Sandy Everlasting ( Helichrysum arenarium (L.) Moench): Botanical, Chemical and Biological Properties

Dejan Pljevljakušić, Dubravka Bigović, Teodora Janković, Slavica Jelačić, Katarina Šavikin, Dejan Pljevljakušić, Dubravka Bigović, Teodora Janković, Slavica Jelačić, Katarina Šavikin

Abstract

Sandy everlasting [Helichrysum arenarium (L.) Moench] is herbaceous perennial plant belonging to Asteraceae family and it is native to Europe, Central Asia, and China. It belongs to the section HELICHRYSUM (Asteraceae family, genus Helichrysum) along with H. plicatum DC. Prodr., which very similar phenolic profile and H. italicum (Roth), which is widely used for essential oil extraction. Its flowers have a long tradition in European ethnomedicine as a cholagogue, choleretic, hepatoprotective, and detoxifying herbal drug. The flowers are rich in phenolic compounds including flavonoids, chalcones, phenolic acids, coumarins, and pyrones. Apart from polyphenols, other compounds such as sterols, lignans, and glycosides of aromatic compounds have been also isolated from H. arenarium. The majority of authors confirm that the most important group of compounds responsible for biological activities is flavonoids. Moreover, significant activities of naringenin, one of the main flavonoids of H. arenarium, were reported. On the other hand, there are no clinical data about testing the extracts or preparations based on H. arenarium. Although H. arenarium is well known in phytotherapy for its potential in the treatment of gallbladder disease and are classified as endangered species in a number of European countries, very few data about its cultivation are available in the literature.

Keywords: Helichrysi flos; chemistry; cholagogue; everlasting; immortelle; naringenin; sandy.

Figures

Figure 1
Figure 1
Distribution map for Helichrysum arenarium. Source: The virtual flora. Naturhistoriska Riksmuseet, Sweden, with permission of Anderberg and Anderberg (2005).
Figure 2
Figure 2
Chemical structures of three characteristic flavonoids originating from H. arenarium inflorescence [redrawn from WHO, 2015].
Figure 3
Figure 3
Chemical structures of two characteristic yellow pigments α-pyrons: arenol and homoarenol from the H. arenarium inflorescences [redrawn from Wichtl (2001)].
Figure 4
Figure 4
Chemical structures of two characteristic phthalides from the H. arenarium inflorescences [redrawn from Kurkina et al. (2012)].

