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ISSN (Print): 2210-3155
ISSN (Online): 2210-3163

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Research Article

Antioxidant Activity and Chemical Composition of Helichrysum lacteum Coss. & Dur.

Author(s): Souad Arrif*, Mohammed Benkhaled, Hamada Haba and Soumia Mouffouk

Volume 10, Issue 4, 2020

Page: [429 - 439] Pages: 11

DOI: 10.2174/2210315509666190603083300

Price: $65

Abstract

Objective: The objective of the present study was to measure antioxidant activity and to evaluate the phytochemical constitution of Helichrysum lacteum growing in Algeria.

Methods: The structure elucidation of the isolated compounds was performed by spectroscopic methods. Antioxidant activity of the extracts the crude extracts (PE, EtOAc, and n-BuOH) and pure compound (noryangonin (3)) was investigated by 5 methods, including DPPH free radical scavenging activity, reducing power and ferric thiocyanate methods, hydrogen peroxide scavenging capacity, and total antioxidant activity by phosphomolybdate assay.

Results: The chemical investigation of the EtOAc extract of the aerial parts of H. lacteum led to the isolation of two flavonoids, astragalin (1) and isoquercitrin (2), together with a styryl pyrone, noryangonin (3), and a cyclobutane dimer, achyrodimer C (4) as well as two triterpenoid compounds, β-sitosterol (5) and oleanolic acid (6). The highest phenolic and flavonoid contents were detected in the ethyl acetate extract. Noryangonin exhibited the highest antioxidant activity than those of the references and all the tested extracts, with a value of IC50 at 1.45±0.44 μg/mL in DPPH scavenging. In hydrogen peroxide scavenging essay, the results revealed that EtOAc extract exhibited the highest percent inhibition (63.15 %) as compared to the ascorbic acid (63.36 %) at the concentration of 100 μg/mL. In the phosphomolybdenum method, the EtOAc extract showed the strongest activity (36.85±0.02 μg EAA/mg ex) as compared to those of n-BuOH and PE extracts.

Conclusion: The antioxidant property shown in these findings needs further investigation, especially with the pure compound (3).

Keywords: Helichrysum lacteum, flavonoid, NMR, antioxidant activity, ascorbic acid, ferric thiocyanate.

