Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states
A study has been conducted on adsorption of semisynthetic flavonoid venoruton on the surface of highly dispersed silica (HDS) modified with polyvinylpyrrolidone (PVP). It has been found that an adsorption value of venoruton for the modified silica was 20% higher than that of hydroxylated silica surf...
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Chuiko Institute of Surface Chemistry National Academy of Sciences of Ukraine
2002
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| author | Kulik, T. V. Galagan, N. P. Pogorelyi, V. K. Pokrovskiy, V. A. |
| author_facet | Kulik, T. V. Galagan, N. P. Pogorelyi, V. K. Pokrovskiy, V. A. |
| author_institution_txt_mv | [
{
"author": "T. V. Kulik",
"institution": "Інститут хімії поверхні НАН України"
},
{
"author": "N. P. Galagan",
"institution": "Інститут хімії поверхні НАН України"
},
{
"author": "V. K. Pogorelyi",
"institution": "Інститут хімії поверхні НАН України"
},
{
"author": "V. A. Pokrovskiy",
"institution": "Інститут хімії поверхні НАН України"
}
] |
| author_sort | Kulik, T. V. |
| baseUrl_str | |
| collection | OJS |
| datestamp_date | 2018-11-27T09:42:19Z |
| description | A study has been conducted on adsorption of semisynthetic flavonoid venoruton on the surface of highly dispersed silica (HDS) modified with polyvinylpyrrolidone (PVP). It has been found that an adsorption value of venoruton for the modified silica was 20% higher than that of hydroxylated silica surface. By the temperature-programmed desorption technique with the mass‑spectrometric registration of volatile constituents (TPD MS) a research has also been made into decomposition of venoruton adsorbed by system PVP-HDS. It has been shown that the number of stages of thermolysis of carbohydrate parts of venoruton molecules adsorbed on the modified surface decreases down to one while in the case of the condensed state there are two stages of carbohydrate portion thermolysis and in the situation with the adsorption on the hydroxylated HDS surface there are three stages. As far as the system venoruton-PVP-HDS is concerned, the maximum rate of volatile constituent elimination (destruction of carbohydrate parts of molecules) is shifted towards high temperature region by 130°C in comparison with the condensed state and by 200°C in comparison with the state set up during adsorption on the hydroxylated HDS surface. The increase in the thermal stability of venoruton adsorbed by the PVP-HDS system is related to the effect of PVP polymer chains, which block the access of venoruton molecules to active sites of the silica surface. |
| first_indexed | 2025-07-22T19:30:12Z |
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143
MASS-SPECTROMETRIC STUDY OF THERMAL
DECOMPOSITION OF SOME POLYKETIDES
IN CONDENSED AND ADSORBED STATES
T.V. Kulik, N.P. Galagan, V.K. Pogorelyi, and V.A. Pokrovskiy
Institute of Surface Chemistry, National Academy of Sciences
Gen. Naumov Str. 17, 03680 Kyiv-164, UKRAINE
Abstract
A study has been conducted on adsorption of semisynthetic flavonoid venoruton on the
surface of highly dispersed silica (HDS) modified with polyvinylpyrrolidone (PVP). It has been
found that an adsorption value of venoruton for the modified silica was 20% higher than that of
hydroxylated silica surface. By the temperature-programmed desorption technique with the
mass-spectrometric registration of volatile constituents (TPD MS) a research has also been
made into decomposition of venoruton adsorbed by system PVP-HDS. It has been shown that
the number of stages of thermolysis of carbohydrate parts of venoruton molecules adsorbed on the
modified surface decreases down to one while in the case of the condensed state there are two
stages of carbohydrate portion thermolysis and in the situation with the adsorption on the
hydroxylated HDS surface there are three stages. As far as the system venoruton-PVP-HDS is
concerned, the maximum rate of volatile constituent elimination (destruction of carbohydrate parts
of molecules) is shifted towards high temperature region by 130°C in comparison with the
condensed state and by 200°C in comparison with the state set up during adsorption on the
hydroxylated HDS surface. The increase in the thermal stability of venoruton adsorbed by the PVP-
HDS system is related to the effect of PVP polymer chains, which block the access of venoruton
molecules to active sites of the silica surface.