References

    1. Afoulous S., Ferhout H., Raoelison E. G., Valentin A., Moukarzel B., Couderc F., et al. . (2011). Helichrysum gymnocephalum essential oil: chemical composition and cytotoxic, antimalarial and antioxidant activities, attribution of the activity origin by correlations. Molecules 16, 8273–8291. 10.3390/molecules16108273
    1. Agus S., Achmadi S. S., Mubarik N. R. (2017). Antibacterial activity of naringenin-rich fraction of pigeon pea leaves toward Salmonella thypi. Asian Pac. J. Trop. Biomed. 7, 725–728. 10.1016/j.apjtb.2017.07.019
    1. Albayrak S., Aksoy A., Sagdic O., Budak U. (2010). Phenolic compounds and antioxidant and antimicrobial properties of Helichrysum species collected from eastern Anatolia, Turkey. Turk. J. Biol. 34, 463–473. 10.3906/biy-0901-4
    1. Amirdowlat Amasyaci (1990). Nenuzhnoe dlja neuczej (Needless for Ignoramus). Moscow: Nauka.
    1. Anderberg A., Anderberg A.-L. (2005). Den Virtuella Floran. Available online at: Naturhistoriska riksmuseet, Stockholm. Information collected (Accessed December 1, 2005).
    1. Bigović D., Brankovic S., Kitic D., Radenkovic M., Jankovic T., Savikin K., et al. . (2010). Relaxant effect of the ethanol extract of Helichrysum plicatum (Asteraceae) on isolated rat ileum contractions. Molecules 15, 3391–3401. 10.3390/molecules15053391
    1. Bigović D., Savikin K., Janković T., Menković N., Zdunić G., Stanojković T., et al. . (2011). Antiradical and cytotoxic activity of different Helichrysum plicatum flower extracts. Nat. Prod. Commun. 6, 819–822.
    1. Bisset N. G., Wichtl M. (1994). Herbal Drugs and Phytopharmaceuticals: A Handbook for Practice on a Scientific Basis. Stuttgart: Medpharm Scientific Publishers.
    1. Blumenthal M., Busse W. R., Goldberg A., Gruenwald J., Hall T., Riggins C. W., et al. (1998). The complete German commission E, in Monographs?Therapeutic Guide to Herbal Medicines, eds S. Klein, and R. S. Rister (Austin, TX: American Botanical Council; Boston: Integrative Medicine Communication; ), 198–199.
    1. Bryksa-Godzisz M., Weglarz Z., Przyby J. (2006). Phenolic compounds in yellow everlasting Helichrysum arenarium L. Moench growing wild in the middle part of the Bug river valley. Herba Polonica 52, 26–31. Available online at:
    1. Buchwald W. (1992). Sandy everlasting as a vanishing species. Wiad. Ziel. 34, 5–6.
    1. Butorac B. (1999). Helichrysum arenarium (L.) Moench subsp. Arenarium, in Red Data Book of Flora of Serbia, 1. Extinct and critically endangered taxa, str ed V. Stevanović (Belgrade: Ministry of environment of the Republic of Serbia; ), 294–296.
    1. Charaux C., Rabaté J. (1931). Contribution à l'étude biochimique du genre “Salix”, III. Un nouveau glucoside liydrolvsable par l'émulsine retiré de l'écorce de “Salix purpurea” L., le salipurposide. IV. La constitution chimique du salipurposide. Bull. Soc. Ch. Biol. 13, 588–814.
    1. Cicin N. W. (1962). Atlas Lekarstvennych Rastenij SSSR. Moscow: Izd Med Lit.
    1. Cosar G., Cubukcu B. (1990). Antibacterial activity of Helichrysum species growing in Turkey. Fitoterapia 61, 161–164.
    1. Czinner E., Hagymási K., Blázovics A., Kéry A., Szoke E., Lemberkovics E. (2001). The in vitro effect of Helichrysi flos on microsomal lipid peroxidation. J. Ethnopharmacol. 77, 31–35.
    1. Czinner E., Kéry A., Hagymási K., Blázovics A., Lugasi A., Szöke E., et al. . (1999). Biologically active compounds of Helichrysum arenarium (L.) Moench. Eur. J. Drug Metab. Pharmacokinet. 24, 309–313. 10.1007/BF03190038
