Graduate School of Integrated Pharmaceutical and Nutritional Sciences , University of Shizuoka , 52-1 Yada , Suruga-ku, Shizuoka 422-8526 , Japan.
Department of Chemical Engineering, Faculty of Engineering , Universitas Indonesia , Baru UI, Depok 16424 , Indonesia.
J Nat Prod. 2019 Feb 22;82(2):205-210. doi: 10.1021/acs.jnatprod.8b00541. Epub 2019 Feb 5.
Three new compounds, namely, 4-(4'-hydroxy-3'-methoxyphenyl)-3,5,7-trihydroxycoumarin (1) and sulawesins A (2) and B (3), were isolated from the propolis of stingless bees ( Tetragonula aff. biroi) collected on South Sulawesi, Indonesia. In addition, five known compounds, glyasperin A, broussoflavonol F, (2 S)-5,7-dihydroxy-4'-methoxy-8-prenylflavanone, (1' S)-2- trans,4- trans-abscisic acid, and (1' S)-2- cis,4- trans-abscisic acid, were identified. The structures of the new compounds were determined by a combination of methods that included mass spectrometry and NMR spectroscopy. The absolute configuration of sulawesin A (2), a new podophyllotoxin derivative, was determined by X-ray crystallography. The absolute configuration of sulawesin B (3) was also determined by the ECD calculation. 4-(4'-Hydroxy-3'-methoxyphenyl)-3,5,7-trihydroxycoumarin (1) and sulawesin A (2) were examined for xanthine oxidase (XO) inhibitory activity; 1 exhibited XO inhibitory activity, with an IC value of 3.9 μM.
三种新化合物，即 4-(4'-羟基-3'-甲氧基苯基)-3,5,7-三羟基香豆素（1）和 sulawesins A（2）和 B（3），从印度尼西亚南苏拉威西采集的无刺蜜蜂（Tetragonula aff. biroi）的蜂胶中分离得到。此外，还鉴定了五种已知化合物，glyasperin A、broussoflavonol F、(2S)-5,7-二羟基-4'-甲氧基-8-烯丙基黄烷酮、(1'S)-2-反式、4-反式-脱落酸和(1'S)-2-顺式、4-反式-脱落酸。新化合物的结构通过质谱和 NMR 光谱等方法的组合确定。通过 X 射线晶体学确定了新的鬼臼毒素衍生物 sulawesin A（2）的绝对构型。通过 ECD 计算确定了 sulawesin B（3）的绝对构型。对 4-(4'-羟基-3'-甲氧基苯基)-3,5,7-三羟基香豆素（1）和 sulawesin A（2）进行了黄嘌呤氧化酶（XO）抑制活性测试；1 表现出 XO 抑制活性，IC 值为 3.9 μM。
