Antiparasitic Derivatives of the Furoquinoline Alkaloids Kokusaginine And Flindersiamine

Valdez, María Belén; Giménez, Diana; Fernández, Liliana Patricia; Musikant, Alejandro Daniel; Ferri, Gabriel; Saenz, Daniel; Venosa, Gabriela Di; Casas, Adriana; Avigliano, Esteban; Edreira, Martín M.; Palermo, Jorge Alejandro

doi:10.1002/cmdc.202100784

Cited by 5 publications

(4 citation statements)

References 45 publications

(44 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…The mechanism of their action might be related to epinephrine α receptors, the M-receptor, and the calcium channel receptor [ 61 ]. Derivatives of cocusaginine and flindersiamine, the primary alkaloids isolated from the bark of Balfourodendron riedelianum , have shown superior in vitro activity against Trypanosoma cruzi compared with positive controls [ 62 ].…”

Section: Discussionmentioning

confidence: 99%

Furoquinoline Alkaloids: Insights into Chemistry, Occurrence, and Biological Properties

Szewczyk,

Pęczek

2023

IJMS

View full text Add to dashboard Cite

Furoquinoline alkaloids exhibit a diverse range of effects, making them potential candidates for medicinal applications. Several compounds within this group have demonstrated antimicrobial and antiprotozoal properties. Of great interest is their potential as acetylcholinesterase inhibitors and anti-inflammatory agents in neurodegenerative diseases. The promising biological properties of furoquinoline alkaloids have motivated extensive research in this field. As a result, new compounds have been isolated from this group of secondary metabolites, and numerous pharmacological studies have been conducted to investigate their activity. It is crucial to understand the mechanisms of action of furoquinoline alkaloids due to their potential toxicity. Further research is required to elucidate their mechanisms of action and metabolism. Additionally, the exploration of derivative compounds holds significant potential in enhancing their pharmacological benefits. In vitro plant cultures offer an alternative approach to obtaining alkaloids from plant material, presenting a promising avenue for future investigations.

show abstract

Section: Discussionmentioning

confidence: 99%

Furoquinoline Alkaloids: Insights into Chemistry, Occurrence, and Biological Properties

Szewczyk,

Pęczek

2023

IJMS

View full text Add to dashboard Cite

show abstract

“…Kokusaginine also displays modest cholinesterase inhibitory activities (IC 50 = 41.46 and 70.24 µg/mL against butyrylcholinesterase and acetylcholinesterase, respectively) [ 38 , 39 ]. The compound has been used as a starting point to the design of antiparasitic molecules active against Trypanosoma cruzi responsible for the Chagas disease [ 40 ]. Kokusaginine is an isomer of skimmianine and a close analogue of dictamnine, both furoquinolines commonly found in Ruta species and endowed with anticancer properties [ 41 , 42 , 43 ].…”

Section: Bioactive Phytochemicals From R Angustifolia ...mentioning

confidence: 99%

Ruta angustifolia Pers. (Narrow-Leaved Fringed Rue): Pharmacological Properties and Phytochemical Profile

Bailly

2023

Plants

View full text Add to dashboard Cite

The genus Ruta in the family Rutaceae includes about 40 species, such as the well-known plants R. graveolens L. (common rue) or R. chalepensis L. (fringed rue), but also much lesser-known species such as R. angustifolia Pers. (narrow-leaved fringed rue). This rue specie, originating from the Mediterranean region, is well-distributed in Southeast Asia, notably in the Indo-Chinese peninsula and other territories. In some countries, such as Malaysia, the plant is used to treat liver diseases and cancer. Extracts of R. angustifolia display antifungal, antiviral and antiparasitic effects. Diverse bioactive natural products have been isolated from the aerial parts of the plant, notably quinoline alkaloids and furocoumarins, which present noticeable anti-inflammatory, antioxidant and/or antiproliferative properties. The present review discusses the main pharmacological properties of the plant and its phytoconstituents, with a focus on the anticancer activities evidenced with diverse alkaloids and terpenoids isolated from the aerial parts of the plant. Quinoline alkaloids such as graveoline, kokusaginine, and arborinine have been characterized and their mode of action defined. Arborinine stands as a remarkable inhibitor of histone demethylase LSD1, endowed with promising anticancer activities. Other anticancer compounds, such as the furocoumarins chalepin and rutamarin, have revealed antitumor effects. Their mechanism of action is discussed together with that of other bioactive natural products, including angustifolin and moskachans. Altogether, R. angustifolia Pers. presents a rich phytochemical profile, fully consistent with the traditional use of the plant to treat cancer. This rue species, somewhat neglected, warrant further investigations as a medicinal plant and a source of inspiration for drug discovery and design.

show abstract

“…Indeed, more active and safer pesticides might be chemically derived from the compounds described here. For example, Valdez et al found that certain derivatives of kokusagenine (7) and flindersiamine (3) were more active against the human parasite Trypanosoma cruzi than the natural compounds without any cytotoxicity to three human cell types [41].…”

Section: Compounds Rankingmentioning

confidence: 99%

Antifungal and Phytotoxic Activities of Isolated Compounds from Helietta parvifolia Stems

Ribeiro,

Bajsa-Hirschel,

Tamang

et al. 2023

Molecules

View full text Add to dashboard Cite

The identification of natural and environmentally friendly pesticides is a key area of interest for the agrochemical industry, with many potentially active compounds being sourced from numerous plant species. In this study, we report the bioassay-guided isolation and identification of phytotoxic and antifungal compounds from the ethyl acetate extract of Helietta parvifolia stems. We identified eight compounds, consisting of two coumarins and six alkaloids. Among these, a new alkaloid, 2-hydroxy-3,6,7-trimethoxyquinoline-4-carbaldehyde (6), was elucidated, along with seven known compounds. The phytotoxicity of purified compounds was evaluated, and chalepin (4) was active against Agrostis stolonifera at 1 mM with 50% inhibition of seed germination and it reduced Lemna pausicotata (duckweed) growth by 50% (IC50) at 168 μM. Additionally, we evaluated the antifungal activity against the fungal plant pathogen Colletotrichum fragariae using a thin-layer chromatography bioautography assay, which revealed that three isolated furoquinoline alkaloids (flindersiamine (3), kokusagenine (7), and maculine (8)) among the isolated compounds had the strongest inhibitory effects on the growth of C. fragariae at all tested concentrations. Our results indicate that these active natural compounds, i.e., (3), (4), (7), and (8), could be scaffolds for the production of more active pesticides with better physicochemical properties.

show abstract

Antiparasitic Derivatives of the Furoquinoline Alkaloids Kokusaginine And Flindersiamine

Cited by 5 publications

References 45 publications

Furoquinoline Alkaloids: Insights into Chemistry, Occurrence, and Biological Properties

Furoquinoline Alkaloids: Insights into Chemistry, Occurrence, and Biological Properties

Ruta angustifolia Pers. (Narrow-Leaved Fringed Rue): Pharmacological Properties and Phytochemical Profile

Antifungal and Phytotoxic Activities of Isolated Compounds from Helietta parvifolia Stems

Contact Info

Product

Resources

About