Seven ferns of Pteridaceae, grown in a botanical garden or wild, harvested in France were investigated for their Volatile Organic Compounds (VOC) profile using GC-MS: Adiantum pedatum L., Adiantum peruvianum Klotzsch, Anogramma leptophylla (L.) Link, Cheilanthes maderensis Lowe, Cryptogramma crispa (L.) R. Br., Pteris cretica L. and Pteris vittata L. Fifty-three VOC biosynthesized from lipidic, shikimic, terpenic and carotenoid pathways were identified. The two Adiantum species show different VOC composition. The main linalool (10.8%) in A. pedatum has several biological activities of great interest. This Maidenhair fern contains the highest proportion (57.9%) of isoprenoid flavor precursors, i.e., ionone derivatives with various scent notes. The two major odorant unsaturated hexenoic acids derivatives of A. peruvianum are used as flavouring agents. Anogramma leptophylla concentrates 6-methoxymellein (71.5%), a bitter phytoallexin which contributes to stress or pathogen resistance. Cheilanthes maderensis produces mainly coumarin (89%) and vanillin (3.5%) with a low odor detection threshold, both used in perfumery and cosmetic industry or as flavouring agent and drug additives. Cryptogramma crispa accumulates a broad-spectrum of carotenoid derivatives (52.1%) and three major shikimic derivatives: the spicy 4-vinylguaiacol (flavouring agent), the floral phenylethanal and benzyl alcohol with floral, balsamic scent. Pteris cretica accumulates mostly furan derivatives, i.e., 5-hydroxymethylfurfural (33.2%) and 3-hydroxy-2,3-dihydromaltol (18.3%) used as food and beverage additives with caramel or roasty flavour and also found in fortified wines, toasty or heat-treated foods. Pteris vittata produces predominantly shikimic derivatives applied in perfumery and food industries as benzaldehyde (26%, with almond scent), benzyl alcohol (22%, floral fruity balsamic scent), nonanal (19.8% cucumber note) and phenylethanal (11%; floral note). Pteridaceae resources are of great interest as a reservoir of odorous and bioactive compounds.
(a) PrelliR., BoudrieM. (2001) Les fougères et plantes alliées de France et d'Europe occidentale, Belin, Paris, 1–432; (b) Schuettpelz E, Schneider H, Huiet L, Windham MD, Pryer KM. (2007) A molecular phylogeny of the fern family Pteridaceae: Assessing overall relationships and the affinities of previously unsampled genera. Molecular Phylogenetics and Evolution, 44, 1172–1185; (c) Mannar Mannan M, Maridass M, Victor B. (2008) A review on the potential uses of Ferns. Ethnobotanical Leaflets, 12, 281–285; (d) Benniamin A. (2011) Medicinal ferns of North Eastern India with special reference to Anapurna Pradesh. Indian Journal of Traditional Knowledge, 10, 516–522; (e) Maridass M, Raju G. (2010) Conservation status of Pteridophytes, Western Ghats, South India. Indian Journal of Biotechnology, 1 (Special Issue), 42–57; (f) May LW. (1978) The economic uses and associated folklore of Ferns and Fern Allies. The Botanical Review, 44, 491–528.
2.
