Le Tuoi Thi, Trang Nguyen Thu, Pham Van Thuy Thi, Quang Dang Ngoc, Phuong Hoa Le Thi
Faculty of Biology, Hanoi National University of Education, 136 Xuan Thuy, Cau Giay, Hanoi 100000, Vietnam.
Institute of Microbiology and Biotechnology, Vietnam National University, 144 Xuan Thuy, Cau Giay, Hanoi 100000, Vietnam.
R Soc Open Sci. 2023 Aug 16;10(8):230676. doi: 10.1098/rsos.230676. eCollection 2023 Aug.
Beta-mangostin is a xanthone commonly found in the genus . Unlike α-mangostin, to date, there have only been a few studies on the biological activity and derivatization of β-mangostin. In this study, two novel glycosylated derivatives of β-mangostin were successfully synthesized via a one-pot enzymatic reaction. These derivatives were characterized as β-mangostin 6-O-β-d-glucopyranoside and β-mangostin 6-O-β-d-2-deoxyglucopyranoside by TOF ESI/MS and H and C NMR analyses. Beta-mangostin showed cytotoxicity against KB, MCF7, A549 and HepG2 cancer cell lines, with IC values ranging from 15.42 to 21.13 µM. The acetylcholinesterase and α-glucosidase inhibitory activities of β-mangostin were determined with IC values of 2.17 and 27.61 µM, respectively. A strong anti-microbial activity of β-mangostin against Gram-positive strains (, and ) was observed, with IC values of 0.16, 0.18 and 1.24 µg ml, respectively. Beta-mangostin showed weaker activity against Gram-negative strains (, and ) as well as fungus, with IC and MIC values greater than the tested concentration (greater than 32 µg ml). The new derivatives of β-mangostin showed weaker activities than those of β-mangostin, demonstrating the important role of the hydroxyl group at C-6 of β-mangostin in its bioactivity.
β-山竹黄酮是一种常见于该属的氧杂蒽酮。与α-山竹黄酮不同，迄今为止，关于β-山竹黄酮的生物活性和衍生化的研究仅有少数。在本研究中，通过一锅法酶促反应成功合成了两种新型的β-山竹黄酮糖基化衍生物。通过飞行时间电喷雾电离质谱（TOF ESI/MS）以及氢和碳核磁共振（H和C NMR）分析，将这些衍生物表征为β-山竹黄酮6-O-β-D-吡喃葡萄糖苷和β-山竹黄酮6-O-β-D-2-脱氧吡喃葡萄糖苷。β-山竹黄酮对KB、MCF7、A549和HepG2癌细胞系表现出细胞毒性，IC值范围为15.42至21.13μM。测定了β-山竹黄酮的乙酰胆碱酯酶和α-葡萄糖苷酶抑制活性，IC值分别为2.17和27.61μM。观察到β-山竹黄酮对革兰氏阳性菌株（、和）具有较强的抗菌活性，IC值分别为0.16、0.18和1.24μg/ml。β-山竹黄酮对革兰氏阴性菌株（、和）以及真菌的活性较弱，IC和MIC值大于测试浓度（大于32μg/ml）。β-山竹黄酮的新衍生物表现出比β-山竹黄酮较弱的活性，表明β-山竹黄酮C-6位羟基在其生物活性中的重要作用。
