Then the aqueous solution was extracted three times with a chloroform-methanol-NH4OH solution in 9: 1 aspect ratio. Analyses were repeated three times. Calibration curves were established with three replicates at each concentration. All the used extractive methods revealed the presence of LSA in seeds of Ipomoea violacea , but the system with ammonium hydroxide, methanol and chloroform, provided excellent results in terms of yield compared to other systems adopted in preliminary screening tests.
In the variety of Ipomoea Rubrocerulea the active compound had been quantified around a mean value of 0. Currently the seeds of these plants can be purchased in smart shops or on the internet. In addition, these plants are usually sold as ornamentals. In this case, seeds are treated with chemical substances and antifungals. There are sites on the internet in which the users tell their experiences and explain how to extract LSA from ornamental seeds at home Bilgrey, The Italian law divides different drugs in various tables depending on their compounds.
The decision to prohibit the spread of Salvia divinorum in , another plant with psychoactive properties, was determined by few episodes of addiction. Since , in Table 1 , following an episode of suicide after ingestion, as a specific item, seeds of plants of Argyreia nervosa and Ipomoea violacea , containing as an active ingredient the lysergic acid amide were added to the table. This finding is in agreement with what was indicated in the literature, as the ingestion of seeds would lead to a dose of approximately 6 mg of LSA, able to provoke hallucinogenic effects.
The analysis of mg of Ipomoea seeds detected an average concentration of LSA of 0. It is therefore possible to have hallucinogenic effects from Ipomoea seeds that are commonly marketed. However, the high amount of seeds that would need to be ingested to have the hallucinogenic effects would give considerable toxicity in the gastrointestinal tract, remember that each of these seeds is treated with fungicides and other toxic substances.
The most important limit was the small sample size. In a social context that demonstrates a consistent rise in drug abuse Isabella Mercurio et al. In this work we identified the presence of LSA in all the Ipomoea seeds analysed. In the varieties used and sold for ornamental purposes, doses of LSA 0. The detection of very different concentrations of LSA in all varieties of Ipomoea may be related to genetic and environmental factors, as well as intrinsic factors such as maturity and the age of the seeds of the same variety.
All of these variables should be studied by increasing the number of seeds from different lots. In the absence of data on the toxicity resulting from the ingestion of seeds for ornamental purposes, especially that related to fungicides, we believe that further research on the actual safety of ornamental seeds is necessary, to assess if they can be considered as herbal highs. Arch Intern Med Article Google Scholar. Aoun, P. Christopher, J. Ingraham Emerging drugs of abuse: clinical and legal considerations.
R I Med J 97 6 —5. Int J Drug Policy —8. Brady ET Jr A note on morning glory seed intoxication. Am J Hosp Pharm 25 2 — PubMed Google Scholar. Cohen S Suicide following morning glory seed ingestion. Am J Psychiatr — Crawford K. J Forensic Sci 15 4 Flach C A case of morning-glory- ipomoea -seed psychosis. Nordisk Psykiatrisk Tidsskrift 21 4 — Hawaii Med J — Pharmacol Ther Bot Museum Leaflets Harvard Univ 20 6 — CAS Google Scholar. Ingram AL Jr Morning glory seed reaction. J Am Med Assoc — Samples of seeds were ground finely in a ball mill and weighed carefully to Two kinds of samples were prepared: samples of single seeds of a given type and samples representative for the whole pack of seeds.
The latter were prepared by grinding 1. Such prepared system was ready for subsequent extraction. The extracts were then cooled to room temperature. Seed extracts were centrifuged, filtered through a 0.
In preliminary experiments conducted using the UAE-B technique, the sample and solvent amount as well as the extracting solvent type were evaluated. After preliminary experiments for assessing the amount of sample, solvent, and the solvent type, the three-factor Doehlert experimental design with response surface methodology RSM was used in order to optimize three main factors for MAE and UAE-B: time, temperature, and solvent composition: methanol to water content.
Doehlert experimental design enables the analysis of each factor on multiple levels, distributed evenly thorough optimization range, and thus enables empirical construction of a second-order model [ 24 ]. It is also one of the most efficient experimental designs, as for the three-factorial model, only 13 experiments with different factor values are required. It was therefore directly connected with extraction efficiency. Then, the desirability function D was constructed as the normalized sum of ergine and ergometrine response models, so that it would have value 1 for best parameter values highest extraction efficiency and 0 for unfavorable ones.
