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Phytochemistry of Harmal
Published in Ephraim Shmaya Lansky, Shifra Lansky, Helena Maaria Paavilainen, Harmal, 2017
Ephraim Shmaya Lansky, Shifra Lansky, Helena Maaria Paavilainen
Unlike the more classical harmala alkaloids such as harmine, tetrahydroharmine, harmaline, harmalol, and harmol—usually listed as constituents of P. harmala or of the Ayahuasca liana, Banisteriopsis caapi—harmane seems rarely mentioned in these contexts (Figure 6.37). However, the presence of harmane in P. harmala has been recently confirmed (Tascón et al. 2016)—it is probably a major constituent (Bensalem et al. 2014), and so, its presence should be taken into consideration when considering the pharmacology of the whole plant, its extracts, and its total alkaloid fractions. Harmane is also among the β-carbolines found in the flowering tops of another plant better known as a carrier of harmine, i.e., the passion flower, Passiflora incarnata (Avula et al. 2012), and is among the MAO-A inhibitors in tobacco smoke (Truman et al. 2017) (Figure 6.38).
Insomnia
Published in Ethan Russo, Handbook of Psychotropic Herbs, 2015
Great controversy has arisen due to the putative presence of beta-carboline alkaloids in some cultivars of Passiflora incarnata. These include harmane, harmaline, and others. In physiological doses, these are monoamine oxidase inhibitors (MAOIs). Literature has even supported the use of maypop, ingested or smoked, as an“ayahuasca analogue” that serves as the MAOI which permits oral activity of DMT (dimethyltryptamine)-containing plants (e.g., Ba-nisteriopsis caapi, Phalaris, etc.) (Ott, 1994, 1996). However, such alkaloids are trace elements in select maypop samples, while most commercial preparations are devoid of these components (ESCOP, 1996–1997). No hypertensive crises or other clinical sequelae have been reported in relation to such activity after use of Passiflora incarnata. Interestingly, most experimenters taking such alkaloids in isolation have reported mild levels of sedation, and no antidepressant or stimulatory effect (Ott, 1994).
Inhibitory effect of norharmane on Serratia marcescens NJ01 quorum sensing-mediated virulence factors and biofilm formation
Published in Biofouling, 2021
Huai-Zhi Luo, Jin-Wei Zhou, Bing Sun, Huan Jiang, Shi Tang, Ai-Qun Jia
The virulence factors and biofilm inhibitory effect of norharmane and its derivatives on S. marcescens NJ01 were assessed at 20 μg ml−1 (Figure 4). Norharmane significantly inhibited QS and biofilm formation compared with other compounds including VNA (positive control). When the hydrogen linked to nitrogen was substituted by a methyl (9-methylnorharmane), and the hydrogen at 3 position was substituted by carboxyl (β-carboline-3-carboxylic acid), inhibition of these virulence factors was significantly weakened. Bioactivity was also reduced when the hydrogen at 1 position was substituted by methyl (harmane), and the hydrogen of harmane at 7 position was substituted by methoxy (harmine). However, when the hydrogen of harmane at 7 position was substituted by a hydroxyl group (harmol), the inhibition of protease, lipase and hemolysin production by S. marcescens NJ01 was slightly greater compared with norharmane treatment. Interestingly, the compound 3-methoxycarbonyl-β-carboline, in which the hydrogen at 3 position was substituted by carboxymethyl, had no obvious inhibition effect on QS and biofilm formation, especially in the production of prodigiosin, which was in sharp contrast with other compounds (Figure 4a). For biofilm formation, 53.9% inhibition was observed in treatment with norharmane, better than obtained by the QS inhibitor VNA, whose application resulted in 30.7% inhibition. The inhibition of harmine and harmane on the biofilm was only 17.3% and 19.9%, respectively, and the other compounds showed scarcely any inhibition activity on biofilm formation by S. marcescens NJ01 (Figure 4f).
Syrian rue seeds interacted with acacia tree bark in an herbal stew resulted in N,N-dimethyltryptamine poisoning
Published in Clinical Toxicology, 2019
Chuan-Huai Liu, Wei-Lan Chu, Shu-Chen Liao, Chen-Chang Yang, Chih-Chuan Lin
Ingestion of an herbal stew made from Acacia tree bark and Syrian rue seeds has similar clinical effects as drinking an ayahuasca brew. Normally, ingested DMT is inactived because it is metabolized by gastrointestinal MAO. However, Syrian rue seed contains alkaloids (e.g., harmaline, harmine, and harmane) with MAO-A inhibitor activity and may allow for orally administered DMT to reach psychoactive levels.