BIOSYNTHESIS OF MUSTARD OIL GLUCOSIDES: IV. THE ADMINISTRATION OF METHIONINE-C14 AND RELATED COMPOUNDS TO HORSERADISH

1964 ◽  
Vol 42 (7) ◽  
pp. 1033-1040 ◽  
Author(s):  
M. D. Chisholm ◽  
L. R. Wetter
Keyword(s):  
Degradation Products ◽  
Allyl Isothiocyanate ◽  
Chemical Degradation ◽  
Mustard Oil ◽  
Methyl Group ◽  
Armoracia Lapathifolia ◽  
Related Compounds

The administration of C14-labelled compounds to horseradish (Armoracia lapathifolia Gilib.) demonstrated that both methionine and acetate were efficiently incorporated into the aglycone (allyl isothiocyanate) of sinigrin. Chemical degradation of the aglycone showed that the methyl group of acetate appeared in the "isothiocyanate carbon" and that carbons 2, 3, and 4 of methionine were incorporated into carbons 2, 3, and 4 respectively of the aglycone with very little randomization. Homocysteine was the only other compound that was incorporated into the aglycone. Other degradation products of methionine did not appear to be incorporated into allyl isothiocyanate.

BIOSYNTHESIS OF MUSTARD OIL GLUCOSIDES: I. ADMINISTRATION OF C14-LABELLED COMPOUNDS TO HORSERADISH, NASTURTIUM, AND WATERCRESS

1962 ◽  
Vol 40 (1) ◽  
pp. 1505-1514 ◽  
Author(s):  
E. W. Underhill ◽  
M. D. Chisholm ◽  
L. R. Wetter
Keyword(s):  
Allyl Isothiocyanate ◽  
The Other ◽  
Mustard Oil ◽  
Methyl Carbon ◽  
Nasturtium Officinale ◽  
Other Hand ◽  
Tropaeolum Majus ◽  
Armoracia Lapathifolia ◽  
Carboxyl Carbon

Biosynthetic investigations with C14-labelled compounds indicate that the aromatic isothiocyanate moieties of mustard oil glucosides obtained from garden nasturtium (Tropaeolum majus L.) and watercress (Nasturtium officinale R.Br.) are derived from phenylalanine. Similar investigations on sinigrin, the mustard oil glucoside isolated from horseradish (Armoracia lapathifolia Gilib.) demonstrate that glycine is incorporated into allyl isothiocyanate. The methyl carbon of acetate was readily incorporated into sinigrin and gluconasturtium and was found almost exclusively in the 'isothiocyanate carbon'; on the other hand the carboxyl carbon is a poor precursor of sinigrin.

BIOSYNTHESIS OF MUSTARD OIL GLUCOSIDES: VII. FORMATION OF SINIGRIN IN HORSERADISH FROM HOMOMETHIONINE-2-14C AND HOMOSERINE-2-14C

1966 ◽  
Vol 44 (12) ◽  
pp. 1625-1632 ◽  
Author(s):  
M. D. Chisholm ◽  
L. R. Wetter
Keyword(s):  
Amino Acids ◽  
Allyl Isothiocyanate ◽  
Valeric Acid ◽  
The Other ◽  
Mustard Oil ◽  
Armoracia Lapathifolia ◽  
Hydroxyvaleric Acid

Five 14C-labeled amino acids were administered to horseradish (Armoracia lapathifolia Gilib.) leaves. Three of the amino acids, DL-homoserine-2-14C, DL-methionine-2-14C, and DL-homomethionine-2-14C (2-amino-5-(methylthio)-valeric acid), were precursors of the aglycone (allyl isothiocyanate) of sinigrin. The other two, DL-allylglycine-2-14C (2-amino-4-pentenoic acid) and DL-2-amino-5-hydroxyvaleric acid-2-14C, were incorporated in insignificant amounts. The relationships of the three efficient precursors are discussed. The syntheses of four 14C-labeled amino acids used in this investigation are described.