As MAE oven is equipped with airtight vessels, it is possible to exceed the methanol boiling point during extraction procedure. UAE-S has to be performed in open vessels, and due to the excessive heat production during extraction, there is no feasible way to control solvent temperature.
As it was assumed that optimal solvent composition should be the same as in the case of UAE-B, only time of extraction was optimized by the single variable optimization, in the range from 0.
Temperature of the solvent was measured directly after every extraction to assure that it does not reach the boiling point of the solvent. Validation was performed following rules of validation guideline for food analysis and bioanalysis [ 25 — 27 ]. The linearity of the method was tested using the set of calibrators: 0. The recovery and matrix effect were evaluated according to the method proposed by Matuszewski et al. In case of matrix effect, a standard was added to the sample after the entire preparation procedure, directly before analysis, and in case of other parameters, standard was added to the sample before extraction.
Repeatability and intermediate precision were calculated using within- and between-day variations, calculated by the ANOVA approach [ 30 ], according to Eqs. Preliminary experiments were carried out to evaluate sample and solvent amount and eliminate solvents with lower efficiency.
As the weight of Ipomoea seeds varies from 15 to 65 mg, a 10 mg sample was chosen, as it would enable analysis of a single seed. Then, using UAE-B, the following solvents were tested: methanol, acetonitrile, and methanol:water mix with and without addition of 0. It was assessed that methanol and methanol:water mixture result in highest extraction efficiency. Therefore, during optimization of extraction methods, methanol:water mixture in different ratios was taken into consideration.
During preliminary experiments, six ergot alkaloids Fig. One should note that in the case of ergine, the first peak originates from ergine and isoergine and it has the same RT as ergine standard used in the experiments.
As those peak RTs overlap perfectly even if other chromatographic gradient programs or columns are used, it was hypothesized that LSH molecule rearranges into ergine due to too aggressive ionization conditions Fig. Chromatograms acquired using the optimized LC-MS method. Ion chromatograms were extracted from the full scan spectrum. Moreover, for 10 mg samples, 10 mL of solvent was sufficient to determine both ergine and ergometrine within linearity range of the LC-MS method.
One should notice that none of the ergot alkaloids was found in samples of IP-MC and IP, even using 50 mg of seeds for extraction. In the case of microwave-assisted extraction, this approach seemed to work perfectly at first glance and enabled prediction of optimal extraction conditions.
Indeed, as response models of both ergine and LSH concentration were calculated, it was assessed that the same factors were significant in both functions, but with inverse coefficients data not shown. This outcome indicated that MAE cannot therefore be used herein, as ergine should be accurately determined. Please note the clear maximum of both the MeOH concentration and the time of extraction are visible on graph C.
Theoretically, higher extraction efficiency could be accessible for higher temperature; however, such experiment could not be conducted, as it is not feasible to use higher temperature of MeOH-water mixture in non-airtight vessels. The extraction efficiency was evaluated by subjecting the same sample to the extraction procedure twice.
Yet, because every sample had to be treated separately and there was no possible automation of the process, this technique was characterized by low throughput and, therefore, it was rejected for further development because of its unsuitability for analysis of a large number of samples.
The linearity of the method covers the range from 5. The LOD and LOQ values estimated using diluted standard solutions and spiked seeds free from analytes were consistent with each other. Particularly, concertation of 1. All of the validation parameters were considered sufficient for applying the developed method to analysis of Ipomoea seeds samples. For quantitative analysis of samples 10 mg each from seeds packs, mean value with standard deviation of ergine or ergometrine concentration is given, whereas for single seed samples, concentration range is listed.
Since there were no available standards for other identified ergot alkaloids, the relative abundance estimation was performed by calculating compound to IS areas ratio for the most abundant isomer of each compound to express differences between samples and Ipomoea cultivars. Determination of ergine, ergometrine in Morning Glory seeds and relative abundance of other ergot alkaloids identified in the samples.
