Sesquiterpenes in Fresh Food

  1. Durán, Alexandra G. 1
  2. Rial, Carlos 1
  3. Gutiérrez, M. Teresa 1
  4. Molinillo, José M. G. 1
  5. Macías, Francisco A. 1
  1. 1 Universidad de Cádiz
    info

    Universidad de Cádiz

    Cádiz, España

    ROR https://ror.org/04mxxkb11

Libro:
Handbook of Dietary Phytochemicals

Editorial: Springer

ISBN: 9789811317453 9789811317453

Año de publicación: 2019

Páginas: 1-66

Tipo: Capítulo de Libro

DOI: 10.1007/978-981-13-1745-3_47-1 GOOGLE SCHOLAR lock_openAcceso abierto editor

Resumen

Sesquiterpenes are secondary metabolites that have interesting health-promoting functions, including anti-inflammatory, cardiovascular, gastro-protective, and anticancer properties. The potential of these compounds in human health will be further discussed throughout this chapter, being incorporated as part of a balanced diet and as pharmaceutical agents. Several foods consumed daily are a rich source of these compounds such as fruits, vegetables, algae, edible medicinal plants, and mushrooms. An overview of the bioactive constituents found in these aliments, metabolism routes and bioavailability, benefits for human health, safety upon ingestion, and market products will be described. Moreover, a deep understanding of the chemical constituents and biological activity observed will be detailed (structure-activity relationship studies). On the other hand, some of the peculiar aspects of these compounds (for instance, sesquiterpene lactones) is the bitterness that they confer to foods such as chicory, lettuce, or dandelion. This bitter taste is a direct consequence to their role as antifeedants, and this characteristic might help to ascertain the appropriate daily doses of sesquiterpenes. Little is known about the intake of sesquiterpenes in our diet. This chapter provides an understanding of the role of sesquiterpenes in health and human diet and the importance of increase their comsumption.

