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Bioscience, Biotechnology, and Biochemistry ISSN: 0916-8451 (Print) 1347-6947 (Online) Journal homepage: https://tandfonline.com/loi/tbbb20 Root Growth-promoting Activities of N-Acyl-L- proline Derivatives Motonori Tsuji, Eiichi Kuwano, Tetsuya Saito & Morifusa Eto To cite this article: Motonori Tsuji, Eiichi Kuwano, Tetsuya Saito & Morifusa Eto (1992) Root Growth-promoting Activities of N-Acyl-L-proline Derivatives, Bioscience, Biotechnology, and Biochemistry, 56:5, 778-782, DOI: 10.1271/bbb.56.778 To link to this article: https://doi.org/10.1271/bbb.56.778 Published online: 12 Jun 2014. Submit your article to this journal Article views: 80 Citing articles: 2 View citing articles Full Terms & Conditions of access and use can be found at https://tandfonline.com/action/journalInformation?journalCode=tbbb20 Biosci. Biotech. Biochem., 56 (5), 778-782, 1992 Root Growth-promoting Activities of N-Acyl-L-proline Derivatives Motonori TSUJI, Eiichi KuwANO, t Tetsuya SAITO, and Morifusa ETO Department of Agricultural Chemistry, Kyushu University, Fukuoka 812, Japan Received November 21, 1991 A number of N-acyl-L-proline derivatives were synthesized and their biological activities were investigated by using lettuce (Lactuca sativa L. cv. Sacramento) seedling test. A wide variety of these compounds promoted root growth at 25°C both under light and in darkness. Of the compounds tested, N-(2-fluorobenzoyl)-L-proline methyl ester (4) showed the highest activity and caused a 270% increase in the root elongation compared to the control. N-(2-Naphthoyl)-L-proline methyl ester (14) promoted the root growth, while N-(I-naphthoyl)-L-proline methyl ester inhibited it. L-Proline, benzoic acid, and 2-naphthoic acid had no significant effect on lettuce seedlings. Compounds 4 and 14, and N-(2-chlorobenzoyl)-L-proline methyl ester (7) reduced the inhibitory effect of 1 ppm ABA on the root growth, while the D-isomer of 4 was less activite than compound 4. Compounds 4, 7, and 14 did not show any rescue-activity for the complete inhibition of germination that was caused by treating 10 ppm of ABA. Proline has been thought to be an anti-stress compound in some plants1) and is known to accumulate in response to environmental stress such as chilling,2) salt,3) and air pollution.4) It has also been shown that an increase of proline levels in plants is induced by addition of abscisic acid (ABA). 5) Ienaga et al. have reported that a diketopiperadine derived from trans-4-hydroxY-L-proline and L-proline, which was isolated from rabbit skin tissue, conferred significant resistance to water-stress caused by sodium chloride or mannitol solution. 6) However, there has been no report on plant growth regulating activity of proline derivatives other than diketopiperadines. We therefore synthesized a number of proline derivatives and examined their effects on the growth of lettuce seedlings. This report describes the activity of acylproline derivatives to promote the root growth of the lettuce seedlings and to partially reduce the inhibitory effect of ABA on root growth. for Z-L-tryptophan. None of the compounds in Table I showed any clear effect on the growth of the hypocotyl at IOppm. Since N-benzoyl-L-proline had root-promoting activity comparable to that of Z-L-proline, we examined the structure-activity relationships of a number of benzoyl- proline derivatives. In Table II there are presented the effects of benzoylproline derivatives and related compounds on the root growth of lettuce seedlings in light. N- Benzoylpyrroli- dine (1) had no activity at 10 ppm, indicating that the presence of a carboxy moiety of the benzoylproline was essential for the activity. The methyl ester of benzoylproline (3) showed much higher activity than benzoylproline. The introduction of a 2-fluoro (4) or 3-fluoro (5) substituent Table II. Effects of N-Benzoyl-L-proline Derivatives and Related Compounds on Root Growth of Lettuce Seedlings in Light Results and Discussion Table I shows the effects of L- and D-proline and several benzyloxycarbonyl (Z)-L-amino acids on the growth of lett

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