Introduction
Recently the interest in phytopreparations of folk medicine increased throughout the
world [1-2]. Active components of most of them are polyketides. Formerly we studied the
following series of polyketides: bioflavonoid quercetin, semisynthetic flavonoid venoruton,
alizarin red S antraquinone, and structural isomer of quercetin, namely morin [3-5]. The results
achieved revealed a correlation between the chemical structure of morin and venoruton and
mechanisms of their thermolysis which occurred trough rupture of chemical bonds by three
main routes A, B and C. The thermolysis of morin took place in three stages whereas that of
venoruton proceeded in four stages. The presence of a carbohydrate residue in a venoruton
molecule brought about additional thermolysis stages corresponding to destruction of this
carbohydrate fragment.
Research into adsorption of polyketide (flavonoids in particular) on the surface of
highly dispersed mineral matrices may to some extent clear up the processes, which occur on
the cell membrane surface in the presence of biomolecules. The role played in these processes
by the hydroxyl group in the para position of a carbonaceous ring was not completely
elucidated yet, although this group is known to be responsible for biological activity of
flavonoids. Venoruton is analogous to flavonoids acting in living systems. The rate of its
adsorption from water on the dispersed silica surface is more than two orders of magnitude
144
larger than that of morin, quercetin, and alizarin red S from water-ethanol mixtures. The
comparison drawn between the available physicochemical parameters of venoruton adsorption
and those obtained in our previous works has shown that the venoruton adsorption on the
HDS surface takes place by binding carbohydrate residues. This inference is corroborated by
the experimental data collected when investigating thermal decomposition of venoruton in the
condensed state and that of venoruton adsorbed on dispersed silica by the method of
temperature-programmed desorption with mass-spectrometric registration of volatile
constituents.
Results and Discussion
Venoruton in the condensed state (Fig. 1) and in the state set up after its adsorption on
the surface of highly dispersed silica (HDS) was already studied by the TPD MS technique [4].
In general, it was found that the routes of its decomposition did not change during its
adsorption on the surface of HDS. However, in the case of the adsorbed state in the low-
temperature region there appeared additional peaks for 109, 110, 111 m/z. (at about 220°C;
destruction by mechanism C) and for 72, 97, 126 m/z (at 180°C; destruction of carbohydrate
residues) (Fig. 2). The formation of these peaks was related to the character of adsorption on
the surface, namely to the fact that it was carbohydrate residues that directly participated in
binding with the surface. At higher temperatures the number of thermal decomposition stages,
their temperature intervals, and their sequence were approximately identical to those observed
for the condensed state (Table).
I, arb. u.
102
126
102
72
97
72
0
0.2
0.4
0.6
0.8
70 140 210 280 350 420 490 T, C
o
Fig. 1. Thermograms of m/z: 126, 102, 97, 102; decomposition of carbohydrate substitutient -
glucose-rhamninose for venoruton in the condensed state.
145
72
97
72
102
126
I, arb. u
0
0.1
0.2
0.3
0.4
T, C
o
60 120 180 240 300 360 420 480
Fig. 2. Thermograms of m/z: 126, 102, 97, 102; decomposition of carbohydrate substitutient -
glucose-rhamninose for venoruton adsorbed on highly dispersed silica surface.
Thus, as is seen from Table, the thermolysis of morin proceeds in three main stages.
The presence of a carbohydrate substituent in the structure of chromone (venoruton) leads to
appearance of an additional stage of the thermal decomposition, with the carbohydrate residue
decomposition and chromone decomposition (routes B and C) proceeding in synchronism. The
observation result is explained by the fact that ramnoglucosyl is in position 3 of chromone, i.e.
it is a component of the structure whose fragments are detected in the mass spectra recorded in
the case of the thermolysis by route B. The adsorption occurred on the silica surface manifests
itself by peaks in a low-temperature region. During the first stage of the carbohydrate residue
thermolysis under these conditions the chromone thermolysis by route B is somewhat delayed
from that of sugar (approximately by 40°C), while during the other two stages (II and III) the
chromone thermolysis by route B and carbohydrate residue thermolysis proceed at the same
rate.
