Simultaneous quantitative analysis of biologically important Amaryllidaceae alkaloids in Narcissus tazetta L. subsp. tazetta by HPLC/PDA

Çiğdem Karakoyun; Nehir Ünver-somer

Simultaneous quantitative analysis of biologically important Amaryllidaceae alkaloids in Narcissus tazetta L. subsp. tazetta by HPLC/PDA

Abstract

The present study was conducted for the quantitative determination of biologically active Amaryllidaceae alkaloids, galanthamine and lycorine, in the bulbs and aerial parts of a subspecies naturally growing in Turkey namely, Narcissus tazetta L. subsp. tazetta collected from Muğla/Turkey. A reverse phase high performance liquid chromatographic method using an isocratic system consisting of trifluoroacetic acid:water:acetonitrile (0.01:90:10) with a flow rate of 1 mL/min was carried out. Photodiode array detection was employed to determine the UV-visible spectral characteristics of the alkaloids. Determination of acetylcholinesterase and butyrylcholinesterase inhibitory activities of different parts of mentioned subspecies were accomplished using a microplate assay modified from Ellman’s method. This is the first report of the galanthamine content of Narcissus tazetta subsp. tazetta of Turkish origin. 0.0051% and 0.0055% galanthamine was detected in the bulbs and aerial parts of the plant, respectively. Also, lycorine was determined as 0.0250% in the bulbs and 0.0672 % in the aerial parts.

Keywords

References

[1] Nair JJ, Bastida J, Codina C, Viladomat F, van Staden J. Alkaloids of the South African Amaryllidaceae: A review. Nat Prod Commun. 2013; 8(9): 1335-1350. [CrossRef]
[2] Nair JJ, van Staden J. Pharmacological and toxicological insights to the South African Amaryllidaceae. Food Chem Toxicol. 2013; 6: 262-275. [CrossRef]
[3] Nair JJ, van Staden J. Traditional usage, phytochemistry and pharmacology of the South African medicinal plant Boophone disticha (L.f.) Herb. (Amaryllidaceae). J Ethnopharmacol. 2014; 151(1): 12-26. [CrossRef]
[4] Cimmino A, Masi M, Evidente M, Superchi S, Evidente A. Amaryllidaceae alkaloids: Absolute configuration and biological activity. Chirality. 2017; 29: 486-499. [CrossRef]
[5] He M, Qu C, Gao O, Hu X, Hong X. Biological and pharmacological activities of amaryllidaceae alkaloids. RSC Adv. 2015; 5: 16562-16574. [CrossRef]
[6] Dasari R, Banuls LMY, Masi M, Pelly SC, Mathieu V, Green IR, van Otterlo WAL, Evidente A, Kiss R, Kornienko A. C1,C2-ether derivatives of the Amaryllidaceae alkaloid lycorine: Retention of activity of highly lipophilic analogues against cancer cells. Bioorg Med Chem Lett. 2014; 24: 923-927. [CrossRef]
[7] Su J, Liu H, Guo K, Chen L, Yang M, Chen Q. Research advances and detection methodologies for microbe-derived acetylcholinesterase inhibitors: A systemic review. Molecules. 2017; 22(1): pii 176. [CrossRef]
[8] Heinrich M, Teoh HL. Galanthamine from snowdrop—the development of a modern drug against Alzheimer’s disease from local Caucasian knowledge. J Ethnopharmacol. 2004; 92: 147-162. [CrossRef]

