purine alkaloids
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2021 ◽  
Vol 22 (24) ◽  
pp. 13394
Author(s):  
Xiaomin Chen ◽  
Shuxian Shao ◽  
Ruxing Yang ◽  
Mengya Gu ◽  
Pengjie Wang ◽  
...  

Jiaocheng kucha is the first reported tea germplasm resource which contains theacrine founded in Fujian Province. Currently, the anabolic mechanism of theacrine within tea leaves is clear, but there are few studies focused on its flowers. In order to further explore the mechanism of theacrine synthesis and related genes in flowers, current study applied Jiaocheng kucha flowers (JC) as test materials and Fuding Dabaicha flowers (FD) as control materials to make transcriptome sequencing, and determination of purine alkaloid content in three different developmental periods (flower bud stage, whitening stage and full opening stage). The results showed that the flower in all stages of JC contained theacrine. The theacrine in the flower bud stage was significantly higher than in the other stages. The differentially expressed genes (DEGs) at three different developmental stages were screened from the transcriptome data, and were in a total of 5642, 8640 and 8465. These DEGs related to the synthesis of theacrine were primarily annotated to the pathways of purine alkaloids. Among them, the number of DEGs in xanthine synthesis pathway was the largest and upregulated in JC, while it was the smallest in caffeine synthesis pathway and downregulated in JC. Further weighted gene co-expression network (WGCNA) indicated that ADSL (CsTGY03G0002327), ADSL (CsTGY09G0001824) and UAZ (CsTGY06G0002694) may be a hub gene for the regulation of theacrine metabolism in JC. Our results will contribute to the identification of candidate genes related to the synthesis of theacrine in tea flowers, and explore the molecular mechanism of theacrine synthesis in JC at different developmental stages.


Author(s):  
Л.А. МАРЧЕНКО ◽  
Н.Я. МОКШИНА ◽  
О.А. ПАХОМОВА ◽  
А.В. СОКОЛОВА ◽  
В.Н. НИЖИВЕНКО

Контроль содержания алкалоидов в пищевых продуктах и напитках в соответствии с нормируемыми показателями – актуальная задача для биотехнологии. Рассмотрена экстракция кофеина и теобромина из растительного сырья – чая черного и зеленого с использованием в качестве экстрагента блок-сополимера плюроник, представляющего собой чередующиеся фрагменты этиленоксида (20 мономерных звеньев) и пропиленоксида (70 мономерных звеньев). Экстракционные системы на основе водорастворимых полимеров отвечают всем требованиям «зеленой» экстракции и могут применяться в технологических процессах, связанных с контролем качества исходного сырья. Исследованы условия процесса извлечения пуриновых алкалоидов, установлены его оптимальные параметры: концентрация экстрагента 0,25 г/см3, температура процесса 95°С, степень измельчения для черного и зеленого чая 0,4 и 0,8 мм соответственно, соотношение водной и органической фаз 10 : 1 соответственно. По результатам экстракции рассчитаны коэффициенты распределения и степень извлечения кофеина и теобромина, которая составляет 95–99% в зависимости от сорта чая. Содержание кофеина и теобромина в фазе органического растворителя после экстракции определяли методом капиллярного электрофореза по электрофореграммам образцов черного и зеленого чая. На основании разработанной экстракционно-электрофоретической методики определения кофеина и теобромина в различных сортах чая предложен механизм взаимодействия пуриновых алкалоидов с экстрагентом плюроник. Наличие в цепи полимера концевых НО-групп, а также в основной цепи атомов кислорода способствует взаимодействию полимера с аналитами с образованием водородных связей. Представленные схемы образования Н-связей подтверждают эффективность применения блок-сополимера плюроник в качестве экстрагента пуриновых алкалоидов. Monitoring the content of alkaloids in food and beverages in accordance with the normalized indicators is an urgent task for biotechnology. The extraction of caffeine and theobromine from vegetable raw materials – black and green tea using the pluronic block copolymer as an extractant is considered. The pluronic block copolymer consists of alternating fragments of ethylene oxide (20 monomer units) and propylene oxide (70 monomer units). Extraction systems based on water-soluble polymers meet all the requirements of «green» extraction and can be used in technological processes related to quality control of feedstock. The conditions of the purine alkaloid extraction process have been investigated, its optimal parameters have been established: the extractant concentration is 0,25 g/cm3, the process temperature is 95°C, the degree of grinding for black and green tea is 0,4 and 0,8 mm respectively, the ratio of aqueous and organic phases is 10 : 1 respectively. According to the extraction results, the distribution coefficients and the degree of extraction of caffeine and theobromine, which is 95–99%, depending on the tea variety, are calculated. The content of caffeine and theobromine in the organic solvent phase after extraction was determined by capillary electrophoresis from electrophoregrams of black and green tea samples. The presence of terminal HO-groups in the polymer chain, as well as in the main chain of oxygen atoms, promotes the interaction of the polymer with analytes with the formation of hydrogen bonds. The presented schemes for the formation of H-bonds confirm the effectiveness of using the pluronic block copolymer as an extractant of purine alkaloids.