A research was also conducted into kinetics of venoruton adsorption on the surface of
silica modified with polyvinylpyrrolidone (PVP) (Fig. 3). It was found that the adsorption
value was 16–20% larger in comparison with the hydroxylated surface. The
mass-spectrometric investigations were made using samples of highly dispersed silica modified
with polyvinylpyrrolidone and samples of venoruton adsorbed by system HDS-PVP. The
adsorption of PVP from an aqueous solution on the surface of highly dispersed silica was affected
under steady-state conditions at room temperature. A weighed sample (1.1 g) of HDS was added to
110 mL of 10% solution of polyvinylpyrrolidone in distilled water. The suspension was let stand 5 h
with periodic stirring, following which it was centrifuged, washed two times with water (2´50 mL),
and dried at room temperature. To 0.1 g of the silica modified with polyvinylpyrrolidone 5 mL of
solution of venoruton in distilled water were added, and the mixture was let stand 1 h with periodic
stirring. Then, the suspension was centrifuged, washed with water, and dried.
The samples prepared have been studied by the TPD MS technique. It has been shown
that the onset of thermal destruction of venoruton adsorbed by the HDS-PVP system takes
place at a temperature above 210°C as it was in the case for the free state. During the first
stage the main contribution to the thermolysis is made by destruction of venoruton molecules
according to route C (release of pyrocatechin in its molecular form). The destruction of a
venoruton molecule by route C proceeds at temperatures up to 450°C and leads to formation
of two peaks at 280°C and at about 370°C.
143
Table. Data on decomposition of venoruton
Т, 0С
Venoruton condensed Venoruton adsorbed
on highly dispersed silica
Venoruton adsorbed
on PVP-highly dispersed silica
Stage Destruction type (m/z)
Stage Destruction
type
(m/z) Stage Destruction
type
(m/z)
180
- - - І Carbohydrate: 126, 97, 72. - - -
220 - - - І Chromone type:
С
109, 110, 111.
- - -
250 І Carbohydrate:
Chromone type:
В
С
126, 97, 72;
112, 95;
109, 110, 111.
- - - - - -
280 - - - ІІ Carbohydrate:
Chromone type:
В
С
126, 97, 72;
112, 95;
110.
І Chromone type:
С
109, 110, 111.
360 ІІ Carbohydrate:
Chromone type:
В
С
126, 97, 72;
112, 95;
111.
ІІІ Carbohydrate:
Chromone type:
В
С
126, 97, 72;
112, 95;
110.
- - -
380 - - - ІV Chromone type:
А
136, 108, 91
ІІ Carbohydrate:
Chromone type:
А
В
С
126, 97, 72;
136, 108, 91;
141, 123, 95;
110.
420
ІІІ Chromone type: А 136, 108, 91. - - - - - -
450 - - - V Chromone
type: А
108, 91
- - -
480
ІV Chromone type: А 136, 108, 91. - - - - - -
144
143
0
100
200
300
400
500
0 5 25 50 75 160 200
t, min
А
, m
g/
g
1
2
Fig. 3. Kinetics of venoruton adsorption by highly dispersed silica (1) and PVP-HDS (2).
Of note here is the fact that in the mass spectra recorded at temperatures below 320°C there
are no lines which might be attributed to the thermal decomposition of carbohydrate substituents
and to destruction by route B, whereas during the first stage of the free venoruton thermolysis (the
thermal destruction maximum is observed at 280°C) some contribution to the process is made by
the carbohydrate residue decomposition and by the destruction of molecules by route B.
The kinetics curves characterizing the destruction of a venoruton molecule by routes A
and B have peaks at about 380°C. The thermal analysis curves plotted for fragments of 141,
108, 95, 91 m/z (destruction by route B) have a gently sloping trailing edge, with the release of
the fragments being observed at temperatures above 500°C.
