Investigation of hallucinogenic and related β-carbolines

Grella, Brian; Dukat, Małgorzata; Young, Richard; Teitler, Milt; Herrick‐Davis, Katharine; Gauthier, C; Glennon, Richard A.

doi:10.1016/s0376-8716(97)00163-4

Cited by 79 publications

(55 citation statements)

References 18 publications

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“…73) Furthermore, plants containing harmala alkaloids have long been used in traditional medicine to treat asthma, jaundice, lumbago, and other ailments. [19][20][21] Certain b-carboline alkaloids have a wide spectrum of neuropharmacological and psychopharmacological actions on the central nervous system such as tremorogenesis, 74,75) hypothermia, 76) hallucinogenesis, 77,78) monoamine oxidase (MAO) inhibition, 79,80) and convulsive or anticonvulsive actions. 81) The central nervous effects of b-carbolines mainly depend on bcarbolines which have a methoxyl group at the C-7 position in their structures.…”

Section: Discussionmentioning

confidence: 99%

The .BETA.-Carboline Alkaloid Harmol Induces Cell Death via Autophagy but Not Apoptosis in Human Non-small Cell Lung Cancer A549 Cells

Abe

Yamada

Moriya

et al. 2011

Biological & Pharmaceutical Bulletin

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Lung cancer is a leading cause of death worldwide, and the long-term survival rate of lung cancer patients is one of the lowest among cancers.1,2) Two major types of lung cancer have been identified: non-small cell lung cancer (NSCLC) and small cell lung cancer (SCLC). NSCLC, the most prevalent subtype, is relatively resistant to chemotherapy and radiation therapy. On the other hand, SCLC is initially highly sensitive to chemotherapy and radiation therapy, but shows resistance to treatment in the majority of patients.3) The high mortality in NSCLC is due to the difficulty of early diagnosis and its high potential for local invasion and distant metastasis. Although relatively effective chemotherapeutic agents have been developed, lung cancer still has a low cure rate. Furthermore, the adverse effects of chemotherapeutic compounds often hamper the quality of life of lung cancer patients. Therefore, the discovery of effective novel prophylactic, diagnostic, and therapeutic treatments for NSCLC is urgently needed."Apoptosis" has been used as a synonym for programmed cell death (PCD), and is a well-known form of PCD. Since the 1960s, various morphological forms of PCD have been recognized. Clarke classified cell death into 4 types, including type I PCD (apoptosis) and type II PCD (autophagy). 4)Numerous studies have demonstrated that most chemotherapy agents and certain naturally occurring compounds induce cell death by activating the apoptotic pathway. It is thought that apoptosis induction in tumor cells with either drugs or natural products is effective therapy for cancer and immune system diseases. On the other hand, autophagy is one of the major regulatory mechanisms in the degradation of intracellular proteins and organelles. 5,6) During autophagy, the cytosol and whole organelles become encased in double-membrane vacuoles such as autophagosomes, and subsequently fuse with lysosomes.5) Degradation of the sequestered material generates nucleotides, amino acids, and free fatty acids that are recycled for macromolecular synthesis and ATP generation.7) Although originally characterized as a survival response to nutrient deficiency, autophagy is now recognized as frequently induced in response to a variety of stressors to maintain cellular homeostasis. [8][9][10][11][12] In recent years, the importance of autophagy has been emphasized in various biological fields, including cancer. 9,[13][14][15] Furthermore, cancer cells show less autophagy than normal cells. 16,17) These findings indicate that autophagy induction is an attractive modality of anticancer therapy.b-Carboline alkaloids occur in a number of medicinal plants such as Peganum harmala, Passiflora edulis, Passiflora incarnata, and Banisteriopsis caapi.18,19) These plants have been used in traditional medicine to treat asthma, jaundice, lumbago, and other human ailments.19-21) Recently, it has been reported that certain b-carboline alkaloids and their related compounds have cytotoxic effects on cancer cells. [22][23][24] We also reported previously that harm...

