Misuda Nodoka, Watanabe Mizuki, Nishikawa Hirotaka, Yasuda Shin, Miyashita Hiroyuki, Yokomizo Kazumi, Yoshimitsu Hitoshi, Tsuchihashi Ryota, Okawa Masafumi, Kinjo Junei, Ono Masateru
School of Agriculture, Tokai University, 871-12 Sugido, Mashiki-Cho, Kamimashiki-Gun, Kumamoto, 861-2205, Japan.
Faculty of Pharmaceutical Sciences, Sojo University, 4-22-2 Ikeda, Nishi-Ku, Kumamoto, 860-0082, Japan.
J Nat Med. 2025 Mar;79(2):341-356. doi: 10.1007/s11418-024-01868-1. Epub 2024 Dec 27.
Ipomoea alba L. (Convolvulaceae) is an annual vine native to tropical America that is cultivated primarily for ornamental purposes. Its seeds are used in traditional medicine as a laxative, and young shoots are consumed as food. In this study, ten new resin glycosides, ipoalbins I (1)-X (10), were isolated from I. alba seeds. The structures of 1-10 were determined based on spectroscopic data. All compounds had intramolecular cyclic ester structures (jalapins). The sugar moieties in 1-10 were partially acylated by organic acids, including isobutyric, (E)-2-methylbut-2-enoic, and 2S-methyl-3S-hydroxybutyric acids. Notably, one of these compounds has a rare jalapin structure characterized by an ester linkage between the carboxyl group of the aglycone moiety and the hydroxyl group of an organic acid attached to the sugar moiety. In contrast, other compounds exhibited typical macrolactone structures. Furthermore, the cytotoxic activity of 1-10 against HL-60 human promyelocytic leukemia cells and their antiviral activity against herpes simplex virus type 1 (HSV-1) were evaluated. All tested compounds, except 3, were comparable to or slightly less cytotoxic than cisplatin, the positive control. In addition, all the compounds showed anti-HSV-1 activity; notably, 5 showed an EC value lower than that of acyclovir, the positive control. However, the selectivity indices of these compounds were lower than that of acyclovir.
白花牵牛（旋花科）是一种原产于热带美洲的一年生藤本植物，主要用于观赏。其种子在传统医学中用作泻药，嫩枝可作为食物食用。在本研究中，从白花牵牛种子中分离出了10种新的树脂糖苷，即白牵牛苷I（1）-X（10）。根据光谱数据确定了1-10的结构。所有化合物都具有分子内环酯结构（jalapins）。1-10中的糖部分被包括异丁酸、（E）-2-甲基-2-丁烯酸和2S-甲基-3S-羟基丁酸在内的有机酸部分酰化。值得注意的是，其中一种化合物具有罕见的jalapin结构，其特征在于苷元部分的羧基与连接在糖部分上的有机酸的羟基之间存在酯键。相比之下，其他化合物表现出典型的大环内酯结构。此外，评估了1-10对HL-60人早幼粒细胞白血病细胞的细胞毒性活性及其对单纯疱疹病毒1型（HSV-1）的抗病毒活性。除3外，所有测试化合物的细胞毒性与阳性对照顺铂相当或略低于顺铂。此外，所有化合物均显示出抗HSV-1活性；值得注意的是，5的EC值低于阳性对照阿昔洛韦。然而，这些化合物的选择性指数低于阿昔洛韦。
