[논문]α-Glucosidase inhibitory caged xanthones from the resin of Garcinia hanburyi

Jin, Young Min; Kim, Jeong Yoon; Lee, Soo Min; Tan, Xue Fei; Park, Ki Hun

doi:10.3839/jabc.2019.012

α-Glucosidase inhibitory caged xanthones from the resin of Garcinia hanburyi 원문보기

Journal of applied biological chemistry, v.62 no.1, 2019년, pp.81 - 86

Jin, Young Min (Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University) , Kim, Jeong Yoon (Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University) , Lee, Soo Min (Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University) , Tan, Xue Fei (Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University) , Park, Ki Hun (Division of Applied Life Science (BK21 plus), IALS, Gyeongsang National University)

Abstract ▼ AI-Helper

A yellow resin (gamboge) from Garcinia hanburyi has been widely used as folk medicine due to its antibacterial and antitumor activities. We isolated four ${\alpha}$-glucosidase inhibitory compounds from the methanol extract of gamboge. The compounds (1-4) were identified as gambogoic acid (1), moreollic acid (2), gambogic acid (3), and 10-methoxygambogenic acid (4), respectively through spectroscopic data including 2D-NMR and HREIMS. All compounds were examined in the enzyme inhibition assay against ${\alpha}$-glucosidase to identify their inhibitory potencies and kinetic behavior. All compounds (1-4) showed enzyme inhibition against ${\alpha}$-glucosidase, but the activity was significantly affected by the methoxy group on C-10 of ring A and pentenyl pyran moiety of ring D. For example, compound 1 ($IC_{50}=41.4{\mu}M$) bearing pyran ring eight times effective that 4 ($IC_{50}=350.6{\mu}M$) having geranyl group itself. Most active compound was found out to be gambogoic acid (1) which was analyzed most abundant metabolite in gamboge by LC-ESI-MS/MS. In kinetic study, compounds 1 and 2 were proved as noncompetitive inhibitors.

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제안 방법

3298) in the HREIMS. The analysis of individual carbon atoms was conducted by ¹H-NMR, ¹³C-NMR, and the result of DEPT experiments. The compound 1 had the following functional groups: 5 methylenes (sp³), 8 methines (sp²), 1 methine (sp³), 9 methyls and 16 quaternary carbons.

대상 데이터

PJ01318601), Republic of Korea. The BK21 Plus program supported scholarships for students.
The Bruker AM 500 spectrometer (Bruker, Karlsruhe, Germany) was used for ¹H-NMR, ¹³C NMR, and 2D NMR data. Mass spectrometry data were obtained by a JEOL JMS-700 (JEOL Ltd.
, Tokyo, Japan), respectively. The HPLC analysis was carried out by using the Agilent (Santa Clara, CA, USA) 1100 series system equipped with a diode array detector. Enzyme assay was screened by Spectra Max M3 Multi-Mode Microplate Reader (Molecular Devices, Sunnyvale, CA, USA).
5 mL/min. The chromatogram was detected at 254 nm. The methanol extract of gamboge was ionized using electrospray ionization (ESI) source in positive and negative ion modes.

데이터처리

values. The kinetic parameters (K_m: Michaelis-Menten constant, V_max: maximal velocity) were analyzed using a nonlinear regression program, Sigma plot (SPCC Inc., Chicago, IL, USA). The inhibition constant (K_i) was determined according to Dixon plot [14].

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