ゼアチンおよびN6-イソペンテニルアデニンの1′-メチル誘導体とそれらのリボヌクレオシド体のレタス種子発芽におけるサイトカイニン活性について〔英文〕

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  • Cytokinin Activities of 1'-Methyl Derivatives of Zeatin and N^6-(Δ^2-Isopentenyl) adenine and of their 9-β-D-Ribofuranosides in Lettuce Seed Germination (A. NATURAL SCIENCE)
  • ゼアチン オヨビ N6 イソペンテニルアデニン ノ 1 メチル ユウドウタイ
  • ゼアチンおよび N^6- イソペンテニルアデニンの 1'- メチル誘導体とそれらのリボヌクレオシド体のレタス種子発芽におけるサイトカイニン活性について(A. 理学)

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説明

Cytokinin activities of trans- and cis-zeatins (1 and 2), N^6-(Δ^2-isopentenyl)-adenine (3), their 1'-methyl derivatives [(1'R)-1,(1'S)-1,(1'R)-2OH-1,(1'S)-2OH-1,(1'R)-2,(1'S)-2,(1'R)-3,and (1'S)-3,listed in Table 1], and of their 9-β-D-ribofuranosides [4,(1"R)-4,(1"S)-4,5,(1"R)-5,(1"S)-5,6,(1"R)-6,and (1"S)-6,listed in Table 1] except for those of (1'R)-2OH-1,and (1'S)-2OH-1,assayed by lettuce seed germination, are summarized, and structure-activity relationships are reviewed. (1) 1'- or 1"- Methylation in 1,2,4,and 6 resulted in slightly less active (1'R)-1,(1'R)-2,(1"R)-4,and (1"R)-6,respectively, and did in much less active (1'S)-1,(1'S)-2,(1"S)-4,and (1"S)-6,respectively. However, 1'-methylation gave no effect on 3 : (1'R)-3 and (1'S)-3 were nearly as active as 3. On the other hand, 1"-methylation in 5 gave slightly more active (1"R)-5 and completely inactive (1"S)-5. The 2-hydroxy derivative (1'R)-2OH-1 was more active than (1'S)-2OH-1. Thus, all the R-enantiomers were more active than the corresponding S-enantiomers, respectively. (2) The trans-isomers [1,(1'R)-1,(1'S)-1,4,(1"R)-4,and (1"S)-4] were more active than the corresponding cis-isomers [2,(1'R)-2,(1'S)-2,5,(1"R)-5,and (1"S)-5], respectively. (3) Hydroxylation at the 2-position of the purine ring in (1'R)-1 and (1'S)-1 gave much less active (1'R)-2OH-1 and (1'S)-2OH-1,respectively. (4) Ribosidations at the 9-position in 1,(1'R)-1,(1'S)-1,2,(1'R)-2,(1'S)-2,3,(1'R)-3,and (1'S)-3 all reduced the cytokinin activity. In the cis series, 5 still possessed a very weak cytokinin activity, but its 2'-deoxy derivative [9-(2'-deoxy-β-D-ribofuranosyl)-cis-zeatin (2'H-5)] did not exhibit any cytokinin activity even at the highest concentration tested.

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