Du X, Sun N, Tamura T, Mohri A, Sugiura M, Yoshizawa T, Irino N, Hayashi J, Shoyama Y
Graduate School of Pharmaceutical Sciences, Kyushu University, Fukuoka, Japan.
Biol Pharm Bull. 2001 Jan;24(1):65-9. doi: 10.1248/bpb.24.65.
A higher concentration of kinsenoside, 3-(R)-3-beta-D-glucopyranosyloxybutanolide (1), was detected in the crude drug Anoectochilusformosanus, and A. koshunensis by HPLC analysis. A methylation reaction occurred to give methyl ester (4) when the lactone ring of 1 was cleaved by silica gel catalysis using methanol containing solvent used in the purification step resulting in difficulty to purify 1. To avoid the cleavage reaction, a reversed-phase or silica gel column without methanol was used to give a high yield of 1. In an anti-hyperliposis assay using high-fat diet rats, 1 significantly reduced the weights of body and liver, and also decreased the triglyceride level in the liver compared to those of control rats. On the other hand, the epimer of 1, 3-(S)-3-beta-glucopyranosy-loxybutanolide (2), trivially named goodyeroside A, which was isolated from Goodyera species, had no effect for anti-hyperliposis. In aurothioglucose-induced obese mouse, 1 suppressed the body and liver weight increase, significantly ameliorated the triglyceride level in the liver, and also reduced the deposition of uterine fat-pads.
通过高效液相色谱分析在粗药金线莲和高雄金线莲中检测到较高浓度的金线莲苷，即3-(R)-3-β-D-吡喃葡萄糖氧基丁内酯(1)。当使用纯化步骤中含甲醇的溶剂通过硅胶催化裂解1的内酯环时，发生甲基化反应生成甲酯(4)，导致难以纯化1。为避免裂解反应，使用不含甲醇的反相柱或硅胶柱以高产率得到1。在使用高脂饮食大鼠的抗高血脂试验中，与对照大鼠相比，1显著降低了体重和肝脏重量，还降低了肝脏中的甘油三酯水平。另一方面，1的差向异构体，3-(S)-3-β-吡喃葡萄糖氧基丁内酯(2)，俗称古氏苷A，从斑叶兰属植物中分离得到，对抗高血脂没有作用。在金硫葡萄糖诱导的肥胖小鼠中，1抑制了体重和肝脏重量的增加，显著改善了肝脏中的甘油三酯水平，还减少了子宫脂肪垫的沉积。