Referencias bibliográficas

  • Abad MJ, Bedoya LM, Apaza L, Bermejo P (2012) The Artemisia L. genus: a review of bioactive essential oils. Molecules 17:2542–2566
  • Aberham A, Cicek SS, Schneider P, Stuppner H (2010) Analysis of sesquiterpene lactones, lignans, and flavonoids in Wormwood (Artemisia absinthium L.) using High-Performance Liquid Chromatography (HPLC)−Mass Spectrometry, reversed phase HPLC, and HPLC−Solid Phase Extraction−Nuclear Magnetic Resonance. J Agric Food Chem 58:10817–10823
  • Aharoni A, Verstappen FWA, Bouwmeester HJ, Beekwilder J (2005) Fruit flavor formation in wild and cultivated strawberry. Acta Hortic 682:233–236
  • Ahlemeyer B, Krieglstein J (2003) Pharmacological studies supporting the therapeutic use of Ginkgo biloba extract for Alzheimer’s disease. Pharmacopsychiatry 36:8–14
  • Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS (2016) Alimentary pharmacology and therapeutics investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther 43:596–611
  • Alarif WM, Al-Footy KO, Zubair MS, Halid Ph M, Ghandourah MA, Basaif SA, Al-Lihaibi SS, Ayyad SE, Badria FA (2016) The role of new eudesmane-type sesquiterpenoid and known eudesmane derivatives from the red alga Laurencia obtusa as potential antifungal-antitumour agents. Nat Prod Res 30:1150–1155
  • Anderson DM (1995) Toxic red tides and harmful algal blooms: a practical challenge in coastal oceanography. Rev Geophys 33:1189–1200
  • Antonious GF, Kochhar TS (2003) Zingiberene and curcumene in wild tomato. J Environ Sci Health B 38:489–500
  • Araújo MJC, Câmara CAG, Born FS, Moraes MM, Badji CA (2012) Acaricidal activity and repellency of essential oil from Piper aduncum and its components against Tetranychus urticae. Exp Appl Acarol 57:139–155
  • Avula B, Wang YH, Wang M, Smillie TJ, Khan IA (2012) Simultaneous determination of sesquiterpenes and pyrrolizidine alkaloids from the rhizomes of Petasites hybridus (L.) G.M. et Sch. and dietary supplements using UPLC-UV and HPLC-TOF-MS methods. J Pharm Biomed Anal 70:53–63
  • Avula B, Sagi S, Gafner S, Upton R, Wang YH, Wang M, Khan IA (2015) Identification of Ginkgo biloba supplements adulteration using high performance thin layer chromatography and ultra high performance liquid chromatography-diode array detector-quadrupole time of flight-mass spectrometry. Anal Bioanal Chem 407:7733–7746
  • Bangmei X, Abbott IA (1987) Edible seaweeds of China and their place in the Chinese diet. Econ Bot 41:341–353
  • Barrière V, Lecompte F, Nicot PC, Maisonneuve B, Tchamitchian M, Lescourret F (2014) Lettuce cropping with less pesticides. A review. Agron Sustain Dev 34:175–198
  • Barry TN (1998) The feeding value of chicory (Cichorium intybus) for ruminant livestock. J Agric Sci 131:251–257
  • Barsby R, Salan U, Knight D, Hoult J (1993a) Feverfew and vascular smooth muscle: extracts from fresh and dried plants show opposing pharmacological profiles, dependent upon sesquiterpene lactone content. Planta Med 59:20–25
  • Barsby RWJ, Knight RW, Mcfadzean I (1993b) A chloroform extract of the herb feverfew blocks voltage-dependent potassium currents recorded from single smooth muscle cells. J Pharm Pharmacol 45:641–645
  • Beekman AC, Woerdenbag HJ, van Uden W, Pras N, Konings AWT, Wikström HV, Schmidt TJ (1997) Structure−cytotoxicity relationships of some helenanolide-type sesquiterpene lactones. J Nat Prod 60:252–257
  • Berger T, Dieckmann D, Efferth T, Schultz E, Funk J-O, Baur A, Schuler G (2005) Artesunate in the treatment of metastatic uveal melanoma–first experiences. Oncol Rep 14:1599–1603
  • Bickel D, Röder T, Bestmann H, Brune K (1994) Identification and characterization of inhibitors of peptido-leukotriene-synthesis from Petasites hybridus. Planta Med 60:318–322
  • Bourgou S, Bettaieb Rebey I, Mkadmini K, Isoda H, Ksouri R, Ksouri WM (2017) LC-ESI-TOF-MS and GC-MS profiling of Artemisia herba-alba and evaluation of its bioactive properties. Food Res Int 99:702–712
