Biotransformation of Isoprenoids and Shikimic Acid Derivatives by a Vegetable Enzymatic System

2004 ◽  
Vol 59 (3-4) ◽  
pp. 201-204 ◽  
Author(s):  
Wanda Krystyna Mączka ◽  
Agnieszka Mironowicz
Keyword(s):  
Daucus Carota ◽  
Shikimic Acid ◽  
Methyl Esters ◽  
Reversible Reaction ◽  
Apium Graveolens ◽  
Enzymatic System ◽  
Aromatic Acids ◽  
Daucus Carota L ◽  
Enzymatic Systems ◽  
Armoracia Lapathifolia

In biotransformations carried out under similar conditions enzymatic systems from carrot (Daucus carota L.), celeriac (Apium graveolens L. var. rapaceum) and horse-radish (Armoracia lapathifolia Gilib.) hydrolyzed the ester bonds of acetates of phenols or alicyclic alcohols. Nevertheless, methyl esters of aromatic acids did not undergo hydrolysis. Alcohols were oxidized to ketones in a reversible reaction.

scholarly journals Plant-Mediated Biotransformations of S(+)- and R(–)-Carvones

2018 ◽  
Vol 8 (12) ◽  
pp. 2605 ◽  
Author(s):  
Wanda Mączka ◽  
Daria Sołtysik ◽  
Katarzyna Wińska ◽  
Małgorzata Grabarczyk ◽  
Antoni Szumny
Keyword(s):  
Solanum Tuberosum L ◽  
Apium Graveolens ◽  
Petroselinum Crispum ◽  
Enzymatic System ◽  
Enantiomerically Pure ◽  
Daucus Carota L ◽  
Pyrus Communis L ◽  
Substrate Conversion ◽  
Diastereomeric Excess ◽  
Reduction Of Ketones

The enzymatic system of vegetables is well known as an efficient biocatalyst in the stereoselective reduction of ketones. Therefore, we decided to use the comminuted material of several plants including five vegetables (Apium graveolens L., Beta vulgaris L., Daucus carota L., Petroselinum crispum L., and Solanum tuberosum L.) and three fruits (Malus pumila L. “Golden” and “Kortland” as well as Pyrus communis L. “Konferencja”) to obtain enantiomerically pure carveol, which is commercially unavailable. Unexpectedly, all of the used biocatalysts not only reduced the carbonyl group of (4R)-(–)-carvone and (4S)-(+)-carvone, but also reduced the double bond in the cyclohexene ring. The results revealed that (4R)-(–)-carvone was transformed into (1R, 4R)- and (1S, 4R)-dihydrocarvones, and (1R,2R,4R)-dihydrocarveol. Although the enzymatic system of the potato transformed the substrate almost completely, the %de was not the highest. Potato yielded 92%; however, when carrot was used as the biocatalyst, it was possible to obtain 17% of (1R, 4R)-(+)-dihydrocarvone with 100% diastereomeric excess. In turn, the (4S)-(+)-carvone was transformed, using the biocatalysts, into (1R, 4S)- and (1S, 4S)-dihydrocarvones and dihydrocarveols. Complete substrate conversion was observed in biotransformation when potato was used. In the experiments using apple, (1R, 4S)-dihydrocarvone with 100% diastereomeric excess was obtained. Using NMR spectroscopy, we confirmed both diastereoisomers of 4(R)-1,2-dihydrocarveols, which were unseparated in the GC condition. Finally, we proved the high usefulness of vegetables for the biotransformation of both enantiomers of carvone as well as dihydrocarvone.

Screening of somatic hybrids of celery (Apium graveolens L.) and carrot (Daucus carota L.) with the chloroplast marker DcMP

2020 ◽  
pp. 91-94
Author(s):  
S. Bruznican ◽  
T. Eeckhaut ◽  
E. De Keyser ◽  
J. Van Huylenbroeck ◽  
D. Geelen
Keyword(s):  
Daucus Carota ◽  
Somatic Hybrids ◽  
Apium Graveolens ◽  
Daucus Carota L ◽  
Chloroplast Marker

Protein bodies in umbelliferous seeds. III. Characterization of calcium-rich crystals

1982 ◽  
Vol 60 (8) ◽  
pp. 1399-1403 ◽  
Author(s):  
Ernest Spitzer ◽  
John N. A. Lott
Keyword(s):  
Chemical Composition ◽  
Daucus Carota ◽  
Protein Bodies ◽  
Apium Graveolens ◽  
X Ray Diffraction ◽  
Anethum Graveolens ◽  
Foeniculum Vulgare ◽  
X Ray ◽  
Daucus Carota L

