Tags

Type your tag names separated by a space and hit enter

Trimeric and Tetrameric A-Type Procyanidins from Peanut Skins.
J Nat Prod. 2017 02 24; 80(2):415-426.JN

Abstract

Peanut skins are a rich source of oligomeric and polymeric procyanidins. The oligomeric fractions are dominated by dimers, trimers, and tetramers. A multistep chromatographic fractionation led to the isolation of four new A-type procyanidins of tri- and tetrameric structures. The structures of the new trimers were defined by NMR, electronic circular dichroism, and MS data as epicatechin-(4β→8,2β→O→7)-epicatechin-(4β→8,2β→O→7)-catechin, peanut procyanidin B (3), and epicatechin-(4β→8,2β→O→7)-epicatechin-(4β→6)-catechin, peanut procyanidin C (4). The new tetramers were defined as epicatechin-(4β→8,2β→O→7)-epicatechin-(4β→6)-epicatechin-(4β→8,2β→O→7)-catechin, peanut procyanidin E (1), and epicatechin-(4β→8,2β→O→7)-epicatechin-(4β→6)-epicatechin-(4β→8,2β→O→7)-epicatechin, peanut procyanidin F (2). In addition, both A-type dimers A1, epicatechin-(4β→8,2β→O→7)-catechin, and A2, epicatechin-(4β→8,2β→O→7)-epicatechin, as well as two known peanut trimers, ent-epicatechin-(4β→6)-epicatechin-(4β→8,2β→O→7)-catechin, peanut procyanidin A (5), and epicatechin-(4β→8)-epicatechin-(4β→8,2β→O→7)-catechin, peanut procyanidin D (6), were also isolated. Dimer A1, the four trimers, and two tetramers were evaluated for anti-inflammatory activity in an in vitro assay, in which LPS-stimulated macrophages were responding with secretion of TNF-α, a pro-inflammatory cytokine. Tetramer F (2) was the most potent, suppressing TNF-α secretion to 82% at 8.7 μM (10 μg/mL), while tetramer E (1) at the same concentrations caused a 4% suppression. The results of the TNF-α secretion inhibition indicate that small structural differences, as in peanut procyanidin tetramers E and F, can be strongly differentiated in biological systems.

Authors+Show Affiliations

Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences , Sienkiewicza 112, 90-363 Lodz, Poland. Physical Chemistry Department, Medical University of Warsaw , Banacha 1, 02-097 Warsaw, Poland.Planta Analytica LCC , 461 Danbury Road, New Milford, Connecticut 06776, United States.Planta Analytica LCC , 461 Danbury Road, New Milford, Connecticut 06776, United States.DSTest-Laboratories LLC , Purdue Research Park, 5225 Exploration Drive, Indianapolis, Indiana 46241, United States.Centre of Molecular and Macromolecular Studies, Polish Academy of Sciences , Sienkiewicza 112, 90-363 Lodz, Poland.Planta Analytica LCC , 461 Danbury Road, New Milford, Connecticut 06776, United States.

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

28231711

Citation

Dudek, Marta K., et al. "Trimeric and Tetrameric A-Type Procyanidins From Peanut Skins." Journal of Natural Products, vol. 80, no. 2, 2017, pp. 415-426.
Dudek MK, Gliński VB, Davey MH, et al. Trimeric and Tetrameric A-Type Procyanidins from Peanut Skins. J Nat Prod. 2017;80(2):415-426.
Dudek, M. K., Gliński, V. B., Davey, M. H., Sliva, D., Kaźmierski, S., & Gliński, J. A. (2017). Trimeric and Tetrameric A-Type Procyanidins from Peanut Skins. Journal of Natural Products, 80(2), 415-426. https://doi.org/10.1021/acs.jnatprod.6b00946
Dudek MK, et al. Trimeric and Tetrameric A-Type Procyanidins From Peanut Skins. J Nat Prod. 2017 02 24;80(2):415-426. PubMed PMID: 28231711.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Trimeric and Tetrameric A-Type Procyanidins from Peanut Skins. AU - Dudek,Marta K, AU - Gliński,Vitold B, AU - Davey,Matthew H, AU - Sliva,Daniel, AU - Kaźmierski,Sławomir, AU - Gliński,Jan A, Y1 - 2017/02/13/ PY - 2017/2/25/entrez PY - 2017/2/25/pubmed PY - 2017/7/15/medline SP - 415 EP - 426 JF - Journal of natural products JO - J Nat Prod VL - 80 IS - 2 N2 - Peanut skins are a rich source of oligomeric and polymeric procyanidins. The oligomeric fractions are dominated by dimers, trimers, and tetramers. A multistep chromatographic fractionation led to the isolation of four new A-type procyanidins of tri- and tetrameric structures. The structures of the new trimers were defined by NMR, electronic circular dichroism, and MS data as epicatechin-(4β→8,2β→O→7)-epicatechin-(4β→8,2β→O→7)-catechin, peanut procyanidin B (3), and epicatechin-(4β→8,2β→O→7)-epicatechin-(4β→6)-catechin, peanut procyanidin C (4). The new tetramers were defined as epicatechin-(4β→8,2β→O→7)-epicatechin-(4β→6)-epicatechin-(4β→8,2β→O→7)-catechin, peanut procyanidin E (1), and epicatechin-(4β→8,2β→O→7)-epicatechin-(4β→6)-epicatechin-(4β→8,2β→O→7)-epicatechin, peanut procyanidin F (2). In addition, both A-type dimers A1, epicatechin-(4β→8,2β→O→7)-catechin, and A2, epicatechin-(4β→8,2β→O→7)-epicatechin, as well as two known peanut trimers, ent-epicatechin-(4β→6)-epicatechin-(4β→8,2β→O→7)-catechin, peanut procyanidin A (5), and epicatechin-(4β→8)-epicatechin-(4β→8,2β→O→7)-catechin, peanut procyanidin D (6), were also isolated. Dimer A1, the four trimers, and two tetramers were evaluated for anti-inflammatory activity in an in vitro assay, in which LPS-stimulated macrophages were responding with secretion of TNF-α, a pro-inflammatory cytokine. Tetramer F (2) was the most potent, suppressing TNF-α secretion to 82% at 8.7 μM (10 μg/mL), while tetramer E (1) at the same concentrations caused a 4% suppression. The results of the TNF-α secretion inhibition indicate that small structural differences, as in peanut procyanidin tetramers E and F, can be strongly differentiated in biological systems. SN - 1520-6025 UR - https://www.unboundmedicine.com/medline/citation/28231711/Trimeric_and_Tetrameric_A_Type_Procyanidins_from_Peanut_Skins_ L2 - https://doi.org/10.1021/acs.jnatprod.6b00946 DB - PRIME DP - Unbound Medicine ER -