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Absolute configuration of isosilybin A by X-ray crystallography of the heavy atom analogue 7-(4-Bromobenzoyl)isosilybin A.
J Nat Prod 2012; 75(11):1879-81JN

Abstract

Isosilybin A (1) is one of the major flavonolignans that constitute silymarin, an extract of the fruits (achenes) of milk thistle (Silybum marianum). The chemistry of the Silybum flavonolignans has been studied for over four decades, and the absolute configuration of 1 has been determined previously by electronic circular dichroism and X-ray crystallography via correlating the relative configuration of the phenylpropanoid moiety to the established absolute configuration of the 3-hydroxyflavanone portion of the molecule. Herein we report the X-ray crystallographic structure of the product of the reaction of 1 with 4-bromobenzoyl chloride, and, thus, the absolute configuration of 1 was established as (2R, 3R, 7″R, 8″R) directly via X-ray crystallography of an analogue that incorporated a heavy atom. The results were consistent with previously reported assignments and verified the absolute configuration of the diastereoisomer of 1, isosilybin B, and the related diastereoisomeric regioisomers, silybin A and silybin B.

Authors+Show Affiliations

Department of Chemistry and Biochemistry, University of North Carolina at Greensboro , Greensboro, North Carolina 27402, United States.No affiliation info availableNo affiliation info available

Pub Type(s)

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

Language

eng

PubMed ID

23116206

Citation

Sy-Cordero, Arlene A., et al. "Absolute Configuration of Isosilybin a By X-ray Crystallography of the Heavy Atom Analogue 7-(4-Bromobenzoyl)isosilybin A." Journal of Natural Products, vol. 75, no. 11, 2012, pp. 1879-81.
Sy-Cordero AA, Day CS, Oberlies NH. Absolute configuration of isosilybin A by X-ray crystallography of the heavy atom analogue 7-(4-Bromobenzoyl)isosilybin A. J Nat Prod. 2012;75(11):1879-81.
Sy-Cordero, A. A., Day, C. S., & Oberlies, N. H. (2012). Absolute configuration of isosilybin A by X-ray crystallography of the heavy atom analogue 7-(4-Bromobenzoyl)isosilybin A. Journal of Natural Products, 75(11), pp. 1879-81. doi:10.1021/np3005369.
Sy-Cordero AA, Day CS, Oberlies NH. Absolute Configuration of Isosilybin a By X-ray Crystallography of the Heavy Atom Analogue 7-(4-Bromobenzoyl)isosilybin A. J Nat Prod. 2012 Nov 26;75(11):1879-81. PubMed PMID: 23116206.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Absolute configuration of isosilybin A by X-ray crystallography of the heavy atom analogue 7-(4-Bromobenzoyl)isosilybin A. AU - Sy-Cordero,Arlene A, AU - Day,Cynthia S, AU - Oberlies,Nicholas H, Y1 - 2012/11/01/ PY - 2012/11/3/entrez PY - 2012/11/3/pubmed PY - 2014/5/9/medline SP - 1879 EP - 81 JF - Journal of natural products JO - J. Nat. Prod. VL - 75 IS - 11 N2 - Isosilybin A (1) is one of the major flavonolignans that constitute silymarin, an extract of the fruits (achenes) of milk thistle (Silybum marianum). The chemistry of the Silybum flavonolignans has been studied for over four decades, and the absolute configuration of 1 has been determined previously by electronic circular dichroism and X-ray crystallography via correlating the relative configuration of the phenylpropanoid moiety to the established absolute configuration of the 3-hydroxyflavanone portion of the molecule. Herein we report the X-ray crystallographic structure of the product of the reaction of 1 with 4-bromobenzoyl chloride, and, thus, the absolute configuration of 1 was established as (2R, 3R, 7″R, 8″R) directly via X-ray crystallography of an analogue that incorporated a heavy atom. The results were consistent with previously reported assignments and verified the absolute configuration of the diastereoisomer of 1, isosilybin B, and the related diastereoisomeric regioisomers, silybin A and silybin B. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/23116206/Absolute_configuration_of_isosilybin_A_by_X_ray_crystallography_of_the_heavy_atom_analogue_7__4_Bromobenzoyl_isosilybin_A_ L2 - https://dx.doi.org/10.1021/np3005369 DB - PRIME DP - Unbound Medicine ER -