The greatest changes brought about by the adsorption are characteristic of the thermolysis
stages that involve destruction of the carbohydrate part of a molecule. The venoruton adsorption
on the surface of the system HDS-PVP leads to a decrease in the number of the peaks observed
on the thermal analysis curves plotted for volatile constituents released during destruction of
carbohydrate fragments (in the case of the free state and the state set up upon adsorption on
HDS there are two and three peaks respectively). It is well illustrated by Fig. 4 and Table. The
maximum on the thermal analysis curves for 126, 97, 72 m/z (destruction of the carbohydrate
part of a molecule; 380°C) in the case of the system venoruton-HDS-PVP is shifted towards
high temperatures by 130°C in comparison with the free state and by 200 C in comparison with
the state set up after the adsorption on hydroxylated silica.
The observed enhancement of the thermal stability of venoruton in the state set up
during its adsorption by the system HDS-PVP in comparison with the state after its adsorption
on the HDS surface may be explained by the influence of polyvinylpyrrolidone polymer chains
that block approach of venoruton molecules to active sites on the silica surface which function
as agents of dehydroxylation. The active sites on the surface facilitate the thermal
decomposition of carbohydrate residues, with the decomposition involving abstraction of water
if the venoruton molecule is in the state set up during its adsorption on the hydroxylated silica
144
surface. It should be emphasized that it is the carbohydrate fragment that makes a main
contribution to binding with the highly dispersed silica surface.
Fig. 4. Thermograms of m/z: 126, 102, 97, 102; decomposition of carbohydrate
substitutient - glucose-rhamninose for venoruton adsorbed by PVP-HDS surface.
The destruction of the carbohydrate part and chromone by routes A and B takes place
in the narrow interval of temperatures 320–450°C with the maximum of the elimination rate
for volatile constituents at 380°C, i.e. in the temperature region where destruction of
polyvinylpyrrolidone proceeds. Thus, one can infer that decomposition of the prevailing majority
of venoruton molecules occurs in synchronism with destruction of polymer chains of
polyvinylpyrrolidone.
Conclusions
The changes in the silica surface structure caused by modification of silica with
polyvinylpyrrolidone (PVP) lead to corresponding changes in thermal desorption curves
characteristic of the thermal decomposition of venoruton in the system PVP-highly dispersed
silica. The most significant changes are observed during the thermolysis stages, which involve
the destruction of carbohydrate fragments of molecules. The number of the decomposition
stages for the system venoruton-PVP-HDS reduces to one, whereas in the case of the
condensed and adsorbed states there are two stages and three stages respectively. The
maximum of the carbohydrate fragment decomposition for the system venoruton-PVP-HDS is
shifted towards high temperatures by 130 C in comparison with the condensed state and by
200 C in comparison with the state set up as a result of adsorption on the hydroxylated silica
surface.
The enhancement of the thermal stability characteristic of venoruton adsorbed by the
silica-PVP system in comparison with that characteristic of the substance adsorbed by highly
145
dispersed silica may be explained by influence of polyvinylpirrolidone whose polymer chains
impede access of venoruton molecules to active sites of silica surface which possesses
dehydroxylation properties. The active sites present on silica surface promote thermal
decomposition of carbohydrate residues, with the decomposition being accompanied by
elimination of water. It should be emphasized that the main contribution to binding with the
silica surface is made by carbohydrate residues.
References
1. Doerge D.R., Churchwel M.I., and Delclos K.B. On-line sample preparation using
restricted-access media in the analysis of the soya isoflavones, genistein and daidzein, in
rat serum using liquid chromatography electrospray mass spectrometry // Rapid
Commun. Mass Spectrom. – 2000. – V.14. – P.673-678.
2. Pogorelyi V.K., Barvinchenko V.N., Lipkovska N.A., Turov V.V., and Chuiko A.A.
Adsorption of bioactive molecules of medical plants // Chemistry, Physics and
Technology of Surfaces. - Issues 4-6. - Kyiv.- 2001. - P.301-309.
3. Kulik T.V., Galagan N.P., Pogorelyi V.K., and Pokrovskiy V.A. TPD MS studies of
several polyketides in solid state and adsorbed on silica surface // Proc. 15th
International Mass Spectrometry Conference. – Barselona, 28 August–1 September
2000. - Book Abstr. - P.105.