[9] Torras-Claveria L, Berkov S, Codina C, Viladomat F, Bastida J. Daffodils as potential crops of galanthamine. Assessment of more than 100 ornamental varieties for their alkaloid content and acetylcholinesterase inhibitory activity. Ind Crops Prod. 2013; 43: 237-244. [CrossRef]
[10] Berkov S, Georgieva L, Kondakova V, Atanassov A, Viladomat F, Bastida J, Codina C. Plant sources of galanthamine: phytochemical and biotechnological aspects. Biotechnol Biotechnol Equip. 2009; 23(2): 1170-1176. [CrossRef]
[11] Uzmay A, Durmaz S, Örümlü AE. A Study on the Problems of Narcissus Farming in Mordoğan. Ege Üniv Ziraat Fak Derg. 2001; 38(1): 39-46.
[12] Selles M, Bastida J, Viladomat, Codina C. Quantitative evaluation of galanthamine and related alkaloids in wild plants and tissue cultures of Narcissus confusus by high performance liquid chromatography. Analysis. 1997; 25: 156-158. [CrossRef]
[13] Khonakdari MR, Mirjalili MH, Gholipour A, Rezadoost H, Farimani MM. Quantification of galantamine in Narcissus tazetta and Galanthus nivalis (Amaryllidaceae) populations growing wild in Iran. Plant Genet Resour. 2018; 16(2): 188-192. [CrossRef]
[14] Lubbe A, Pomahacova B, Choi YV, Verporte R. Analysis of metabolic variation and galanthamine content in Narcissus bulbs by 1H NMR. Phytochem Anal. 2010; 21(1): 66-72. [CrossRef]
[15] Moraes Cerdeira RM, Burandt CL, Bastos JK, Nanayakkara NPD, Mikell J, Thurn J, McChesney JD. Evaluation of four Narcissus cultivars as potential sources for galanthamine production. Planta Med. 1997; 63(5): 472-474. [CrossRef]
[16] Laura TC, Strahil B, Carles C, Francesc V, Jaume B. Daffodils as potential crops of galanthamine. Assessment of more than 100 ornamental varieties for their alkaloid content and acetylcholinesterase inhibitory activity. Ind Crops Prod. 2013; 43: 237-244. [CrossRef]
[17] Kreh M. Studies on galanthamine extraction from Narcissus and other Amaryllidaceae. In: Hanks GR, (Eds). Narcissus and Daffodil—The genus Narcissus. Taylor & Francis Ltd, New York, 2002, pp. 256-272.
[18] Mustafa NR, Rhee IK, Verpoorte R. Rapid method for determination of galanthamine in Amaryllidaceae plants using HPLC. J Liq Chromatogr Relat Technol. 2003; 26(19): 3217-3233. [CrossRef]
[19] Hanks GR. Commercial production of Narcissus bulbs. In: Hanks GR. (Eds). Narcissus and Daffodil—The genus Narcissus. Taylor & Francis Ltd, New York, 2002, pp. 53-130.
[20] Abdallah OM. Narcisine, an alkaloid from Narcissus tazetta. Phytochemistry. 1993; 34(5): 1447-1448. [CrossRef]
[21] Ramakrishna A, Ravishankar GA. Influence of abiotic stress signals on secondary metabolites in plants. Plant Signal Behav. 2011; 6(11): 1720-1731. [CrossRef]
[22] Orhan I, Sener B. Bioactivity-directed fractionation of alkaloids from some Amaryllidaceae plants and their anticholinesterase activity. Chem Nat Compd. 2003; 39(4): 383-386. [CrossRef]
[23] Sener B, Koyuncu M, Bingöl F, Muhtar F. Production and bioactive alkaloids from Turkish geophytes. Pure Appl Chem. 1998; 70: 2131.
[24] Lopez S, Bastida J, Viladomat F, Codina C. Galanthamine Pattern in Narcissus confusus plants. Planta Med. 2003; 69: 1166-1168. [CrossRef]
[25] Lubbe A, Choi YH, Vreeburg P, Verporte R. Effect of fertilizers on galanthamine and metabolite profiles in Narcissus bulbs by 1H NMR. J Agric Food Chem. 2011; 59(7): 3155–3161. [CrossRef]
[26] Bergonon S, Codina C, Bastida J, Viladomat F, Mele E. Galanthamine production in ''shoot-clump'' cultures of Narcissus confusus in liquid-shake medium. Plant Cell Tissue Organ Cult. 1996; 45(3): 191-199. [CrossRef]
[27] Selles M, Bergonon S, Viladomat F, Bastida J, Codina C. Effect of sucrose on growth and galanthamine production in shoot-clump cultures of Narcissus confusus in liquid-shake medium. Plant Cell Tissue Organ Cult. 1997; 49(2): 129-136.
[28] Selles M, Viladomat F, Bastida J, Codina C. Callus induction, somatic embryogenesis and organogenesis in Narcissus confusus: correlation between the state of differentiation and the content of galanthamine and related alkaloids. Plant Cell Rep. 1999; 18(7-8): 646-651. [CrossRef]
[29] Colque R, Viladomat F, Bastida J, Codina C. Improved production of galanthamine and related alkaloids by methyl jasmonate in Narcissus confusus shoot-clumps. Planta Med. 2004; 70(12): 1180-1188. [CrossRef]
[30] Carles C. Production of galanthamine by Narcissus tissues in vitro. In: Hanks GR. (Eds). Narcissus and Daffodil—The genus Narcissus. Taylor & Francis Ltd, New York, 2002, pp. 215-241.
[31] Ellman GL, Courtney KD, Andres V Jr, Feather-Stone RM. A new and rapid colorimetric determination of acetylcholinesterase activity. Biochem Pharmacol. 1961; 7: 88-95. [CrossRef]
[32] Lopez S, Bastida J, Viladomat F, Codina C. Acetylcholinesterase inhibitory activity of some Amaryllidaceae alkaloids and Narcissus extracts. Life Sci. 2002; 71(21): 2521-2529. [CrossRef]