Although concentration of ergine in all three seed pack samples is similar and comparable to the one reported in the literature [ 6 ], it is clearly visible that in the case of single seeds, the amount of both ergine and ergometrine varies substantially, from concentration close or below LOD to two times greater than the mean concentration, which may create a risk of overdose for people experimenting with Morning Glory seeds.
Alkaloids abundance in all three HB cultivars is comparable, with most significant difference for LSH, which varies from 0. As has been demonstrated in this study, LSH is a labile compound, and therefore the variances in its concentration may be due to different age and storage conditions of the seeds rather than difference in plant metabolism.
High relative abundance of penniclavine is an interesting observation; however, it cannot be directly connected with high concentration of this clavine. As there is significant difference in ionization efficiency of different compounds in ESI ion source, comparison with standard is required for assessing penniclavine concentration. The extracts of plant tissue leaves with stems were prepared in a similar manner to seeds extracts, with the difference of 50 mg of sample being used to provide higher alkaloids concentration in the extract.
Extracts were purified with graphitized carbon by vortexing 1. The sample:carbon ratio was established on the basis of our unpublished work devoted to preparation of samples containing chlorophyll. It was also experimentally checked and confirmed that the graphitized carbon does not absorb ergine, ergometrine, or IS from the solution.
The found concentration of ergine and ergometrine were Presence of investigated alkaloids in the tissue of glasshouse plants can be explained by probable fungal infection during cultivation. Endophytes can be transmitted through seeds vertical path or from the environment [ 31 , 32 ], and the composition of species and their occurrence is dynamic and depends on many factors [ 33 ].
It is hard to track down how the fungi had colonized the examined plants. According to the presence of alkaloids in seeds from the same source , the most likely is a vertical path, especially since ergine and ergometrine concentration is fold lower in plant samples than in seeds. However, an old tropical greenhouse est. Only UAE-B has proven to be suitable for such analysis and the method was optimized in terms of temperature, time, and solvent composition.
The use of ultrasound-assisted extraction enabled significant shortening of extraction time in comparison to similar seed samples [ 17 ]. The method was validated and proven to be suitable for the analysis of Morning Glory seeds from different sources. However, it is known that microwave energy may induce the decay of analytes, which is one of the mayor drawbacks of the MAE technique discussed by Zhang et al.
LSA has a similar chemical structure to lysergic acid diethylamide LSD and produces hallucinogenic effects. Therefore, some people view morning glory seeds as a legal alternative to the potent psychedelic.
However, the fact that they are legal and widely available does not necessarily mean they are safe. Here is our complete guide to morning glory and LSA, including their uses, effects, side effects, and more.
Morning glory is a member of a plant family known as Convolvulaceae. They are creeping vines with heart-shaped leaves and trumpet-like flowers. There are many different varieties of the plant, and morning glory flowers can be white, purple, or blue. One of the most common varieties is Heavenly Blue Ipomoea tricolor , which is popular for its striking turquoise blooms.
Therefore, Heavenly Blue morning glory seeds are widely available in garden centers and nurseries, along with other related species. Their accessibility means that some individuals may consider using these seeds for their psychoactive effects. They contain a range of alkaloid compounds , including LSA, that can produce altered mental states and hallucinations.
Other plants that contain the same chemicals include Hawaiian Baby Woodrose Argyreia nervosa and Ololiuqui Rivea corymbosa. This ancient healing system promotes its use for gonorrhea, difficult urination, ulcers, diabetes, and more.
Meanwhile, Ololiuqui is native to Central America, and the Aztecs and their neighboring tribes used it in religious ceremonies. They also recommended Ololiuqui for treating flatulence, venereal diseases, pain, and tumors. However, there is currently little scientific evidence supporting the medicinal uses of either plant. Morning glory seedlings look fairly similar to many other young plants. Therefore, correctly identifying wild morning glory seedlings can be difficult and is not recommended.
The best way to reduce the risk of confusing these plants with other species is by growing them from seed. However, readers should note that commercial morning glory seeds are usually treated with antifungals and other chemicals.
Therefore, they may be toxic and should not be consumed. According to a report by Albert Hofmann, the Aztecs used Ololiuqui to induce a delirious state and communicate with the Gods. However, Hofmann described his own experience with the drug somewhat differently. A study found that LSA extract from A. LSA-containing plants can also cause numerous unpleasant side effects, and there have been several reports of fatalities after using them.
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