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Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, Isolated from Silybum marianum (milk thistle).
J Nat Prod 2003; 66(9):1171-4JN

Abstract

Two pairs of diastereoisomeric flavonolignans, silybin A, silybin B, isosilybin A, and isosilybin B, were successfully separated from Silybum marianum by sequential silica gel column chromatography, preparative reversed-phase HPLC, and recrystallization. Complete stereochemical assignments at C-2, C-3, C-7', and C-8' of these flavonolignans have been achieved. On the basis of X-ray crystallographic analysis and optical rotation data, coupled with comprehensive (1)H and (13)C NMR spectral data interpretation including COSY, HMQC, and HMBC, the stereochemistry of these diastereoisomers was determined unambiguously as silybin A (4), 2R, 3R, 7'R, 8'R; silybin B (5), 2R, 3R, 7'S, 8'S; isosilybin A (6), 2R, 3R, 7'R, 8'R; and isosilybin B (7), 2R, 3R, 7'S, 8'S.

Authors+Show Affiliations

Bio-Organic and Natural Product Laboratory, McLean Hospital/Harvard Medical School, 115 Mill Street, Belmont, Massachusetts 02478, USA. dlee@mclean.harvard.eduNo affiliation info available

Pub Type(s)

Journal Article
Research Support, U.S. Gov't, P.H.S.

Language

eng

PubMed ID

14510591

Citation

Lee, David Y-W, and Yanze Liu. "Molecular Structure and Stereochemistry of Silybin A, Silybin B, Isosilybin A, and Isosilybin B, Isolated From Silybum Marianum (milk Thistle)." Journal of Natural Products, vol. 66, no. 9, 2003, pp. 1171-4.
Lee DY, Liu Y. Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, Isolated from Silybum marianum (milk thistle). J Nat Prod. 2003;66(9):1171-4.
Lee, D. Y., & Liu, Y. (2003). Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, Isolated from Silybum marianum (milk thistle). Journal of Natural Products, 66(9), pp. 1171-4.
Lee DY, Liu Y. Molecular Structure and Stereochemistry of Silybin A, Silybin B, Isosilybin A, and Isosilybin B, Isolated From Silybum Marianum (milk Thistle). J Nat Prod. 2003;66(9):1171-4. PubMed PMID: 14510591.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Molecular structure and stereochemistry of silybin A, silybin B, isosilybin A, and isosilybin B, Isolated from Silybum marianum (milk thistle). AU - Lee,David Y-W, AU - Liu,Yanze, PY - 2003/9/27/pubmed PY - 2004/3/5/medline PY - 2003/9/27/entrez SP - 1171 EP - 4 JF - Journal of natural products JO - J. Nat. Prod. VL - 66 IS - 9 N2 - Two pairs of diastereoisomeric flavonolignans, silybin A, silybin B, isosilybin A, and isosilybin B, were successfully separated from Silybum marianum by sequential silica gel column chromatography, preparative reversed-phase HPLC, and recrystallization. Complete stereochemical assignments at C-2, C-3, C-7', and C-8' of these flavonolignans have been achieved. On the basis of X-ray crystallographic analysis and optical rotation data, coupled with comprehensive (1)H and (13)C NMR spectral data interpretation including COSY, HMQC, and HMBC, the stereochemistry of these diastereoisomers was determined unambiguously as silybin A (4), 2R, 3R, 7'R, 8'R; silybin B (5), 2R, 3R, 7'S, 8'S; isosilybin A (6), 2R, 3R, 7'R, 8'R; and isosilybin B (7), 2R, 3R, 7'S, 8'S. SN - 0163-3864 UR - https://www.unboundmedicine.com/medline/citation/14510591/Molecular_structure_and_stereochemistry_of_silybin_A_silybin_B_isosilybin_A_and_isosilybin_B_Isolated_from_Silybum_marianum__milk_thistle__ L2 - https://dx.doi.org/10.1021/np030163b DB - PRIME DP - Unbound Medicine ER -