BIOSYNTHESIS OF MUSTARD OIL GLUCOSIDES: I. ADMINISTRATION OF C14-LABELLED COMPOUNDS TO HORSERADISH, NASTURTIUM, AND WATERCRESS

1962 ◽  
Vol 40 (11) ◽  
pp. 1505-1514 ◽  
Author(s):  
E. W. Underhill ◽  
M. D. Chisholm ◽  
L. R. Wetter
Keyword(s):  
Allyl Isothiocyanate ◽  
The Other ◽  
Mustard Oil ◽  
Methyl Carbon ◽  
Nasturtium Officinale ◽  
Other Hand ◽  
Tropaeolum Majus ◽  
Armoracia Lapathifolia ◽  
Carboxyl Carbon

Biosynthetic investigations with C14-labelled compounds indicate that the aromatic isothiocyanate moieties of mustard oil glucosides obtained from garden nasturtium (Tropaeolum majus L.) and watercress (Nasturtium officinale R.Br.) are derived from phenylalanine. Similar investigations on sinigrin, the mustard oil glucoside isolated from horseradish (Armoracia lapathifolia Gilib.) demonstrate that glycine is incorporated into allyl isothiocyanate. The methyl carbon of acetate was readily incorporated into sinigrin and gluconasturtium and was found almost exclusively in the 'isothiocyanate carbon'; on the other hand the carboxyl carbon is a poor precursor of sinigrin.

scholarly journals Volatile glucosinolate breakdown products and the essential oil of Descurainia sophia (L.) webb ex Prantl (Brassicaceae)

2017 ◽  
Vol 15 (2) ◽  
pp. 95-102
Author(s):  
Milan Dekic ◽  
Niko Radulovic ◽  
Jelena Danilovic-Lukovic ◽  
Dalibor Stojanovic
Keyword(s):  
Essential Oil ◽  
Degradation Products ◽  
Allyl Isothiocyanate ◽  
Cuticular Wax ◽  
Mustard Oil ◽  
Breakdown Product ◽  
Volatile Constituents ◽  
Descurainia Sophia ◽  
Whole Plant ◽  
Peak Areas

Volatile constituents obtained by autolysis of aerial and underground parts of D. sophia and the essential oil obtained by hydrodistillation of whole plant samples were analyzed in detail by GC and GC-MS. In total, 71 constituents were identified, accounting for more than 90% of the total peak areas in the chromatograms. Both aerial and underground autolysates contained considerable amounts of lignan arctigenin and cuticular wax compounds. The essential oil was dominated by glucosinolate breakdown product 4-pentenenitrile. Glucosinolate degradation products identified in the essential oil and autolysates, 3-butenyl isothiocyanate, 4-pentenenitrile and allyl isothiocyanate, suggested the presence of gluconapin and sinigrin in this species as the most likely ?mustard oil? precursors.

scholarly journals In VitroActivity of Glucosinolates and Their Degradation Products against Brassica-Pathogenic Bacteria and Fungi

2014 ◽  
Vol 81 (1) ◽  
pp. 432-440 ◽  
Author(s):  
T. Sotelo ◽  
M. Lema ◽  
P. Soengas ◽  
M. E. Cartea ◽  
P. Velasco
Keyword(s):  
Pseudomonas Syringae ◽  
Xanthomonas Campestris ◽  
Pathogenic Bacteria ◽  
Degradation Products ◽  
Allyl Isothiocyanate ◽  
Leaf Extracts ◽  
Soil Pathogens ◽  
Content Type ◽  
Positive Effects

ABSTRACTGlucosinolates (GSLs) are secondary metabolites found inBrassicavegetables that confer on them resistance against pests and diseases. Both GSLs and glucosinolate hydrolysis products (GHPs) have shown positive effects in reducing soil pathogens. Information about theirin vitrobiocide effects is scarce, but previous studies have shown sinigrin GSLs and their associated allyl isothiocyanate (AITC) to be soil biocides. The objective of this work was to evaluate the biocide effects of 17 GSLs and GHPs and of leaf methanolic extracts of different GSL-enrichedBrassicacrops on suppressingin vitrogrowth of two bacterial (Xanthomonas campestrispv. campestris andPseudomonas syringaepv. maculicola) and two fungal (AlternariabrassicaeandSclerotiniascletoriorum)Brassicapathogens. GSLs, GHPs, and methanolic leaf extracts inhibited the development of the pathogens tested compared to the control, and the effect was dose dependent. Furthermore, the biocide effects of the different compounds studied were dependent on the species and race of the pathogen. These results indicate that GSLs and their GHPs, as well as extracts of differentBrassicaspecies, have potential to inhibit pathogen growth and offer new opportunities to study the use ofBrassicacrops in biofumigation for the control of multiple diseases.