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Section: Discussionmentioning

confidence: 99%

The .BETA.-Carboline Alkaloid Harmol Induces Cell Death via Autophagy but Not Apoptosis in Human Non-small Cell Lung Cancer A549 Cells

Abe

Yamada

Moriya

et al. 2011

Biological & Pharmaceutical Bulletin

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“…[11,12]. It was also reported that among these alkaloids harmaline and harmine are known as monoamineoxidase (MAO-B) inhibitors and they have several types of activities such as antioxidant, antiviral and anticancer [12,13].…”

Section: Kinetic Analysis For Inhibition Studymentioning

confidence: 99%

Inhibition of catechol-O-methyltransferase (COMT) by some plant-derived alkaloids and phenolics

Yalçın

Bayraktar

2010

Journal of Molecular Catalysis B: Enzymatic

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a b s t r a c tIn this study, as an alternative to the medicines, natural compounds extracted from plant species (Peganum harmala, Cistus parviflorus and Vitex agnus-cactus) were investigated in order to inhibit the catechol-O-metyhltranferase (COMT) activity. In fluorometric enzyme assay, S-adenosylmethionine (SAM) and aesculetin (ES) were used as methyl donor and acceptor substrates, respectively. Their K m values were determined as 3.5 ± 0.3 M and 6.4 ± 0.4 M in absence of inhibitor. Inhibition performances of the plantderived polyphenolics and alkaloids were determined. Inhibitory effect of alkaloids extracted from P. harmala seeds was found the highest among the plant extracts; however, it was lower than that of 3,5-DNC. In case of inhibition mechanism, mixed type inhibition was observed for alkaloid extract whereas uncompetitive inhibition was observed for 3,5-DNC. In case of polyphenolic extracts obtained from C. parviflorus and V. agnus-cactus leaves, mechanism were also explained as mixed type inhibition and their K i values were calculated as 1.99 ± 0.35 g/ml and 9.48 ± 0.58 g/ml, respectively.

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“…This plant is used in traditional medicine as an anthelmintic, lactogogue, antispasmodic, antipyretic, abortifacient, emetic (Kirtikar & Basu 1935;Chopra et al 1958), anticancerous (Bellakhdar 1997;Berrougui et al 2005), antiviral (Rashan et al 1989) and anti-hypertensive agent (Hmamouchi 1999). Hallucinogenesis (Grella et al 1998) and central monoamine oxidase inhibition effect (Fuller et al 1986), such as binding to various receptors including 5-HT receptors and the benzodiazepine-binding site of GABA A receptors (Rommelspacher et al 1980(Rommelspacher et al , 1985 have been reported also. The principal compounds of this plant are -carboline alkaloids such as harmine, harmaline, harmalol, harman, vasicine and vasicinon (Kartal et al 2003;Monsef et al 2004).…”

Section: Introductionmentioning

confidence: 99%

Protective effects of Peganum harmala L. extract, harmine and harmaline against human low-density lipoprotein oxidation

Berrougui

Isabelle

Cloutier

et al. 2006

Journal of Pharmacy and Pharmacology

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Oxidative modification of low-density lipoprotein (LDL) particles has been implicated in the process of atherogenesis. Antioxidants that prevent LDL from oxidation may reduce atherosclerosis. We have investigated the protective effect of Peganum harmala-extract (P-extract) and the two major alkaloids (harmine and harmaline) from the seeds of P. harmala against CuSO 4 -induced LDL oxidation. Through determination of the formation of malondialdehyde (MDA) and conjugated diene as well as the lag phase, the extract (P-extract) and compounds were found to possess an inhibitory effect. Moreover, harmaline and harmine reduced the rate of vitamin E disappearance and exhibited a significant free radical scavenging capacity (DPPH . ). However, harmaline had a markedly higher antioxidant capacity than harmine in scavenging or preventive capacity against free radicals as well as inhibiting the aggregation of the LDL protein moiety (apolipoprotein B) induced by oxidation. The results suggested that P. harmala compounds could be a major source of compounds that inhibit LDL oxidative modification induced by copper.

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Investigation of hallucinogenic and related β-carbolines

Cited by 79 publications

References 18 publications

The .BETA.-Carboline Alkaloid Harmol Induces Cell Death via Autophagy but Not Apoptosis in Human Non-small Cell Lung Cancer A549 Cells

The .BETA.-Carboline Alkaloid Harmol Induces Cell Death via Autophagy but Not Apoptosis in Human Non-small Cell Lung Cancer A549 Cells

Inhibition of catechol-O-methyltransferase (COMT) by some plant-derived alkaloids and phenolics

Protective effects of Peganum harmala L. extract, harmine and harmaline against human low-density lipoprotein oxidation

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