  • Brown GD (2010) The biosynthesis of artemisinin (Qinghaosu) and the phytochemistry of Artemisia annua L. (Qinghao). Molecules 15:7603–7698
  • Bruno M, Rosselli S, Maggio A, Raccuglia RA, Bastow KF, Lee K-H (2005) Cytotoxic activity of some natural and synthetic guaianolides. J Nat Prod 68:1042–1046
  • Campos A, Souza CB, Lhullier C, Falkenberg M, Schenkel EP, Ribeiro-Do-Valle RM, Siqueira JM (2012) Anti-tumour effects of elatol, a marine derivative compound obtained from red algae Laurencia microcladia. J Pharm Pharmacol 64:1146–1154
  • Cejudo-bastante MJ, Durán-Guerrero E, Natera-Marín R, Castro-Mejías R, García Barroso C (2012) Characterisation of commercial aromatised vinegars: phenolic compounds, volatile composition and antioxidant activity. J Sci Food Agric 93:1284–1302
  • Chadwick M, Trewin H, Gawthrop F, Wagstaff C (2013) Sesquiterpenoids lactones: benefits to plants and people. Int J Mol Sci 14:12780–12805
  • Chadwick M, Gawthrop F, Michelmore RW, Wagstaff C, Methven L (2016) Perception of bitterness, sweetness and liking of different genotypes of lettuce. Food Chem 197:66–74
  • Chakraborty K, Paulraj R (2010) Sesquiterpenoids with free-radical-scavenging properties from marine macroalga Ulva fasciata Delile. Food Chem 122:31–41
  • Chakraborty K, Lipton AP, Paulraj R, Chakraborty RD (2010) Guaiane sesquiterpenes from seaweed Ulva fasciata Delile and their antibacterial properties. Eur J Med Chem 45:2237–2244
  • Chaturvedi D, Dwivedi PK, Mishra M (2015) Sesquiterpene lactones: a versatile class of structurally diverse natural products and their semisynthetic analogs as potential anticancer agents. In Bioactive natural products: chemistry and biology, Wiley, Weinheim, pp 321–348
  • Chen HC, Chang WT, Hseu YC, Chen HY, Chuang CH, Lin CC, Lee MS, Lin MK (2016) Immunosuppressive effect of Litsea cubeba L. Essential oil on dendritic cell and contact hypersensitivity responses. Int J Mol Sci 17:1319
  • Chiu KY, Wu CC, Chia CH, Hsu SL, Tzeng YM (2016) Inhibition of growth, migration and invasion of human bladder cancer cells by antrocin, a sesquiterpene lactone isolated from Antrodia cinnamomea, and its molecular mechanisms. Cancer Lett 373:174–184
  • Chizzola R, Langer T, Franz C (2006) An approach to the inheritance of the sesquiterpene chemotypes within Petasites hybridus. Planta Med 72:1254–1256
  • Christaki E, Bonos E, Florou-Paneri P (2012) Nutritional and functional properties of cynara crops (globe artichoke and cardoon) and their potential applications: a review. Int J Appl Sci Technol 2:64–70
  • Da Silva Machado FL, Ventura TLB, De Souza Gestinari LM, Cassano V, Resende JALC, Kaiser CR, Lasunskaia EB, Muzitano MF, Soares AR (2014) Sesquiterpenes from the Brazilian red alga Laurencia dendroidea J. Agardh. Molecules 19:3181–3192
  • Dai YY, Chuang CH, Tsai CC, Sio HM, Huang SC, Chen JC, Hu ML (2003) The protection of Anthrodia camphorata against acute hepatotoxicity of alcohol in rats. J Food Drug Anal 11:177–185
  • Dai DN, Thang TD, Ogunmoye A, Eresanya OI, Ogunwande IA (2015) Chemical constituents of essential oils from the leaves of Tithonia diversifolia, Houttuynia cordata and Asarum glabrum grown in Vietnam. Am J Essent Oil Nat Prod 2:17–21
  • Davyt D, Fernandez R, Suescun L, Mombrú AW, Saldaña J, Domínguez L, Fujii MT, Manta E (2006) Bisabolanes from the red alga Laurencia scoparia. J Nat Prod 69:1113–1116
  • De Smet PAGM (2002) Herbal Remedies. N Engl J Med 347:2046–2056
  • Defeudis FV (2002) Bilobalide and neuroprotection. Pharmacol Res 46:565–568
  • Demirel Z, Yilmaz-Koz FF, Karabay-Yavasoglu NU, Ozdemir G, Sukatar A (2011) Antimicrobial and antioxidant activities of solvent extracts and the essential oil composition of Laurencia obtusa and Laurencia obtusa var. pyramidata. Rom Biotechnol Lett 16:5927–5936
