Organ-to-organ and seasonal statistical variations were also detected for some of the individual alkaloids detected in each of these species. Seasonal variation in Amaryllidaceae alkaloid content (mg 100 g-1 dry weight) observed in different organs of Crinum moorei for the. Seasonal variation in Amaryllidaceae alkaloid content (mg 100 g-1 dry weight) detected in different organs of Crinum moorei for.
Seasonal variation in the alkaloid content of Amaryllidaceae. mg 100 g-1 dry weight) detected in various organs of Crinum.
CD 3 COOD
Literature Review
Identification and Structure Elucidation .1 NMR Spectra
- Central nervous system
- Antimalarial activity
In the case of the unsubstituted benzyl protons, the most deprotected appears at b 4.71 ppm as in diacetylnarcissidine 17 (KIHARA et al. 1995). It has been observed that slight changes in stereochemistry of Amaryllidaceae alkaloids are often sufficient to cause significant differences in the mass spectra of many of the stereoisomers (DUFFIELD et al. 1965). Crinamines are the main antibacterial constituents of the bulbs of Crinum jagus (VILADOMAT et al. 1996).
An ascending gradient in thebaine content was found from upper to lower parts of Papaver bracteatum roots (LEVY et al. 1988).
Aims of This Study
The third group is distinguished only by the presence of the matrine alkaloids and a fourth group is characterized by the absence of all these alkaloids (IZADDOOST 1975). The only chemotaxonomic criterion distinguishing the genus Ochrosia from the closely related Neisosperma is the presence of the antitumor alkaloid ellipticine, or its derivatives in the former, and their absence in the latter (AMARASEKERA and ARAMBEWELA 1986; SEVENET 1991). An example is the discovery of high sanguinarine content in the roots of Argemone subfusiformis taxa, compared to the aerial parts.
The cultivars Ice Follice and Mount Hood had a high content of galanthamine compared to the cultivars Geranium and white cheerf (MORAES-CERDEIRA et al. 1997).
Materials and Methods
Alkaloid Extraction and isolation
The plant material was sliced and dried in an oven at 55°C until constant dry weight was obtained and pulverized using a grinder. The dried and powdered non-flowering whole plants (198.5 g for C. bulbispermum, 62.5 g for C moorei and 865 g for C. macowanit) were extracted according to the method of GHOSAL et al. The solution was basified with NH 4 OH to pH 9.5 after removal of neutral material with diethyl ether (100 mL x 4).
The basic solution was extracted with diethyl ether, ethyl acetate and n-butanol (100 mL x 4 each) respectively to give fractions A, Band C.
Purification of alkaloids .1 Crinum bulbispermum
The remaining crude extract was developed on a VLC packed with silica gel using chloroform and then chloroform enriched with 5% methanol and then with 2.5% methanol at a time. The first was developed on TLC using dichloromethane:methanol:ammonia (16:1:1) to give crinine (9 mg) and bulbispermine (7 mg). Fractions eluted with 85% and 82.5% chloroform were combined and developed on a preparative TLC using chloroform:methanol (6:1) to give an impure fraction of 34 mg, which was further developed using chloroform:diethylamine (20 :1) to achieve.
Fraction C was developed using VLC eluted with chloroform and then with chloroform enriched gradually with 5% methanol up to 50% methanol.
Quantification of alkaloids for the study of variations .1 Plant material
- Sample collection
- Data processing
- Cherylline 106
- Mooreine 104
- Epivittatine 107
- Year 1998/1999
- Year 1999/2000
The surface area percentage of crinin extracted was extrapolated with the linear response curve of crinin for. In the 13C NMR spectrum (Table 3.2) the presence of a carbon resonance of the methoxy group at 56.7, a carbon resonance of the N-methyl group at 42.5 and an aliphatic carbon group at 45.3 along with four olefinic singlets and four doublets suggest the presence of tazetin type . of the alkaloid (ZE-L1N et al. The presence of the ethoxy substituent at the 8-position is not common in natural product chemistry.
As an alternative, crinine was used to determine the recovery of alkaloids and the effectiveness of the methods used. In addition, there were no variations in the different classes of Amaryllidaceae alkaloids, expressed as a percentage of the total alkaloid content. It represented the total alkaloid yield of the root while it was a minor component of the other organs.
The leaves had the highest crinine-type alkaloids expressed as a percentage of the total alkaloid content throughout the year (Figure 4.2). In the first year of the study, the bulbs had a significantly higher crini level in the winter while, in the year bulbs had a significantly higher crini level in the summer. However, the Iycorine content in leaves was significantly lower than that of other organs.
Crinamine was only detected in leaves and bulbs in summer in the second year of the study period. During the winter of the first study year, the bulbs had the highest 3-0-acetyl hamaine content followed by the flower stems and leaves. Wald statistics showed highly significant seasonal differences in crin content of the organs examined.
An exception was the low yield (20%) of leaves in the summer of the second year of the study.
