Isolation, structure elucidation and PTP1B inhibitory activity of serrulatane diterpenoids from the roots of Myoporum insulare
Research output: Contribution to journal › Journal article › Research › peer-review
Standard
Isolation, structure elucidation and PTP1B inhibitory activity of serrulatane diterpenoids from the roots of Myoporum insulare. / Kjaerulff, Louise; Jensen, Alexander Bækager Just; Ndi, Chi; Semple, Susan J.; Møller, Birger Lindberg; Stærk, Dan.
In: Phytochemistry Letters, Vol. 39, 2020, p. 49-56.Research output: Contribution to journal › Journal article › Research › peer-review
Harvard
APA
Vancouver
Author
Bibtex
}
RIS
TY - JOUR
T1 - Isolation, structure elucidation and PTP1B inhibitory activity of serrulatane diterpenoids from the roots of Myoporum insulare
AU - Kjaerulff, Louise
AU - Jensen, Alexander Bækager Just
AU - Ndi, Chi
AU - Semple, Susan J.
AU - Møller, Birger Lindberg
AU - Stærk, Dan
PY - 2020
Y1 - 2020
N2 - A methylene chloride extract of Myoporum insulare R. Br. (Scrophulariaceae) root material was investigated by dual high-resolution PTP1B/α-glucosidase inhibition profiling and LC-PDA-HRMS. Subsequent analytical-scale separation of the crude extract afforded serrulatanes 1-9 of which 2 ((1R,11S,18R)-5,18-epoxyserrulat-3,14-dien-8,18-diol or myoporulatane A), 6 ((1R,4S,11S)-8-hydroxy-serrulat-14-en-18,5-olide or myoporulatane B), 7 ((1R,4S,11S)-serrulat-14-en-5,8,18-trione or myoporulatane C), and 9 ((1S, 2R,4S,11S)-2β-hydroxy-serrulat-14-ene or myoporulatane D) are previously unreported. The structures of all isolated compounds were established by HRMS as well as 1D and 2D NMR analysis. Relative configurations were determined from combined analyses of chemical shifts, J-coupling constants and ROESY correlations, and absolute configurations were tentatively assigned by comparison to previous studies and from biosynthetic arguments. Compounds correlated with PTP1B inhibitory activity in the high-resolution inhibition profile were tested after isolation. However, the pure compounds exhibited weak or essentially no inhibitory activity against PTP1B with IC50 values of 97.4 μM for 2, 3.0 mM for 4, and > 100 μM for 7. This is the first study of the root chemistry of M. insulare.
AB - A methylene chloride extract of Myoporum insulare R. Br. (Scrophulariaceae) root material was investigated by dual high-resolution PTP1B/α-glucosidase inhibition profiling and LC-PDA-HRMS. Subsequent analytical-scale separation of the crude extract afforded serrulatanes 1-9 of which 2 ((1R,11S,18R)-5,18-epoxyserrulat-3,14-dien-8,18-diol or myoporulatane A), 6 ((1R,4S,11S)-8-hydroxy-serrulat-14-en-18,5-olide or myoporulatane B), 7 ((1R,4S,11S)-serrulat-14-en-5,8,18-trione or myoporulatane C), and 9 ((1S, 2R,4S,11S)-2β-hydroxy-serrulat-14-ene or myoporulatane D) are previously unreported. The structures of all isolated compounds were established by HRMS as well as 1D and 2D NMR analysis. Relative configurations were determined from combined analyses of chemical shifts, J-coupling constants and ROESY correlations, and absolute configurations were tentatively assigned by comparison to previous studies and from biosynthetic arguments. Compounds correlated with PTP1B inhibitory activity in the high-resolution inhibition profile were tested after isolation. However, the pure compounds exhibited weak or essentially no inhibitory activity against PTP1B with IC50 values of 97.4 μM for 2, 3.0 mM for 4, and > 100 μM for 7. This is the first study of the root chemistry of M. insulare.
U2 - 10.1016/j.phytol.2020.07.001
DO - 10.1016/j.phytol.2020.07.001
M3 - Journal article
VL - 39
SP - 49
EP - 56
JO - Phytochemistry Letters
JF - Phytochemistry Letters
SN - 1874-3900
ER -
ID: 244029036