504 



Y. Suiniki tnid A. Kaxvarnda 



ReUtion Between Chemical Structure ana Physiol ogicdl Activity 



HO 



HO 



H 



CH, 



COOM 



)H (i sp activityi 



rep, 



y^ 



CH, 



\ 



OH 



(^, S6 4) ° 



HO 



MO 



fCQ, 



COOH \H} 



A {Mttittr ± ) 



Hoor 



3H (-f-. /OO 0) HO 



COOH 



CKj 



COOH 



=CH, 



CH 



COOH 



H5 ( — ) 



OH (-) 

 J-CHj 



(fie titer ± ) 



no 



/\ 



HOt^C 



COOH 



(+, 7J / ) HO-l. "0^ 

 ^^^i CHs 



/>« ejff r ± ) 



CHiOH 



■OH ( — ) 

 =CH, 



HO 



x^ 



CHj 



COOH 

 J-b'bb A, 



OH (-) 

 tCH, 



CIVIH 



HO 



CHj 



^CO 



HO 



CH3 



( + , 2S g) 



Ch5 



COOM 



HO 



HO 



'^5, 



CH, 



•OH (+, ,ff,) 



COOH 



rc?, 



HO 



HO 



CHj 



^^9, 



COOH 



to (-) 

 -COOH 



CHj 



COOH 

 a-.tb c 



iO 



tP, 



CHj 



•CHjBr (+, / / /; 



COOM 



iC 



■CH, ( — ) 



COOH 

 /JO- S.'»t Ai 



CH,Br( + , / C f) 



' COOH 



COOH 



but attiviiy is decreased on catalytic hydrogenation or ozonolysis; (b) 

 also, tertiary hydroxyl (bridge head) is not important; (c) by opening 

 D-ring, the activity disappears. 



LITERATURE CITED 



1. Kitamura, H.. Seta. V., Takaliashi, N., Kawarada. A., and Siimiki, Y. Biochemical 

 studies on "Hakanae" fungus. Part 19. Chemical structure of gibhercUins. Part 



XIV. Bui. Agr. Chem. Soc. Japan. 23: 408-411. 1959. 



2. Seta, Y., Takahashi, N., Kawarada, A., Kitamura, H., and Sumiki, Y. Biochemical 

 studies on "Bakanac" fungus. Part 50. Chemical structure of gibbcrellins. Part 



XV. Bui. Agr. Chem. Soc. Japan. 23: 412-417. 1959. 



3. , Takahashi, N., Kitamura, H., Takai. .\I., Tamura, S., and Sumiki, Y. 



Biochemical studies on "Bakanae" fungus. Part 52. Chemical structure of gib- 

 bcrellins. Part XVII 1. Bui. Agr. Chem. Soc. Japan. 23: 499-509. 1959. 



4. Takahashi, N., Kitamura, H., Kawarada. A., Seta. V., Takai, M., Tamura, S., 

 and Sumiki, Y. Biochemical studies on "Bakanae" fungus. Part 34. (Isolation of 

 gibbcrellins and their properties.) Bui. Agr. Chem. Soc. Japan. 19: 267-277. 

 1955. 



5. , Seta, Y., Kitanuiia, H., and Sumiki, \. Bioduinical stuilics on '"Bakanae" 



fungus. Part 42. (A new gibberellin, gibberellin A,.) Bui. Agr. Chem. Soc. Japan. 

 '21: 396-398. 1957. 