2021 ◽  
Vol 12 (6) ◽  
pp. 7438-7468

Xanthine and its derivatives belong to the class of purine alkaloids. They are natural bases holding nitrogen atoms within the molecular structure, and they have an effective pharmacological alteration in both animals and human beings. Substituted xanthine, theophylline/caffeine being prototype, is one of the derivatives which have shown prominent binding to adenosine receptors as agonist or antagonist. Various mechanistic approaches are involved in exerting bronchospasmolytic, neuroprotective, hypoglycemic, MAO modulatory, along cardiac effects. Mostly, xanthine derivatives reduce inflammation and bronchospasm in asthmatic conditions. Other therapeutics effects are in the management of cancer, Alzheimer's disease, vasoconstriction, and also possess excellent central nervous system-penetration ability; thus, they can also be used as stimulants and anti-depressants. Their actions are relatively very weak, but their pharmacological effects are also associated with snarl-up adenosine-mediated functions. An assortment of the biological profile of the xanthine scaffold attracted many research groups over the years to explore this nucleus vividly. The present review is aimed to cover every aspect of the xanthine moiety reported in the earlier years. This review covers all the major biological roles and various synthetic strategies adopted to synthesize xanthine moiety and its derivatives.


Author(s):  
Mateusz Gołdyn ◽  
Anna Komasa ◽  
Mateusz Pawlaczyk ◽  
Aneta Lewandowska ◽  
Elżbieta Bartoszak-Adamska

The study of various forms of pharmaceutical substances with specific physicochemical properties suitable for putting them on the market is one of the elements of research in the pharmaceutical industry. A large proportion of active pharmaceutical ingredients (APIs) occur in the salt form. The use of an acidic coformer with a given structure and a suitable pK a value towards purine alkaloids containing a basic imidazole N atom can lead to salt formation. In this work, 2,6-dihydroxybenzoic acid (26DHBA) was used for cocrystallization of theobromine (TBR) and caffeine (CAF). Two novel salts, namely, theobrominium 2,6-dihydroxybenzoate, C7H9N4O2 +·C7H5O4 − (I), and caffeinium 2,6-dihydroxybenzoate, C8H11N4O2 +·C7H5O4 − (II), were synthesized. Both salts were obtained independently by slow evaporation from solution, by neat grinding and also by microwave-assisted slurry cocrystallization. Powder X-ray diffraction measurements proved the formation of the new substances. Single-crystal X-ray diffraction studies confirmed proton transfer between the given alkaloid and 26DHBA, and the formation of N—H...O hydrogen bonds in both I and II. Unlike the caffeine cations in II, the theobromine cations in I are paired by noncovalent N—H...O=C interactions and a cyclic array is observed. As expected, the two hydroxy groups in the 26DHBA anion in both salts are involved in two intramolecular O—H...O hydrogen bonds. C—H...O and π–π interactions further stabilize the crystal structures of both compounds. Steady-state UV–Vis spectroscopy showed changes in the water solubility of xanthines after ionizable complex formation. The obtained salts I and II were also characterized by theoretical calculations, Fourier-transform IR spectroscopy (FT–IR), thermogravimetric analysis (TGA), differential scanning calorimetry (DSC) and elemental analysis.


Nutrients ◽  
2021 ◽  
Vol 13 (11) ◽  
pp. 3706
Author(s):  
Anna Gawron-Gzella ◽  
Justyna Chanaj-Kaczmarek ◽  
Judyta Cielecka-Piontek

Bearing in mind the growing interest in Yerba Mate, a comprehensive study has been prepared containing the most important aspects and possibilities of its use. The introduction of the work contains the species characteristics of Yerba Mate, as well as information about the origin and places of cultivation. The next part focuses on the analysis of the composition, pointing to purine alkaloids, polyphenols, saponins, and minerals as groups of active compounds responsible for the clinical activity of Yerba Mate. The review of the results of preclinical and clinical studies indicates activity in relation to the stimulating effect, reducing weight by stimulating lipolysis, cardioprotective, anti-diabetic, and anti-inflammatory effects. The information about the action of Yerba Mate is supplemented by the characteristics of its potential toxicity in terms of PAHs content (in particular benzo[α]pyrene) and preparation as a determinant of increased irritation. The current data on the effects of Yerba Mate and the wide safety margin of its use position this raw material as a valuable component of functional food. The growing frequency of consuming Yerba Mate, conditioned by the availability resulting from the globalization of the market and the information provided about it’s the pro-health effects, will position Yerba Mate's popularity among wider population groups.


