a Department of Natural Product Chemistry , Jinan University , Guangzhou 510632 , P.R. China.
Nat Prod Res. 2012;26(15):1388-94. doi: 10.1080/14786419.2011.589055. Epub 2011 Oct 20.
A new sesquiterpene glycoside, artemisinic acid 3-β-O-β-D-glucopyranoside (3, 31.24%) and other two biotransformation products, 3-β-hydroxyartemisinic acid (2, 36.69%) and 3-β-hydroxyartemisinic acid β-D-glucopyranosyl ester (4, 7.03%), were biosynthesised after artemisinic acid (1) was administered to the cultured cells of Averrhoa carambola. The three biotransformation products were obtained for the first time by using the suspension-cultured cells of A. carambola as a new biocatalyst system, and their structures were identified on the basis of the physico-chemical properties, NMR and mass spectral analyses. The results indicate that the cultured cells of A. carambola have the abilities to hydroxylate and glycosylate sesquiterpene compounds in a regio- and stereoselective manner. Furthermore, the anti-tumour activity of compounds 3 and 4 was evaluated against K562 and HeLa cell lines. Compound 4 showed strong activity against HeLa cell line, with the IC₅₀ value of 0.56 µmol mL⁻¹.
一种新的倍半萜糖苷，青蒿酸 3-β-O-β-D-吡喃葡萄糖苷（3，31.24%）和另外两种生物转化产物，3-β-羟基青蒿酸（2，36.69%）和 3-β-羟基青蒿酸β-D-吡喃葡萄糖苷（4，7.03%），在青蒿酸（1）被给予车前草培养细胞后生物合成。这三种生物转化产物首次通过使用车前草悬浮培养细胞作为一种新的生物催化系统获得，并根据物理化学性质、NMR 和质谱分析鉴定了它们的结构。结果表明，车前草培养细胞具有区域和立体选择性羟化和糖基化倍半萜化合物的能力。此外，还评估了化合物 3 和 4 对 K562 和 HeLa 细胞系的抗肿瘤活性。化合物 4 对 HeLa 细胞系表现出很强的活性，IC₅₀值为 0.56µmol·mL⁻¹。
