Identification of reaction products of 9-hydroxy-10-oxo-12(Z),15(Z)-octadecadienoic acid (KODA) and norepinephrine that strongly induce flowering in Lemna

Yokoyama, Mineyuki; Yamaguchi, Syuhei; Suzuki, Masayuki; Tanaka, Osamu; Kobayashi, Katsuhei; Yanaki, Toshio; Watanabe, Naoharu

doi:10.5511/plantbiotechnology.25.547

Cited by 5 publications

(1 citation statement)

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“…The reaction products of 1 with norepinephrine and epinephrine showed strong flower-inducing activities towards Lemna. 1,2 1 has been also identified in the leaves of Pharbitis nil cv. Violet 3 and in immature flower buds of Dianthus caryophyllus L., Dendranthema grandiflorum Kitam, and Eustoma russellianum Griseb.…”

Section: Introductionmentioning

confidence: 88%

Enantio-selective reduction of the flowering related compound KODA and its analogues in Pharbitis nil cv. Violet

et al. 2012

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Plant oxylipins are an important class of signaling molecules in plants. The cyclic adducts of epinephrine or norepinephrine with the naturally occurring oxylipin (12Z,15Z)-9-hydroxy-10oxo-octadeca-12,15-dienoic acid (KODA, 1) or its synthetic analogues (2-6) have been reported to possess flower-inducing activity towards Lemna paucicostata. By in vivo and in vitro experiments with seedlings of Pharbitis nil cv. Violet carbonyl groups of the -ketols (1 and 3) and the ketones (7 and 9) were enantio-selectively reduced to give their corresponding vicinal diols (2 and 4) and alcohols (8 and 10). The stereo-chemistry at the oxymethine carbon was determined based on the long-range C-H coupling constants and the modified Mosher's method. Orientation of the adjacent hydroxyl group in (1 and 3) did not affect the enantioselectivity, whereas the conversion was slightly affected and higher yields were obtained with the R enantiomers of the -ketols.

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Section: Introductionmentioning

confidence: 88%