    1. Czinner E., Kusinszki L., Baumann D., Hamburger M., Kéry Á., Szoke É., et al. (2002). Phytochemical study of phenolic compounds from Helichrysi flos by LC-DAD –MS, in Natural Products in the New Millenium: Prospects and Industrial Application, eds A. P. Rauter, F. B. Palma, J. Justino, M. E. Araújo, and S. Pina dos Santos (Kluwer Acadenic Publishers; ), 99–109
    1. Czinner E., Lemberkovics É., Bihátsi-Karsai É., Vitányi G., Lelik L. (2000). Composition of the essential oil from the inflorescence of Helichrysum arenarium (L.) Moench. J. Essent. Oil Res. 12, 728–730. 10.1080/10412905.2000.9712202
    1. DAC (2005) Deutscher Arzneimittel-Codex – German Pharmaceutical Codex: A Supplementary Pharmacopoeia to the European and German Pharmacopoeia. Berlin: Federal Union of German Associations of Pharmacists.
    1. Derkach A. I., Komissarenko N. F., Chornobay V. T. (1986). Kumarini sotsvetiy Calendula officinalis i Helichrysum arenarium [Coumarinin florescences Calendula officinalis and Helichrysum arenarium]. Int. J. Chem. Nat Comp. 6:777.
    1. Dombrowicz E., Swiatek L., Kopycki W. (1992). Phenolic acids in inflorenscentia Helichrysi and herba Hieracii pilosella. Pharmazie 47, 469–470.
    1. EMA (2015) Assessment report on Helichrysum arenarium (L.) Moench flos (Rapporteur: Wojciech Dymowski). European Medicines Agency, EMA/HMPC/41109/2015.
    1. Erhardt W., Götz E., Bödeker N., Seybold S. (2008). Der große Zander, Eugen Ulmer. K. G. Stuttgart.
    1. Eshbakova K. A., Aisa H. A. (2009). Components of Helichrysum arenarium. Chem. Nat. Comp. 45, 929–930. 10.1007/s10600-010-9462-3
    1. Esmagambetova A. B., Ahmetzanova A. I. (2006). Methods of cultivation sandy everlasting in conditions of Central Kazakhstan. Bull. Karaganda State Univ. 3, 3–6. Available online at:
    1. Fijalkowski D., Seroczynska M. (1974). Sandy everlasting [Helichrysum arenarium (L.) Moench] in Lubelskie voivodship and its cultivation. Herba Pol. 20, 363–372.
    1. Flora Europea (2006). Flora Europea Volume IV, Plantaginaceae to Compositae (and Rubiaceae). Cambridge: Cambridge University Press.
    1. Gajić M. (1975). Helichrysum Mill, in Flora SR Srbije, ed M. Josifović (Beograd: Srpska Akademija Nauka i Umetnosti; ), 45–46.
    1. Galbany-Casals M., Garcia-Jacas N., Sáez L., Benedí C., Susanna A. (2009). Phylogeny, biogeography, and character evolution in Mediterranean, Asiatic, and Macaronesian Helichrysum (Asteraceae, Gnaphalieae) inferred from nuclear phylogenetic analyses. Int. J. Plant Sci. 170, 365–380. 10.1086/596332
    1. GBIF (2013) The Global Biodiversity Information Facility: GBIF Backbone Taxonomy 2013-07-01. GBIF.
    1. Greuter W. (2006). Compositae (pro parte majore), in Compositae. Euro+Med PlantBase - The Information Resource for Euro-Mediterranean Plant Diversity, eds W. Greuter and E. von Raab-Straube. Available online at:
    1. Hänsel R., Heise D. (1959). Zwei diastereomere Naringen-B-D-glukoside aus Flores Stoechados. Arch. Pharm. 292, 398–411.
    1. Hänsel R., Pinkewitz G., Langhammer L., Hase D. (1960). Das gelbe pigment der flores Stoechados. Arch. Pharm. 65, 485–486. 10.1002/ardp.19602930504
    1. Heise D. (1959). Two diastereoisomeric naringenine-D-glucosides from dry flowers of Helichrysum arenarium. Arch. Pharm. Ber. Deutsch Pharm. Ges. 9, 398–411.
    1. Jarzycka A., Lewinska A., Gancarz R., Wilk K. A. (2013). Assessment of extracts of Helichrysum arenarium, Crataegus monogyna, Sambucus nigra in photoprotective UVA and UVB; photostability in cosmetic emulsions. J. Photochem. Photobiol. B 128, 50–57. 10.1016/j.jphotobiol.2013.07.029
