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Aquatic Plants Native to Europe
Published in Namrita Lall, Aquatic Plants, 2020
Isa A. Lambrechts, Lydia Gibango, Antonios Chrysargyris, Nikolaos Tzortzakis, Namrita Lall
The alkaloids, tryptamine, bufotenidine, gramine, and arundamine, have previously been isolated from A. donax. Five indole-3-alkylamine bases, N-methyltryptamine, 5-methoxy-N,N-dimethyl-tryptamine, bufotenine, bufotenidine, and dehydro-bufotenine, were previously isolated from the rhizomes (Figure 5.2). Other compounds previously isolated from this species include triacontanol, tricin, gramine, tetramethyl-N,N-bis-2,6 dimethylphenyl cyclobutane-1,3-diimine, arundine, deoxyvasicinone, N-phenylnaphthylamine, donaxine, donaxarine, and donaxaridine (Al-Snafi 2015, Khnzhaev and Aripova 1995).
Xenobiotic Biotransformation
Published in Robert G. Meeks, Steadman D. Harrison, Richard J. Bull, Hepatotoxicology, 2020
Indolethylamine N-methyltransferases are enzymes, present in various tissues, that are both specific and nonspecific for N-methylation of amines. There is a broad substrate specificity for the methyl donor. Enzyme activity is generally assayed with tryptamine, N-methylserotonin, N-methyltryptamine, or β-phenylethylamine as a substrate. The enzymes are subject to end-product inhibition by N-methylated indoleamines. Substrates include endogenous biogenic amines, amine drugs such as amphetamine, and xenobiotic amines such as aniline.
Natural Products Structures and Analysis of the Cerrado Flora in Goiás
Published in Luzia Valentina Modolo, Mary Ann Foglio, Brazilian Medicinal Plants, 2019
Lucilia Kato, Vanessa Gisele Pasqualotto Severino, Aristônio Magalhães Teles, Aline Pereira Moraes, Vinicius Galvão Wakui, Núbia Alves Mariano Teixeira Pires Gomides, Rita de Cássia Lemos Lima, Cecilia Maria Alves de Oliveira
From the leaves of P. hoffmannseggiana (Schult.) Müll. Arg. several alkaloids were isolated, such as N-methyltryptamine (22), harmane (23), N-methyl-1,2,3,4-tetrahydro-β-carboline (24), (+) chimonantine (25) and the major alkaloid strictosidinic acid (3) (Naves, 2014). Strictosidinic acid (3), first isolated from P. myriantha Müll. Arg., was assayed on rat hippocampus showing a decrease in the serotonin (5-HT) levels, possibly indicating an inhibition of the precursor enzymes of the 5-HT biosynthesis. Tryptamine and β-carboline type alkaloids were also isolated from the leaves of P. capitata Ruiz & Pav., with bufotenine (26) and its N-oxide derivative (27) as the major alkaloids (Wakui, 2015). Although early studies (Moraes et al., 2011) have shown the presence of β-carboline alkaloids in P. capitata ethanol extract, only 6-hydroxy-2-methyl-1,2,3,4-tetrahydro-β-carboline (28) was identified. From P. goyazensis Müll. Arg., the quinolone alkaloid calycanthine (6) was isolated together with strictosidinic acid (3) and harmane (23), so far, the first report of the occurrence of a monoterpene indole and a quinolinic type alkaloid in the same species of Psychotria (Januário, 2015) (Figure 11.9).
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
Indole alkaloids are the characteristic constituents of TR, including evodiamine and rutaecarpine, which show diverse bioactivities, such as anti-inflammatory, antimicrobial, anti-HIV, antioxidant, and anticancer activities (Tian et al. 2019). The typical structure of indole alkaloids contains a bicyclic structure formed by the fusion of a benzene ring and a five-membered pyrrole ring (Rosales et al. 2020). Dehydroevodiamine (25), evodiamine (67) and rutaecarpine (71) were used to summarise the mass spectral fragmentation pathways of the indole alkaloids. Dehydroevodiamine displayed diagnostic fragmentation ion m/z 286.10 (Figure 4A), which formed a big conjugation system by fusing with π-bonds and was rather stable, while both evodiamine and rutaecarpine displayed fragmentation ions m/z 171.09, 134.06 and 169.08, 120.04, which was caused by the split of ring-D (Figure 4B). The fragmentation pathways of indole alkaloids are summarised as follows (Kumar et al. 2016, 2018): (1) If a double bond existed between C-3 and C-14, no mass fragments of ring split were found because a stable conjugation structure was formed by π-bonds. If not, a fragment ion from reverse the Diels-Alder split of ring-D would be discovered. (2) If the bonds between C-2 and C-3, C-3, and C-14 break, ring-C and ring-D would not exist. No Diels-Alder cleavage is observed, and the broken active sites are amide and quaternary amide bond. (3) If only the ring-C is open, an amide bond, a quaternary amide bond, and a Diels-Alder cleavage will simultaneously appear. (4) For linear indoleamine alkaloids, the diagnostic ion m/z 160.1 (C10H10NO) could be obtained after the loss of the corresponding alkylamine group. Based on the diagnostic fragmentation ions and accurate mass measurements, peaks 8, 9, 10, 12, 31, 56, 59, 61, 62, 68, 70 and 72 were assigned to N-methyltryptamine, 5-methoxy-α-methyltryptamine, N, N-dimethyl-5-methoxytryptamine, 6-methoxy-N-methyl-1,2,3,4-tetrahydro-β-carboline, evodianinine, 14-formyldihydroxyrutaecarpine, evodiamide, dehydrorutaecarpine, Nβ-demethylevodiamide, goshuyuamide II, goshuyuamide I, and hydroxyrutaecarpine, respectively. Typical mass spectra and fragmentation pathways of 14-formyldihydroxyrutaecarpine are exhibited in Figure 5.