Le Thi-Kim-Dung, Danova Ade, Aree Thammarat, Duong Thuc-Huy, Koketsu Mamoru, Ninomiya Masayuki, Sawada Yoshiharu, Kamsri Pharit, Pungpo Pornpun, Chavasiri Warinthorn
Center of Excellence in Natural Products Chemistry, Department of Chemistry, Faculty of Science, Chulalongkorn University, Pathumwan, Bangkok 10330, Thailand.
Department of Chemistry, Ho Chi Minh City University of Education, 280 An Duong Vuong Street, District 5, Ho Chi Minh City 748342, Vietnam.
J Nat Prod. 2022 Apr 22;85(4):776-786. doi: 10.1021/acs.jnatprod.1c00765. Epub 2022 Mar 9.
Six new compounds, globunones A-F (-), and two new flavonoids ( and ) together with nine known compounds (-) were isolated from the stems of The chemical structures of - were elucidated by an analysis of their NMR and high-resolution electrospray ionization mass spectrometry data as well as by comparison with literature values. The absolute configurations were determined using time-dependent density functional theory electronic circular dichroism (TD-DFT-ECD). Globunones A-E (-) represent the initial combined structures of a flavan-3-ol core and a 1,4-benzoquinone core. Globunone F () is the first flavanone-type compound bearing a 2-(2,4-dihydroxyphenyl)-2-oxoethyl group found to date in Nature. Compounds - and - were tested for their yeast α-glucosidase inhibitory activity. All compounds tested (except for and ) showed potent inhibition toward α-glucosidase with IC values in the range 0.4-26.6 μM. Calodenin A () was the most active compound with an IC value of 0.4 μM (the positive control, acarbose, IC 93.6 μM). A kinetic analysis of revealed that it is a noncompetitive inhibitor with a value of 3.4 μM.
从 Globuna paniculata 的茎中分离出 6 种新化合物，即球穗酮 A - F（-）、2 种新黄酮类化合物（和）以及 9 种已知化合物（-）。通过对它们的核磁共振（NMR）和高分辨率电喷雾电离质谱数据进行分析，并与文献值进行比较，阐明了化合物 - 的化学结构。使用含时密度泛函理论电子圆二色性（TD - DFT - ECD）确定绝对构型。球穗酮 A - E（-）代表了黄烷 - 3 - 醇核心和 1,4 - 苯醌核心的初始组合结构。球穗酮 F（）是迄今为止在自然界中发现的首个带有 2 -（2,4 - 二羟基苯基）- 2 - 氧代乙基的黄烷酮类化合物。对化合物 - 和 - 进行了酵母 α - 葡萄糖苷酶抑制活性测试。所有测试的化合物（除了和）对 α - 葡萄糖苷酶均表现出强效抑制作用，IC 值在 0.4 - 26.6 μM 范围内。卡洛地宁 A（）是活性最强的化合物，IC 值为 0.4 μM（阳性对照阿卡波糖的 IC 为 93.6 μM）。对的动力学分析表明它是一种非竞争性抑制剂，值为 3.4 μM。