2021 ◽  
Vol 14 (03) ◽  
Author(s):  
A. Ramakrishna Reddy ◽  
J. Prasad ◽  
M. Bhooshan ◽  
K. C. Rajanna ◽  
A. Panasa Reddy ◽  
...  

2021 ◽  
Vol 33 (5) ◽  
pp. 1051-1057
Author(s):  
A. Ramakrishna Reddy ◽  
Bhooshan Muddam ◽  
A. Sambashiva Rao ◽  
K.C. Rajanna ◽  
A. Panasa Reddy ◽  
...  

Brønsted acid (HClO4, H2SO4) catalyzed Mn(VII) oxidation of purine alkaloids such as caffeine, theophylline and theobromine in aqueous acetonitrile and sodium fluoride medium revealed first order kinetics in both [(Mn(VII)] and [Alkaloid] at constant acidity and temperature. Sodium fluoride was added to the reaction mixture in order to avoid/suppress auto catalytic reaction due to the generation of Mn(III) and Mn(IV) species during the course of Mn(VII) oxidations in acidic solutions. An increase in the Brønsted acids (HClO4, H2SO4) concentration accelerated the rate of oxidation. Rate enhancements observed here in are analyzed by Zucker-Hammett, Bunnett and Bunnett-Olsen criteria of acidity functions. On the basis of observed Bunnett-Olsen criteria of acidity functions, the most plausible mechanism has been proposed with the involvement of water molecule in the slow step (as proton transferring agent).


2020 ◽  
Vol 7 ◽  
Author(s):  
Yue-Yue Sheng ◽  
Jing Xiang ◽  
Ze-Shi Wang ◽  
Jing Jin ◽  
Ying-Qi Wang ◽  
...  

Theacrine, i.e., 1,3,7,9-tetramethyluric acid, is one of the major purine alkaloids found in leaf of a wild tea plant species Camellia kucha Hung T. Chang. Theacrine has been attracted great attentions academically owing to its diverse health benefits. Present review examines the advances in the research on the health beneficial effects of theacrine, including antioxidant effect, anti-inflammatory effect, locomotor activation and reducing fatigue effects, improving cognitive effect, hypnotic effect, ameliorating lipid metabolism and inhibiting breast cancer cell metastasis effect. The inconsistent results in this research field and further expectations were also discussed.


Nutrients ◽  
2020 ◽  
Vol 12 (3) ◽  
pp. 654 ◽  
Author(s):  
Trisha A. VanDusseldorp ◽  
Matthew T. Stratton ◽  
Alyssa R. Bailly ◽  
Alyssa J. Holmes ◽  
Michaela G. Alesi ◽  
...  

Methylliberine (Dynamine®; DYM) and theacrine (Teacrine®; TCR) are purine alkaloids purported to have similar neuro-energetic effects as caffeine. There are no published human safety data on DYM, and research on TCR is limited. The purpose of this study was to examine the effect of four weeks of DYM supplementation with and without TCR on cardiovascular function and blood biomarkers. One-hundred twenty-five men and women (mean age 23.0 yrs, height 169.7 cm, body mass 72.1 kg; n = 25/group) were randomly assigned to one of five groups: low-dose DYM (100 mg), high-dose DYM (150 mg), low-dose DYM with TCR (100 mg + 50 mg), high-dose DYM with TCR (150 mg + 25 mg), and placebo. Regardless of group and sex, significant main effects for time were noted for heart rate, systolic blood pressure, and QTc (p < 0.001), high-density lipoproteins (p = 0.002), mean corpuscular hemoglobin (p = 0.018), basophils (p = 0.006), absolute eosinophils (p = 0.010), creatinine (p = 0.004), estimated glomerular filtration rate (p = 0.037), chloride (p = 0.030), carbon dioxide (p = 0.023), bilirubin (p = 0.027), and alanine aminotransferase (p = 0.043), among others. While small changes were found in some cardiovascular and blood biomarkers, no clinically significant changes occurred. This suggests that DYM alone or in combination with TCR consumed at the dosages used in this study does not appear to negatively affect markers of health over four weeks of continuous use.


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