N-caffeoyl-4-amino-n-butyric acid, a new flower-specific metabolite in cultured tobacco cells and tobacco plants.
PUT cells were selected from the XD line of cultured tobacco cells (Nicotiana tabacum L. cv. Xanthi-nc) for the ability to utilize putrescine as sole nitrogen source. Previous work had indicated that hydroxycinnamoylputrescines (principally caffeoylputrescine) and 4-amino-n-butyric acid (GABA) are obligatory intermediates in the assimilation of putrescine by PUT cells. The apparent absence in these cells of diamine or polyamine oxidase and pyrroline dehydrogenase, enzymes which catalyze putrescine oxidation in some plant species, led us to propose the following pathway for putrescine oxidation in PUT cells: putrescine----hydroxycinnamoylputrescine----hydroxycinnamoyl - 4-aminobutyraldehyde----hydroxycinnamoyl-GABA----GABA. We tested the hypothesis by looking for the predicted compound, caffeoyl-GABA. A chemical synthesis was developed, and chromatographic and mass spectroscopic procedures were devised for identifying the compound in extracts of cells and plant tissues. Caffeoyl-GABA was found in extracts of PUT cells in micromolar concentrations but was not present in XD cells. Thus, its occurrence in PUT cells appears to be a direct result of selection for the ability to catabolize putrescine. Caffeoyl-GABA has the same distribution in tobacco plants as caffeoylputrescine, i.e. flower buds greater than open flowers greater than floral leaves, green fruit; absent in vegetative tissues.
D002109:Caffeic Acids / Q000032:analysis* / Q000138:chemical synthesis; D002460:Cell Line; D055598:Chemical Phenomena; D002621:Chemistry; D002845:Chromatography; D002851:Chromatography, High Pressure Liquid; D002934:Cinnamates / Q000032:analysis*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D010944:Plants / Q000032:analysis* / Q000378:metabolism; D010947:Plants, Toxic; D011700:Putrescine / Q000378:metabolism; D011760:Pyrrolidinones / Q000032:analysis / Q000138:chemical synthesis; D014026:Nicotiana; D005680:gamma-Aminobutyric Acid / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis / Q000378:metabolism
D002109:Caffeic Acids; D002934:Cinnamates; D011760:Pyrrolidinones; C053363:N-(3,4-diacetoxycinnamoyl)-2-pyrrolidone; C053362:N-caffeoyl-4-aminobutyric acid; D005680:gamma-Aminobutyric Acid; D011700:Putrescine