| Autor: |
Jing SX, McDermott CM; Department of Chemistry, Grandview University, Des Moines, Iowa 50316, United States., Flanders PL, Reis-Havlat M, Chen SN, Bedran-Russo AK, McAlpine JB, Ambrose EA, Pauli GF |
| Jazyk: |
angličtina |
| Zdroj: |
Journal of natural products [J Nat Prod] 2024 May 24; Vol. 87 (5), pp. 1416-1425. Date of Electronic Publication: 2024 Apr 30. |
| DOI: |
10.1021/acs.jnatprod.4c00231 |
| Abstrakt: |
In nature, proanthocyanidins (PACs) with A-type linkages are relatively rare, likely due to biosynthetic constraints in the formation of additional ether bonds to be introduced into the more common B-type precursors. However, A-type linkages confer greater structural rigidity on PACs than do B-type linkages. Prior investigations into the structure-activity relationships (SAR) describing how plant-derived PACs with B- and complex AB-type linkages affect their capacity for dentin biomodification indicate that a higher ratio of double linkages leads to a greater interaction with dentin type I collagen. Thus, A-type PACs emerge as particularly intriguing candidates for interventional functional biomaterials. This study employed a free-radical-mediated oxidation using DPPH to transform trimeric and tetrameric B-type PACs, 2 and 4 , respectively, into their exclusively A-type linked analogues, 3 and 5 , respectively. The structures and absolute configurations of the semisynthetic products, including the new all-A-type tetramer 5 , were determined by comprehensive spectroscopic analysis. Additionally, molecular modeling investigated the conformational characteristics of all trimers and tetramers, 1 - 5 . Our findings suggest that the specific interflavan linkages significantly impact the flexibility and low-energy conformations of the connected monomeric units, which conversely can affect the bioactive conformations relevant for dentin biomodification. |
| Databáze: |
MEDLINE |
| Externí odkaz: |
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