The chemical composition of the calcium-rich crystal inclusions present in the seed protein bodies of carrot (Daucus carota L. cv. Imperator 408), wild carrot (Daucus carota L.), caraway (Carum carvi L.), anise (Pimpinella anisum L.), dill (Anethum graveolens L.), celery (Apium graveolens L. cv. Tall Utah), fennel (Foeniculum vulgare Mill.), parsnip (Pastinaca sativa L. cv. Hollow Crown), parsley (Petroselinum sativum L. cv. Moss Curled), and chervil (Anthriscus cerefolium L. cv. Curled) was determined. Using a variety of methods including X-ray diffraction, infrared spectroscopy, microincineration, energy dispersive X-ray analysis, solubility studies, and staining, the chemical composition of the calcium-rich crystal inclusions was identified as calcium oxalate.

scholarly journals Plant-Mediated Enantioselective Transformation of Indan-1-one and Indan-1-ol. Part 2

Molecules ◽  
2019 ◽  
Vol 24 (23) ◽  
pp. 4342
Author(s):  
Mączka ◽  
Wińska ◽  
Grabarczyk ◽  
Galek
Keyword(s):  
Daucus Carota ◽  
Enantiomeric Excess ◽  
Callus Cultures ◽  
Enzymatic System ◽  
Daucus Carota L ◽  
Satisfactory Yield ◽  
Reduction And Oxidation ◽  
Competing Reactions

The main purpose of this publication was to obtain the S-enantiomer of indan-1-ol with high enantiomeric excess and satisfactory yield. In our research, we used carrot callus cultures (Daucus carota L.), whereby the enzymatic system reduced indan-1-one and oxidized indan-1-ol. During the reaction of reduction, after five days, we received over 50% conversion, with the enantiomeric excess of the formed S-alcohol above 99%. In turn, during the oxidation of racemic indan-1-ol after 15 days, 36.7% of alcohol with an enantiomeric excess 57.4% S(+) remained in the reaction mixture. In addition, our research confirmed that the reactions of reduction and oxidation are competing reactions during the transformation of indan-1-ol and indan-1-one in carrot callus cultures.

Calcium mobilization into developing seedlings of umbelliferous plants

1982 ◽  
Vol 60 (8) ◽  
pp. 1404-1408 ◽  
Author(s):  
John N. A. Lott ◽  
Ernest Spitzer ◽  
Catherine M. Vollmer
Keyword(s):  
Calcium Oxalate ◽  
Daucus Carota ◽  
Polarized Light ◽  
Calcium Mobilization ◽  
Apium Graveolens ◽  
Calcium Oxalate Crystals ◽  
Anethum Graveolens ◽  
Foeniculum Vulgare ◽  
Daucus Carota L ◽  
Oxalate Crystals

Calcium mobilization into developing seedlings of several umbelliferous plants including carrot (Daucus carota L. cv. Imperator 408), wild carrot (Daucus carota L.), caraway (Carum carvi L.), anise (Pimpinella anisum L.), dill (Anethum graveolens L.), celery (Apium graveolens L. cv. Tall Utah), fennel (Foeniculum vulgare Mill.), parsnip (Pastinaca sativa L. cv. Hollow Crown), parsley (Petroselinum sativum L. cv. Moss Curled), and chervil (Anthriscus cerefolium L. cv. Curled) was investigated with emphasis on carrot and celery. Calcium determinations using atomic absorption spectrometry of carrot and celery embryos obtained from dry mericarps and carrot and celery seedlings collected when the pericarp plus testa plus endosperm remains fell off the seedlings, revealed that some calcium uptake occurred in carrot and possibly celery. It is possible that some of the calcium obtained by the seedlings came from the calcium oxalate crystals but the calcium could also have originated from other calcium sources within the endosperm. Polarized light studies of endosperm remains from carrot, celery, and the other members of the family Umbelliferae investigated, revealed that large numbers of calcium oxalate crystals were present in the endosperm remains after separation from the seedlings. The results of these studies indicate that calcium oxalate crystals are not used extensively as a calcium source during germination and early seedling growth.

