A Brief Up-to-Date Overview of Amaryllidaceae Alkaloids: Phytochemical Studies of <i>Narcissus tazetta</i> subsp. <i>tazetta</i> L., Collected in Turkey

Karakoyun, Çiğdem; Masi, Marco; Cimmino, Alessio; Önür, Mustafa; Somer, Nehir Unver; Kornienko, Alexander; Evidente, Antonio

doi:10.1177/1934578x19872906

Cited by 5 publications

(7 citation statements)

References 56 publications

(94 reference statements)

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“…Pseudolycorine was obtained from bulbs of Narcissus tazetta subsp. tazetta L., collected in Turkey [ 71 ]. Epi -epoformin was extracted from the culture filtrates of D. quercivora [ 39 ].…”

Section: Methodsmentioning

confidence: 99%

Activity of Some Plant and Fungal Metabolites towards Aedes albopictus (Diptera, Culicidae)

Ganassi

Masi

Grazioso

et al. 2021

Toxins

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Aedes albopictus (Skuse) is a widespread mosquito, a vector of important human arboviruses, including Chikungunya, Dengue and Zika. It is an extremely difficult species to control even for the onset of resistances to chemicals insecticides, therefore ecofriendly products are urgently needed. In this study, the activity of Amaryllidaceae alkaloids and some of their semisynthetic derivatives, of 2-methoxy-1,4-naphthoquinone and two analogues, of cyclopaldic acid and epi-epoformin on the survival and development of Ae. albopictus larvae was evaluated. First-instar larval exposure for 24 and 48 h to cyclopaldic acid, resulted in mortality mean per-centage of 82.4 and 96.9 respectively; 1,2-O,O-diacetyllycorine 48h post-treatment caused 84.7% mortality. Larval and pupal duration were proved to decrease significantly when larvae were exposed to cyclopaldic acid, 1,2-O,O-diacetyllycorine and N-methyllycorine iodide. The mean number of third-instar larvae surviving to 2-methyl-1,4-naphthoquinone, 2-hydroxy-1,4-naphthoquinone and 2-methoxy-1,4-naphthoquinone was significantly lower than the number of correspondent control larvae over the time. This study indicated that 1,2-O,O’-diacetyllycorine, N-methyllycorine iodide, cyclopaldic acid and 1,4-naphthoquinone structural derivatives have good potential for developing bioinsecticides for mosquito control programs. The obtained results are of general interest due to the global importance of the seri-ous human diseases such a vector is able to spread.

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“…Pseudolycorine was obtained from bulbs of Narcissus tazetta subsp. tazetta L., collected in Turkey [ 71 ]. Epi -epoformin was extracted from the culture filtrates of D. quercivora [ 39 ].…”

Section: Methodsmentioning

confidence: 99%

Activity of Some Plant and Fungal Metabolites towards Aedes albopictus (Diptera, Culicidae)

Ganassi

Masi

Grazioso

et al. 2021

Toxins

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“…Galanthamine, lycorine pseudolycorine and 11-hydroxygalanthine ( 1 , 2 , 93 and 99 ) were isolated from the bulb organic extract of Narsissus tazetta subsp. tazetta , collected during the flowering period in Akçapınar/Muğla, Turkey [ 81 ]. Other alkaloids were isolated and identified as narwedine, anhydrolycorine, 9- O -demethylhomolycorine, 4′,O-methylnorbelladine, 8- O -demethylmaritidine, pseudolycorine, 1- O -acetyl-3- O -methylnarcissidine, 11-hydroxygalanthine, narcissidine, saguinine ( 14 , 17 , 50 , 86 , 88 , 93 , 97 , 99 , 120 , 124 ) and 9- O -methylpseudolycorine ( 139 , Figure 9 ) and pancratinine C ( 51 ) [ 81 ].…”

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

confidence: 99%

“…tazetta , collected during the flowering period in Akçapınar/Muğla, Turkey [ 81 ]. Other alkaloids were isolated and identified as narwedine, anhydrolycorine, 9- O -demethylhomolycorine, 4′,O-methylnorbelladine, 8- O -demethylmaritidine, pseudolycorine, 1- O -acetyl-3- O -methylnarcissidine, 11-hydroxygalanthine, narcissidine, saguinine ( 14 , 17 , 50 , 86 , 88 , 93 , 97 , 99 , 120 , 124 ) and 9- O -methylpseudolycorine ( 139 , Figure 9 ) and pancratinine C ( 51 ) [ 81 ]. All the alkaloids isolated were assayed for their ability to inhibit AChE and BuAchE, and 11-hydroxygalanthine and narcissidine ( 99 and 120 ) showed significant activity on acetylcholinesterase (AChE) [ 81 ].…”

