Abstract
In order to obtain the biological active compound, α-mangostin, from the traditional native mangosteen (Garcinia mangostana L.), an extraction method for industrial application was explored. A high yield of α-mangostin (5.2%) was obtained by extraction from dried mangosteen pericarps with subsequent purification on macroporous resin HPD-400. The chemical structure of α-mangostin was verified mass spectrometry (MS), nuclear magnetic resonance (1H NMR and 13C NMR), infrared spectroscopy (IR) and UV-Vis spectroscopy. The purity of the obtained α-mangostin was 95.6% as determined by HPLC analysis. The binding of native α-mangostin to human serum albumin (HSA) or transferrin (TRF) was explored by combining spectral experiments with molecular modeling. The results showed that α-mangostin binds to HSA or TRF as static complexes but the binding affinities were different in different systems. The binding constants and thermodynamic parameters were measured by fluorescence spectroscopy and absorbance spectra. The association constant of HSA or TRF binding to α-mangostin is 6.4832×105 L/mol and 1.4652×105 L/mol at 298 K and 7.8619×105 L/mol and 1.1582×105 L/mol at 310 K, respectively. The binding distance, the energy transfer efficiency between α-mangostin and HSA or TRF were also obtained by virtue of the Förster theory of non-radiation energy transfer. The effect of α-mangostin on the HSA or TRF conformation was analyzed by synchronous spectrometry and fluorescence polarization studies. Molecular docking results reveal that the main interaction between α-mangostin and HSA is hydrophobic interactions, while the main interaction between α-mangostin and TRF is hydrogen bonding and Van der Waals forces. These results are consistent with spectral results.
Highlights
Mangosteen (Garcinia mangostana L.) is a member of the Garcinia genus, which mainly grows in Thailand, Vietnam, Malaysia, Indonesia, Philippines and other Southeast Asian countries
The reaction mechanism between α-mangostin and human serum albumin (HSA)/TRF has been studied by fluorescence and UV spectroscopy, as well as by computer molecular simulation
The experimental results show that the fluorescence quenching mechanism between α-mangostin and HSA/TRF were both static quenching and the binding distances between αmangostin and HSA/TRF were both less than 7 nm, indicating that an energy transfer exists between the α-mangostin and HSA/TRF
Summary
Mangosteen (Garcinia mangostana L.) is a member of the Garcinia genus, which mainly grows in Thailand, Vietnam, Malaysia, Indonesia, Philippines and other Southeast Asian countries. It is widely cultivated in Guangxi, Hainan and Zhejiang provinces as well as other areas of China. Xanthones are the main active substance in mangosteen, wherein α-mangostin (1,3,6-trihydroxy7-methoxy-2,8-bis(3-methyl-2-butenyl)-9H-xanthen-9-one) (Fig 1) is one of the most important natural xanthone derivative [7] It can be used as a drug for the treatment of diabetes, reduction of blood lipids, cardiovascular protection, inhibiting leukemia HL-60 cells growth and inhibiting HIV-1 protease. As a health care product, it has the function of antioxidant and anti-aging [8] and it is used in cosmetics
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