Identification and determination of metabolites in plant cell biotechnology by gas chromatography and gas chromatography/mass spectrometry

Groneman, A.F.; Posthumus, M.A.; Tuinstra, L.G.M.Th.; Traag, W.A.

doi:10.1016/s0003-2670(00)81492-0

Cited by 18 publications

(4 citation statements)

References 9 publications

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“…Tertiary calli of T. minuta did not contain HPLC-UVdetectable levels of thiophenes. The decrease of the content of secondary metabolites (thiophenes) in calli and cell suspensions (Groneman et al 1984) relative to intact plants is in agreement with a number of investigations in other plant species (Knoop and Beiderbeck 1983). This impoverishment of the secondary metabolite pattern may be due to the dedifferentiated state of the cells in calli and fine suspensions Yeoman 1983, Misawa andSuzuki 1982).…”

Section: Discussionsupporting

confidence: 91%

“…Primary calli of T. minuta had only 4 to 11% of the thiophene content of leaves and this value was 0 to 3% in secondary callus and 0% in tertiary callus. The rapid decrease in thiophene content upon subculturing of callus explains the absence of thiophenes in cell suspensions (Groneman et al 1984). A large variation occurred in the relative thiophene content of primary calli of T. patula (16-156%) and T. ereeta (19-100%).…”

Section: Discussionmentioning

confidence: 98%

“…Mass spectrometry of some of the putative thiophenes indicated that their mass and number of S atoms per molecule corresponded with some known di-and trithiophenes (cf. Groneman et al 1984).…”

Section: Discussionmentioning

confidence: 99%

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Morphological differentiation and occurrence of thiophenes in leaf callus cultures from Tagetes species: Relation to the growth medium of the plants

Ketel¹

1986

Physiologia Plantarum

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The morphology, and the number and concentration of thiophene‐like compounds were studied in leaves, roots and calli of Tagetes species grown with different nutrient solutions. The type of nutrient solution exerted no effect on the number of thiophene‐like compounds, but altered the type of morphological differentiation and thiophene content of calli. Calli of T. minuta L. showed little differentiation and resulted in suspensible callus after two passages. Calli of T. erecta L. cv. Rose d'Inde differentiated rapidly and turned dark brown after one passage. The morphology of calli from T. patula L. cv. Nana furia was intermediate. Tertiary callus of T. patula contained more thiophene‐like compounds and higher concentrations than did the corresponding calli of T. minuta. The content of thiophene‐like compounds decreased after various callus passages, but the relative decrease varied between species.

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Section: Discussionsupporting

confidence: 91%

Section: Discussionmentioning

confidence: 98%

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Morphological differentiation and occurrence of thiophenes in leaf callus cultures from Tagetes species: Relation to the growth medium of the plants

Ketel¹

1986

Physiologia Plantarum

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“…ert'cta and the related Tagetes patula (Siitfeld, 1982;Croes et al, 1989;Mukundan and Hjortso, 1990). Low concentrations of some C,, thiophenes have been incidentally reported (Bohlmann et al, 1967;Groneman et al, 1984;Ketel, 1986;Caniato et al, 1990). We did find AcOCH,BBT at low concentrations in roots and hypocotyls of wild-type T. (zrecta, and AcOCH,BBT and BPT at low concentrations in T. patula (Jacobs et al, 1994).…”

Section: Discussionmentioning

confidence: 47%

Isolation and Characterization of Mutants of Thiophene Synthesis in Tagetes erecta

Jacobs

Arroo²,

Koning³

et al. 1995

Plant Physiol.