The Pyrolytic Rearrangement of 1-Alkynoyl-3-methylpyrazoles: Synthesis of Pyrazolo[1,5-a]pyridin-5-ols and Related Compounds

1994 ◽  
Vol 47 (6) ◽  
pp. 991 ◽  
Author(s):  
RFC Brown ◽  
FW Eastwood ◽  
GD Fallon ◽  
SC Lee ◽  
RP Mcgeary
Keyword(s):  
Carbon Chain ◽  
Ring Structure ◽  
High Yield ◽  
Methyl Group ◽  
X Ray ◽  
X Ray Crystallography ◽  
Flash Vacuum Pyrolysis ◽  
Vacuum Pyrolysis ◽  
Fused Ring ◽  
Related Compounds

Flash vacuum pyrolysis of 1-(alkyn-2′-oyl)-3-methylpyrazoles at 650°/0.03 mm forms pyrazolo[1,5-a]pyridin-5-ols, often in high yield, which may bear substituents at C2, C3 or C7. In the absence of a 3-methyl group in the precursor, N-ethynylpyrazoles are formed in low yield. The formation of both types of product is interpreted as involving 3-(N-pyrazolyl)propadienones formed by N1 → N2 migration of the N-alkynoyl group with inversion of the three-carbon chain. The fused-ring structure of 2-methylpyrazolo[1,5-a]pyridin-5-ol (25) was established by X-ray crystallography of the O-benzoyl derivative (27).

Phase I Study of the Novel Epothilone Analog Ixabepilone (BMS-247550) in Patients With Advanced Solid Tumors and Lymphomas

2007 ◽  
Vol 25 (9) ◽  
pp. 1082-1088 ◽  
Author(s):  
Carol Aghajanian ◽  
Howard A. Burris ◽  
Suzanne Jones ◽  
David R. Spriggs ◽  
Marvin B. Cohen ◽  
...  
Keyword(s):  
Plasma Concentration ◽  
Solid Tumors ◽  
Dose Escalation ◽  
Mononuclear Cells ◽  
Degradation Products ◽  
Standard Dose ◽  
Chemical Degradation ◽  
Maximum Plasma ◽  
Advanced Solid Tumors ◽  
Phase Ii Studies

Purpose To establish the maximum-tolerated dose (MTD), dose-limiting toxicity (DLT), safety, pharmacokinetics, and pharmacodynamics of ixabepilone when administered as a 1-hour infusion every 3 weeks to patients with advanced solid tumors or relapsed/refractory non-Hodgkin's lymphoma. Dosing schedules of 40 mg/m2 and 50 mg/m2 over 3 hours were also evaluated. Patients and Methods Sixty-one patients were enrolled using an initial accelerated dose-escalation phase followed by a standard dose-escalation phase, with doses of ixabepilone ranging from 7.4 to 65 mg/m2. The pharmacokinetics of ixabepilone and two of its chemical degradation products were evaluated. Plasma pharmacodynamics were evaluated for both 1- and 3-hour infusions using an assay that measures the amount of endogenous tubulin in peripheral-blood mononuclear cells that exists in the polymerized versus the unpolymerized state. Response evaluation was performed every 6 weeks. Results The most common DLTs were neutropenia, stomatitis/pharyngitis, myalgia, and arthralgia. The MTD of ixabepilone as a 1-hour infusion every 3 weeks was established as 50 mg/m2. The maximum plasma concentration and area under the plasma concentration time curve appeared to increase less than proportionally to dose. Durable objective responses were seen in eight patients, including two complete responses. Five of the responders had experienced treatment failure with a taxane. Conclusion The recommended dose of ixabepilone for the initiation of phase II studies on the basis of these results is 50 mg/m2 over 1 hour every 3 weeks. The promising efficacy and tolerability results demonstrated by ixabepilone in this study warrant its continued development.

Identification of new aqueous chemical degradation products of isophosphoramide mustard

2001 ◽  
Vol 25 (3-4) ◽  
pp. 669-678 ◽  
Author(s):  
Stéphane Breil ◽  
Robert Martino ◽  
Véronique Gilard ◽  
Myriam Malet-Martino ◽  
Ulf Niemeyer
Keyword(s):  
Degradation Products ◽  
Chemical Degradation ◽  
Isophosphoramide Mustard
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