Details

Primary Language

English

Subjects

Pharmacognosy

Journal Section

Research Article

Authors

Çiğdem Karakoyun ^* This is me
Türkiye

Nehir Ünver-somer This is me
Türkiye

Publication Date

June 27, 2025

Submission Date

September 27, 2018

Acceptance Date

November 22, 2018

Published in Issue

Year 2019 Volume: 23 Number: 3

IZ

https://izlik.org/JA97WT58RN

Cite

RIS / Bibtex

APA

Karakoyun, Ç., & Ünver-somer, N. (2025). Simultaneous quantitative analysis of biologically important Amaryllidaceae alkaloids in Narcissus tazetta L. subsp. tazetta by HPLC/PDA. Journal of Research in Pharmacy, 23(3), 498-505. https://izlik.org/JA97WT58RN

AMA

1.Karakoyun Ç, Ünver-somer N. Simultaneous quantitative analysis of biologically important Amaryllidaceae alkaloids in Narcissus tazetta L. subsp. tazetta by HPLC/PDA. J. Res. Pharm. 2025;23(3):498-505. https://izlik.org/JA97WT58RN

Chicago

Karakoyun, Çiğdem, and Nehir Ünver-somer. 2025. “Simultaneous Quantitative Analysis of Biologically Important Amaryllidaceae Alkaloids in Narcissus Tazetta L. Subsp. Tazetta by HPLC PDA”. Journal of Research in Pharmacy 23 (3): 498-505. https://izlik.org/JA97WT58RN.

EndNote

Karakoyun Ç, Ünver-somer N (June 1, 2025) Simultaneous quantitative analysis of biologically important Amaryllidaceae alkaloids in Narcissus tazetta L. subsp. tazetta by HPLC/PDA. Journal of Research in Pharmacy 23 3 498–505.

IEEE

[1]Ç. Karakoyun and N. Ünver-somer, “Simultaneous quantitative analysis of biologically important Amaryllidaceae alkaloids in Narcissus tazetta L. subsp. tazetta by HPLC/PDA”, J. Res. Pharm., vol. 23, no. 3, pp. 498–505, June 2025, [Online]. Available: https://izlik.org/JA97WT58RN

ISNAD

Karakoyun, Çiğdem - Ünver-somer, Nehir. “Simultaneous Quantitative Analysis of Biologically Important Amaryllidaceae Alkaloids in Narcissus Tazetta L. Subsp. Tazetta by HPLC PDA”. Journal of Research in Pharmacy 23/3 (June 1, 2025): 498-505. https://izlik.org/JA97WT58RN.

JAMA

1.Karakoyun Ç, Ünver-somer N. Simultaneous quantitative analysis of biologically important Amaryllidaceae alkaloids in Narcissus tazetta L. subsp. tazetta by HPLC/PDA. J. Res. Pharm. 2025;23:498–505.

MLA

Karakoyun, Çiğdem, and Nehir Ünver-somer. “Simultaneous Quantitative Analysis of Biologically Important Amaryllidaceae Alkaloids in Narcissus Tazetta L. Subsp. Tazetta by HPLC PDA”. Journal of Research in Pharmacy, vol. 23, no. 3, June 2025, pp. 498-05, https://izlik.org/JA97WT58RN.

Vancouver

1.Çiğdem Karakoyun, Nehir Ünver-somer. Simultaneous quantitative analysis of biologically important Amaryllidaceae alkaloids in Narcissus tazetta L. subsp. tazetta by HPLC/PDA. J. Res. Pharm. [Internet]. 2025 Jun. 1;23(3):498-505. Available from: https://izlik.org/JA97WT58RN