(a) LimayeA.S., DeoreG.B., ShindeB.M., LawareS.L. (2010) Assessment of Adiantum trapeziforme L. for antioxidant activities. Asian Journal Experimental Biological Sciences, Special Vol 1, 79–84; (b) Ghorpade PN, Thakar SB, Dongare MM, Kale MV, Jadhav JP. (2016) Potential of antioxidant capacity and phenol content in four Cheilanthes species from Northern Western Ghats. Asian Journal of Pharmaceutical and Clinical Research, 9, 378–382; (c) Singh M, Govindarajan R, Rawat AKS, Khare PB. (2008) Antimicrobial flavonoid rutin from Pteris vittata L. against pathogenic gastrointestinal microflora. American Fern Journal, 98, 98–103; (d) De Britto AJ, Gracelin DHS, Kumar PBJR. (2012) Pteris biaurita L.: A potential antibacterial fern against Xanthomonas and Aeromonas bacteria. Journal of Pharmacy Research, 5, 678–680; (e) Paul T, Das B, Apte KG, Banerjee S, Saxena RC. (2012) Hypoglycemic activity of Pteris vittata L., a fern on alloxan induced diabetic rats. Inventi Rapid: Planta Activa, 2, 88–91; (f) Gong XL, Chen ZH, Liang NC (2007) Advances in study on chemical constituents and pharmacological activities of plants of genus Pteris. China Journal of Chinese Materia Medica, 32, 1382–1387; (g) Pham HN, Michalet S, Bodillis J, Nguyen TD, Nguyen TKO, Le TPQ, Haddad M, Nazaret S, Dijoux-Franca MG (2017) Impact of metal stress on the production of secondary metabolites in Pteris vittata L. and associated rhizosphere bacterial communities. Environmental Science and Pollution Research, 24, 16735–16750; (h) Li JH, He CW, Liang NC, Mo LE, Zhang X. (1999) Effects of antitumor compounds isolated from Pteris semipinnata L. on DNA topoisomerases and cell cycle of HL- 60 cells. Zhongguo Yao Li Xue Bao, 20, 541–545; (i) Patil SD, Chaudhari MA, Sapkale PV, Chaudhari RB (2013) A recent review on anticancer herbal drugs. Journal of Drug Discovery and Therapeutics, 1, 77–84; (j) Wu MJ, Weng CY, Wang L, Lian TW. (2005) Immunomodulatory mechanism of the aqueous extract of sword brake fern (Pteris ensiformis Burm.). Journal of Ethnopharmacolgy, 98, 73–81.
3.
(a) JonesD.L. (1987) Encyclopedia of ferns.Lothian, Port Melbourne, 1–433; (b) Fons F, Rapior S, Eyssartier G, Bessière JM. (2003) Volatile compounds in the Cantharellus, Craterellus and Hydnum genera. Cryptogamie, Mycologie, 24, 367–376; (c) Rapior S, Fons F, Bessière JM. (2003) Volatile flavor constituents of Lepista nebularis (clouded Clitocybe). Cryptogamie, Mycologie, 24, 159–166; (d) Fons F, Rapior S, Fruchier A, Saviuc P, Bessière JM. (2006) Volatile composition of Clitocybe amoenolens, Tricholoma caligatum and Hebeloma radicosum. Cryptogamie, Mycologie, 27, 45–55; (e) Fons F, Rapior S, Gargadennec A, Andary C, Bessière JM. (1998) Volatile components of Plantago lanceolata. Acta botanica Gallica, 145, 265–269; (f) Maggi F, Papa F, Vittori S. (2012) Gas chromatography for the characterization of the mushroom-like flavor in Melittis melissophyllum L. (Lamiaceae). Journal of Essential Oil Research, 24, 321–337; (g) Froissard D, Fons F, Bessière JM, Fruchier A, Buatois B, Rapior S. (2014) Volatile organic compounds of six French Dryopteris species: Natural odorous and bioactive resources. Natural Product Communications, 6, 1723–1726; (h) Fons F, Froissard D, Bessière JM, Fruchier A, Buatois B, Rapior S. (2013) Fougères et parfumerie. Annales de la Société d'Horticulture et d'Histoire Naturelle de l'Hérault, 153, 96–108; (i) AsakawaY, Nii K, Higuchi M. (2015) Identification of sesquiterpene lactones in the Bryophyta (mosses) Takakia: Takakia species are closely related chemically to the Marchantiophyta (liverworts). Natural Product Communications, 10, 5–8; (j) Asakawa Y, Ludwiczuk A, Nagashima F. (2013) Chemical constituents of Bryophytes. Bio- and chemical diversity, biological activity, and chemosystematics. In Progress in the Chemistry of Organic Natural Products. Vol. 95, Kinghorn AD, Falk H, Kobayashi J. (Eds.). Springer, Vienna, 1–796.
4.
