Two new pyridine-containing limonoids, xylogranatopyridines A and B (1 and 2) and their formal precursor, prexylogranatopyridine (3) were isolated from the twigs and leaves of the Chinese mangrove, Xylocarpus granatum. Xylogranatopyridine B (2) possesses an unprecedented rearranged B-ring together with a seco-ring A, supporting the biogenetic connection of 1e2 with 3. The chemical structures were elucidated by means of detailed spectroscopic analysis and X-ray single-crystal diffraction. The absolute configurations were assigned using electronic solid-state circular dichroism (ECD) supported by timedependent density functional theory (TDDFT) ECD calculations and X-ray analysis. Xylogranatopyridine A (1) exhibited a significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) with an IC50 value of 22.9 mM. This is the first report of PTP1B inhibitory activity of limonoids
Bioactive rearranged limonoids from the Chinese mangroveXylocarpus granatum Koenig / Z., Zhou; H., Liu; W., Zhang; Ti, Kurtán; A., Mándi; A., Bényei; J., Li; TAGLIALATELA SCAFATI, Orazio; Y., Guo. - In: TETRAHEDRON. - ISSN 0040-4020. - 70:(2014), pp. 6444-6449. [10.1016/j.tet.2014.07.027]
Bioactive rearranged limonoids from the Chinese mangroveXylocarpus granatum Koenig
TAGLIALATELA SCAFATI, ORAZIO;
2014
Abstract
Two new pyridine-containing limonoids, xylogranatopyridines A and B (1 and 2) and their formal precursor, prexylogranatopyridine (3) were isolated from the twigs and leaves of the Chinese mangrove, Xylocarpus granatum. Xylogranatopyridine B (2) possesses an unprecedented rearranged B-ring together with a seco-ring A, supporting the biogenetic connection of 1e2 with 3. The chemical structures were elucidated by means of detailed spectroscopic analysis and X-ray single-crystal diffraction. The absolute configurations were assigned using electronic solid-state circular dichroism (ECD) supported by timedependent density functional theory (TDDFT) ECD calculations and X-ray analysis. Xylogranatopyridine A (1) exhibited a significant inhibitory activity against protein tyrosine phosphatase 1B (PTP1B) with an IC50 value of 22.9 mM. This is the first report of PTP1B inhibitory activity of limonoidsI documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
