Matthiola

Figueiredo, P. et al., Anthocyanin intramolecular interactions a new mathematical approach to account for the remarkable colorant properties of the pigments extracted from Matthiola incana, J. Am. Chem. Soc., 118, 4788, 1996. 

Flavonol synthase (FLS E.C.l.14.11.23) catalyzes the committed step in the production of fiavonols by introduction of a double bond between C2 and C3 of the corresponding dihydroflavonols. Like E3H, ELS has been described as a 2-oxoglutatarate-dependent dioxygenase based on its cofactor requirements for 2-oxoglutarate, Fe, and ascorbate. FLS was initially identified in enzyme preparations from illuminated parsley cell suspension cultures [67]. Subsequently, FLS was characterized from the flower buds of Matthiola incana and carnation (Dianthus caryophyllus L.), and it was suggested that there was regulation between flavonol and anthocyanidin biosynthesis [83, 84]. 

Dihydroflavonol 4-reductase (DFR EC 1.1.1.219) is a member of the short-chain dehydrogenase/reductase family and catalyzes the stereospecific conversion of (+)-(2R,3R)-dihydroflavonols to the corresponding (2R,3S,4S) flavan-3,4-cw-diols (leucoanthocyanidins), with NADPH as a required cofactor. The enzyme activity was first identified in cell suspension cultures of Douglas fir (Pseudotsuga menziesii) and was shown to be related to the accumulation of flavan-3-ols and proanthocyanidins [96]. Leucoanthocyanidins and DFR were later shown to be required for anthocyanidin formation by complementation of Matthiola incana mutants blocked between dihydroflavonol and anthocyanidin biosynthesis [97, 98], DFR has been purified to apparent homogeneity and biochemically analyzed from flower buds of Dahlia variabilis [99]. DFR was shown to accept different substrates depending on the plant species from which it was isolated (reviewed in 100). 

SpribiUe R, Forkmann G (1984) Conversion of dihydroflavonols to flavonols with enzyme extracts from flower buds of Matthiola incana. Z Naturforsch 39C 714-719... 

HeUer W, Britsch L, Eorkmann G, Grisebach H (1985) Leucoanthocyanidins as intermediates in anthocyanin biosynthesis in flowers of Matthiola incana. R. Br. Planta 163(2) 191-196... 

HeUer W, Forkmann G, Britsch L, Grisebach H (1985) Enzymatic reduction of (+)-dihydroflavonols to flavan-3,4-cu-diols with flower extracts from Matthiola incana and its role in anthocyanin biosynthesis. Planta 165(2) 284-287... 

Ramsay, N.A. et ah. Two basic helix-loop-helix genes (MYC-146 and GL3) from Arabidopsis can activate anthocyanin biosynthesis in a white-flowered Matthiola incana mutant. Plant Mol Biol, 52, 679, 2003. 

Saito, N. et al., Acylated pelargonidin 3-sambubioside-5-glucosides in Matthiola incana, Phytochemistry, 41, 1613, 1996. 

FORKMANN, G., HELLER, W., GRISEBACH, H Anthocyanin biosynthesis in flowers of Matthiola incana flavanone 3-hydroxylase and flavonoid 3 -hydroxylase. Z. Naturforsch, 1980,35c, 691-695. 

Teusch, M., Forkmann, C. and Seyffert, W. (1987) Cenetic control of hydroxycin-namoylcoenzyme A anthocyanidin 3-glycoside-hydroxycinnamoyltransferases from petals oi Matthiola incana. Phytochemistry, 26, 991. ... 

Sulforaphene (Raphanin) (CH2)2-CH = CH-SO-CH3 C6H9NOS2 175.26 oil (a]D-108° 2404-46-8 (CHCI3) seeds of radish (Raphanus sativus var. alba), radish and stock Matthiola blcomis... 

Approximately 1030 flavonols are known (Harbome, 1991). Most of these are glycosides derived from approximately 300 flavonoid aglycones. Flavonol biosynthesis probably occurs via a 2-hydroxy intermediate with subsequent dehydration, in a manner similar to that proposed for formation of flavones. Flavonol formation with extracts from flowers of Matthiola and Petunia requires a soluble 2-oxo-glutarate-dependent dioxygenase (Heller and Forkmann, 1988). 

Hhllkr. W.. L. Bri isch. G. Forkm.xnn. and H. Grishbach, Leu-coanthocyanidins as intermediates in anthocyanidin biosynthesis in flowers of Matthiola incana, Planta, 163, 191-196 (1985a). 

Drinker, A. M. and G. F. Spencer, Herbicidal activity of sulforaphene from stock (Matthiola incana), J. Chem. Ecol., 19, 2279-2284 (1993). 

C12H21NO10S3 435.497 Isol. from Matthiola bicornis and Matthiola fruticulosa. Needles +lH20(EtOH) (as tetra-Ac, K salt). 

Isol. from petals of Matthiola incana (as chloride), k 280, 508 nm (MeOH/HCl). Present in acylated form in the plant. 

Similar results were obtained by Kristiansen (71) and Grisebach and co-workers (61) on crude enzyme preparations from Hordeum vulgare and Matthiola in-cana, respectively. Kristiansen (71) further showed that the enzymic product was a minor species in the sodium borohydride reduction of taxifolin, the 4R and 4S products being formed in a ratio of approximately 95 5. This enabled the properties of the enzymically and chemically produced 4S isomers to be directly compared. Stafford and Lester (132) have also shown that (2i ,3i )-dihydromyricetin may be converted to 3,3, 4,4, 5,5, 7-heptahydroxy-flavan by the Pseudotsuga menziesii enzyme complex, thereby establishing the sequence for prodelphinidins as well. 

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