Graphical Abstract

[1]
Mutanyatta-Comar, J.; Phale, O.J.K.; Abegaz, B.M.; Croft, K. Phloroglucinol derivatives and flavones from Helichrysum paronychioides. Bull. Chem. Soc. Ethiop., 2006, 20, 61-68.
[2]
Drewes, S.E.; Mudau, K.E.; van Vuuren, S.F.; Viljoen, A.M. Antimicrobial monomeric and dimeric diterpenes from the leaves of Helichrysum tenax var. tenax. Phytochemistry, 2006, 67(7), 716-722.
[http://dx.doi.org/10.1016/j.phytochem.2005.12.015] [PMID: 16434071]
[3]
Lv, H.; Sabir, G.; Kungurhan, B.; Liu, Y.; Akber Aisa, H. New phthalide glycosides from Helichrysum arenarium (L.). Moench. J. Asian Nat. Prod. Res., 2009, 11(4), 352-356.
[http://dx.doi.org/10.1080/10286020902819772] [PMID: 19431016]
[4]
Öztürk, B.; Özek, G.; Özek, T.; Hüsnü, K.; Başer, C. Chemical diversity in volatiles of Helichrysum plicatum DC. subspecies in Turkey. Rec. Nat. Prod., 2014, 8(4), 373-384.
[5]
Al-Rehaily, A.J.; Albishi, O.A.; El-Olemy, M.M.; Mossa, J.S. Flavonoids and terpenoids from Helichrysum forskahlii. Phytochemistry, 2008, 69(9), 1910-1914.
[http://dx.doi.org/10.1016/j.phytochem.2008.03.025] [PMID: 18485427]
[6]
Kutluk, I.; Aslan, M.; Orhan, I.E.; Özçelik, B. Antibacterial antifungal and antiviral bioactivities of selected Helichrysum species. S. Afr. J. Bot., 2018, 119, 252-257.
[http://dx.doi.org/10.1016/j.sajb.2018.09.009]
[7]
Albayrak, S.; Aksoy, A.; Sağdiç, O.; Budak, U. Phenolic compounds and antioxidant and antimicrobial properties of Helichrysum species collected from eastern Anatolia Turkey. Turk. J. Biol., 2010, 34, 463-473.
[8]
Süzgeç, S.; Meriçli, A.H.; Houghton, P.J.; Cubukçu, B. Flavonoids of Helichrysum compactum and their antioxidant and antibacterial activity. Fitoterapia, 2005, 76(2), 269-272.
[http://dx.doi.org/10.1016/j.fitote.2004.12.006] [PMID: 15752647]
[9]
Quezel, P.; Santa, S. Nouvelle Flore de l′Algérie et des régions désertiques méridionales; CNRS: Paris, France, 1963, Vol. 1 & 2, .
[10]
Bouchaala, M.; Ramdani, M.; Lograda, T.; Chalard, P.; Figueredo, G. Chemical composition, antibacterial activity and chromosome number of Helichrysum lacteum endemic from Algeria. Int. J. Pharma. Res. Health Sci., 2017, 5(1), 1539-1545.
[11]
Blois, M.S. Antioxidant determinations by the use of a stable free radical. Nature, 1958, 181, 1199-1200.
[http://dx.doi.org/10.1038/1811199a0]
[12]
Oyaizu, M. Antioxidative activities of products of browning reaction prepared from glucosamine. Jpn. J. Nutr., 1986, 44(6), 307-315.
[http://dx.doi.org/10.5264/eiyogakuzashi.44.307]
[13]
Ruch, R.J.; Cheng, S.J.; Klaunig, J.E. Prevention of cytotoxicity and inhibition of intercellular communication by antioxidant catechins isolated from Chinese green tea. Carcinogenesis, 1989, 10(6), 1003-1008.
[http://dx.doi.org/10.1093/carcin/10.6.1003] [PMID: 2470525]
[14]
Prieto, P.; Pineda, M.; Aguilar, M. Spectrophotometric quantitation of antioxidant capacity through the formation of a phosphomolybdenum complex: Specific application to the determination of vitamin E. Anal. Biochem., 1999, 269(2), 337-341.
[http://dx.doi.org/10.1006/abio.1999.4019] [PMID: 10222007]
[15]
Takao, T.; Kitatani, F.; Watanabe, N.; Yagi, A.; Sakata, K. A simple screening method for antioxidant and isolation of several antioxidants produced by Marin bacteria from fish and shellfish. Biosci. Biotechnol. Biochem., 1994, 58, 1780-1783.
[http://dx.doi.org/10.1271/bbb.58.1780]
[16]
Demirezer, L.Ö.; Gürbüz, F.; Güvenalp, Z.; Ströch, K.; Zeeck, A. Iridoids flavonoids and monoterpene glycosides from Galium verum subsp. Verum. Turk. J. Chem., 2006, 30, 525-534.
[17]
Süzgeç-Selçuk, S.; Birteksöz, A.S. Flavonoids of Helichrysum chasmolycicum and its antioxidant and antimicrobial activities. S. Afr. J. Bot., 2011, 77(1), 170-174.
