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Xanthones with pancreatic lipase inhibitory activity from the pericarps of Garcinia mangostana L. (Guttiferae)

Chae, Hee‐Sung, Kim, Eun‐Young, Han, Ling, Kim, Na‐Rae, Lam, Bunthoeun, Paik, Jin Hyub, Yoon, Kee Dong, Choi, Young Hee, Chin, Young‐Won
European journal of lipid science and technology 2016 v.118 no.9 pp. 1416-1421
Garcinia mangostana, absorption, inhibitory concentration 50, kinetics, nuclear magnetic resonance spectroscopy, oleic acid, spectral analysis, triacylglycerol lipase, xanthone
Bioactivity‐guided isolation of natural compounds from the pericarps of Garcinia mangostana, using a pancreatic lipase assay, led to the identification of 13 xanthones including α‐mangostin (1), β‐mangostin (2), γ‐mangostin (3), 1‐isomangostin (4), gartanin (5), garcinone D (6), 9‐hydroxycalabaxanthone (7), smeathxanthone A (8), tovophyllin A (9), 8‐ deoxygartanin (10), mangostanin (11), calocalabaxanthone (12), and 1,7‐dihydroxy‐3‐methoxy‐2‐(3‐methylbut‐2‐enyl) xanthen‐9‐one (13). The inhibitory activities of the isolated xanthones against pancreatic lipase were evaluated and α‐mangostin (1) was found to possess the most potent inhibitory activity (IC₅₀ 5.0 µM) in a non‐competitive manner, compared with the positive control, orlistat (IC₅₀ 3.9 µM). Practical applications: Pancreatic lipase is a key enzyme in lipid absorption. A total of 13 compounds were isolated from the pericarps of G. mangostana. Their structures were characterized by HRESI‐MS, and 1D and 2D‐NMR spectroscopic data. Our results show that all the isolates exhibited inhibitory activity against pancreatic lipase. Of the active xanthones, α‐mangostin displayed the most potent lipase inhibition, with an IC₅₀ value of 5.0 μM. Furthermore, kinetic analysis of α‐mangostin was carried out. In the Lineweaver–Burk plot, the apparent Vₘₐₓ values in the presence of 1, 2, 4, and 10 µM α‐mangostin were decreased compared with those without α‐mangostin, whereas the Kₘ values of 4‐MU oleate with and without α‐mangostin were both close to 3.22 μM. Finally, it is evident that xanthone derivatives isolated from G. mangostana possess pancreatic lipase inhibitory activities. A total of 13 compounds are isolated from the pericarps of Garcinia mangostana. α‐Mangostin is found to possess the most potent lipase inhibitory activity.