Cytotoxicity and Antiviral Properties of Alkaloids Isolated from Pancratium maritimum

Masi, Marco; Lecce, Roberta Di; Mérindol, Natacha; Girard, Marie-Pierre; Berthoux, Lionel; Desgagné‐Penix, Isabel; Calabrò, Viola

doi:10.3390/toxins14040262

Cited by 12 publications

(16 citation statements)

References 63 publications

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“…Several studies demonstrated the antiviral effect of AAs against several types of viruses [ 18 , 19 , 20 , 21 , 22 , 23 , 36 , 37 , 38 ]. Here, the virus used to perform DENV GFP infections corresponded to dengue serotype 2.…”

Section: Discussionmentioning

confidence: 99%

“…Here, the virus used to perform DENV GFP infections corresponded to dengue serotype 2. Recently, we also uncovered that the Amaryllidaceae alkaloids haemanthamine, pancracine, and haemanthidine, which were isolated from Pancratium maritimum , inhibited DENV-2 infection [ 23 ]. This study added to the growing evidence that AA structures could be optimized to develop potent inhibitors against this potentially fatal disease.…”

Section: Discussionmentioning

confidence: 99%

“…Lycorine, like many other AAs, exhibits anticancer (i.e., cytotoxic activity) [ 13 , 14 , 15 , 16 , 17 ], but also exerts an inhibitory effect against flaviviruses, such as DENV (dengue virus), and viruses belonging to other families [ 18 , 19 , 20 , 21 ]. Recently, we demonstrated that the AAs cherylline, pancracine, haemanthamine, and haemanthidine display antiviral effects against DENV, and except for cherylline, also against human immunodeficiency virus (HIV-1) [ 22 , 23 ]. The development of antiviral therapeutics based on AAs may provide decisive medical solutions to catastrophic pandemics.…”

Section: Introductionmentioning

confidence: 99%

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Chemical Synthesis and Biological Activities of Amaryllidaceae Alkaloid Norbelladine Derivatives and Precursors

et al. 2022

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Amaryllidaceae alkaloids (AAs) are a structurally diverse family of alkaloids recognized for their many therapeutic properties, such as antiviral, anti-cholinesterase, and anticancer properties. Norbelladine and its derivatives, whose biological properties are poorly studied, are key intermediates required for the biosynthesis of all ~650 reported AAs. To gain insight into their therapeutic potential, we synthesized a series of O-methylated norbelladine-type alkaloids and evaluated their cytotoxic effects on two types of cancer cell lines, their antiviral effects against the dengue virus (DENV) and the human immunodeficiency virus 1 (HIV-1), and their anti-Alzheimer’s disease (anti-cholinesterase and -prolyl oligopeptidase) properties. In monocytic leukemia cells, norcraugsodine was highly cytotoxic (CC50 = 27.0 μM), while norbelladine was the most cytotoxic to hepatocarcinoma cells (CC50 = 72.6 μM). HIV-1 infection was impaired only at cytotoxic concentrations of the compounds. The 3,4-dihydroxybenzaldehyde (selectivity index (SI) = 7.2), 3′,4’-O-dimethylnorbelladine (SI = 4.8), 4′-O-methylnorbelladine (SI > 4.9), 3′-O-methylnorbelladine (SI > 4.5), and norcraugsodine (SI = 3.2) reduced the number of DENV-infected cells with EC50 values ranging from 24.1 to 44.9 μM. The O-methylation of norcraugsodine abolished its anti-DENV potential. Norbelladine and its O-methylated forms also displayed butyrylcholinesterase-inhibition properties (IC50 values ranging from 26.1 to 91.6 μM). Altogether, the results provided hints of the structure–activity relationship of norbelladine-type alkaloids, which is important knowledge for the development of new inhibitors of DENV and butyrylcholinesterase.

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Section: Discussionmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Chemical Synthesis and Biological Activities of Amaryllidaceae Alkaloid Norbelladine Derivatives and Precursors

et al. 2022

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“…Lycorine and haemanthidine ( 1 and 59 ) showed cytotoxic activity on Hacat cells and A431 and AGS cancer cells, while pancracine ( 41 ) exhibited selective cytotoxicity against A431 cells [ 104 ]. Alkaloids 2 , 5 , 41 and 59 also showed antiretroviral activity, inhibiting pseudotyped human immunodeficiency virus (HIV)−1 with EC 50 values of 25.3 and 18.5 µM, respectively [ 104 ]. In addition, all the alkaloids were able to avoid dengue virus (DENV) replication with EC 50 values ranging from 0.34 to73.59 µM at low non-cytotoxic concentrations (CC 50 ranged from 6.25 µM to >100 µM [ 104 ]).…”