(a) The Good Scents Company (2017) http://www.thegoodscentscompany.com (2017/07/18); (b) PubChem, Open Chemistry Database (2017) https://pubchem.ncbi.nlm.nih.gov/compound (2017/07/18); (c) Xie L, Chen X. (2017) Mosquito attractant for controlling Aedes albopictus and Culex quinquefasciatus. Faming Zhuanli Shenqing, CN 106305773 A 20170111, 1–14; (d) Kline DL. (1994) Olfactory attractants for mosquito surveillance and control: 1-octen-3-ol. Journal of the American Mosquito Control Association, 10, 280–287; (e) Aprotosoaie AC, Hancianu M, Costache II, Miron A. (2014) Linalool: a review on a key odorant molecule with valuable biological properties. Flavour and Fragrance Journal, 29, 193–219; (f) Metoui N, Gargouri S, Amri I, Fezzani T, Jamoussi B, Hamrouni L. (2015) Activity antifungal of the essential oils; aqueous and ethanol extracts from Citrus aurantium L. Natural Product Research, 29, 2238–2241; (g) Marquez FM, Moll CN, Herrera PM, Galindo PP, Yuste MM, Sanchez JM. (2004) Activity of the monoterpene derivatives carvacrol, linalool and α-terpineol, Obtained from Aromatic Plants, on Leishmania infantum. Multidisciplinarity for Parasites, Vectors and Parasitic Diseases, Proceedings of the European Multicolloquium of Parasitology, 9th, Valencia, Spain, July 18–23, 2004, Ed. Mas-Coma, Santiago, 2, 93–96; (h) Müller GC, Junnila A, Butler J, Kravchenko VD, Revay EE, Weiss RW, Schlein Y. (2009) Efficacy of the botanical repellents geraniol, linalool, and citronella against mosquitoes. Journal of Vector Ecology, 34, 2–8; (i) Kamatou GPP, Viljoen A. (2008) Linalool – a review of a biologically active compound of commercial importance. Natural Product Communications, 3, 1183–1192; (j) The Pherobase (2017) http://www.pherobase.com/database/kovats/kovats-detail-E,E-pseudoionone.php (2017/07/18).
5.
(a) FonsF., FroissardD., BessièreJ.M., BuatoisB., RapiorS. (2010) Biodiversity of volatile organic compounds from five French ferns. Natural Product Communications, 5, 1655–1658; (b) Froissard D, Fons F, Bessière JM, Buatois B, Rapior S. (2011) Volatiles of French ferns and “fougère” scent in perfumery. Natural Product Communications, 6, 1723–1726; (c) Fons F, Froissard D, Bessière JM, Fruchier A, Buatois B, Rapior S. (2013) Volatile composition of six horsetails: prospects and perspectives, Natural Product Communications, 8, 509–512; (d) Gildemeister E. (1913) The Volatile Oils, Vol 1. John Wiley & Sons, New York, 1–712.
6.
(a) HammerschmidtR. (2012) Secondary metabolites and defense: The story continues. Physiological and Molecular Plant Pathology, 80, iii–iv; (b) De Girolamo A, Solfrizzo M, Vitti C, Visconti A. (2004) Occurrence of 6-methoxymellein in fresh and processed carrots and relevant effect of storage and processing. Journal of Agricultural and Food Chemistry, 52, 6478–6484; (c) Krammer M, Bufler G, Ulrich D, Leitenberger M, Conrad J, Carle R, Kammerer DR. (2012) Effect of ethylene and 1-methylcyclopropene on bitter compounds in carrots (Daucus carota L.). Postharvest Biology and Technology, 73, 28–36; (d) Magid AA, Voutquenne-Nazabadioko L, Moroy G, Moretti C, Lavaud C. (2007) Dihydroisocoumarin glucosides from stem bark of Caryocar glabrum. Phytochemistry, 68, 2439–2443; (e) Krohn K, Bahramsari R, Flörke U, Ludewig K, Kliche-Spory C, Michel A, Aust HJ, Draeger S, Schulz B, Antus S. (1997) Dihydroisocoumarins from fungi: isolation, structure elucidation, circular dichroism and biological activity. Phytochemistry, 45, 313–320.
