Passakorn Teerapongpisan. Chemical constituents and biological activities of Phaeanthus iucidus oliv, Trivalvaria costata (Hookf & Thomson) IMTurner, and Uvaria rufa blume. Doctoral Degree(Applied Chemistry). Mae Fah Luang University. Learning Resources and Educational Media Center. : Mae Fah Luang University, 2022.
Chemical constituents and biological activities of Phaeanthus iucidus oliv, Trivalvaria costata (Hookf & Thomson) IMTurner, and Uvaria rufa blume
Abstract:
The phytochemical investigation of Phaeanthus lucidus Oliv., Trivalvaria costata (Hook.f. & Thomson) I.M.Turner, and Uvaria rufa Blume led to the isolation and identification of 16 new compounds along with 19 known compounds. All new compounds were fully characterized by spectroscopic methods and mass spectrometry. Some isolated compounds were evaluated for their antidiabetic activities, including α-glucosidase, α-amylase inhibitory activities, and glucose consumption.
Ten new dimeric aporphine alkaloids, trivalcostatines A−J (2.1−2.10) and a new isoquinolone alkaloid, trivalcostatine K (2.15) were isolated from the twig extract of T. costata. Four known aporphine alkaloids (2.11−2.14) were also isolated. Compounds 2.1, 2.3, and 2.14 were also confirmed by single crystal X-ray diffraction analysis. All dimeric aporphine alkaloids were atropisomers and most of them were resolved by chiral HPLC. Their absolute configurations were determined by calculated and experimental ECD analysis. Compounds 2.11−2.14 showed α-glucosidase inhibitory activities with IC50 values in the range of 4.14−10.9 μM, which better than standard control (acarbose, IC50 = 185.7 µM). The first phytochemical investigation of the twigs of P. lucidus resulted in the isolation and identification of four new isoquinoline alkaloid derivatives, including two aporphine dimers, phaeanthuslucidines A (3.2) and B (3.3), an aristolactam-aporphine hybrid, phaeanthuslucidine C (3.4), and a CN linked aporphine dimer, phaeanthuslucidine D (3.5), together with two known compounds (3.1 and 3.6). Dimeric compounds 3.1−3.4 were mixture of atropisomers, which were further resolved by chiral HPLC. The absolute configurations of each pure atroisomers were determined by ECD analysis. Compounds 3.1−3.3 and 3.6 showed α-glucosidase inhibitory activities with IC50 values in the range of 6.7−29.2 μM. A new C-benzylated flavone, uvariaruflavone (4.1), along with 13 known compounds (4.2−4.14) were isolated from the twig and leaf extracts of U. rufa. Uvariaruflavone (4.1) showed the α-glucosidase inhibitory activity with an IC50 value of 44.3 µM, while ferrudiol (4.12) displayed the highest α-amylase inhibitory activity with an IC50 value of 73.5 µM.
Mae Fah Luang University. Learning Resources and Educational Media Center