Enantioselective Hydrolysis of Bromo- and Methoxy-Substituted 1-Phenylethanol Acetates Using Carrot and Celeriac Enzymatic Systems

2007 ◽  
Vol 62 (5-6) ◽  
pp. 397-402 ◽  
Author(s):  
Wanda K. Mączka ◽  
Agnieszka Mironowicz
Keyword(s):  
Aromatic Ring ◽  
Opposite Effect ◽  
Bromine Atom ◽  
Apium Graveolens ◽  
Enantioselective Hydrolysis ◽  
Daucus Carota L ◽  
Oxidation Of Alcohols ◽  
Enzymatic Systems ◽  
Hydrolysis Of ◽  
Substituted 1

Enantioselective hydrolysis of bromo- and methoxy-substituted 1-phenylethanol acetates was conducted using comminuted carrot (Daucus carota L.) and celeriac (Apium graveolens L. var. rapaceum) roots. Hydrolysis of the acetates led to alcohols, preferentially to R-(+)- enantiomers. Efficiencies of both reactions - hydrolysis of the acetates with an electrondonating methoxy group and oxidation of the resulting alcohols - increased in the following order: ortho < meta < para. The presence of an electron-withdrawing bromine atom in the aromatic ring had the opposite effect. Oxidation of alcohols with both types of substituents in the aromatic ring showed that location of a substituent had stronger impact on the oxidation rate than its electronic properties.

Protein bodies in umbelliferous seeds. II. Elemental composition

1982 ◽  
Vol 60 (8) ◽  
pp. 1392-1398 ◽  
Author(s):  
Ernest Spitzer ◽  
John N. A. Lott
Keyword(s):  
Elemental Composition ◽  
Daucus Carota ◽  
Protein Bodies ◽  
Apium Graveolens ◽  
Pastinaca Sativa ◽  
Anethum Graveolens ◽  
Foeniculum Vulgare ◽  
X Ray ◽  
Daucus Carota L ◽  
Wild Carrot

The elemental composition of the protein bodies from several members of the Umbelliferae including carrot (Daucus carota L. cv. Imperator 408), wild carrot (Daucus carota L.), caraway (Carum carvi L.), anise (Pimpinella anisum L.), dill (Anethum graveolens L.), celery (Apium graveolens L. cv. Tall Utah), fennel (Foeniculum vulgare Mill.), parsnip (Pastinaca sativa L. cv. Hollow Crown), parsley (Petroselinum sativum L. cv. Moss Curled), and chervil (Anthriscus cerefolium L. cv. Curled) was determined using energy dispersive X-ray analysis. Globoid crystals in the endosperm usually contained P, K, and Mg or infrequently P, K, Mg, and Ca. In the embryos of carrot and caraway, P was always present with a combination of K, Mg, or Ca. Calcium was the only element detectable in the calcium-rich crystals. The proteinaceous matrix always contained S and K regardless of the inclusion present in the protein body.Quantitative determinations of P, Mg, K, and Ca are presented for all members studied except wild carrot, chervil, celery, and fennel. In all species analysed in this manner K or Ca were present in the highest amounts followed by P and Mg. Calcium-localization studies showed that most of the Ca is located in the endosperm and pericarp portions of the mericarp.

Protein bodies in umbelliferous seeds. I. Structure

1982 ◽  
Vol 60 (8) ◽  
pp. 1381-1391 ◽  
Author(s):  
Ernest Spitzer ◽  
John N. A. Lott
Keyword(s):  
Daucus Carota ◽  
Light And Electron Microscopy ◽  
Protein Bodies ◽  
Apium Graveolens ◽  
Anethum Graveolens ◽  
Foeniculum Vulgare ◽  
Daucus Carota L ◽  
The Family ◽  
The 19Th Century ◽  
Structural Aspects

The structure of the protein bodies from seeds of the family Umbelliferae has not been studied extensively since late in the 19th century. Using light and electron microscopy structural aspects of the protein bodies of carrot (Daucus carota L. cv. Imperator 408), wild carrot (Daucus carota L.), caraway (Carum carvi L.), anise (Pimpinella anisum L.), dill (Anethum graveolens L.), celery (Apium graveolens L. cv. Tall Utah), fennel (Foeniculum vulgare Mill), parsnip (Pastinaca sativa L. cv. Hollow Crown), parsley (Petroselinum sativum L. cv.Moss Curled), and chervil (Anthriscus cerefolium L. cv. Curled) were studied. Both endosperm and embryo protein bodies were investigated. Structurally, the protein bodies from all these genera were similar in that two types of protein bodies were found. One type consisted of a homogeneous, proteinaceous matrix and a number of variously sized, globoid crystal inclusions. The other type consisted of a homogeneous, proteinaceous matrix and either an individual or, more commonly, an aggregate of calcium-rich crystals arranged in a cluster usually termed a druse. Both types of protein bodies were never found in the same cell. Only globoid crystals were found in the embryo protein bodies. Protein bodies in the embryos were smaller, more numerous per cell, and often contained a flocculent, proteinaceous matrix.

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