  • Desrosiers MR, Weathers PJ (2016) Effect of leaf digestion and artemisinin solubility for use in oral consumption of dried Artemisia annua leaves to treat malaria. J Ethnopharmacol 190:313–318
  • Di Campli E, Di Bartolomeo S, Pizzi PD, Di Giulio M, Grande R, Nostro A, Cellini L (2012) Activity of tea tree oil and nerolidol alone or in combination against Pediculus capitis (head lice) and its eggs. Parasitol Res 111:1985–1992
  • Domínguez H (2013) Functional ingredients from algae for foods and nutraceuticals, 1st edn. Elsevier Science, Cambridge
  • dos Santos AO, Veiga-Santos P, Ueda-Nakamura T, Filho BPD, Sudatti DB, Bianco EM, Pereira RC, Nakamura CV (2010) Effect of elatol, isolated from red seaweed Laurencia dendroidea, on Leishmania amazonensis. Mar Drugs 8:2733–2743
  • Duke SO, Vaughn KC, Croom EM Jr, Elsohly HN (1987) Artemisinin, a constituent of annual wormwood (Artemisia annua), is a selective phytotoxin. Weed Sci 35:499–505
  • Duncan RE, Archer MC (2008) Farnesol decreases serum triglycerides in rats: identification of mechanisms including up-regulation of PPAR α and down-regulation of fatty acid synthase in hepatocytes. Lipids 43:619–627
  • Eckstein-Ludwing U, van Goethem IDA, East JM, Lee AG, Kimura M, O’Neill PM, Bray PG, Ward SA, Krishna S (2003) Artemisinins target the SERCA of Plasmodium falciparum. Nature 424:957–961
  • Edwards PA, Ericsson J (1999) Sterols and isoprenoids: signalin molecules derived from the cholesterol biosynthetic pathway. Annu Rev Biocem 68:157–185
  • El Gamal AA (2010) Biological importance of marine algae. Saudi Pharm J 18:1–25
  • Emendörfer F, Emendörfer F, Bellato F, Noldin VF, Cechinel-Filho V, Yunes RA, Delle Monache F, Cardozo AM (2005) Antispasmodic activity of fractions and cynaropicrin from Cynara scolymus on guinea-pig ileum. Biol Pharm Bull 28:902–904
  • Esatbeyoglu T, Obermair B, Dorn T, Siems K, Rimbach G, Birringer M (2017) Sesquiterpene lactone composition and cellular Nrf2 induction of Taraxacum officinale leaves and roots and taraxinic acid β-D-glucopyranosyl ester. J Med Food 20:71–78
  • Falara V, Akhtar TA, Nguyen TTH, Spyropoulou EA, Bleeker PM, Schauvinhold I, Matsuba Y, Bonini ME, Schilmiller AL, Last RL, Schuurink RC, Pichersky E (2011) The tomato terpene synthase gene family. Plant Physiol 157:770–789
  • Feng Z-M, Song S, Xia P-F, Jiang J-S, Zhang P-C (2009) Three new sesquiterpenoids from Chrysanthemum indicum L. Helv Chim Acta 92:1823–1828
  • Ferreria L, Perestrelo R, Caldeira M, Cámara JS (2009) Characterization of volatile substances in apples from Rosaceae family by headspace solid-phase microextraction followed by GC-qMS. J Sep Sci 32:1875–1888
  • Fiebich BL, Grozdeva M, Hess S, Hüll M, Danesch U, Bodensieck A, Bauer R (2005) Petasites hybridus extracts in vitro inhibit COX-2 and PGE 2 release by direct interaction with the enzyme and by preventing p42/44 MAP kinase activation in rat primary microglial cells. Planta Med 71:12–19
  • Fonsêca DV, Salgado PRR, de Carvalho FL, Salvadori MGSS, Penha ARS, Leite FC, Borjes CJ, Piuvezam MR, Pordeus LC, Sousa DP, Almeida RN (2016) Nerolidol exhibits antinociceptive and anti.inflammatory activity: involvement of the gabaergic system and proinflammatory cytokines. Fundam Clin Pharmacol 30:14–22
  • Foster JG, Clapham WM, Belesky DP, Labreveux M, Hall MH, Sanderson MA (2006) Influence of cultivation site on sesquiterpene lactone composition of forage chicory (Cichorium intybus L.). J Agric Food Chem 54:1772–1778
  • Francisco MEY, Erickson KL (2001) Ma’iliohydrin, a cytotoxic chamigrene dibromohydrin from a Philippine Laurencia Species. J Nat Prod 64:790–791
  • Garcia-Casal MN, Pereira AC, Leets I, Ramirez J, Quiroga MF (2007) High iron content and bioavailability in humans from four species of marine algae. J Nutr 137:2691–2695