    1. Judzentiene A., Butkiene R. (2006). Chemical composition of the essential oils of wild Helichrysum arenarium (L.) with differently colored inflorescences from Eastern Lithuania. J. Essent. Oil Res. 18, 80–83. 10.1080/10412905.2006.9699391
    1. Kažemekaitis A. (2010). Änderungen des Europäischen Bestandes an Arznei- und Heilpflanzen Durch die Erweiterung der Europäischen Union: Einflussmöglichkeiten am Beispiel der baltischen Republik Litauen. Zürich, Institut für Naturheilkunde.
    1. Kirpičnikov M. E. (1959). Rod cmin, Bessmerntik Helichrysum Mill. Flora USSR 25, 404–405. Available online at:
    1. Kroeber L. (1951). Cat's Foot, Gnaphalium dioecum L., Antennaria dioeca, Gnapha- lium arenarium, Helichrysum arenarium DC. as cholagogues and choleretics. Pharmazie 6, 615–617.
    1. Kurkina A., Ryzhov V., Avdeeva E. (2012). Assay of isosalipurposide in raw material and drugs from the dwarf everlast (Helichrysum arenarium). Pharm. Chem. J. 46, 171–176. 10.1007/s11094-012-0753-9
    1. Lemberkovics E., Czinner E., Balázs A., Bihátsi-Karsai E., Vitányi G., Lelik L., et al. . (2001). New data on composition of esssential oil from inflorescence of everlasting (Helichrysum arenarium (L.) Moench.) Acta Pharm. Hung. 71, 187–191.
    1. Lemberkovics E., Czinner E., Szentmihalyi K., Balazs A., Szoke E. (2002). Comparative evaluation of Helichrysi flos herbal extracts as dietary sources of plant polyphenols, and macro- and microelements. Food Chem. 78, 119–127. 10.1016/S0308-8146(02)00204-2
    1. Leonardi M., Ambryszewska K. E., Melai B., Flamini G., Cioni P. L., Parri F., et al. . (2013). Essential-oil composition of Helichrysum italicum (ROTH) G.DON ssp. italicum from Elba Island (Tuscany, Italy). Chem. Biodivers. 10, 343–355. 10.1002/cbdv.201200222
    1. Liang J., Halipu Y., Hu F., Yakeya B., Chen W., Zhang H., et al. . (2017). Naringenin protects keratinocytes from oxidative stress injury via inhibition of the NOD2-mediated NF-κB pathway in pemphigus vulgaris. Biomed. Pharmacother. 92, 796–801. 10.1016/j.biopha.2017.05.112
    1. Lilleleht V. (1998). Red Data Book of Estonia, Tartu: Eesti Teaduste Akadeemia Looduskaitse Komisjon; (In Estonian with English summary.). Available online at:
    1. Mao Z., Gan C., Zhu J., Ma N., Wu L., Wang L., et al. . (2017). Anti-atherosclerotic activities of flavonoids from the flowers of Helichrysum arenarium L. MOENCH through the pathway of anti-inflammation. Bioorg. Med. Chem. Lett. 27, 2812–2817. 10.1016/j.bmcl.2017.04.076
    1. Maznev N. I. (2004). Entsiklopediia Lekarstvennykh Rastenii (Encyclopedia of Medicinal Plants). Moscow: Martin Press.
    1. Morikawa T., Wang L. B., Nakamura S., Ninomiya K., Yokoyama E., Matsuda H., et al. . (2009a). Medicinal flowers. XXVII. New flavanone and chalcone glycosides, arenariumosides I, II, III, and IV, and tumor necrosis factor-alpha inhibitors from everlasting, flowers of Helichrysum arenarium. Chem. Pharm. Bull. 57, 361–367. 10.1248/cpb.57.361
    1. Morikawa T., Wang L. B., Ninomiya K., Nakamura S., Matsuda H., Muraoka O., et al. . (2009b). Medicinal flowers. XXX. Eight new glycosides, everlastosides F-M, from the flowers of Helichrysum arenarium. Chem. Pharm. Bull. 57, 853–859. 10.1248/cpb.57.853
    1. Moroz I., Bojcenko S., Kondratenko S., Seludko P. (1976). Sandy everlasting in Ukraine and the possibility of introducing it to the culture, in New Culture in the National Economy and Medicine - Cultivation of Medicinal Plants in Western Siberia and Central Kazakhstan, eds V. B. Zagumennikov, S. E. Dzmitruk, T. N. Zagumennikova, S. M. Adekenov, and A. F. Khristenko (Tomsk: NLT; ), 37–38.
