Chapter 11 Colchicine and Related Compounds

Wildman, W. C.; Pursey, B.A.

doi:10.1016/s1876-0813(08)60123-2

Cited by 15 publications

(19 citation statements)

References 117 publications

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“…Moreover, the hydrogen at C-8 in sepedonin (or anhydrosepedonin) should exchange more rapidly than the one at C-5 if it is located between two oxygen functions as shown in 1 and 4. Finally, the chemical shifts of the two tropolone ring hydrogens in sepedonin and anhydrosepedonin are consistent with those found in similar environments in other tropolones (5).…”

Section: Structuresupporting

confidence: 82%

Structure of sepedonin, a tropolone metabolite of Sepedomumchrysospermum Fries

Wright¹,

McInnes²,

Smith³

et al. 1970

Can. J. Chem.

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Section: Structuresupporting

confidence: 82%

Structure of sepedonin, a tropolone metabolite of Sepedomumchrysospermum Fries

Wright¹,

McInnes²,

Smith³

et al. 1970

Can. J. Chem.

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“…10,11 The MS methods have been used to establish fragmentation patterns of some colchicine analogues and for detection and identification of components in Colchicum species, whereas mass spectrometry with liquid chromatography, LC/ESI-MS/MS or LC-APCI-MS, have found application in detection of colchicine in sheep serum and milk and in human blood plasma. 10,[12][13][14][15][16][17][18] In the present work five 10-alkylthiocolchicine derivatives ( Figure 1) were investigated for the principal fragmentation pathways of the molecular ions using EI and protonated molecules using MALDI mass spectrometry. Colchicine was used as the reference compound and its fragmentation spectra were compared with literature data, obtained by using other methods of soft ionization.…”

Section: Introductionmentioning

confidence: 99%

Mass spectrometric study of colchicine and its synthetic derivatives 10-alkylthiocolchicines

Kurek

Nowakowska

Bartkowiak

2015

ACSi

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The mass spectra behaviour of five 10-alkylthiocolchicine derivatives has been studied using electron ionization and MALDI-TOF MS techniques. Fragmentation patterns of colchicines derivatives after EI have been investigated, as well as mass spectra after collision-induced dissociation (CID) MALDI have been used to gain structural information. To the best of our knowledge, this is the first time that the MALDI MS/MS data for colchicine and its alkylthio derivatives have been described. It has been shown also that the data derived from mass spectra can be used for identification/quantitative determination of natural and modified alkaloids of colchicine group. The detailed fragmentation pathways proposed here could be helpful for the characterization of other colchicines of these type. The utility of different ionization techniques for analysis of compounds of this class has been evaluated. Due to the cytotoxic activity towards tumour cell lines, 10-alkylthiocolchicines may be considered as the active ingredients of anticancer agents. If these compounds find use in medical treatment, their distribution in organism and their metabolism will have to be monitored by spectroscopic or spectrometric methods. The characteristic fragment ions may be used by Selected Reaction Monitoring method for determination of colchicine analogues.

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“…Even though the proton assignments for H-C(I 1) and H-C(12) in colchicine and derivatives of the normal series seem well established, these assignments in the is0 series have not been as clear [14]. Again, it would seem logical to assign H-C(12) to the most downfield doublet based on the well established principle that the 8-proton always resonates at lower field than the a-proton in an a,P-unsaturated system.…”

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confidence: 98%

“…C ( 8 ) can be assigned by selective SFORD experiments (6,= 8.07, H-C (8)). Since the proton assignments for H-C(l1) and H-C(12) are not unambiguously known [14] [15] selective SFORD cannot be used to assign C (1 1) and C (12). However, C (1 1) can be assigned to the signal at 124.5 ppm and C(12) to the signal at 141.8, based upon the following argument.…”

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confidence: 99%

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¹³C‐ and ¹H‐NMR. Assignments for colchicine derivatives

Hufford¹,

Capraro²,

Brossi³

1980

Helvetica Chimica Acta

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SummaryThe I3C-NMR. spectra of a number of colchicine derivatives are given comprising examples of the normal series (4+10), is0 series (11416) and colchiceine series (17), which were either reported in the literature or obtained by partial synthesis or degradation reactions. The I3C-NMR. assignments were made by comparisons with known compounds and selective single-frequency offresonance decoupling experiments. Selective proton decoupling experiments have also allowed assignments of the H-C(l1) and H-C(12) protons of the is0 and colchiceine series.In a recent publication, the results of a study of the microbial transformation of colchicine (1) were reported [l]. With the aid of the proton-coupled I3C-NMR. data, selective single-frequency off-resonance decoupling experiments and by comparison of the data with those of 1 and its hydrolysis products 10-0-demethylcolchicine (colchiceine, 18) and trimethylcolchicinic acid (19), the correct structure to the metabolites obtained, 2-0-demethylcolchicine (2) and 3-0-demethylcolchicine (3) was assigned.We have now examined the 13C-NMR. spectra of other colchicine derivatives comprising examples from the normal series (4 + lo), is0 series (11 + 16) and colchiceine series (17). The I3C-NMR. spectra offer an excellent way to distinguish between derivatives of each series. These compounds are natural products (eg. 2,3, 6, 7) [2], or obtained by partial synthesis (e.g. 8, 9, 11-15, 17) [3-71, or by degradations (e.g. 4, 5, 10, 16, 18, 19) [8-11]9, and have recently been prepared again in connection with another project [7].1-0-Demethylcolchicine (4) was reported to be a microbial metabolite of colchicine (1) [ 121, although only 2-0-demethylcolchicine (2) and 3-0-demethylcolchicine (3) were identified as microbial metabolites using the fermentation I )The isomeric 0-methyl ethers 10 and 16 were obtained by methylation of Woodwarcfs dehydrodeacetylaminocolchiceine, an intermediate in Eschenmoser's total synthesis of colchicine (1) [ 1 I] with CH2N2. The position of the double bond in ring B of 10 and 16 is not firmly established and may well have to be assigned to the 5,6-position.

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Chapter 11 Colchicine and Related Compounds

Cited by 15 publications

References 117 publications

Structure of sepedonin, a tropolone metabolite of Sepedomumchrysospermum Fries

Structure of sepedonin, a tropolone metabolite of Sepedomumchrysospermum Fries

Mass spectrometric study of colchicine and its synthetic derivatives 10-alkylthiocolchicines

¹³C‐ and ¹H‐NMR. Assignments for colchicine derivatives

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Chapter 11 Colchicine and Related Compounds

Cited by 15 publications

References 117 publications

Structure of sepedonin, a tropolone metabolite of Sepedomumchrysospermum Fries

Structure of sepedonin, a tropolone metabolite of Sepedomumchrysospermum Fries

Mass spectrometric study of colchicine and its synthetic derivatives 10-alkylthiocolchicines

13C‐ and 1H‐NMR. Assignments for colchicine derivatives

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¹³C‐ and ¹H‐NMR. Assignments for colchicine derivatives