College of Science and Technology, Nihon University, 1-8-14 Kanda Surugadai, Tokyo 101-8308, Japan.
Chem Biodivers. 2012 Aug;9(8):1490-9. doi: 10.1002/cbdv.201200030.
A new iridoid glycoside, 10-O-(4"-O-methylsuccinoyl)geniposide (7), and two new pyronane glycosides, jasminosides Q and R (13 and 14, resp.), along with nine known iridoid glycosides, 1-6 and 8-10, and two known pyronane glycosides, 11 and 12, were isolated from a MeOH extract of Gardeniae Fructus, the dried ripe fruit of Gardenia jasminoides (Rubiaceae). The structures of new compounds were elucidated on the basis of extensive spectroscopic analyses and comparison with literature. Upon evaluation of compounds 1-14 on the melanogenesis in B16 melanoma cells induced with α-melanocyte-stimulating hormone (α-MSH), three compounds, i.e., 6-O-p-coumaroylgeniposide (3), 7, and 6'-O-sinapoyljasminoside (12), exhibited inhibitory effects with 21.6-41.0 and 37.5-47.7% reduction of melanin content at 30 and 50 μM, respectively, with almost no toxicity to the cells (83.7-106.1% of cell viability at 50 μM).
从栀子（茜草科栀子属）的干燥成熟果实栀子果实的甲醇提取物中分离得到了 10-O-(4"-O-甲基琥珀酰基)京尼平苷（7）和两个新的吡喃烷糖苷，即栀子苷 Q 和 R（13 和 14），以及 9 个已知的环烯醚萜糖苷和 2 个已知的吡喃烷糖苷，11 和 12。新化合物的结构是根据广泛的光谱分析和与文献的比较来阐明的。在评估化合物 1-14 对α-促黑素细胞激素（α-MSH）诱导的 B16 黑素瘤细胞中的黑色素生成的影响时，三种化合物，即 6-O-对香豆酰京尼平苷（3）、7 和 6'-O-芥子酰基栀子苷（12），在 30 和 50 μM 时表现出抑制作用，黑色素含量分别降低了 21.6-41.0%和 37.5-47.7%，对细胞几乎没有毒性（在 50 μM 时细胞活力为 83.7-106.1%）。
