Saito T, Kamiya Y, Yamane H, Sakurai A, Murofushi N, Takahashi N
a Department of Agricultural Chemistry , The University of Tokyo , Bunkyo-ku , Tokyo 113 , Japan.
b The Institute of Physical and Chemical Research , Wako-shi , Saitama 351-01 , Japan.
Biosci Biotechnol Biochem. 1992 Jan;56(7):1046-52. doi: 10.1271/bbb.56.1046.
Six 3-methylgibberellin analogs were synthesized, and their effects on the GA 3β-hydroxylases from immature seeds of Phaseolus vulgaris and Cucurbita maxima, and/or on the growth of dwarf rice (Oryza sativa L. cv. Tan-ginbozu) and cucumber (Cucumis sativus L. cv. Spacemaster) were investigated. 3-Methyl-GA5 and 2, 3-didehydro-3-methyl-GA9· inhibited the conversion of [2, 3-(3)H2]GA9 to [2-(3)H]GA4 by GA 3β-hydroxylases from both P. vulgaris and C. maxima at 3 μM and higher. Their C/D-ring-rearranged isomers, 2, 3-didehydro-3-methyl-DGC and 16-deoxo-2, 3-didehydro-3-methyl-DGC, inhibited 3β-hydroxylation by the enzyme from P. vulgaris threefold more strongly than the non-C/D-ring-rearranged compounds, but exhibited no effect on 3β-hydroxylation by the enzyme from C. maxima. In a dwarf rice seedling assay, 3-methyl-GA5 and 2, 3-didehydro-3-methyl-GA9 promoted shoot elongation at doses of 300 ng/plant and higher, and 3α-methyl-GA1 and 3α-methyl-GA4 at doses of 30 ng/plant and higher. In contrast 2, 3-didehydro-3-methyl-DGC inhibited shoot growth to half that of the control at a dose of 300 ng/plant, and 16-deoxo-2, 3-didehydro-3-methyl-DGC showed no effect on growth. In a cucumber seedling assay, 3α-methyl-GA4 promoted hypocotyl elongation at doses of 300 ng/plant and higher. The other C-3 methyl compounds showed no effect on the hypocotyl elongation of cucumber seedlings.
合成了六种3-甲基赤霉素类似物，并研究了它们对菜豆和南瓜未成熟种子中GA 3β-羟化酶的影响，和/或对矮生水稻（Oryza sativa L. cv. Tan-ginbozu）和黄瓜（Cucumis sativus L. cv. Spacemaster）生长的影响。3-甲基-GA5和2,3-二脱氢-3-甲基-GA9在3 μM及更高浓度下抑制菜豆和南瓜的GA 3β-羟化酶将[2,3-(3)H2]GA9转化为[2-(3)H]GA4。它们的C/D环重排异构体，2,3-二脱氢-3-甲基-DGC和16-脱氧-2,3-二脱氢-3-甲基-DGC，对菜豆酶的3β-羟化抑制作用比非C/D环重排化合物强三倍，但对南瓜酶的3β-羟化没有影响。在矮生水稻幼苗试验中，3-甲基-GA5和2,3-二脱氢-3-甲基-GA9在剂量为300 ng/株及更高时促进茎伸长，3α-甲基-GA1和3α-甲基-GA4在剂量为30 ng/株及更高时促进茎伸长。相反，2,3-二脱氢-3-甲基-DGC在剂量为300 ng/株时抑制茎生长至对照的一半，而16-脱氧-2,3-二脱氢-3-甲基-DGC对生长没有影响。在黄瓜幼苗试验中，3α-甲基-GA4在剂量为300 ng/株及更高时促进下胚轴伸长。其他C-3甲基化合物对黄瓜幼苗的下胚轴伸长没有影响。