(a) LasekanO. (2013) Volatile constituents of roasted tigernut oil (Cyperus esculentus L.). Journal of the Science of Food and Agriculture, 93, 1055–1061. (b) Zhao YP, Wang L, Li JM, Pei GR, Liu QS. (2011) Comparison of volatile compounds in two brandies using HS-SPME coupled with GC-O, GC-MS and Sensory evaluation. South African Journal of Enology & Viticulture, 32, 9–20; (c) Sigma Aldrich, Ingredients Catalog: Flavors and Fragrances (http://www.sigmaaldrich.com//ifb/fnf_2014); (d) Merck & Co., Inc. (1996) The Merck Index, An Encyclopedia of Chemicals, Drugs, and Biologicals, 12th Ed. Merck and Co., Inc., Whitehouse Station, NJ, 1–1741; (e) Abraham K, Gürtler R, Berg K, Heinemeyer G, Lampen A, Appel KE. (2011) Toxicology and risk assessment of 5-hydroxymethylfurfural in food. Molecular Nutrition & Food Research, 55, 667–678; (f) Amanpour A, Selli S. (2016) Differentiation of volatile profiles and odor activity values of turkish coffee and French press coffee. Journal of Food Processing and Preservation, 40, 1116–1124; (g) Perestrelo R, Silva CL, Câmara JS. (2015) Quantification of furanic derivatives in fortified wines by a highly sensitive and ultrafast analytical strategy based on digitally controlled microextraction by packed sorbent combined with ultrahigh pressure liquid chromatography. Journal of Chromatography A, 1381, 54–63; (h) Paravisini L, Gourrat-Pernin K, Gouttefangeas C, Moretton C, Nigay H, Dacremont C, Guichard E. (2012) Identification of compounds responsible for the odorant properties of aromatic caramel. Flavour and Fragrance Journal, 27, 424–432.
9.
(a) FroissardD., RapiorS., BessièreJ.M., BuatoisB., FruchierA., SolV., FonsF. (2015) Asplenioideae species as a reservoir of volatile organic compounds with potential therapeutic properties. Natural Product Communications, 10, 1079–1083; (b) Zodrow EL, Helleur R, Werner-Zwanziger U, Chen B, D'Angelo JA. (2013) Spectrochemical study of coalified Trigonocarpus grandis (Pennsylvanian tree-fern ovule, Canada): Implications for fossil–organ linkage. International Journal of Coal Geology, 109–110, 24–35; (c) Chen Y, Tao Y, Lian X, Wang L, Zhao Y, Jiang J, Zhang Y. (2010) Chemical constituents of Angiopteris esculenta including two new natural lactones. Food Chemistry, 122, 1173–1175; (d) Cuong NX, Minh CV, Kiem PV, Huong HT, Ban NK, Nhiem NX, Tung NH, Jung JW, Kim HJ, Kim SY, Kim JA, Kim YH. (2009) Inhibitors of osteoclast formation from rhizomes of Cibotium barometz. Journal of Natural Products, 72, 1673–1677; (e) Fang CW, Chen JJ, Liu SJ. (2010) Studies on the chemical constituents of rhizome of Coniogramme japonica. Zhong Yao Cai, 33, 557–559; (f) Leach H, Barber GD, Evans IA, Evans WC. (1971) Isolation of an active principle from the bracken fern that is mutagenic, carcinogenic and lethal to mice on intraperitoneal injection. Proceedings of the Biochemical Society, 124, 13P-14P; (g) Kessler M, Connor E, Lehnert M. (2015) Volatile organic compounds in the strongly fragrant fern genus Melpomene (Polypodiaceae). Plant Biology, 17, 430–436.
10.
(a) ZhangJ.H., SunH.L., ChenS.Y., ZengL., WangT.T. (2017) Anti-fungal activity, mechanism studies on α-phellandrene and nonanal against Penicillium cyclopium. Botanical Studies58: 13. DOI: 10.1186/s40529-017-0168-8.; (b) Xu P, Zhu F, Buss GK, Leal WS. (2015) 1-Octen-3-ol – the attractant that repels. F1000Research, 4, 156. DOI: 10.12688/f1000research.6646.1; (c) Chen YC, Tsai WJ, Wu MH, Lin LC, Kuo YC. (2007) Suberosin inhibits proliferation of human peripheral blood mononuclear cells through the modulation of the transcription factors NF-AT and NF-kappaB. British Journal of Pharmacology, 150, 298–312; (d) Kim JK, Kim JY, Kim HJ, Park KG, Harris RA, Cho WJ, Lee JT, Lee IK. (2013) Scoparone exerts anti-tumor activity against DU145 prostate cancer cells via inhibition of STAT3 activity. PLoS One. Nov 15;8(11):e80391. DOI: 10.1371/journal.pone.0080391. eCollection 2013.
11.
(a) National Institute of Standard, and Technology. (2005) PC version of the NIST / EPA / NIH Mass Spectra Database, Gaithersburg, Maryland, USA; (b) Adams RP. (2007) Identification of Essential Oil Components by Gas Chromatography/Mass Spectroscopy. 4th Ed., Allured, Carol Stream, IL, USA.