Total quantified alkaloid content
In the first year of the study, seven alkaloids belonging to three ring types of Amaryllidaceae alkaloids were identified. In addition to the above, 1-epideacetylbovdensine 108 and crinamidine 36 were also detected in the second year of the research. 1-0-Acetylicorine was excluded from the quantitative changes between organs and seasonal changes due to poor separation from the unidentified compound (Appendix 2).
In the second year of the study, alkaloids of the crinine type were expressed as a percentage of all alkaloids represented in winter and spring. As in the first year, the bulbs contained the highest levels of crinine-type alkaloids in all seasons, in the range of 63.3-65% in summer and winter, respectively. In percentage terms, after the leaves (0%), the flowering stems had a low content of crinine-type alkaloids (24.8%).
The roots had the highest cronin-type alkaloid yield (%) in summer followed by winter (Table 5.4).
Variation in individual alkaloid levels .1 Organ-to-organ variation
- Lycorine 1
- Seasonal variation in individual alkaloids
- Crinine 32
- Crinamine 34
Crinines were detected in bulbs and roots throughout the study period and in flower stems in the first year of the study. Powellin was detected in bulbs and roots in winter and in roots in summer the first year. In the second year, powellina was discovered in the roots in all seasons and in the bulbs in the spring.
Cherylline was present in bulbs throughout the study period and in flowering stems in the second year of the study. Bulbs had a clear pattern of variation in crinine content in different seasons throughout the study period. The level of lycorine in the roots was significantly higher in spring than in winter.
Crinina was detected in the flowering stems and bulbs throughout the study period and in the roots in the spring of the first year of the study. The highest amount of crinamine was detected in the bulbs during the spring, followed by the roots of the flowering bulbs inside and from the flowering stems in the second year of the study period. 3-0-Acetylhamayne was detected in bulbs and roots and as a trace in flowering stems.
No significant differences were detected in the 3-O-acetylhamayne content of bulbs and roots collected during summer and winter. No significant differences were observed in the yield of the above alkaloids for the bulbs of C.
Flowering stalks
Crinin was added to the dilute acid solution at a rate of 100 µg mr1 and extracted in the same way as the alkaloids from the plant material. There are also reports on the occurrence of alkaloids in the flowers of Lycoris incamata (LEWIS 1996), L. In the second year, the decrease in total alkaloid yield was between spring (High) and winter (Iow).
The high variation among plants of the same species was particularly noticeable for those sampled in the same season. An exception was the relatively low yield (20%) of leaves in summer in the second year of the study. Crinin-type alkaloids with an ethane bridge in the ~ position, lacking a double bond between 1 and 2, were not detected in all organs of C.
Crinamidin was detected only at relatively low levels in bulbs and roots; and. The fact that no Iycorine or only traces of this compound was detected in the leaves of C. Since the modified leaves that form the bulb protect the apical meristem, it seems logical that the plant accumulates significant amounts of alkaloids in the bulb instead of the leaves.
The amounts of epibuphanisin in the various organs corresponded to the amounts of crinine and powellin. An increase in the levels of crinin and powellin was accompanied by an increase in epibuphanisin.
Conclusions
The isolation of the related alkaloids Iycorine, 1-0-acetyllycorine and the quaternary alkaloid mooreine is also biosynthetically important. The presence of quaternary alkaloids in plants has been shown to be vital intermediates with biosynthetic and translocation roles (COURT 1983). The second part of the current study focused on the seasonal and interspecific variation of Crinum alkaloids between organs.
Using shorter intervals between successive samplings (once every week or two weeks) will provide a better understanding of the biosynthetic interconversion, translocation and accumulation of these alkaloids in the different organs and in different seasons. The great variation between the individual plants tested made it difficult to draw a clear conclusion about the organ and seasonal yield of the alkaloids. Complete assignment of the NMR spectra of papyramine and 6-epipapyramine by two-dimensional NMR spectroscopy.
A rapid quantitative method for the analysis of galantamine and other Amaryllidaceae alkaloids by capillary gas chromatography. Distribution of total alkaloids and major constituents in different organs of Datura metal var. Proton magnetic resonance spectral studies of some Amaryllidaceae alkaloids of the 5,1 series Obethanophenanthridine and criwelline and tazettine.
High-resolution mass spectrometry in molecular structure studies-VI: The fragmentation of Amaryllis alkaloids in the crinine series. 1Hand 13C NMR spectra of the isolated alkaloids arranged in numerical order by their appearance in the results sections of Chapter 3.
![Table 3.4. 13C-NMR Data (CD30D) for 3-[4'-(2'-minoethyl)phenoxy]bulbispermine 103 and bulbispermine.](https://thumb-ap.123doks.com/thumbv2/pubpdfnet/10629089.0/75.834.105.635.323.1004/table-nmr-data-cd30d-minoethyl-phenoxy-bulbispermine-bulbispermine.webp)
