Isolation of two steroidal saponins with antileishmanial activity from Allium giganteum L.

Farnaz Chaparian, Zeinab Delazar, Masoud Sadeghi Dinani

Abstract


Background and purpose: Alliums are rich sources of steroidal saponins, flavonoids, and sulphoric compounds of which steroidal saponins have recently received more attention due to their important pharmacological activities. Allium giganteum (giant onion) which is named locally “Couria” in the Northeast of Iran, is grown widely in “Kouh-Sorkh” mountains in Khorasan province.

Experimental approach: Phytochemical investigation of chloroform-methanol and aqueous extract of the plant resulted in the isolation and identification of two steroidal saponins, using comprehensive spectroscopic methods including 1D and 2D NMR and MS.

Findings/Results: The chemical structures of the isolated saponins were determined as (22S)-cholesta-1b,3b,16b,22b-tetraol 5-en, and 3-O-β-D-glucopyranosyl 26-O-β-D-glucopyranosside and (25R)-26-O-β-D-glucopyranosyl-5α-furostan-1α,3β,22α,26-tetraol3-O-{β-D-galactopyranosyl-(1→2)-O-[β-D-xylopyranosyl-(1→3)]-O-β-D-glucopyranosyl-(1→4)-β-D-galactopyranoside}. Investigation of in vitro antileishmanial activity of the isolated compounds at 10, 50, and 100 μg/mL exhibited significant leishmanicidal against the promastigotes of Leishmania major.

Conclusion and implications: The results established a valuable basis for further studies about A. giganteum and the anti-parasitic activity of steroidal saponins.


Keywords


Allium giganteum; Leishmania; Saponins; Structure elucidation.

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References


Evans WC. Trease and Evans' pharmacognosy E-book. 16th ed. Elsevier Health Sciences; 2009. pp. 40.

Chehri Z, Zolfaghari B, Sadeghi Dinani M. Isolation of cinnamic acid derivatives from the bulbs of Allium tripedale. Adv Biomed Res. 2018;7:60,1-5.DOI: 10.4103/abr.abr_34_17.

Hosseinzadeh Namin H, Saeidi Mehrvarz S, Zarre S, Fritsch R. Pollen morphology of selected species of Allium (Alliaceae) distributed in Iran. Nord J Bot. 2009;27(1):54-60.DOI: 10.1111/j.1756-1051.2009.00319.x.

Movafeghi A, Miryeganeh M. Scape anatomy of Allium sect. Allium (Alliaceae) in Iran. J Sci. 2009;35(1):1-5.

Ozturk M, Gucel S, Altay V, Altundag E. Alliums, an underutilized genetic resource in the east Mediterranean. Acta Hort. 2012;969:303-310.DOI: 10.17660/ActaHortic.2012.969.39.

Lanzotti V. Bioactive polar natural compounds from garlic and onions. Phytochem Rev. 2012;11(2-3):179-196.DOI: 10.1007/s11101-012-9247-3.

Sadeghi M, Safaeian L, Aghaye Ghazvini MR, Ramezani M. Evaluation of fibrinolytic and antioxidant effects of Allium affine hydroalcoholic extract. Res Pharm Sci. 2017;12(4):299-306.DOI: 10.4103/1735-5362.212047.

Rezaee F, Zolfaghari B, Sadeghi Dinani M. Isolation of dioscin-related steroidal saponin from the bulbs of Allium paradoxum L. with leishmanicidal activity. Res Pharm Sci. 2018;13(5):469-475.DOI: 10.4103/1735-5362.236875.

Cui M, Song F, Zhou Y, Liu Z, Liu S. Rapid identification of saponins in plant extracts by electrospray ionization multi‐stage tandem mass spectrometry and liquid chromatography/tandem mass spectrometry. Rapid Commun Mass Spectrom. 2000;14(14):1280-1286.DOI: 10.1002/1097-0231(20000730)14:14<1280::AID-RCM26>3.0.CO;2-C.

Sadeghi M, Zolfaghari B, Senatore M, Lanzotti V. Spirostane, furostane and cholestane saponins from Persian leek with antifungal activity. Food Chem. 2013;141(2):1512-1521.DOI: 10.1016/j.foodchem.2013.04.009.

Sang S, Mao S, Lao A, Chen Z, Ho CT. New steroid saponins from the seeds of Allium tuberosum L. J Agric Food Chem. 2001;49(3):1475-1478.DOI: 10.1021/jf001062b.

Zhang T, Liu H, Liu XT, Xu DR, Chen XQ, Wang Q. Qualitative and quantitative analysis of steroidal saponins in crude extracts from Paris polyphylla var. yunnanensis and P. polyphylla var. chinensis by high performance liquid chromatography coupled with mass spectrometry. J Pharm Biomed Anal. 2010;51(1):114-124.DOI: 10.1016/j.jpba.2009.08.020.

