PTP1B-inhibiting branched-chain fatty acid dimers from Eremophila oppositifolia subsp. angustifolia identified by high-resolution PTP1B inhibition profiling and HPLC-PDA-HRMS-SPE-NMR analysis
Publikation: Bidrag til tidsskrift › Tidsskriftartikel › fagfællebedømt
Standard
PTP1B-inhibiting branched-chain fatty acid dimers from Eremophila oppositifolia subsp. angustifolia identified by high-resolution PTP1B inhibition profiling and HPLC-PDA-HRMS-SPE-NMR analysis. / Pedersen, Hans Albert; Ndi, Chi; Semple, Susan J.; Buirchell, Bevan; Møller, Birger Lindberg; Stærk, Dan.
I: Journal of Natural Products, Bind 83, 07.04.2020, s. 1598-1610.Publikation: Bidrag til tidsskrift › Tidsskriftartikel › fagfællebedømt
Harvard
APA
Vancouver
Author
Bibtex
}
RIS
TY - JOUR
T1 - PTP1B-inhibiting branched-chain fatty acid dimers from Eremophila oppositifolia subsp. angustifolia identified by high-resolution PTP1B inhibition profiling and HPLC-PDA-HRMS-SPE-NMR analysis
AU - Pedersen, Hans Albert
AU - Ndi, Chi
AU - Semple, Susan J.
AU - Buirchell, Bevan
AU - Møller, Birger Lindberg
AU - Stærk, Dan
PY - 2020/4/7
Y1 - 2020/4/7
N2 - Ten new branched-chain fatty acid (BCFA) dimers with a substituted cyclohexene structure, five new monomers, and two known monomers, (2E,4Z,6E)-5-(acetoxymethyl)tetradeca-2,4,6-trienoic acid and its 5-hydroxymethyl analogue, were identified in the leaf extract of Eremophila oppositifolia subsp. angustifolia using a combination of HPLC-PDA-HRMS-SPE-NMR analysis and semi-preparative-scale HPLC. The dimers could be classified as three types of Diels-Alder reaction products formed between monomers at two different sites of unsaturation of the dienophile. Two of the monomers represent potential biosynthetic intermediates of branched-chain fatty acids. Several compounds were found by high-resolution bioactivity profiling to inhibit PTP1B and were purified subsequently by semi-preparative-scale HPLC. The dimers were generally more potent than the monomers with IC50 values ranging from 2-66 μM, compared to 38-484 μM for the monomers. The ten fatty acid dimers represent both a novel class of compounds and a novel class of PTP1B inhibitors
AB - Ten new branched-chain fatty acid (BCFA) dimers with a substituted cyclohexene structure, five new monomers, and two known monomers, (2E,4Z,6E)-5-(acetoxymethyl)tetradeca-2,4,6-trienoic acid and its 5-hydroxymethyl analogue, were identified in the leaf extract of Eremophila oppositifolia subsp. angustifolia using a combination of HPLC-PDA-HRMS-SPE-NMR analysis and semi-preparative-scale HPLC. The dimers could be classified as three types of Diels-Alder reaction products formed between monomers at two different sites of unsaturation of the dienophile. Two of the monomers represent potential biosynthetic intermediates of branched-chain fatty acids. Several compounds were found by high-resolution bioactivity profiling to inhibit PTP1B and were purified subsequently by semi-preparative-scale HPLC. The dimers were generally more potent than the monomers with IC50 values ranging from 2-66 μM, compared to 38-484 μM for the monomers. The ten fatty acid dimers represent both a novel class of compounds and a novel class of PTP1B inhibitors
U2 - 10.1021/acs.jnatprod.0c00070
DO - 10.1021/acs.jnatprod.0c00070
M3 - Journal article
C2 - 32255628
VL - 83
SP - 1598
EP - 1610
JO - Journal of Natural Products
JF - Journal of Natural Products
SN - 0163-3864
ER -
ID: 238498506