    1. Šohina N. K., Valuckaya A. G. (1984). Experimental introduction Helichrysum arenarium (L.) Moench in the Novosibirsk region. Rast. Resursy 20:515.
    1. Olsson K., Pihlik U., Radušiene J., Wedelsbäck B. K. (2005). Helichrysum arenarium (L.) Moench (Everlasting) in Spice- and Medicinal Plants in the Nordic and Baltic Countries Conservation of Genetic Resources Report from the SPIMED-project group at the Nordic Gene Bank, Alnarp, Sweden, 55–65.
    1. Pacholak H., Zalecki R. (1979). Sposoby rozmnazania kocanek piaskowych./Sandy Everlasting propagation methods. Wiad. Ziel. 3, 10–11.
    1. Pafumi I., Festa M., Papacci F., Lagostena L., Giunta C., Gutla V., et al. . (2017). Naringenin impairs two-pore channel 2 activity and inhibits VEGF-induced Angiogenesis. Sci. Rep. 7:5121. 10.1038/s41598-017-04974-1
    1. Park S., Lim W., Bazer F. W., Song G. (in press). Naringenin suppresses growth of human placental choriocarcinoma via reactive oxygen species-mediated P38 JNK MAPK pathways. Phytomedicine 10.1016/j.phymed.2017.08.026
    1. PDR (1998) Fleming T. (ed). Physician's Desk Reference (PDR) for Herbal Medicines, 1st Edn. Montvale, NJ: Medical Economics.
    1. Ph. Eur. 7.0. (2011) European Pharmacopoeia 7.0. Strasbourg: EDQM.
    1. Ph. Helv. VII (1987) Pharmacopoeia Helvetica Vol.1, 7th Edn. Berne, Département fédéral de l'intérieur.
    1. Ph USSR (1990) The State Pharmacopoeia of the USSR 11th Edn. Part 2. Moscow: USSR.
    1. Polish Ph VI (2002). Farmakopea Polska–Wydanie VI/Polish Pharmacopoeia−6th Edn, Rzeczpospolita Polska Minister Zdrowa, Urzad Rejestracji Produktów Leczniczych. Warszawa: Wyrobów Medycznych i Produktów Biobójczych.
    1. Roth H. J., Schmid W. (1976). Hagers Handbuch der Pharmazeutischen Praxis. Berlin: Springer.
    1. Sarić P. M. (1989). Lekovite biljke SR Srbije. Beograd: SANU.
    1. Sawilska A. K. (2006). The impact of environmental factors on the course of flowering Helichrysum arenarium (L.) Moench. Acta Agrobot. 59, 241–249. 10.5586/aa.2006.024
    1. Sawilska A. K. (2007). The influence of origin of Helichrysum arenarium (L.) Moench individuals on their inflorescence yield and germination ability. Acta Agrobot 60, 111–116. 10.5586/aa.2007.038
    1. Sawilska A. K. (2008). Dynamics of Helichrysum arenarium (L.) Moench populations growing in fallow field on barren soil. Ecol. Quest. 9, 93–101. 10.2478/v10090-009-0024-x
    1. Sawilska A. K., Jendrzejczak E. (2013). Efficiency of sandy everlasting [Helichrysum arenarium (L.) Moench] cultivation from in vitro seedlings and achenes. Ind. Crops Prod. 43, 50–55. 10.1016/j.indcrop.2012.07.009
    1. Sawilska A. K., Jendrzejczak E., Welc M., Kieliszewska-Rokicka B. (2009). Influence of mycorrhizal fungi on the growth and development of sandy everlasting [Helichrysum arenarium (L.) Moench]. Acta Agrobot. 62, 67–76. 10.5586/aa.2009.008
    1. Shass E. Y. (1952). Phytotherapy. Moscow: Academy of Medicinal Science of USSR.
    1. Shikov A. N., Pozharitskaya O. N., Makarov V. G., Wagner H., Verpoorte R., Heinrich M. (2014). Medicinal plants of the Russian Pharmacopoeia; their history and applications. J. Ethnopharmacol. 154, 481–536. 10.1016/j.jep.2014.04.007
    1. Skakun N. P., Stepanov N. Y. (1988). Comparative evaluation of the heptaprotective, antioxidant and choleretic activity of flavonoids drugs. Vracebnoe Delo. 12, 52–54.