Section: Alkaloids Isolated From Amaryllidacae Plants Collected In Me...mentioning

confidence: 99%

Advances on the Amaryllidacea Alkaloids Collected in South Africa, Andean South America and the Mediterranean Basin

Evidente

2023

Molecules

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The alkaloids are one of the most represented family of natural occurring biological active compounds. Amaryllidaceae are also very well known for their beautiful flower and are thus used as ornamental plants in historic and public gardens. The Amaryllidacea alkaloids constitute an important group that is subdivided into different subfamilies with different carbon skeletons. They are well known from ancient times for their long application in folk medicine, and in particular, Narcissus poeticus L. was known to Hippocrates of Cos (ca. B.C. 460–370), who treated uterine tumors with a formulate prepared from narcissus oil. To date, more than 600 alkaloids of 15 chemical groups exhibiting various biological activities have been isolated from the Amaryllidaceae plants. This plant genus is diffused in regions of Southern Africa, Andean South America and the Mediterranean basin. Thus, this review describes the chemical and biological activity of the alkaloids collected in these regions in the last two decades as weel those of isocarbostyls isolated from Amaryllidaceae in the same regions and same period.

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“…Among these there are alkaloids isolated from Amaryllidaceae and alkylamides [7,8], with the latter being a broad and expanding group found in at least 33 plant families [8]. Alkylamides and alkaloids have been observed to have antimicrobial [9][10][11][12][13][14], antiprotozoal [11,15], antiviral [16,17], insecticidal [18][19][20][21], nematocidal [22], cytotoxic [17], anticancer [23][24][25][26][27][28][29][30][31][32], acetylcholinesterase inhibition [27,28], and bioherbicidal activities [20,30]. Some plant extracts with potential herbicidal activity were also appropriately formulated in biopolymers [31,32].…”

Section: Introductionmentioning

confidence: 99%

Biochemical Analyses of Bioactive Extracts from Plants Native to Lampedusa, Sicily Minor Island

Lecce

Mérindol

Pérez

et al. 2022

Plants

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Major threats to the human lifespan include cancer, infectious diseases, diabetes, mental degenerative conditions and also reduced agricultural productivity due to climate changes, together with new and more devastating plant diseases. From all of this, the need arises to find new biopesticides and new medicines. Plants and microorganisms are the most important sources for isolating new metabolites. Lampedusa Island host a rich contingent of endemic species and subspecies. Seven plant species spontaneously growing in Lampedusa, i.e., Atriplex halimus L. (Ap), Daucus lopadusanus Tineo (Dl), Echinops spinosus Fiori (Es) Glaucium flavum Crantz (Gf) Hypericum aegypticum L: (Ha), Periploca angustifolia Labill (Pa), and Prasium majus L. (Pm) were collected, assessed for their metabolite content, and evaluated for potential applications in agriculture and medicine. The HPLC-MS analysis of n-hexane (HE) and CH2Cl2 (MC) extracts and the residual aqueous phases (WR) showed the presence of several metabolites in both organic extracts. Crude HE and MC extracts from Dl and He significantly inhibited butyrylcholinesterase, as did WR from the extraction of Dl and Pa. HE and MC extracts showed a significant toxicity towards hepatocarcinoma Huh7, while Dl, Ha and Er HE extracts were the most potently cytotoxic to ileocecal colorectal adenocarcinoma HCT-8 cell lines. Most extracts showed antiviral activity. At the lowest concentration tested (1.56 μg/mL), Dl, Gf and Ap MC extracts inhibited betacoronavirus HCoV-OC43 infection by> 2 fold, while the n-hexane extract of Pm was the most potent. In addition, at 1.56 μg/mL, potent inhibition (>10 fold) of dengue virus was detected for Dl, Er, and Pm HE extracts, while Pa and Ap MC extracts dampened infections to undetectable levels. Regarding to phytotoxicity, MC extracts from Er, Ap and Pm were more effective in inhibiting tomato rootlet elongation; the same first two extracts also inhibited seed cress germination while its radicle elongation, due to high sensitivity, was affected by all the extracts. Es and Gf MC extracts also inhibited seed germination of Phelipanche ramosa. Thus, we have uncovered that many of these Lampedusa plants displayed promising biopesticide, antiviral, and biological properties.

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Cytotoxicity and Antiviral Properties of Alkaloids Isolated from Pancratium maritimum

Cited by 12 publications

References 63 publications

Chemical Synthesis and Biological Activities of Amaryllidaceae Alkaloid Norbelladine Derivatives and Precursors

Chemical Synthesis and Biological Activities of Amaryllidaceae Alkaloid Norbelladine Derivatives and Precursors

Advances on the Amaryllidacea Alkaloids Collected in South Africa, Andean South America and the Mediterranean Basin

Biochemical Analyses of Bioactive Extracts from Plants Native to Lampedusa, Sicily Minor Island

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