Boyce Thompson Institute, Tower Road, 14853, Ithaca, New York.
J Chem Ecol. 1993 Jul;19(7):1355-69. doi: 10.1007/BF00984881.
Larvae of the cabbage butterfly,Pieris rapae, refuse to feed on the wild mustard,Erysimum cheiranthoides, due to the presence of alcoholextractable deterrents. The active components were extracted inton-BuOH, and this extract was separated into four fractions (I-IV) by reverse-phase HPLC. Fractions III and IV retained the feeding deterrent activity. The activity of fraction III was found to be due to the cardenolide diglycosides 1 and 2, which were previously reported as oviposition deterrents for gravidP. rapae butterflies. Three active compounds were isolated from fraction IV by column chromatography on silica gel followed by reverse-phase HPLC. These compounds were identified as a monoglycoside, digitoxigenin 3-O-β-D-glucoside (4), and two diglycosides, glucodigigulomethyloside (5) and glucodigifucoside (6). An additional cardenolide isolated from fraction II was identified as cheirotoxin (7). All compounds were identified by UV, NMR ((1)H and(13)C), and mass spectrometry, as well as hydrolysis experiments. The feeding deterrent activity of these compounds was compared with that of related commercially available chemicals and other compounds isolated fromE. cheiranthoides.
幼虫的白菜粉蝶， Pieris rapae ，拒绝以野生芥菜，辣根，由于存在醇溶性抑制剂。活性成分提取 inton-BuOH ，和这种提取物分为四个部分（一至四）通过反相高效液相色谱法。第三和第四部分保留的摄食抑制活性。该活动的第三部分是由于 cardenolide 二糖苷 1 和 2 ，这是以前报道的产卵威慑剂 gravidP. rapae 蝴蝶。三个活性化合物从第四部分分离柱色谱硅胶后反相高效液相色谱法。这些化合物被鉴定为单糖苷，洋地黄毒苷 3-O-β-D-葡萄糖苷（ 4 ）和二糖苷， glucodigigulomethyloside （ 5 ）和 glucodigifucoside （ 6 ）。一个额外的 cardenolide 从第二部分分离出来的鉴定为 cheirotoxin （ 7 ）。所有化合物均通过紫外线， NMR （ 1 H和 13 C ），质谱，以及水解实验。摄食抑制活性的这些化合物进行了比较，有关的商业上可利用的化学品和其他化合物分离出来的辣根。