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Two mutants of Tagetes erecfa displaying aberrant thiophene composition were identified by screening more than 300 plants from a mutagenized M, population using high-performance liquid chromatography analysis of root extracts. Both mutants, which may have originated from the same mutational event, contained high amounts of the C,, monothiophene 2-(but-3-en-I -ynyl)-5-(penta-1,3-diynyl)-thiophene that was previously not found in T. erecfa and also high amounts of two C,, bithienyls that were absent or present at low concentrations in the wild type. The mutant phenotype was also expressed in 21 Agrobacterium rhizogenes transformed root clones derived from both mutants. Feeding experiments with root cultures derived from one mutant and from the wild type indicated that the monothiophene accumulating in the mutant is the common precursor for all bithienyl thiophenes in wild-type and mutant Tagefes erecfa. These experiments also showed that one mutant is deficient in demethylation of the monothiophene.Although mutants have been widely applied to investigate metabolic pathways in microorganisms and fungi, they have been used relatively rarely for this purpose in plants. Most metabolic mutants of plants affect primary metabolic processes, such as carbon assimilation (Somerville and Ogren, 1979) and metabolism of starch (Caspar et al., 1985), lipids (Browse et al., 1985;Kunst et al., 1989), and amino acids (Haughn and Somerville, 1986;Kreps and Town, 1991;Frankard et al., 1992;Wright et al., 1992;Wu and King, 1994), whereas only a few mutants of secondary metabolic pathways are known (Haughn et al., 1991;Chapple et al., 1992; Rathjen and Robinson, 1992). This situation exists in spite of the fact that chemically induced loss-of-function mutations can be obtained relatively easily (Haughn and Somerville, 1987).Tugetes species (marigolds) produce, mainly in the roots, aromatic sulfur-containing compounds known as thiophenes, which are toxic to nematodes when ingested Bijloo, 1958, 1959). Co-occurrence patterns and precursor-feeding experiments in related species have led to a generally accepted biogenetic scheme, as depicted in Figure 1 (Bohlmann et al., 1973;Bohlmann and Zdero, 1985). Oleic acid is converted into PYE via repeated steps of desaturation and chain shortening. PYE is then converted into the thiophenes that accumulate in Tagetes * Corresponding author; fax 31-80-553450.species. (Bohlmann and Berger, 1965;Bohlmann and Hinz, 1965;Schulte et al., 1965;Bohlmann et al., 1966). The key step in this conversion is the addition of H,S or its biochemical equivalent to conjugated triple bonds and subsequent ring formation, which is probably a two-step reaction (Bohlmann et al., 1973). In addition to the formation of two or three thiophene rings, remova1 of a terminal methyl group and modification of a vinyl group are necessary to obtain the various thiophenes that finally accumulate (Fig. 1).Not much is known about the order in which these reactions take place in Tugetes or about the specificity of the enzymes involve...

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Optimized gas chromatographic analysis of natural pyrethrins and pyrethroids

Class

1991

J. High Resol. Chromatogr.

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Gas chromatographic analysis of natural pyrethrins in insecticidal pyrethrum extract and in insecticide formulations is achieved by on‐column injection with hydrogen as carrier gas under constant flow and programmed pressure conditions. Short thin‐film fused silica capillaries (DB 5 and DB 1701) coupled to retention gaps separate the pyrethrins (cinerin I and II, jasmolin I and II, and pyrethrin I and II) and their analogue S‐bioallethrin (Esbiol) in less than twelve minutes at temperatures below 210°C without any discrimination, degradation or isomerization of thermally labile pyrethrin I and II. With S‐bioallethrin added as internal standard, spray and powder formulations are extracted with ethyl acetate and analyzed by gas chromatography with flame ionization detection for pyrethrum constituents, for other pyrethroids such as tetramethrin, cyphenothrin, cypermethrin, and for the commonly used synergist piperonl butoxide.

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Identification and determination of metabolites in plant cell biotechnology by gas chromatography and gas chromatography/mass spectrometry

Cited by 18 publications

References 9 publications

Morphological differentiation and occurrence of thiophenes in leaf callus cultures from Tagetes species: Relation to the growth medium of the plants

Morphological differentiation and occurrence of thiophenes in leaf callus cultures from Tagetes species: Relation to the growth medium of the plants

Isolation and Characterization of Mutants of Thiophene Synthesis in Tagetes erecta

Optimized gas chromatographic analysis of natural pyrethrins and pyrethroids

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