4. Pokrovskiy V.A., Galagan N.P., and Kulik T.V. Non-isothermal decomposition of
biomolecules studied by means of temperature-programmed desorption mass
spectrometry // Chemistry, Physics and Technology of Surface.- Issues 4-6. – Kyiv. –
2001. - P.332-347.
5. Kulik T.V., Galagan N.P., Pogorelyi V.K., and Pokrovskiy V.A. TPD MS studies of
several polyketides in solid state and adsorbed on silica surface //Advances in Mass
Spectrometry. – Wiley. – Ed. by E. Gelpi, Chichester, New York, Weinhelm, Brisbane,
Singapore, Toronto, 2001. - V.15. - P.491-492.
T.V. Kulik, N.P. Galagan, V.K. Pogorelyi, and V.A. Pokrovskiy
T.V. Kulik, N.P. Galagan, V.K. Pogorelyi, and V.A. Pokrovskiy
T.V. Kulik, N.P. Galagan, V.K. Pogorelyi, and V.A. Pokrovskiy
T.V. Kulik, N.P. Galagan, V.K. Pogorelyi, and V.A. Pokrovskiy
Gen. Naumov Str. 17, 03680 Kyiv-164, UKRAINE
Abstract
A study has been conducted on adsorption of semisynthetic flavonoid venoruton on the surface of highly dispersed silica (HDS) modified with polyvinylpyrrolidone (PVP). It has been found that an adsorption value of venoruton for the modified silica was 20% higher than that of hydroxylated silica surface. By the temperature-programmed desorption technique with the massspectrometric registration of volatile constituents (TPD MS) a research has also been made into decomposition of venoruton adsorbed by system PVP-HDS. It has been shown that the number of stages of thermolysis of carbohydrate parts of venoruton molecules adsorbed on the modified surface decreases down to one while in the case of the condensed state there are two stages of carbohydrate portion thermolysis and in the situation with the adsorption on the hydroxylated HDS surface there are three stages. As far as the system venoruton-PVP-HDS is concerned, the maximum rate of volatile constituent elimination (destruction of carbohydrate parts of molecules) is shifted towards high temperature region by 130(C in comparison with the condensed state and by 200(C in comparison with the state set up during adsorption on the hydroxylated HDS surface. The increase in the thermal stability of venoruton adsorbed by the PVP-HDS system is related to the effect of PVP polymer chains, which block the access of venoruton molecules to active sites of the silica surface.
Table. Data on decomposition of venoruton
Table. Data on decomposition of venoruton
Table. Data on decomposition of venoruton
Table. Data on decomposition of venoruton
Table. Data on decomposition of venoruton
Table. Data on decomposition of venoruton
Table. Data on decomposition of venoruton
Table. Data on decomposition of venoruton
Conclusions
|
| id | oai:ojs.pkp.sfu.ca:article-92 |
| institution | Surface |
| keywords_txt_mv | keywords |
| language | English |
| last_indexed | 2025-07-22T19:30:12Z |
| publishDate | 2002 |
| publisher | Chuiko Institute of Surface Chemistry National Academy of Sciences of Ukraine |
| record_format | ojs |
| resource_txt_mv | surfacezbircomua/69/a4fa14896001a5438979a2b0a1628a69.pdf |
| spelling | oai:ojs.pkp.sfu.ca:article-922018-11-27T09:42:19Z Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states Kulik, T. V. Galagan, N. P. Pogorelyi, V. K. Pokrovskiy, V. A. A study has been conducted on adsorption of semisynthetic flavonoid venoruton on the surface of highly dispersed silica (HDS) modified with polyvinylpyrrolidone (PVP). It has been found that an adsorption value of venoruton for the modified silica was 20% higher than that of hydroxylated silica surface. By the temperature-programmed desorption technique with the mass‑spectrometric registration of volatile constituents (TPD MS) a research has also been made into decomposition of venoruton adsorbed by system PVP-HDS. It has been shown that the number of stages of thermolysis of carbohydrate parts of venoruton molecules adsorbed on the modified surface decreases down to one while in the case of the condensed state there are two stages of carbohydrate portion thermolysis and in the situation with the adsorption on the hydroxylated HDS surface there are three stages. As far as the system venoruton-PVP-HDS is concerned, the maximum rate of volatile constituent elimination (destruction of carbohydrate parts of molecules) is shifted towards high temperature region by 130°C in comparison with the condensed state and by 200°C in comparison with the state set up during adsorption on the hydroxylated HDS surface. The increase in the thermal stability of