Phosphodiesterase and thymidine phosphorylase-inhibiting salirepin derivatives from Symplocos racemosa.
A re-investigation of the chemical constituents of the stem bark of Symplocos racemosa Roxb. led to the isolation of four new glycosides, symplocomoside (1), symponoside (2), symplososide (3) and symploveroside (4). Benzoylsalireposide (5) and salireposide (6) were re-isolated from this plant. The structures of the new compounds were determined by 1D and 2D-homonuclear and heteronuclear NMR spectroscopy, chemical evidence, and by comparison with the published data of the closely related compounds. The glycosides 1-4 displayed in vitro inhibitory activity against phosphodiesterase I with IC50 values of 122 +/- 0.017, 698 +/- 0.06, 722 +/- 0.03, 909 +/- 0.09 microM, respectively. The compounds 1-6 also showed in vitro inhibitory activity against thymidine phosphorylase with IC50 values of 189.96 +/- 1.02, 195.56 +/- 2.36, 207.61 +/- 1.06, 488.89 +/- 4.10, 427.20 +/- 5.36, 354.2 +/- 5.69 microM, respectively while 1 was also found to be a urease inhibitor with an IC50 value of 54.13 +/- 0.71 microM.
Abbasi
Muhammad Athar
MA
H.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi, Pakistan.
Ahmad
Viqar Uddin
VU
Zubair
Muhammad
M
Fatima
Naheed
N
Farooq
Umar
U
Hussain
Sajjad
S
Lodhi
Muhammad Arif
MA
Choudhary
M Iqbal
MI
D004791:Enzyme Inhibitors / Q000737:chemistry / Q000494:pharmacology*; D029791:Ericaceae; D006027:Glycosides / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D020128:Inhibitory Concentration 50; D009682:Magnetic Resonance Spectroscopy; D043264:Phosphodiesterase I / Q000037:antagonists & inhibitors; D008517:Phytotherapy; D024301:Plant Bark; D010936:Plant Extracts / Q000737:chemistry / Q000494:pharmacology*; D013329:Structure-Activity Relationship; D013939:Thymidine Phosphorylase / Q000037:antagonists & inhibitors; D014510:Urease / Q000037:antagonists & inhibitors
D004791:Enzyme Inhibitors; D006027:Glycosides; D010936:Plant Extracts; D013939:Thymidine Phosphorylase; D043264:Phosphodiesterase I; D014510:Urease