABAergic phthalide dimers from Angelica sinensis (Oliv.) Diels. Phytochemical Analysis : PCA, 17(6), 398-405.
Deng S, et al. GABAergic Phthalide Dimers From Angelica Sinensis (Oliv.) Diels. Phytochem Anal. 2006 Nov-Dec;17(6):398-405. PubMed PMID: 17144247.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - GABAergic phthalide dimers from Angelica sinensis (Oliv.) Diels. AU - Deng,Shixin, AU - Chen,Shao-Nong, AU - Lu,Jian, AU - Wang,Zaijie Jim, AU - Nikolic,Dejan, AU - van Breemen,Richard B, AU - Santarsiero,Bernard D, AU - Mesecar,Andrew, AU - Fong,Harry H S, AU - Farnsworth,Norman R, AU - Pauli,Guido F, PY - 2006/12/6/pubmed PY - 2007/3/17/medline PY - 2006/12/6/entrez SP - 398 EP - 405 JF - Phytochemical analysis : PCA JO - Phytochem Anal VL - 17 IS - 6 N2 - 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 microM, respectively. SN - 0958-0344 UR - https://www.unboundmedicine.com/medline/citation/17144247/GABAergic_phthalide_dimers_from_Angelica_sinensis__Oliv___Diels_ L2 - https://doi.org/10.1002/pca.937 DB - PRIME DP - Unbound Medicine ER -