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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“…Pseudolycorine was obtained from bulbs of Narcissus tazetta subsp. tazetta L., collected in Turkey [66]. Epi-epoformin was extracted from the culture ltrates of D. quercivora [49]; 2-methoxy-1,4-naphthoquinone was obtained from the organic extract of I. glandulifera [63].…”

Section: Natural Compounds Testedmentioning

confidence: 99%

Activity of Some Plant and Fungal Metabolites Towards Aedes Albopictus (Diptera, Culicidae)

Ganassi

Masi

Grazioso

et al. 2020

Preprint

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Background: Aedes albopictus (Skuse), a globally spread species, vector of important human arboviruses, and of Zika virus, is extremely difficult to control even for the onset of resistances to chemicals insecticides. Ecofriendly biopesticides for vector control are urgently needed. In this study, the activity of some plant metabolites as Amaryllidaceae alkaloids and some their semisynthetic derivatives and 2-methoxy-1,4-naphthoquinones, and two analogues, and of the fungal metabolites cyclopaldic acid and epi-epoformin on the development and survival of Ae. albopictus larvae was evaluated. Methods: A preliminary screening, on first-instar larvae, with lycorine semisynthetic derivatives and cyclopaldic acid at 100 ppm was conducted. The living larvae were recorded 24 and 48 h post treatment. Based on the results, first-instar larvae were exposed to increasing doses of the compounds tested until adult emergence. The mean larval and pupal duration was calculated. Third instar larvae were exposed to increasing doses of naphthoquinones for 72 h. The mortality rates were recorded every 24. The larvicide Device® SC-15 was used as control.Results: First instar larval exposure to cyclopaldic acid at 50 and 100 ppm for 48 h, resulted in mortality mean percentage of 82.444 and 96.889% respectively; LC50 and LC90 were 40.119 and 105.092 ppm. 1,2-O,O-diacetyllycorine at 50 ppm, 48h post-treatment caused 84.667% mean percentage mortality with LC50 27.769 and LC90 88.316 ppm. Significant differences in the larval and pupal duration were proved when larvae were exposed to cyclopaldic acid (H=16.386; df 4; P=0.003; H=31.835; df 4; P=0.000), 1,2-O,O-diacetyllycorine (H=9.044; df 3; P=0.029; H=18.115; df 3; P=0.000) and N-methyllycorine iodide (H=19.457; df 4; P=0.001; H=15.400; df 4; P=0.004).Statistical analyses revealed that the number of third-instar larvae surviving to naphthoquinones significantly decreases over the time when exposed to 2-methyl-1,4-naphthoquinone 12.5, 25, 50 ppm; 2-hydroxy-1,4-naphthoquinone 12.5, 25 ppm, 2-metoxy-1,4-naphthoquinone 50 ppm. The mean number of surviving larvae exposed to: 2-methyl-1,4-naphthoquinone 12.5, 25, 50, 100 ppm, 2-hydroxy-1,4-naphthoquinone 25, 50, 100 ppm, 2-metoxy-1,4-naphthoquinone 50, 100 ppm was significantly lower than the number of correspondent control larvae, respectively.Conclusions: This study indicated that 1,2-O,O’-diacetyllycorine, N-methyllycorine iodide, cyclopaldic acid and 1,4-naphtoquinone structural derivatives have good potential to develop bioinsecticides for mosquito control programs.

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A Brief Up-to-Date Overview of Amaryllidaceae Alkaloids: Phytochemical Studies of Narcissus tazetta subsp. tazetta L., Collected in Turkey

Cited by 5 publications

References 56 publications

Activity of Some Plant and Fungal Metabolites towards Aedes albopictus (Diptera, Culicidae)

Activity of Some Plant and Fungal Metabolites towards Aedes albopictus (Diptera, Culicidae)

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

Activity of Some Plant and Fungal Metabolites Towards Aedes Albopictus (Diptera, Culicidae)

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