Katayama Masato, Masui Yuko, Kageyama Eiji, Kawabata Youichi, Kanayama Kozo
Cooperative Research Laboratory for Plant Growth Regulator Development, National Institute of Advanced Industrial Science and Technology, Nagoya, Japan.
Biosci Biotechnol Biochem. 2008 Aug;72(8):2025-33. doi: 10.1271/bbb.80138. Epub 2008 Aug 7.
In our studies on the development of new promoters for the root formation of tree cuttings, 4-trifluoromethylindole-3-acetic acid (4-CF(3)-IAA), a new fluorinated auxin, was synthesized via 4-trifluoromethylindole and 4-trifluoromethylindole-3-acetonitrile by using 2-methyl-3-nitrobenzotrifluoride as the starting material. As a control compound for comparing biological activities, 4-methylindole-3-acetic acid (4-CH(3)-IAA) was also synthesized by using 2,3-dimethylnitrobenzene as the starting material. The biological activities of these compounds were compared by three bioassays with those of indole-3-acetic acid and 4-chloroindole-3-acetic acid (4-Cl-IAA), which, like 4-CF(3)-IAA and 4-CH(3)-IAA, has a substituent at the 4-position of the indole nucleus. 4-CF(3)-IAA showed strong root formation-promoting activity with black gram cuttings which was 1.5 times higher than that of 4-(3-indole)butyric acid at 1x10(-4) M. 4-CH(3)-IAA, however, only weakly promoted root formation in spite of its strong inhibition of hypocotyl growth in Chinese cabbage and promotion of hypocotyl swelling and lateral root formation in black gram. On the other hand, 4-CF(3)-IAA demonstrated weaker activities than 4-CH(3)-IAA and 4-Cl-IAA in these two bioassays.
在我们关于开发促进树木插条生根新启动子的研究中，以2-甲基-3-硝基三氟甲苯为起始原料，通过4-三氟甲基吲哚和4-三氟甲基吲哚-3-乙腈合成了一种新型氟化生长素4-三氟甲基吲哚-3-乙酸（4-CF(3)-IAA）。作为比较生物活性的对照化合物，还以2,3-二甲基硝基苯为起始原料合成了4-甲基吲哚-3-乙酸（4-CH(3)-IAA）。通过三种生物测定法，将这些化合物的生物活性与吲哚-3-乙酸和4-氯吲哚-3-乙酸（4-Cl-IAA）进行了比较，4-Cl-IAA与4-CF(3)-IAA和4-CH(3)-IAA一样，在吲哚核的4位上有一个取代基。4-CF(3)-IAA对黑绿豆插条表现出很强的促生根活性，在1x10(-4) M时，其活性比4-(3-吲哚)丁酸高1.5倍。然而，4-CH(3)-IAA尽管对大白菜下胚轴生长有很强的抑制作用，对黑绿豆下胚轴肿胀和侧根形成有促进作用，但对生根的促进作用却很弱。另一方面，在这两种生物测定中，4-CF(3)-IAA的活性比4-CH(3)-IAA和4-Cl-IAA弱。
