MUSCARI ARMENIACUM LEICHTLIN (GRAPE HYACINTH): PHYTOCHEMISTRY AND BIOLOGICAL ACTIVITIES REVIEW

Abstract

This review focuses on the Muscari armeniacum Leichtlin (Asparagaceae Juss) biologically active substances composition presented in the Aireal and underground parts and finding their possible therapeutic effects. The systematic review is dedicated to the composition of biologically active substances, including recent advances in the biological activity investigation, phytochemical studies, and biotechnology methods of plant material producing. Various electronic search engines such as Google, Google Scholar, scientific literature, publishing sites, and electronic databases such as PubMed, Wiley, Springer, and Science Direct had been searched and data obtained. Other online academic libraries such as E-library and specific ethnopharmacological literature had been searched systematically for more exhaustive information on the crude herbal drug. The chemical composition of M. armeniacum biologically active substances is established; it contains anthocyanins (delphinidin and cyanidin derivatives), homoisoflavonoids, polyhydroxylated pyrrolizidine alkaloids (hyacinthacines A1, A2, A3, and B3), oligoglycosides (Muscarosides), and ribosome-inactivating proteins (musarmins). Recent physicochemical analytical procedures for components determination and hyacinthacines synthesis pathways are mentioned. Moreover, future prospects and trends in the research of this plant have been proposed. We have reviewed researches conducted on M. armeniacum especially in areas of its use in medicine, phytochemicals, biological activity, and developed analytical methods. M. armeniacum possesses antioxidant, antimutagenic activity, and specific glycosidase inhibitory activity; M. armeniacum can be used for the production of potential anticancer, antiviral, antidiabetic, and anti-obesity drugs. It should be noted that more pharmacognostic, pharmacological studies are needed for giving further information on the clinical practice and standardization procedures for the crude herbal drug.

Keywords: Muscari armeniacum, Hyacinthacine, Muscarosides, Musarmin, Homoisoflavonoids, Muscarinin A.

Author Biography

Dmitry Olegovich Bokov, Department of Pharmaceutical and Natural Sciences, Sechenov First Moscow State Medical University, Moscow, Russia.
assistant

References

1. Bhattacharya S, Maity S, Pramanick D, Hazra A, Choudhury M. HPLC of phenolic compounds, antioxidant and antimicrobial activity of bulbs from three Ornithogalum species available in India. Int J Pharm Pharm Sci 2016;8:187-92.
2. Misra B, Kameshwari MN. Extraction and sugar composition of mucilage in Urginea indica/Drimia indica (Roxb) Kunth Hyacinthaceae. Int J Pharm Pharm Sci 2016;8:335-8.
3. Wilson CG, Mathew B. Bulbs: The Bulbous Plants of Europe and their Allies. London: Collins; 1981.
4. Botanical Society of Britain and Ireland. Archived from the Original (xls). Available from: https://www.webcitation.org/6VqJ46atN?url=http://www.bsbi.org.uk/BSBIList2007.xls. [Last accessed on 2018 Jun 06].
5. “Muscari”. Pacific Bulb Society. Available from: http://www.pacificbulbsociety.org/pbswiki/index.php/muscari. [Last accessed on 2018 Jun 06].
6. Grape Hyacinth, Muscari armeniacum. Master Gardener Program. University of Wisconsin-Extension. Available from: https://www.wimastergardener.org/article/grape-hyacinth-muscari-armeniacum/. [Last accessed on 2018 Jun 06].
7. Mükemre M, Behçet L, Çakılcıoğlu U. Survey of wild food plants for human consumption in villages of Çatak (Van-Turkey). Indian J Tradit Knowl 2016;15:183-91.
8. Dogan A. Traditional Natural Therapeutic Products Used in the Treatment of Wound in the Tunceli (Turkey). USA: The 2016 WEI International Academic Conference Proceedings Boston.
9. Tuzlacı E, Doğan A. Turkish folk medicinal plants. IX: Ovacık (Tunceli). Marmara Pharm J 2010;14:136-43.
10. Lozina-Lozinskaya AS. Genus 283. In: Komarov VL, editor. Viper Onion-Muscari. Flora of the USSR. Vol. 4, 30. Moscow-Leningrad: Publishing House of the Academy of Sciences of the USSR; 1935. p. 412-22.