    1. Smirnova L. P., Pervykh L. N. (1998). Quantitative determination of the total content of flavonoids in the flowers of immortelle Helichrysum arenarium. Pharm. Chem. J. 32, 321–324.
    1. Sokolov S. Y. (2000). Phytotherapy and Phytopharmacology: The Manual for Doctors. Moscow: Medical News Agency.
    1. Sroka Z., Kuta I., Cisowski W., Dryś A. (2004). Antiradical activity of hydrolyzed and non-hydrolyzed extracts from Helichrysi inflorescentia and its phenolic contents. Z. Naturforsch. C. 59, 363–367. 10.1515/znc-2004-5-613
    1. Szadowska A. (1962). Pharmacology of galenic preparations and flavonoids from Helichrysum arenarium. Acta Pol. Pharm. 19, 465–479.
    1. Tasić S., Šavikin K., Menković N. (2009). Guide to the World of Medicinal Plants. Alexandria.
    1. Turova A. D. (1974). Lekarstvenniye Rasteniya SSSR i ikh Premeneniye (Medicinal Plants of the USSR and Their Uses). Moscow: Meditisina.
    1. Turova A. D., Sapozhnikova E. N. (1984). Lekarstvennuiye Rasteniya SSSR i ikh Premeneniye (Medicinal Plants of the USSR and Their Uses), 4th Edn. Moscow: Meditisina.
    1. Tyszynska-Kownacka D. (1972). Let us replenish the natural stands of medicine plants. Wiad. Ziel. 11, 8–9.
    1. Vereschagin V. I., Sobolevskaya K. A., Yakubova A. I. (1959). Useful Plants of West Siberia. Moscow-Leningrad: Academy of Science of USSR.
    1. Vrkoč J., Dolejš L., Sedmera P., Vašíčková S., Šorm F. (1971). The structure of arenol and homoarenol, α-pyrone derivatives from Helichrysum arenarium (L.) Moench. Tetrahedron Lett. 12, 247–250 10.1016/S0040-4039(01)96410-X
    1. Vrkoc J., Ubik K., Sedmera P. (1973). Phenolic extractives from the achenes of Helichrysum arenarium. Phytochemistry 12:2062.
    1. Wagner H. (1993). Pharmazeutische Biologie, Drogen und ihre Inhaltsstoffe. Stuttgart; NewYork, NY: Gustav Fischer Verlag.
    1. Wang L. B., Morikawa T., Nakamura S., Ninomiya K., Matsuda H., Muraoka O., et al. (2009). Medicinal Flowers. XXVIII. structures of five new glycosides, everlastosides, A., B, C, D, and E, from the Flowers of Helichrysum arenarium. Heterocycles 78, 1235–1242. 10.3987/COM-08-11618
    1. Wang L., Liu F., Gan C., Dong N., Hou Y., Wang C. (2012). Isolation and identification of chemical constituents in the lipid-lowering fraction of Flos Helichrysum arenarium (II). J. Shenyang Pharm. Univ. 29, 109–112.
    1. WHO (2015). WHO Monographs on Medicinal Plants Commonly Used in the Newly Independent States (NIS). Geneva: World Health Organization.
    1. Wichtl M. (2001). Herbal Medicines and Phytopharmaceuticals, 2nd Edn. Boca Raton, FL: CRC Press.
    1. Yang Y., Huang Y., Gu D., Yili A., Sabir G., Aisa H. A. (2009). Separation and purification of three flavonoids from Helichrysum arenarium (L.) Moench by HSCCC. Chromatographia 69, 963–967. 10.1365/s10337-009-0986-2
    1. Yong F., Aisa H. A., Mukhamatkhanova R. F., Shamyanov I. D., Levkovich M. G. (2011). New flavanone and other constituents of Helichrysum arenarium indigenous to China. Chem. Nat. Comp. 46, 872–875. 10.1007/s10600-011-9772-0
    1. Yousheng C., Shixin Z., Bayer R. J. (2011). Tribe GNAPHALIEAE, genus HELICHRYSUM, Asteraceae (Compositae), in Flora of China Volume 20–21 (Asteraceae), eds Z. Y. Wu, P. H. Raven, and D. Y. Hong, D. Y (Beijing: Science Press; St. Louis, MO: Missouri Botanical Garden Press; ), 818.
    1. Zidenberg-Cherr S., Keen C. L. (1991). Essential trace elements in antioxidant processes, in Trace Elements, Micronutrients, and Free Radicals, ed I. E. Dreosti (Totowa, NJ: Humana Press; ), 107–127.

Source: PubMed

Sponsors and Collaborators

Medical Conditions

Drug Interventions

3
Subscribe