  • Geethangili M, Institute, Y.-M. T (2006) Review of pharmacological effects of Antrodia camphorata and its bioactive compounds. Indian J Exp Biol 44:981–986
  • Ghantous A, Nasser N, Saab I, Darwiche N, Saliba NA (2009) Structure-activity relationship of seco-tanapartholides isolated from Achillea falcata for inhibition of HaCaT cell growth. Eur J Med Chem 44:3794–3797
  • Ghantous A, Gali-Muhtasib H, Vuorela H, Saliba NA, Darwiche N (2010) What made sesquiterpene lactones reach cancer clinical trials? Drug Discov Today 15:668–678
  • Gil B, Ferrándiz ML, Sanz MJ, Terencio MC, Ubeda A, Rovirosa J, San-Martin A, Alcazar MJ, Payá M (1995) Inhibition of inflammatory responses by epitaondiol and other marine natural products. Life Sci 57:PL25–PL30
  • Gliszczynska A, Łysek A, Janeczko T, Switalska M, Wietrzyk J, Wawrzen C (2011) Bioorganic & medicinal chemistry microbial transformation of (+)-nootkatone and the antiproliferative activity of its metabolites. Bioorg Med Chem 19:2464–2469
  • Goldblum S, Warren CB (2014) Nootkatone in various carriers and formulations as an insecticide and insect repellent. WO 2014031790A1. PCT Int Appl
  • Gornik HL, Creager MA (2013) Medical treatment of peripheral artery disease. In: Creager MA, Beckman JA, Loscalzo J (eds) Vascular medicine: a companion to Braunwald’s heart disease. Elsevier, Philadelphia, pp 242–258
  • Gossell-Williams M, Davis A, O’Connor N (2006) Inhibition of testosterone-induced hyperplasia of the prostate of sprague-dawley rats by pumpkin seed oil. J Med Food 9:284–286
  • Guzman ML, Rossi RM, Neelakantan S, Li X, Corbett CA, Hassane DC, Becker MV, Bennett JM, Sullivan E, Lachowicz JL, Vaughan A, Sweeney CJ, Matthews W, Carroll M, Liesveld JL, Crooks PA, Jordan CT (2007) An orally bioavailable parthenolide analog selectively eradicates acute myelogenous leukemia stem and progenitor cells. Blood 110:4427–4435
  • Hamdan D, Ashour ML, Mulyaningsih S, El-shazly A (2013) Chemical composition of the essential oils of variegated pink-fleshed lemon (Citrus x limon L. Burm. f.) and their anti-inflammatory and antimicrobial activities. Z Naturforsch C 68:275–284
  • Harizani M, Ioannou E, Roussis V (2016) The Laurencia paradox: an endless source of chemodiversity. In: Kinghorn AD, Falk H, Gibbons S, Kobayashi J (eds) Progress in the chemistry of organic natural products. Springer, Cham
  • Hassanein HD, Nazif NM, Shahat AA, Hammouda FM, Aboutable ESA, Saleh MA (2014) Chemical diversity of essential oils from Cyperus articulatus, Cyperus esculentus and Cyperus papyrus. J Essen Oil Bear Plants 17:251–264
  • Higa T, Kuniyoshi M (2000) Toxins associated with medicinal and edible seaweeds. J Toxicol Toxin Rev 19:119–137
  • Hinson DD, Chamliss KL, Toth MJ, Tanaka RD, Gibson KM (1997) Post-translational regulation of mevalonate kinase by intermediates of the cholesterol and nonsterol isoprene biosynthetic pathways. J Lipid Res 38:2216–2223
  • Högnadóttir Á, Rouseff RL (2003) Identification of aroma active compounds in orange essence oil using gas chromatography-olfactometry and gas chromatography-mass spectrometry. J Chromatogr A 998:201–211
  • Hseu YC, Wu FY, Wu JJ, Chen JY, Chang WH, Lu FJ, Lai YC, Yang HL (2005) Anti-inflammatory potential of Antrodia Camphorata through inhibition of iNOS, COX-2 and cytokines via the NF-κB pathway. Int Immunopharmacol 5:1914–1925
  • Hudek K, Davis LC, Ibbini J, Erickson L (2014) Commercial products from algae. In: Bajpai R, Prokop A, Zappi M (eds) Algal Biorefineries: volume 1: cultivation of cells and products. Springer, Dordrecht, pp 275–295
  • Hui L, Zhao G, Zhao J (2015) δ-Cadinene inhibits the growth of ovarian cancer cells via caspase-dependent apoptosis and cell cycle arrest. Int J Clin Exp Pathol 8:6046–6056
  • Hunter GL, Brogden JWB (1965) Analysis of the terpene and sesquiterpene hydrocarbons in some citrus oils. J Food Sci 30:383–387