11. Pehlivan S, Ozler H. Pollen morphology of some species of Muscari Miller (Liliaceae-Hyacinthaceae) from Turkey. Flora 2003;198:200 10.
12. Karlén T. Karyotypes and chromosome numbers of five species of Muscari (Liliaceae). Willdenowia 1985;14:313-20.
13. Jia M, Wang F, Jia A, Zheng L. Colchicines induced polyploid plants of Muscari armeniacum. Acta Agric Boreali Occident Sin 2011;1:21.
14. Mulholland DA, Schwikkard SL, Crouch NR. The chemistry and biological activity of the Hyacinthaceae. Nat Prod Rep 2013;30:1165 210.
15. Kayıran SD, Özkan EE, Özhatay N. The Screening Phytochemical Components of Muscari and Bellevalia species Growing in Kahramanmaras and Review of Phytochemical Studies. 11th International Symposium on Pharmaceutical Sciences-Ankara (ISOPS 2015); 2015.
16. Kayıran SD, Özkan EE. The ethnobotanical uses of Hyacinthaceae species growing in Turkey and a review of pharmacological activities. Indian J Tradit Knowl 2017;16:243-50.
17. Plantarium. The Determinant of Plants On-Line. Open Atlas of Plants and Lichens in Russia and Adjacent Countries. Available from: http://www.plantarium.ru/page/image/id/450309.html. [Last accessed on 2018 Oct 06].
18. Nakada M, Komatsu M, Ochiai T, Ohtsu K, Nakazono M, Nishizawa NK, et al. Isolation of MaDEF from Muscari armeniacum and analysis of its expression using laser microdissection. Plant Sci 2006;170:143 50.
19. Yoshida K, Aoki H, Kameda K, Kondo T. Structure of muscarinin A, an acylated anthocyanin, from purplish blue spicate flower petals of Muscari armeniacum. ITE Lett Batter New Technol Med 2002;1:35-8.
20. Mori S, Nakano M, Kondo M, Hoshi Y, Kobayashi H. Isolation and characterization of a cytochrome P450 gene from Muscari armeniacum. Acta Hortic 2005;673:429-35.
21. Chen K, Liu H, Lou Q, Liu Y. Ectopic expression of the grape hyacinth (Muscari armeniacum) R2R3-MYB transcription factor gene, MaAN2, induces anthocyanin accumulation in tobacco. Front Plant Sci 2017;8:965.
22. Williams CA, Grayer RJ. Anthocyanins and other flavonoids. Nat Prod Rep 2004;21:539-73.
23. Wraga K, Placek M. Review of taxons from genus Muscari cultivated in department of ornamental plants in Szczecin. Herba Pol 2009;55:348 53.
24. Dashwood M, Mathew B. Hyacinthaceae–Little Blue Bulbs. Bulletin Number 11. RHS Plant Trials and Awards. Royal Horticultural Society; 2005. Available from: https://www.rhs.org.uk/Plants/PDFs/Plant-trials-and-awards/Plant-bulletins/hyacinthaceae.pdf. [Last accessed on 2018 Nov 08].
25. Lou Q, Wang L, Liu H, Liu Y. Anthocyanin profiles in flowers of grape Hyacinth. Molecules 2017;22:688.
26. Mori S, Asano S, Kobayashi H, Nakano M. Analyses of anthocyanidins and anthocyanins in flowers of Muscari spp. Bulletin of the Faculty of Agriculture-Niigata University (Japan) 2002;551:13-8.
27. Lou Q, Liu Y, Qi Y, Jiao S, Tian F, Jiang L, et al. Transcriptome sequencing and metabolite analysis reveals the role of delphinidin metabolism in flower color in grape hyacinth. J Exp Bot 2014;65:3157 64.
28. Sivamaruthi B, Pengkumsri N, Saelee M, Kesika P, Sirilun S, Peerajan S, et al. Impact of physical treatments on stability and radical scavenging capacity of anthocyanidins. Int J Pharm Pharm Sci 2015;8:162-7.