venoruton adsorbed by the PVP-HDS system is related to the effect of PVP polymer chains, which block the access of venoruton molecules to active sites of the silica surface. A study has been conducted on adsorption of semisynthetic flavonoid venoruton on the surface of highly dispersed silica (HDS) modified with polyvinylpyrrolidone (PVP). It has been found that an adsorption value of venoruton for the modified silica was 20% higher than that of hydroxylated silica surface. By the temperature-programmed desorption technique with the mass‑spectrometric registration of volatile constituents (TPD MS) a research has also been made into decomposition of venoruton adsorbed by system PVP-HDS. It has been shown that the number of stages of thermolysis of carbohydrate parts of venoruton molecules adsorbed on the modified surface decreases down to one while in the case of the condensed state there are two stages of carbohydrate portion thermolysis and in the situation with the adsorption on the hydroxylated HDS surface there are three stages. As far as the system venoruton-PVP-HDS is concerned, the maximum rate of volatile constituent elimination (destruction of carbohydrate parts of molecules) is shifted towards high temperature region by 130°C in comparison with the condensed state and by 200°C in comparison with the state set up during adsorption on the hydroxylated HDS surface. The increase in the thermal stability of venoruton adsorbed by the PVP-HDS system is related to the effect of PVP polymer chains, which block the access of venoruton molecules to active sites of the silica surface. A study has been conducted on adsorption of semisynthetic flavonoid venoruton on the surface of highly dispersed silica (HDS) modified with polyvinylpyrrolidone (PVP). It has been found that an adsorption value of venoruton for the modified silica was 20% higher than that of hydroxylated silica surface. By the temperature-programmed desorption technique with the mass‑spectrometric registration of volatile constituents (TPD MS) a research has also been made into decomposition of venoruton adsorbed by system PVP-HDS. It has been shown that the number of stages of thermolysis of carbohydrate parts of venoruton molecules adsorbed on the modified surface decreases down to one while in the case of the condensed state there are two stages of carbohydrate portion thermolysis and in the situation with the adsorption on the hydroxylated HDS surface there are three stages. As far as the system venoruton-PVP-HDS is concerned, the maximum rate of volatile constituent elimination (destruction of carbohydrate parts of molecules) is shifted towards high temperature region by 130°C in comparison with the condensed state and by 200°C in comparison with the state set up during adsorption on the hydroxylated HDS surface. The increase in the thermal stability of venoruton adsorbed by the PVP-HDS system is related to the effect of PVP polymer chains, which block the access of venoruton molecules to active sites of the silica surface. Chuiko Institute of Surface Chemistry National Academy of Sciences of Ukraine 2002-06-12 Article Article application/pdf https://surfacezbir.com.ua/index.php/surface/article/view/92 Surface; No. 7-8 (2002): Chemistry, Physics and Technology of Surface; 143-149 Поверхность; № 7-8 (2002): Химия, физика и технология поверхности; 143-149 Поверхня; № 7-8 (2002): Хімія, фізика та технологія поверхні; 143-149 3154-8091 3154-8083 en https://surfacezbir.com.ua/index.php/surface/article/view/92/91 Авторське право (c) 2002 T.V. Kulik, N.P. Galagan, V.K. Pogorelyi, V.A. Pokrovskiy |
| spellingShingle | Kulik, T. V. Galagan, N. P. Pogorelyi, V. K. Pokrovskiy, V. A. Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states |
| title | Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states |
| title_alt | Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states |
| title_full | Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states |
| title_fullStr | Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states |
| title_full_unstemmed | Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states |
| title_short | Mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states |
| title_sort | mass-spectrometric study of thermal decomposition of some polyketides in condensed and adsorbed states |
| url | https://surfacezbir.com.ua/index.php/surface/article/view/92 |
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