  • Hwang E-S, Kim G-H (2013) Safety evaluation of Chrysanthemum indicum L. Flower oil by assessing acute oral toxicity, micronucleus abnormalities, and mutagenicity. Prev Nutr Food Sci 18:111–116
  • Ishii T, Nagamine T, Nguyen BCQ, Tawata S (2017) Insecticidal and repellent activities of laurinterol from the okinawan red alga Laurencia nidifica. Rec Nat Prod 11:63–68
  • Janßen IM, Sturtz S, Skipka G, Zentner A, Garrido MV, Busse R (2010) Ginkgo biloba in alzheimer’s disease: a systematic review. Wien Med Wochenschr 160:539–546
  • Janssens D, Delaive E, Remade J, Michiels C (2000) Protection by bilobalide of the ischaemia-induced alterations of the mitochondrial respiratory activity. Fundam Clin Pharmacol 14:193–201
  • Jia R, Yang X, Cai C, He P, Qiu J, Wang W, Tan J, Zhang J (2015) Application of sesquiterpenoid compound derived from Laurencia okamurai as veterinary antibiotic against Streptococcus agalactiae and Vibrio anguillarum. CN104622853A. Faming Zhuanli Shenqing
  • Johnston GAR, Chebib M, Duke RK, Fernandez SP, Hanrahan JR, Hinton T, Mewett KN (2009) Herbal products and GABA receptors. In: Encyclopedia of neuroscience, vol 4. Elsevier, Amsterdam, pp 1095–1101
  • Jovanovic M, Poljacki M, Mimica-Dukic N, Boza P, Vujanovic L, Duran V, Stojanovic S (2004) Sesquiterpene lactone mix patch testing supplemented with dandelion extract in patients with allergic contact dermatitis, atopic dermatitis and non-allergic chronic inflammatory skin diseases. Contact Dermatitis 51:101–110
  • Kabugi Mwangi J, Ndung’u M, Gitu L (2013) Repellent activity of the essential oil from Capparis tomentosa against maize weevil Sitophilus zeamais. J Res Dev Manage 1:9–13
  • Kajiwara T, Ochi S, Kodama K, Matsui K, Hatanaka A, Fujimura T, Ikeda T (1992) Cell-destroying sesquiterpenoid from red tide of Gymnodinium nagasakiense. Phytochemistry 31:783–785
  • Kasrati A, Alaoui Jamali C, Fadli M, Bekkouche K, Hassani L, Wohlmuth H, Leach D, Abbad A (2014) Antioxidative activity and synergistic effect of Thymus saturejoides Coss. essential oils with cefixime against selected food-borne bacteria. Ind Crop Prod 61:338–344
  • Kawasaki BT, Hurt EM, Kalathur M, Duhagon MA, Milner JA, Kim YS, Farrar WL (2009) Effects of the sesquiterpene lactone parthenolide on prostate tumor-initiating cells: an integrated molecular profiling approach. Prostate 69:827–837
  • Kennedy GG (2003) Tomato, pests, parasitoids, and predators: tritrophic interactions involving the genus Lycopersicon. Annu Rev Entomol 48:51–72
  • Kfoury M, Landy D, Ruellan S, Auezova L, Greige-Gerges H, Fourmentin S (2017) Nootkatone encapsulation by cyclodextrins: effect on water solubility and photostability. Food Chem 236:41–48
  • Kim M-M, Mendis E, Kim S-K (2008) Laurencia okamurai extract containing laurinterol induces apoptosis in melanoma cells. J Med Food 11:260–266
  • Kim DS, Na H, Kwack Y, Chun C (2014) Secondary metabolite profiling in various parts of tomato plants. Korean J Hortic Sci Technol 32:252–260
  • Kimura J, Kamada N, Tsujimoto Y (1999) Fourteen chamigrane derivatives from a red alga, Laurencia nidifica. Bull Chem Soc Jpn 72:289–292
  • Kiss T, Szabo A, Oszlanczi G, Lukacs A, Tõmar Z, Tiszlavicz L, Csupor D (2017) Repeated-dose toxicity of common ragweed on rats. PLoS One 12:1–18
  • Klopell FC, Lemos M (2007) Nerolidol, an antiulcer constituent from the essential oil of Baccharis dracunculifolia DC (Asteraceae). Z Naturforsh C 62:537–542
  • Ku CM, Lin JY (2015) Farnesol, a sesquiterpene alcohol in herbal plants, exerts anti-inflammatory and antiallergic effects on ovalbumin-sensitized and-challenged asthmatic mice. Evid Based Complement Alternat Med 2015:1–12
  • Ku C, Lin J (2016) Farnesol, a sesquiterpene alcohol in essential oils, ameliorates serum allergic antibody titres and lipid profiles in ovalbumin-challenged mice. Allergol Inmunopathologia 44:149–159
