Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan; Antiaging Center, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
Pharmaceutical Research and Technology Institute, Kindai University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
Fitoterapia. 2020 Jun;143:104584. doi: 10.1016/j.fitote.2020.104584. Epub 2020 Apr 1.
Three new acylated phenylethanoid glycosides, kurroaosides A (14), B (15), and C (16), and a new acylated cucurbitane-type triterpene glycoside, kurroaoside D (17), were isolated from a methanol extract of the rhizomes of Picrorhiza kurroa Royle ex Benth. (Plantaginaceae) along with 29 known isolates including 10 acylated phenylethanoid glycosides (18-27), three cucurbitane-type triterpene glycosides (32-34), and a nortriterpene glycoside (35). The structures of these new compounds (14-17), including their stereochemistry, were determined based on chemical and physicochemical evidence derived from NMR and MS analysis. Among the isolates, acylated iridoid glycosides, picrosides I (8), II (9), III (10), and IV (11) and 6-feruloylcatalpol (12), phenylethanoid glycosides (14-16), triterpene glycosides, cucurbitacin B 2-O-β-D-glucopyranoside (32) and 25-acetoxy-2-β-D-glucopyranosyloxy-3,16,20-trihydroxy-9-methyl-19-norlanosta-5-en-22-one (35), and an acetophenone glycoside, picein (36), significantly promoted collagen synthesis at 10-30 μM, with no cytotoxicity being observed at the effective concentrations. Furthermore, acylated phenylethanoid glycosides, calceolarioside A (19, IC = 69.2 μM), plantamajoside (20, 51.8 μM), isoplantamajoside (21, 76.8 μM), and scroside E (23, 65.5 μM), exhibited collagenase inhibitory activity equivalent to that of positive agents caffeic acid (75.6 μM) and epigallocatechin 3-O-gallate (75.4 μM).
从 Picrorhiza kurroa Royle ex Benth.（玄参科）根茎的甲醇提取物中分离得到三种新的酰化苯乙醇苷，kurroaosides A（14）、B（15）和 C（16），以及一种新的酰化葫芦烷型三萜糖苷，kurroaoside D（17），以及 29 种已知的分离物，包括 10 种酰化苯乙醇苷（18-27）、三种葫芦烷型三萜糖苷（32-34）和一种木脂素糖苷（35）。这些新化合物（14-17）的结构，包括它们的立体化学，是根据 NMR 和 MS 分析得出的化学和物理化学证据确定的。在分离物中，酰化环烯醚萜糖苷，苦玄参苷 I（8）、II（9）、III（10）和 IV（11）和 6-阿魏酰梓醇（12）、苯乙醇苷（14-16）、三萜糖苷、葫芦素 B 2-O-β-D-吡喃葡萄糖苷（32）和 25-乙酰氧基-2-β-D-吡喃葡萄糖基氧基-3,16,20-三羟基-9-甲基-19-降胆甾烷-5-烯-22-酮（35）和一种苯乙酮糖苷，picein（36），在 10-30 μM 时显著促进胶原蛋白合成，在有效浓度下没有观察到细胞毒性。此外，酰化苯乙醇苷，calceolarioside A（19，IC=69.2 μM）、plantamajoside（20，51.8 μM）、isoplantamajoside（21，76.8 μM）和 scroside E（23，65.5 μM）表现出与阳性药物咖啡酸（75.6 μM）和表没食子儿茶素 3-O-没食子酸酯（75.4 μM）相当的胶原酶抑制活性。