29. Joshi S, Jadhav V, Kadam V. Exotic fruits and vegetable food as nutritional supplement for diabetes, obesity and metabolic diseases. Int J Curr Pharm Res 2018;10:51-5.
30. Adinolfi M, Corsaro MM, Lanzetta R, Laonigro G, Mangoni L, Parrilli M. Ten homoisoflavanones from two Muscari species. Phytochemistry 1986;26:285-90.
31. Grancaiová Z, Mašterová I, Suchý V. Constituents of Muscari armeniacum. Fitoterapia 1992;63:380.
32. Juránek I, Suchý V, Stará D, Maśterová I, Grancaiova Z. Antioxidative activity of homoisoflavonoids from Muscari racemosum and Dracena cinnabari. Pharm 1993;48:310.
33. Miadoková E, Mašterová I, Vlčková V, Dúhová V, Tóth J. Antimutagenic potential of homoisoflavonoids from Muscari racemosum. J Ethnopharmacol 2002;81:381-6.
34. Surburg H, Guentert M, Harder H. Volatile Compounds from Flowers: Analytical and Olfactory Aspects. Bioactive Volatile Compounds from Plants. In ACS Symposium Series (USA); 1993. p. 168-86.
35. Ranwala AP, Miller WB. Analysis of nonstructural carbohydrates in storage organs of 30 ornamental geophytes by high-performance anion-exchange chromatography with pulsed amperometric detection. New Phytol 2008;180:421-33.
36. Barbakadze VV, Targamadze IL, Usov AI. Glucofructan from bulbs of grape hyacinth Muscari szovitsianum Baker (Liliaceae). Bioorg Khim 1996;22:441-5.
37. Sedelnikova LL, Kukushkina TA. The content of reserve and biologically active substances in the vegetative organs of Armenian Muscari (Muscari armeniacum). Chem Sustain Dev 2016;24:647-51.
38. Asano N, Kuroi H, Ikeda K, Kizu H, Kameda Y, Kato A, et al. New polyhydroxylated pyrrolizidine alkaloids from Muscari armeniacum: Structural determination and biological activity. Tetrahedron Asymmetry 2000;11:1-8.
39. Asano N, Nash RJ, Molyneux RJ, Fleet GW. Sugar-mimic glycosidase inhibitors: Natural occurrence, biological activity and prospects for therapeutic application. Tetrahedron Asymmetry 2000;11:1645-80.
40. Watson AA, Fleet GW, Asano N, Molyneux RJ, Nash RJ. Polyhydroxylated alkaloids-natural occurrence and therapeutic applications. Phytochemistry 2001;56:265-95.
41. Ritthiwigrom T, Au CW, Pyne SG. Structure, biological activities and synthesis of hyacinthacine alkaloids and their stereoisomers. Curr Org Synth 2012;9:583-612.
42. Chabaud L, Landais Y, Renaud P. Total synthesis of hyacinthacine A1 and 3-epi-hyacinthacine A1. Org Lett 2005;7:2587-90.
43. Reddy PV, Veyron A, Koos P, Bayle A, Greene AE, Delair P. Approach to the hyacinthacines: First non-chiral pool synthesis of (+)-hyacinthacine A1. Org Biomol Chem 2008;6:1170-2.
44. Chandrasekhar S, Parida BB, Rambabu C. Total synthesis of hyacinthacine A1, a glycosidase inhibitor. J Org Chem 2008;73:7826-8.
45. Si CM, Mao ZY, Ren RG, Du ZT, Wei BG. Flexible approach for the asymmetric synthesis of (−)-hyacinthacine A1 and its 7a-epimer. Tetrahedron 2014;70:7936-41.
46. Calveras J, Casas J, Parella T, Joglar J, Clapés P. Chemoenzymatic synthesis and inhibitory activities of hyacinthacines A1 and A2 stereoisomers. Adv Synth Catal 2007;349:1661-6.
47. D’Adamio G, Goti A, Parmeggiani C, Moreno-Clavijo E, Robina I, Cardona F. Total synthesis of (+)‐hyacinthacine A1,(+)‐7a‐epi‐hyacinthacine A1,(6R)‐6‐hydroxyhyacinthacine A1 and (6S)‐6‐hydroxy‐7a‐epi‐hyacinthacine A1. Eur J Org Chem 2011;35:7155 62.