[http://dx.doi.org/10.1016/j.sajb.2010.07.017]
[18]
Sukito, A.; Tachibana, S. Isolation of hyperoside and isoquercitrin from Camellia sasanqua as antioxidant agents. Pak. J. Biol. Sci., 2014, 17(8), 999-1006.
[http://dx.doi.org/10.3923/pjbs.2014.999.1006] [PMID: 26031018]
[19]
Les, F.; Venditti, A.; Cásedas, G.; Frezza, C.; Guiso, M. Everlasting flower (Helichrysum stoechas Moench) as a potential source of bioactive molecules with antiproliferative, antioxidant, antidiabetic and neuroprotective properties. Ind. Crops Prod., 2017, 108, 295-302.
[http://dx.doi.org/10.1016/j.indcrop.2017.06.043]
[20]
Wiedenfeld, H.; Andrade-Cetto, A. Pyrone glycosides from Acosmium panamense (Benth.) Yacovlev. Z. Natforsch. C J. Biosci., 2003, 58(9-10), 637-639.
[http://dx.doi.org/10.1515/znc-2003-9-1006] [PMID: 14577622]
[21]
Bohlmann, F.; Suwita, A. Weitere phloroglucin-derivate aus Helichrysum-arten. Phytochemistry, 1979, 18(12), 2046-2049.
[http://dx.doi.org/10.1016/S0031-9422(00)82740-5]
[22]
Sagawa, T.; Takaishi, Y.; Fujimoto, Y.; Duque, C.; Osorio, C.; Ramos, F.; Garzon, C.; Sato, M.; Okamoto, M.; Oshikawa, T.; Ahmed, S.U. Cyclobutane dimers from the Colombian medicinal plant Achyrocline bogotensis. J. Nat. Prod., 2005, 68(4), 502-505.
[http://dx.doi.org/10.1021/np040187y] [PMID: 15844937]
[23]
D’Abrosca, B.; Buommino, E.; D’Angelo, G.; Coretti, L.; Scognamiglio, M.; Severino, V.; Pacifico, S.; Donnarumma, G.; Fiorentino, A. Spectroscopic identification and anti-biofilm properties of polar metabolites from the medicinal plant Helichrysum italicum against Pseudomonas aeruginosa. Bioorg. Med. Chem., 2013, 21(22), 7038-7046.
[http://dx.doi.org/10.1016/j.bmc.2013.09.019] [PMID: 24094434]
[24]
De Quesada, T.G.; Rodriguez, B.; Valverde, S. The constituents of Helichrysum stoechas. Phytochemistry, 1972, 11(1), 446-449.
[http://dx.doi.org/10.1016/S0031-9422(00)90048-7]
[25]
Aslan, M.; Deliorman Orhan, D.; Orhan, N.; Sezik, E.; Yesilada, E. In vivo antidiabetic and antioxidant potential of Helichrysum plicatum ssp. Plicatum capitulums in streptozotocin-induced-diabetic rats. J. Ethnopharmacol., 2007, 109(1), 54-59.
[http://dx.doi.org/10.1016/j.jep.2006.07.001] [PMID: 16949229]
[26]
Albayrak, S.; Sagdic, O.; Aksoy, A.; Hamzaoglu, E. Antimicrobial and antioxidant activities of Helichrysum species from the mediterranean region of Turkey. Asian J. Chem., 2008, 20(4), 3143-3152.
[27]
Aiyegoro, O.A.; Okoh, A.I. Preliminary phytochemical screening and in vitro antioxidant activities of the aqueous extract of Helichrysum longifolium DC. BMC Complement. Altern. Med., 2010, 10, 21.
[http://dx.doi.org/10.1186/1472-6882-10-21] [PMID: 20470421]
[28]
Goldansaz, S.M.; Mahboubi, A.; Yazdi-nejad, A.; Jahanbakhsh, M.; Mojab, F. Investigation on total phenolic content antibacterial and antioxidant activity of ethanolic extract of Helichrysum leucocephalum Boiss. Am. J. Essent. Oil Nat. Prod., 2018, 6(1), 20-24.
[29]
Petti, S.; Scully, C. Polyphenols, oral health and disease: A review. J. Dent., 2009, 37(6), 413-423.
[http://dx.doi.org/10.1016/j.jdent.2009.02.003] [PMID: 19303186]
[30]
Pietta, P.G. Flavonoids as antioxidants. J. Nat. Prod., 2000, 63(7), 1035-1042.
[http://dx.doi.org/10.1021/np9904509] [PMID: 10924197]
[31]
Hazra, B.; Biswas, S.; Mandal, N. Antioxidant and free radical scavenging activity of Spondias pinnata. BMC Complement. Altern. Med., 2008, 8, 63.
[http://dx.doi.org/10.1186/1472-6882-8-63] [PMID: 19068130]
[32]
Adnan, L.; Osman, A.; Abdul Hamid, A. antioxidant activity of different extracts of red pitaya (Hylocereus polyrhizus) seed. Int. J. Food Prop., 2011, 14, 1171-1181.
[http://dx.doi.org/10.1080/10942911003592787]

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