Adão CR, da Silva BP, Tinoco LW, Parente JP. Haemolytic activity and immunological adjuvant effect of a new steroidal saponin from Allium ampeloprasum var. porrum. Chem Biodivers. 2012;9(1):58-67.DOI: 10.1002/cbdv.201100005.

Adão CR, da Silva BP, Parente JP. A new steroidal saponin with antiinflammatory and antiulcerogenic properties from the bulbs of Allium ampeloprasum var. porrum. Fitoterapia. 2011;82(8): 1175-1180. DOI: 10.1016/j.fitote.2011.08.003.

Fritsch RM. A preliminary review of Allium subg. Melanocrommyum in central Asia. Leibniz-Institut für Pflanzengenetik und Kulturpflanzenforschung Gatersleben (IPK), Gatersleben; 2016. pp. 168.

Oskuee RK, Jaafari MR, Amani S, Ramezani M. Evaluation of leishmanicidal effect of Euphorbia erythadenia extract by in vitro leshmanicidal assay using promastigotes of Leishmania major. Asian Pac J Trop Biomed. 2014;4(2):S581-S583.DOI: 10.12980/APJTB.4.2014C1018.

Štajner D, Milić-Demarino N, Čanadanović-Brunet J, Štajner M, Popović BM. Screening for antioxidant properties of Allium giganteum. Fitoterapia. 2006;77(4):268-270.DOI: 10.1016/j.fitote.2006.03.015.

Mimaki Y, Nikaido T, Matsomuto K, Sashida Y, Ohmoto T. New steroidal saponins from the bulbs of Allium giganteum exhibiting potent inhibition of cAMP phosphodiesterase activity. Chem Pharm Bull. 1994;42(3):710-714.DOI: 10.1248/cpb.42.710.

Avula B, Wang YH, Wang M, Ali Z, Smillie TJ, Zweigenbaum J, et al. Characterization of steroidal saponins from Dioscorea villosa and D. cayenensis using ultrahigh performance liquid chromatography/electrospray ionization quadrupole time-of-flight mass spectrometry. Planta Med. 2014;80(4):321-329.DOI: 10.1055/s-0033-1360330.

Dong SH, Cai G, Napolitano JG, Nikolić D, Lankin DC, McAlpine JB, et al. Lipidated steroid saponins from Dioscorea villosa (wild yam). Fitoterapia. 2013;91:113-124.DOI: 10.1016/j.fitote.2013.07.018.

Perrone A, Plaza A, Bloise E, Nigro P, Hamed AI, Belisario MA, et al. Cytotoxic furostanol saponins and a megastigmane glucoside from Tribulus p arvispinus. J Nat Prod. 2005;68(10):1549-1553.DOI: 10.1021/np0502138.

Kadria A. Ahmed, Amaal H. Mohamed. A taxonomic study of the genus Tribulus L. in Egypt. Arab Univ J Agric Sci. 2005;13(2):197-206.

Hu K, Dong A, Yao X, Kobayashi H, Iwasaki S. Antineoplastic agents II: four furostanol glycosides from rhizomes of Dioscorea collettii var. hypoglauca. Planta Med. 1997;63(2):161-165.DOI: 10.1055/s-2006-957636.

Pan WB, Chang FR, Wei LM, Wu YC. New flavans, spirostanol sapogenins, and a pregnane genin from Tupistra chinensis and their cytotoxicity. J Nat Prod. 2003;66(2):161-168.DOI: 10.1021/np0203382.

González AG, Hernández JC, León F, Padrón JI, Estévez F, Quintana J, et al. Steroidal saponins from the bark of Dracaena draco and their cytotoxic activities. J Nat Prod. 2003;66(6):793-798.DOI: 10.1021/np020517j.

Dong M, Feng XZ, Wang BX, Wu LG, Ikejima T. Two novel furostanol saponins from the rhizomes of Dioscorea panthaica Prain et Burkill and their cytotoxic activity. Tetrahedron. 2001;57(3):501-506.DOI: 10.1016/S0040-4020(00)01024-3.

Tran QL, Tezuka Y, Banskota AH, Tran QK, Saiki I, Kadota S. New spirostanol steroids and steroidal saponins from roots and rhizomes of Dracaena a ngustifolia and their antiproliferative activity. J Nat Prod. 2001;64(9):1127-1132.DOI: 10.1021/np0100385.

Iorizzi M, Lanzotti V, Ranalli G, De Marino S, Zollo F. Antimicrobial furostanol saponins from the seeds of Capsicum annuum L. var. acuminatum. J Agric Food Chem. 2002;50(15):4310-4316. DOI: 10.1021/jf0116911.


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