Chemopreventive Agents
David E. Thurston, Ilona Pysz in Chemistry and Pharmacology of Anticancer Drugs, 2021
Matrine (Figure 12.23) is a tetracyclo-quinolizidine, and the predominant alkaloid in Sophora plants. It has a structure based on four saturated six-membered rings with two ring-junction nitrogen atoms, making it rich in stereochemistry. Matrine is reported to have both in vitro and in vivo antitumor activity, and is the main bioactive compound in Kushen at a concentration of 1 g/10 kg. It is also a constituent of the herb Sophora flavescens used in Chinese medicine. Structure of the alkaloid matrine.
Biochemistry of Caffeine's Influence On Exercise Performance
Peter M. Tiidus, Rebecca E. K. MacPherson, Paul J. LeBlanc, Andrea R. Josse in The Routledge Handbook on Biochemistry of Exercise, 2020
Caffeine can be found as an alkaloid (pill, powder), but is also naturally occurring in the nuts, beans, leaves, and berries of various plants (61), such as the kola nut, guarana seed, and yerba mate. However, caffeine is most notably recognized as a derivative of tea and coffee—typically the second and third most abundantly consumed beverages in adults worldwide after water. Over the past decade, the number of caffeine-containing foods and beverages available to consumers has increased exponentially. Among children and adolescents, caffeine-containing energy drinks have become popular, with an estimated 74% of youth in North America consuming these products and 16% consuming more than two within a day (75). These statistics are highly concerning, as the low body mass of children can expose them to significant amounts of the drug (39, 40). Aside from naturally caffeinated beverages, the alkaloid form can be an additive to various foods and drinks, including chocolate, gums, candy, and alcohol. Furthermore, caffeine has pharmaceutical properties and can be found in analgesics, cold and sinus preparations, and appetite suppressants (46). Within sport, the majority of studies have examined alkaloid caffeine, although a greater number are now starting to examine alternative forms, including mouthwashes, candy (e.g., jellybeans), energy drinks, gum, and coffee.
An Alternative Approach for Anti-Alzheimer’s Compounds from Plant Extracts
Atanu Bhattacharjee, Akula Ramakrishna, Magisetty Obulesu in Phytomedicine and Alzheimer’s Disease, 2020
Alkaloids constitute an important class of structurally diverse plant compounds that have a nitrogen atom in the heterocyclic ring, and are derived from amino acids. The term ‘alkaloids’ was coined by the German chemist Carl F. W. Meissner in 1819 and the word is derived from the Arabic name al-qali that is related to the plant from which soda was first isolated (Howes et al., 2003; Rinaldia et al., 2017). The alkaloid compounds are low-molecular-weight structures and make up about 20% of plant-based secondary metabolites and they have influenced human history profoundly, due to their wide range of physiological effects on animals and pharmacological properties on humans, such as anticancer and antibiotic properties, along with their potential exploitation as narcotics, stimulants, and poisons (Kaur and Arora, 2018). About 12,000 alkaloids have been isolated from the plant kingdom. Depending upon their biosynthetic precursor and heterocyclic ring system, alkaloids have been classified into different categories, including indole, piperidine, tropane, purine, imidazole, pyrrolidine, pyrrolizidine, quinolizidine, and isoquinoline alkaloids (Ramakrishna et al., 2012; Aniszewski, 2007; Bribi, 2018). They are classified using various signatures, such as natural source or chemical nature. The biological activity of alkaloids, like cytotoxic and CNS activity, and toxicity against herbivores, include anticarcinogenic, antibacterial, antifungal, and antiviral properties in vertebrates (Wirasathien et al., 2006; Padma Kumar et al., 2009; Ramakrishna et al., 2011).
Integrated serum pharmacochemistry and investigation of the anti-gastric ulcer effect of Zuojin pill in rats induced by ethanol
Published in Pharmaceutical Biology, 2022
Jiaying Zhang, Yi Yin, Qianqian Xu, Xiaoqing Che, Chen Yu, Yan Ren, Dongsheng Li, Juanjuan Zhao
Aporphine alkaloids are another type of alkaloid from CC that display various biological activities, such as antitumor, antimicrobial, reversal of multidrug resistance, and antiviral activities (Liu et al. 2014). Aporphine alkaloids are characterised by a tetracyclic aromatic basic skeleton, including the phenol oxidative coupling of a benzylisoquinoline precursor (Ge and Wang 2018). Magnoflorine, a representative aporphine alkaloid found in CC, was first analysed. Molecular ions M+ and fragment ions, including [M-45]+, [M-60]+ and [M-77]+, were easily detected in the magnoflorine spectrum. The fragmentation pathways are shown in Figure 3A, from which we found aporphine alkaloids easily broke and recombined the side chain. According to the diagnostic fragmentation pathways [M-45]+, [M-60]+ and [M-77]+ and accurate mass measurement within 5 ppm error, peaks 14 and 22 were assigned as menisperine and stephabine, respectively. The typical mass spectra of menisperine and its fragmentation pathways are exhibited in Figure 3B.
An integrated analytical strategy to decipher the metabolic profile of alkaloids in Compound Kushen injection based on UHPLC-ESI-QTOF/MSE
Published in Xenobiotica, 2023
Li Zhang, Ruijuan Li, Ting Zheng, Huan Wu, Yanyan Yin
Take matrine (P18) and N-methylcytisine (P12) as examples to illustrate the process of prototype alkaloid identification. P18 with tR of 12.97 min that showed an adduct ion at m/z 249.1965 [M + H]+. It had a molecular formula of C15H25N2O. The molecular formula and its tR were consistent with that of matrine in our chemical database. Furthermore, fragment ions at 218.1552, 190.1585, 176.1442, 162.1292, 150.1281, 148.1117, 134.0970, and 122.0977 were observed (Figure S2). Among these fragments, m/z 218.1552 was the product ion of m/z 249.1965 removal of a molecule of CH3NH2. Then m/z 218.1552 lost CO and C2H2O to form fragment ions m/z 190.1585 and m/z 176.1442, respectively. m/z 190.1585 continuously lost C2H4 to generate fragment ions of m/z 162.1292 and m/z 134.0970. m/z 176.1442 lost C2H2 and C2H4 to form fragment ions m/z 150.1281 and m/z 148.1117, respectively. The cleavage behaviour is consistent with the cleavage mode of matrine. Consequently, P18 was identified as matrine according to its tR, quasi-molecular ion and product ions. This result was also verified using the reference substance of matrine.
Do you know about Kratom?
Published in Postgraduate Medicine, 2020
Ahmed Adel Eladely, Junaid Shahzad, Steven Lippmann
Kratom is a drug derived from the Mitragyna speciosa tree that grows in Asia and Africa [1]. Its alkaloid products are consumed in many ways: chewing fresh leaves; ingested powder, tablet and/or pill forms; smoked; brewed; boiled into tea; and/or mixed with various beverages, yogurt, or other foods [2]. The Drug Enforcement Administration listed kratom as a ‘concern drug,’ which allows it to be less restricted than controlled substances [1]. It exhibits stimulant, analgesic, and/or sedative properties. Stimulation is induced at moderate dosages, while at high doses it sedates and is accompanied by opioid-like activity [1]. About 3–5 million people in United States have used kratom [3]. However, many physicians are unaware of kratom’s easy availability and it has not been perceived as a public health concern.
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