48. Ribes C, Falomir E, Carda M, Marco JA. Stereoselective syntheses of the glycosidase inhibitors hyacinthacine A2, hyacinthacine A3 and 5-epi-hyacinthacine A3. Tetrahedron 2009;65:6965-71.
49. Liu XK, Qiu S, Xiang YG, Ruan YP, Zheng X, Huang PQ. SmI2-mediated radical cross-couplings of α-hydroxylated aza-hemiacetals and N, S-acetals with α, β-unsaturated compounds: Asymmetric synthesis of (+)-hyacinthacine A2,(−)-uniflorine A, and (+)-7-epi-casuarine. J Org Chem 2011;76:4952-63.
50. Izquierdo I, Plaza MT, Franco F. Polyhydroxylated pyrrolizidines. Part 3: A new and short enantiospecific synthesis of (+)-hyacinthacine A2. Tetrahedron Asymmetry 2003;14:3933-5.
51. Duarte MO, Stedele G, Pazinatto M, de Oliveira ER, Eifler-Lima VL. New solid-phase approach to synthesize a hyacinthacine core using the L-proline as a building block. Lett Org Chem 2009;6:90-3.
52. Dewi‐Wülfing P, Blechert S. Enantiospecific synthesis of (+)‐hyacinthacine A2. Eur J Org Chem 2006;8:1852-6.
53. Rambaud L, Compain P, Martin OR. First total synthesis of (+)-hyacinthacine A2. Tetrahedron Asymmetry 2001;12:1807-9.
54. Cardona F, Faggi E, Liguori F, Cacciarini M, Goti A. Total syntheses of hyacinthacine A2 and 7-deoxycasuarine by cycloaddition to a carbohydrate derived nitrone. Tetrahedron Lett 2003;44:2315-8.
55. Desvergnes S, Py S, Vallée Y. Total synthesis of (+)-hyacinthacine A2 based on SmI2-induced nitrone umpolung. J Org Chem 2005;70:1459 62.
56. Delso I, Tejero T, Goti A, Merino P. Synthesis of D-arabinose-derived polyhydroxylated pyrrolidine, indolizidine and pyrrolizidine alkaloids. Total synthesis of hyacinthacine A2. Tetrahedron 2010;66:1220-7.
57. Royzen M, Taylor MT, De Angelis A, Fox JM. Total synthesis of hyacinthacine A2: Stereocontrolled 5-aza-cyclooctene photoisomerization and transannular hydroamination with planar-to-point chirality transfer. Chem Sci 2011;2:2162-5.
58. Izquierdo I, Plaza MT, Franco F. Polyhydroxylated pyrrolizidines. Part 2: The first total synthesis of (+)-hyacinthacine A3. Tetrahedron Asymmetry 2002;13:1581-5.
59. Liu WJ, Ye JL, Huang PQ. A flexible approach for the asymmetric syntheses of hyacinthacines A 2, A 3 and structural confirmation of hyacinthacine A3. Org Biomol Chem 2010;8:2085-91.
60. Christopher WG. Synthesis of hyacinthacine B3 and purported hyacinthacine B 7. Chem Commun 2010;46:713-5.
61. Adinolfi M, Barone G, Corsaro MM, Mangoni L, Lanzetta R, Parrilli M. Glycosides from Muscari armeniacum and Muscari botryoides. Isolation and structure of muscarosides G–N. Can J Chem 1988;66:2787-93.
62. Mahato SB, Nandy AK. Triterpenoid saponins discovered between 1987 and 1989. Phytochemistry 1991;30:1357-90.
63. Stirpe F. Ribosome-inactivating proteins. Toxicon 2004;44:371-83.
64. Arias FJ, Antolı́n P, de Torre C, Barriuso B, Iglesias R, Rojo MA, et al. Musarmins: Three single-chain ribosome-inactivating protein isoforms from bulbs of Muscari armeniacum L. and Miller. Int J Biochem Cell Biol 2003;35:61-78.
65. Antolı́n P, Girotti A, Arias FJ, Barriuso B, Jiménez P, Rojo MA, et al. Bacterial expression of biologically active recombinant musarmin 1 from bulbs of Muscari armeniacum L. and Miller. J Biotechnol 2004;112:313-22.
