Peganum harmala Alkaloids Self-Assembled Supramolecular Nanocapsules with Enhanced Antioxidant and Cytotoxic Activities

In vitro cell-toxicity of Peganum harmala alkaloids on cancerous cell-lines

Fitoterapia ◽

10.1016/s0367-326x(99)00117-3 ◽

2000 ◽

Vol 71 (1) ◽

pp. 50-54 ◽

Cited By ~ 43

Author(s):

F. Lamchouri ◽

A. Settaf ◽

Y. Cherrah ◽

M. Hassar ◽

M. Zemzami ◽

...

Keyword(s):

Cell Lines ◽

Cell Toxicity ◽

Peganum Harmala ◽

Cancerous Cell ◽

Harmala Alkaloids

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XV.—The Harmala Alkaloids in Malaria

Proceedings of the Royal Society of Edinburgh ◽

10.1017/s0370164600009494 ◽

1921 ◽

Vol 40 ◽

pp. 140-149 ◽

Cited By ~ 2

Author(s):

J. A. Gunn ◽

D. G. Marshall

Keyword(s):

Central Nervous System ◽

Nervous System ◽

Pigment Cells ◽

Ciliated Epithelium ◽

Peganum Harmala ◽

Selective Action ◽

Differentiated Cells ◽

The Central Nervous System ◽

Harmala Alkaloids ◽

Heart Blood

In two former contributions to this Society I described the pharmacological actions of harmaline and harmine, the two alkaloids found in the seeds of Peganum harmala. In regard to harmaline I came to the following conclusions:— “It differs from most alkaloids in that it does not exert, to the same extent as they do, a selective action on one kind of tissue. It attacks not only highly specialised tissues such as voluntary muscle, muscle of the heart, blood-vessels and uterus, and cells of the central nervous system, but also less highly differentiated cells, such as pigment cells, protozoa (Raab), and ciliated epithelium (Jacobson).

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Synthesis of quaternary salts of Peganum harmala alkaloids

Chemistry of Natural Compounds ◽

10.1007/s10600-009-9381-3 ◽

2009 ◽

Vol 45 (4) ◽

pp. 601-603

Author(s):

A. Zh. Turmukhambetov ◽

M. T. Agedilova ◽

Zh. S. Nurmaganbetov ◽

A. V. Kazantsev ◽

E. E. Shul′ts ◽

...

Keyword(s):

Peganum Harmala ◽

Quaternary Salts ◽

Harmala Alkaloids

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Green Synthesis of Platinum and Palladium Nanoparticles Using Peganum harmala L. Seed Alkaloids: Biological and Computational Studies

Nanomaterials ◽

10.3390/nano11040965 ◽

2021 ◽

Vol 11 (4) ◽

pp. 965

Author(s):

Sherif Ashraf Fahmy ◽

Iten M. Fawzy ◽

Basma M. Saleh ◽

Marwa Y. Issa ◽

Udo Bakowsky ◽

...

Keyword(s):

Antioxidant Activity ◽

Green Synthesis ◽

Palladium Nanoparticles ◽

Cysteine Proteinase ◽

Breast Adenocarcinoma ◽

Cytotoxic Activities ◽

Gravimetric Analysis ◽

Peganum Harmala ◽

Vis Spectroscopy ◽

Alkaloid Fraction

This study reports a facile and eco-friendly method for the green synthesis of platinum and palladium nanoparticles (Pt NPs and Pd NPs) using Peganum harmala seed alkaloid fraction. The ζ-potential of the synthesized Pt NPs, Pd NPs and Pt–Pd NPs were −11.2 ± 0.5, −9.7 ±1.2, and −12.7 ± 2.1 mV; respectively. Transmission electron microscopy (TEM) revealed the formation of spherical-shaped nanoparticles with smooth margins. The mean diameters of the synthesized Pt NPs, Pd NPs, and Pt–Pd NPs were determined using TEM analysis and were found to be 20.3 ± 1.9, 22.5 ± 5.7, and 33.5 ± 5.4 nm, respectively. The nanoparticles’ bioreduction was confirmed by ultraviolet–visible (UV–vis) spectroscopy, X-ray diffraction (XRD) and Fourier transform infrared (FTIR) spectroscopy, and their organic contents were determined by thermal gravimetric analysis (TGA). The Pt–Pd NPs mixture showed more pronounced antioxidant activity of 843.0 ± 60 μM Trolox equivalent (TE)/mg NPs compared to the individual Pt NPs (277.3 ± 13.5 μM TE/mg NPs) and Pd NPs (167.6 ± 4.8 μM TE/mg NPs). Furthermore, the Pt–Pd NPs exhibited significant cytotoxic activities against lung cancer (A549) and breast adenocarcinoma (MCF-7) cells, IC50 of 8.8 and 3.6 µg/mL, respectively; as compared to Pt NPs (IC50 of 10.9 and 6.7 µg/mL, respectively) and Pd NPs (IC50 of 31 and 10.8 µg/mL, respectively and compared to carboplatin (IC50 of 23 and 9.5 µg/mL, respectively). Moreover, molecular docking studies were conducted to explore the possible anticancer and antioxidant mechanisms of the biogenic nanoparticles. Pt NPs, Pd NPs, and their mixture showed inhibitory activity against cysteine proteinase, which supports their high antitumor activity, but moderate antioxidant activity. In conclusion, Pd-Pt NPs mixture prepared using harmala seed alkaloid fraction showed potential as effective antineoplastic agents.

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New Bioactive Esters and Phosphonates Semisynthesized From (±)-Vasicinone: An Alkaloid Isolated From Peganum harmala

Natural Product Communications ◽

10.1177/1934578x19893544 ◽

2019 ◽

Vol 14 (12) ◽

pp. 1934578X1989354

Author(s):

Insaf Filali ◽

Amira Jelassi ◽

Hichem Ben Jannet

Keyword(s):

Cell Lines ◽

Chloroacetic Acid ◽

Cytotoxic Activities ◽

Protecting Group ◽

Peganum Harmala ◽

Tosyl Chloride ◽

Trialkyl Phosphites ◽

Hct 116 ◽

Mcf 7

A series of N-tosyl α-amino acids 2a-e, prepared using a tosyl chloride protecting group, was condensed with (±)-vasicinone 1, isolated from the seeds of the plant Peganum harmala, to generate the corresponding esters 3a-e and 3b′-e′. (±)-Vasicinone 1 was also reacted with chloroacetic acid chloride to afford a new chlorinated ester 4 which was refluxed with trialkyl phosphites to give 2 new phosphonates 5a,b. All synthesized compounds were characterized with the help of spectroscopic means, including NMR (1H, 13C, and 31P) and ES-HRMS, and then screened for their in vitro anti-acetylcholinesterase (AChE), anti-5-lipoxygenase (5-LOX), and cytotoxic activities (MCF-7, OVCAR-3, and HCT-116 cell lines). Most synthesized derivatives exhibited a cytotoxic activity against 3 cell lines used. The phosphonate derivative 5b was found to be the most active one (IC50 = 63.7 ± 1.4 µM) against AChE enzyme. Only 2 diastereoisomers 3e and 3e′ exhibited activity against 5-LOX enzyme with IC50 values of 63.1 ± 4.2 and 79.2 ± 8.3 µM, respectively.

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