Win Nwet Nwet, Awale Suresh, Esumi Hiroyasu, Tezuka Yasuhiro, Kadota Shigetoshi
Institute of Natural Medicine, University of Toyama, 2630-Sugitani, Toyama 930-0194, Japan.
J Nat Prod. 2007 Oct;70(10):1582-7. doi: 10.1021/np070286m. Epub 2007 Sep 27.
The chloroform extract of rhizomes of Boesenbergia pandurata demonstrated marked preferential cytotoxicity against human pancreatic PANC-1 cancer cells in nutrient-deprived medium. Bioactivity-directed investigation of this extract yielded four new secondary metabolites, geranyl-2,4-dihydroxy-6-phenethylbenzoate ( 1), 2',4'-dihydroxy-3'-(1''-geranyl)-6'-methoxychalcone ( 2), (1' R,2' S,6' R)-2-hydroxyisopanduratin A ( 3), and (2 R)-8-geranylpinostrobin ( 4), and twenty known compounds ( 5- 24). Among the known compounds, (2 S)-6-geranylpinostrobin ( 5), (+/-)-6-methoxypanduratin A ( 6), and (2 S)-7,8-dihydro-5-hydroxy-2-methyl-2-(4''-methyl-3''-pentenyl)-8-phenyl-2 H,6 H-benzo[1,2- b:5,4- b']dipyran-6-one ( 7) were isolated for the first time from a natural source. The structures of these compounds were elucidated using extensive spectroscopic techniques including CD measurements. All the isolated compounds showed varying degrees of in vitro preferential cytotoxicity against PANC-1 cells. Nicolaioidesin B ( 11) and panduratin A ( 17) were most potent, each showing a PC 100 at 2.5 microM.
平卧山姜根茎的氯仿提取物在营养缺乏的培养基中对人胰腺PANC - 1癌细胞表现出显著的优先细胞毒性。对该提取物进行生物活性导向研究，得到了四种新的次生代谢产物，香叶基 - 2,4 - 二羟基 - 6 - 苯乙基苯甲酸酯（1）、2',4'-二羟基 - 3'-(1''-香叶基)-6'-甲氧基查耳酮（2）、(1'R,2'S,6'R)-2 - 羟基异姜黄烯素A（3）和(2R)-8 - 香叶基松属素（4），以及二十种已知化合物（5 - 24）。在这些已知化合物中，(2S)-6 - 香叶基松属素（5）、(±)-6 - 甲氧基姜黄烯素A（6）和(2S)-7,8 - 二氢 - 5 - 羟基 - 2 - 甲基 - 2-(4''-甲基 - 3''-戊烯基)-8 - 苯基 - 2H,6H - 苯并[1,2 - b:5,4 - b']二吡喃 - 6 - 酮（7）首次从天然来源中分离得到。使用包括圆二色光谱测量在内的广泛光谱技术阐明了这些化合物的结构。所有分离出的化合物对PANC - 1细胞均表现出不同程度的体外优先细胞毒性。尼可莱奥苷B（11）和姜黄烯素A（17）最具活性，在2.5微摩尔浓度下均显示出PC100。
