Harman alkaloids

Other flavones in passionflower (vitexin, coumerin, umbelliferone) have not been well characterized for their neuropharmacological action. Vitexin (derived from millet in one study) was found to have antithyroid properties. The remaining constituents, maltol and harman alkaloids, are present in small quantities and not presumed to contribute to the psychotropic effects (Meier 1995). Harman alkaloids in greater quantities are hallucinogenic and presumed to work through 5-HT receptors (Grella et al. 1998). 

A variety of alkaloids bind to or intercalate with DNA or DNA/RNA processing enzymes and affect either transcription or replication (quinine, harmane alkaloids, melinone, berberine), act at the level of DNA and RNA polymerases (vinblastine, coralyne, avicine), inhibit protein synthesis (sparteine, tubulosine, vincrastine, lupanine), attack electron chains (pseudane, capsaicin, solenopsine), disrupt biomembranes and transport processes (berbamine, ellipticine, tetrandrine), and inhibit ion channels and pumps (nitidine, caffeine, saxitoxin). In addition, these natural products attack a variety of other systems that can result in serious biochemical destabilization... 

Passiflora incamata (apricot vine, grenadille, passion flower, passion vine) is widely touted as a herbal sedative and anxiolytic (1). It contains harman alkaloids. 

The authors suggested that the adverse event had been caused by harman alkaloids from P. incamata. 

Sasse et al. reported the analysis of harmane alkaloids in cell suspension cultures by means of HPLC. An octyl column and a mobile phase of methanol - water - formic acid (166 34 1) buffered at pH 8.5 with triethylamine was used for the separation of the alkaloids (Fig.8.4). 

Sasse et al.46 used the difference in fluorescence maxima of harmane alkaloids in the quantitation of the alkaloids after their separation (Fig.8.4). Fluorimetric detection with a detection limit of about 10 pg was about 100 times more sensitive than UV detection. 

The two new alkaloids pauridianthine (162) and pauridianthinine (163) are the first known pyridine—harman alkaloids (194). 

Poindexter, E.H. Jr and R.D. Carpenter The isolation and identification of harmane alkaloids in cigarette smoke 15th Tobacco Chemists Research Conference, Program Booklet and Abstracts, Vol. 15, Paper No. 16, 1961, p. 8 Isolation of harmane and norharmane from cigarette smoke Chem. and Ind. (1962) 176 The isolation of harmane and norharmane from tobacco and cigarette smoke Phytochemistry 1 (1962) 215-221 Poindexter, E.H. Jr,... 

Wilbert 1587). The Shuar likewise drink tobacco juice alternately with ayahuasca (Wilbert 1987). In other words, both the Shuar and Tukano Indians, whose experiences were cited by Flattery as evidence for the psychopharmacology of the harmane alkaloids, commonly brew their with DMT-rich plants, and take it along with tobacco juice and... 

Rehwald, A., O. Sticher, and B. Meier. 1995. Trace analysis of harman alkaloids in Passiflora incarnata by reversed-phase high-performance liquid chromatography. Phytochem. Anal. 6(2) 96-100. 

LissocNnuin alkaloids. Pyrido[2,3,4-k/]acridinone (e.g., diplamine, cf. kuanoniamines) and harman alkaloids from tropical tunicates of the genus Lissocli-... 

All these factors are important for the development of plant cell cultures. For example, cultures of Lupinus polyphyllus only synthesize alkaloids when kept in the light and alkaloid content is correlated with chlorophyll content. This may be explained by a better supply of lysine (formed in the chloroplasts), the fact that the enzymes of alkaloid biosynthesis have a pH optimum of about pH 8, which is created in the chloroplast stroma only in the light, and that the enzymes are subject to activation by reduced thioredoxin which is generated only in the light (Wink, 1987). The alkaloids of Peganum harmala, which are formed in the roots of the plant, act in an opposing manner. Cultures maintained in the light fail to produce the alkaloids, whereas those kept in the dark synthesize harman alkaloids (Barz and Hiisemann,... 

An additional group of alkaloids that arises from anthranilic acid, the harman alkaloids, is discussed in Chapter 35. Avenalumins, 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA), and related compounds are treated in Chapter 7. 

Distribution of Harmane Alkaloids Biological Activity Biosynthetically Related Alkaloids Canthin-6-one and Related Alkaloids Carbazole Alkaloids Alkaloids of Physostigma venenosum Alkaloids of the Calycanthaceae Polyindolenines... 

Many alkaloids contain an indole nucleus as a part of their structure. Monoterpene-derived indole alkaloids see Chapter 34) are the most important of these compounds, but several other significant types of indole alkaloids exist. Ergot alkaloids formed from tryptamine and a mevalonate-derived hemiterpene unit are of medical importance. Others, such as harmane alkaloids, physostigmine and a series of structurally similar alkaloids, Calycanthus alkaloids (Calycanthaceae) and related compounds (principally from the Rubiaceae), and relatively minor types of alkaloids from the Ascelpiada-... 

The results of feeding studies leading to the formation of harmane alkaloids have been tabulated (Leete, 1983). 

Harmane alkaloids inhibit membrane transport and act at serotonin receptors (Robinson, 1979). Harmine (16) inhibits monoamine oxidases and binds to DNA. Harmaline (17) inhibits (Na, K )-ATPase, Na" transport, and monoamine oxidase (Wink, 1993). 

A. Harman Alkaloids. Harman is formed in plants by the reaction of tryptamine with pyruvic acid on the pathway shown in Fig. 258. 1,2,3,4-Tetrahydro-jff-carboline was found in the urine of humans (E 1). It is probably formed from tryptamine and formaldehyde. 

Gill S, Raszeja W 1973 Chromatographic analysis of harman alkaloid derivatives in some plant raw materials. Rozpr Wydz 3 Nauk Mat-Przyr, Gdansk Tow Nauk 8 137-143... 

Another notable example of the production of alkaloids in a cell-suspension culture was with Berberis species ( Berberis stolonifera) where the yield of berberine alkaloids (eg. jatrorrhizine (62) ) was as high as 10% of the dry weight of the cells °. Cell cultures of Peganum harmaZa produce harman alkaloids in minute amounts. ... 

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