Effects of ${\alpha}-ketol$ type oxylipin (KODA) on flowering and its application as a growth regulater

a-Ketol linolenic acid [KODA, 9,10-ketol-octadecadienoic acid, or 9-hydroxy-10 -oxo-12(Z), 15(Z)-octadecadienoic acid] was found as a stress-induced factor in Lemna paucicostata. KODA reacts with catecholamines to generate many products that strongly induce flowering in L. paucicostata, although KODA itself was inactive. KODA contains an asymmetric carbon at the 9-position in the molecule; the 9-hydroxyl group is predominantly 9R, with an enantiomeric excess of 40% (70% 9R and 30% 9S). We analyzed two major products of the reaction between KODA and norepinephrine, named FN1 and FN2. FN1 was identified as a tricyclic a-ketol fatty acid, 9(R)-11-{(2'R,8’R,10'S,11'S)-2',8'-dihydroxy-7'-oxo-11'-[(Z)-2-pentenyl]-9'-oxa-4'-azatricyclo[6.3.1.01.5]dodec-5'en-10'-yl}-9-hydroxy-10-oxoundecanoic acid. FN2 was the C-9 epimer of FN1. FN1 was derived from 9R-type KODA and FN2 from 9S-type. FN1 showed strong flower-inducing activity, but FN2 was inactive. Pharbitis nil (violet) is a typical short-day plant; flowering can be induced by exposing a seedling cultivated under continuous light to a single 16-h dark period. We analyzed endogenous KODA levels and showed that they were closely related to flower induction: KODA sharply increased in the later part of a 16-h dark period, on the other hand, it failed to increase in the night-break experiment. In addition to it, KODA increased transiently in immature flower buds in all the plants we examined, including P. nil. No such increase of KODA was seen in foliar buds of P. nil. When KODA was sprayed on seedlings of Pharbitis, flower induction was promoted only by the (R)-form of KODA. We also found that KODA enhances flowering in garden plants such as carnations and impatienses. These phenomena indicate that KODA may be involved in flowering formationg of plants and it is potentially useful for a regulating agent for commercial plant flowering.