A growth inhibitor, R-(−)-3-hydroxy-β-ionone, from lightgrown shoots of a dwarf cultivar of Phaseolus vulgaris

A novel inhibitor of platelet-activating factor (PAF) acetyltransferase, an essential enzyme in the remodeling pathway of platelet-activating factor synthesis, was identified by a high throughput screen of natural product extracts of microbial origin. The compound, ZG-1494α, was isolated from an ethyl acetate extract of a culture broth of Penicillium rubrum through bioassay guided fractionation. The structure of ZG-1494α was determined by spectroscopic methods. A key feature of the structure, which is relatively rare among natural products, is the 5-hydroxy-3-pyrrolin-2-one moiety. A 13C-13C INADEQUATE was utilized to unambiguously determine the regiochemistry of this molecule.

ZG-1494α, a Novel Platelet-activating Factor Acetyltransferase Inhibitor from Penicilium rubrum, Isolation, Structure Elucidation and Biological Activity

Variations in the content of A-2α and β, novel endogenous growth inhibitors, andcis,trans- andtrans, trans-xanthoxins were determined in 6- or 7-d-old, dark-grown seedlings of peas (Pisum sativum L. cvs. Progress No. 9, dwarf, and Alaska, tall) under various treatments with red light (R), and compared with R-induced growth inhibition. After transfer of the plants to continuous R the contents of the A-2s in cv. Progress increased after a 20-min lag, and reached plateaus after 12 h, whereas they remained almost unchanged in darkness. Both the rates of increase of the A-2s and the plateau levels were proportional to the logarithm of the irradiance applied. After a 10-min R pulse, the contents of both A-2α and β increased with the same rapidity to reach peaks after 6 h, and then gradually decreased to the initial levels after about 24 h. The effect of R was shown to be phytochrome-dependent, being nullified by far-red light. The level of neithercis,trans- nortrans,trans-xanthoxin showed such a close correlation with growth inhibition, although both xanthoxins increased as a result of phytochrome action. It is highly suggestive that the A-2s, rather than the xanthoxins, are responsible for phytochrome-dependent growth inhibition in cv. Progress. In cv. Alaska, in contrast, R-induced increase of the A-2s was rapid but slight, and could not explain the transient growth inhibition, which was found to be as large as that in cv. Progress shortly after the onset of R. The large content of the A-2s in cv. Progress in the steady state under continuous R, compared with that in cv. Alaska, may explain the dwarfism of cv. Progress.

Phytochrome-mediated synthesis of novel growth inhibitors, A-2α and β, and dwarfism in peas.

Jatropham, ( R )-(−)-5-hydroxy-3-methyl-3-pyrrolin-2-one, is synthesized in three steps from citraconic anhydride. Highly regioselective reduction of citraconimide gives racemic jatropham in high yield. Kinetic resolution of racemic jatropham using lipase is also described.

First synthesis of (R)-(−)-5-hydroxy-3-methyl-3-pyrrolin-2-one (jatropham) by lipase-catalyzed kinetic resolution

The effects of 3-hydroxy-β-ionone on the growth of hypocotyls of dark-grown dwarl bean (Phaseolus vulgaris L. cv. Morocco) and tall bean (cv. Kentucky Wonder) were examined. 3-Hydroxy-β-ionone inhibited growth of the hypocotyl of both cultivars at doses higher than 3 ng per plant. Seedlings of the tall cultivar responded to a slightly lesser extent to 3-hydroxy-β-ionone than those of the dwarf cultivar. Changes in the levels of 3-hydroxy-β-ionone in hypocotyls of both cultivars 24 h after the onset of light irradiation, were determined by high-performance liquid chromatography and the results compared with the results of light-induced inhibition of growth. The difference in levels of 3-hydroxy-β-ionone between the two cultivars was considerable, and the changes in its levels in the hypocotyls of each cultivar reflected the light-induced inhibition of growth of the hypocotyls of the respective cultivars. These results suggest that the endogenous growth inhibitor. 3-hydroxy-β-ionone, may play an important role in the inhibition by light of hypocotyl growth of the two cultivars and may serve to distinguish the growth habits of these cultivars.

An endogenous growth inhibitor, 3‐hydroxy‐β‐ionone. I. Its role in light‐induced growth inhibition of hypocotyls of Phaseolus vulgaris

To correlate endogenous growth inhibitors of dwarf pea to its dwarfism a thorough search of growth inhibitors was made in the neutral fraction of an acetone extract from the shoots of light-grown seedlings of Pisum sativum L. cvs Progress No 9 and Alaska. From both cultivars six inhibitors were separated and named A-1, A-2, A-3, B-1, B-2 and B-3 based on their order of elution from the silica gel column. Their contents as determined by cress root bioassay were: in cv. Progress 0.40, 16.5, 6.36, 1.02, 0.11 and 0.10, and in cv. Alaska 0.33, 2.35, 3.51, 0.95, 0.10 and 0.09 cress units (g fresh weight)−1. Their contributions to growth regulation of the relevant pea plants were estimated as the products of the above-stated contents times the ratios of the specific activities of each standard sample in the cress roots and the relevant pea cultivars, and they were; in cv. Progress A-2, 5.44 and A-3, 2.10, and in cv. Alaska A-2, 0.68 and A-3, 0.88, those of A-2 and A-3 constituting more than 90% of the total contribution of the six inhibitors in either cultivar. The great differences in the content and contribution to growth regulation of A-2 and A-3 between the two cultivars suggest that the higher contents of and greater responsiveness to the two inhibitors in cv. Progress may be causes of dwarfism of this cultivar. A-l and A-3 were spectroscopically identified with pisatin and a mixture of cis, trans–, and trans, trans xanthoxins.

Yasuyoshi Takeuchi

Papers

Neutral growth inhibitors in light‐grown dwarf pea shoots –separation, identification and growth regulation

Isolation and characterization of dihydromaleimide and its glucoside as growth inhibitors from dwarf pea