66. da Silva JA, Dobranszki J. Tissue culture of Muscari species: Present achievements and future perspectives. Rend Lincei 2016;27:427-41.
67. Suzuki S, Nakano M. Organogenesis and somatic embryogenesis from callus cultures in Muscari armeniacum Leichtl. Ex Bak. In Vitro Cell Dev Biol Plant 2001;37:382-7.
68. Suzuki S, Nakano M. Effects of antibiotics and bialaphos on the growth and development of embryogenic callus cultures of Muscari armeniacum. Biol Plant 2003;47:425-7.
69. Suzuki S, Nakano M. Agrobacterium-mediated production of transgenic plants of Muscari armeniacum Leichtl. Ex Bak. Plant Cell Rep 2002;20:835-41.
70. Wang S, Yang F, Jiu L, Zhang W, Zhang W, Tian Z, et al. Plant regeneration via somatic embryogenesis from leaf explants of Muscari armeniacum. Biotechnol Biotechnol Equip 2013;27:4243-7.
71. Azad MA, Amin MN. Effects of hormonal and basal nutrient medium on in vitro regeneration of an ornamental plant-Muscari armeniacum Leichtlin. Ex Baker. Plant Tissue Cult Biotechnol 2012;22:113-26.
72. Yücesan BB, Cicek F, Gürel E. Somatic embryogenesis and encapsulation of immature bulblets of an ornamental species, grape hyacinths (Muscari armeniacum Leichtlin ex Baker). Turk J Agric For 2014;38:716-22.
73. Nakano M, Tanaka S, Kagami S, Saito H. Plantlet regeneration from protoplasts of Muscari armeniacum Leichtl. ex Bak. Plant Biotechnol 2005;22:249-51.
74. Bae H, Ahn H, Park S, Yue W, Jung W, Chang Y, et al. Effect of scaling time and scale position on bulblet formation in scaling of Muscari armeniacum ‘early giant’. J Korean Soc Hortic Sci 2000;41:93-5.
75. Choi S, Park S, Jung W, Ahn H, Park I, Chang Y, et al. Effect of leaf cutting time and leaf part on bulblet formation of Muscari armeniacum ‘early giant’. J Korean Soc Hortic Sci 2000;41:87-9.
76. Miyamoto K, Kotake T, Sasamoto M, Saniewski M, Ueda J. Gummosis in grape hyacinth (Muscari armeniacum) bulbs: Hormonal regulation and chemical composition of gums. J Plant Res 2010;123:363-70.
77. Saniewski M, Góraj-Koniarska J, Węgrzynowicz-Lesiak E, Gabryszewska E. Hormonal regulation of the growth of leaves and inflorescence stalk in Muscari armeniacum Leichtl. Acta Agrobot 2016;69:1654.
78. Hanks GR, Jones SK. The cold requirement for forcing Muscari and related plants. Sci Hortic 1987;32:287-96.
79. Inamoto K, Matsubara K, Doi M, Imanishi H. Evaluation of Freezing Hardiness of Ornamental Geophytes. Vol. 886. In 10th International Symposium on Flower Bulbs and Herbaceous Perennials; 2008. p. 105 12.
80. Gürsoy M, Şık L. Comparative anatomical studies on Muscari armeniacum Leichtlin ex Baker and Muscari neglegtum Guss. In West Anatolia. CBU J Sci 2010;6:61-72.
81. Savaspun K, Au CW, Pyne SG. Total synthesis of hyacinthacines B3, B4, and B5 and purported hyacinthacine B7, 7-epi-hyacinthacine B7, and 7a-epi-hyacinthacine B3 from a common precursor. J Org Chem 2014;79:4569-81.
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Bokov, D. O. “MUSCARI ARMENIACUM LEICHTLIN (GRAPE HYACINTH): PHYTOCHEMISTRY AND BIOLOGICAL ACTIVITIES REVIEW”. Asian Journal of Pharmaceutical and Clinical Research, Vol. 12, no. 1, Jan. 2019, pp. 68-72, doi:10.22159/ajpcr.2019.v12i1.30325.
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