  • Kubmarawa D, Ogunwande IA, Okorie DA, Olawore NO, Kasali AA (2005) Chemical constituents of the volatile oil of Cyperus esculentus L. from Nigeria. Flavour Fragr J 20:640–641
  • Kubo I, Ganjian I (1981) Insect antifeedant terpenes, hot-tasting to humans. Experientia 37:1063–1064
  • Kwak JH, Jung GH, Ji OP, Park YJ, Lee MS (2015) Eudesmadiene derivative for alleviating menopause symptoms and allergic disorders. KR1512901 B1 20150416. Repub Korea Patent
  • La Barre S, Potin P, Leblanc C, Delage L (2010) The halogenated metabolism of brown algae (Phaeophyta), its biological importance and its environmental significance. Mar Drugs 8:988–1010
  • Lamikanra O, Richard OA (2004) Storage and ultraviolet-induced tissue stress effects on fresh-cut pineapple. J Sci Food Agric 84:1812–1816
  • Lapczynski A, Bhatia SP, Letizia CS, Api AM (2008) Fragrance material review on nerolidol (isomer unspecified). Food Chem Toxicol 46:S247–S250
  • Li XD, Miao FP, Liang XR, Wang BG, Ji NY (2013) Two halosesquiterpenes from Laurencia composita. RSC Adv 3:1953–1956
  • Li HP, Yang WJ, Qu SX, Pei F, Luo X, Mariga AM, Ma L (2018) Variation of volatile terpenes in the edible fungi mycelia Flammulina velutipes and communications in fungus-mite interactions. Food Res Int 103:150–155
  • Lin YL, Ma LT, Lee YR, Lin SS, Wang SY, Chang TT, Shaw JF, Li WH, Chu FH (2015) MicroRNA-like small RNAs prediction in the development of Antrodia cinnamomea. PLoS One 10:e0123245
  • Lin YL, Ma LT, Lee YR, Shaw JF, Wang SY, Chu FH (2017) Differential gene expression network in terpenoid synthesis of Antrodia cinnamomea in mycelia and fruiting bodies. J Agric Food Chem 65:1874–1886
  • Liu RH (2003) Health benefits of fruit and vegetables are from additive and synergistic combinations of phytochemicals. Am J Clin Nutr 78:517S–520S
  • Liu B, Wang H, Du Z, Li G, Ye H (2011) Metabolic engineering of artemisinin biosynthesis in Artemisia annua L. Plant Cell Rep 30:689–694
  • Liu K, Chen Q, Liu Y, Zhou X, Wang X (2012) Isolation and biological activities of decanal, linalool, valencene, and octanal from sweet orange oil. J Food Res 77:C1156–C1161
  • Liu H, Cao X, Liu X, Xin R, Wang J, Gao J, Xu C, Zhang B, Grierson D, Chen K (2017) UV-B irradiation differentially regulates terpene synthases and terpene content of peach. Plant Cell Environ 40:2261–2275
  • Liu X, Yang J, Niu W, Jia W, Olaleye OE, Wen Q, Duan XN, Huang YH, Wang FQ, Du FF, Zhong CC, Li YF, Xu F, Gao Q, Li L, Li C (2018) Human pharmacokinetics of ginkgo terpene lactones and impact of carboxylation in blood on their platelet-activating factor antagonistic activity. Acta Pharmacol Sin 0:1–12
  • Lněničková K, Svobodová H, Skálová L, Ambrož M, Matoušková P (2017) The impact of sesquiterpenes β-caryophyllene oxide and transnerolidol on xenobiotic-metabolizing enzymes in mice in vivo. Xenobiotica 48:1089–1097
  • Lu L (2002) Study on effect of Cordyceps sinensis and artemisinin in preventing recurrence of lupus nephritis. Chin J Int Tradit West Med 22:169–171
  • Lynn Bissett D, Jewell-Motz EA (1999) Methods for regulating the condition of mammalian keratinous tissue. US6284802B1. US Patent
  • MacArtain P, Gill CIR, Brooks M, Campbell R, Rowland IR (2008) Nutritional value of edible seaweeds. Nutr Rev 65:535–543
  • Macleod AJ, De Troconis NG (1983) Aroma volatiles of aubergine (Solanum Melongena). Phytochemistry 22:2077–2079
  • MacLeod W, McFadden WH, Buigues NM (1966) Lemon oil analysis. II. Gas-liquid chromatography on a temperature-programmed, long open tubular column. J Food Sci 31:591–594
  • Mahmoud ZF, Kassem FF, Abdel-Salam NA, Zdero C (1986) Sesquiterpene lactones from Lactuca sativa. Phytochemistry 25:747–748
  • Malnoe A, Cavin C, Offord-Cavin E, Grigorov M (2004) Compositions against inflammatory processes. US 20040208944A1. US Application
  • Mao SC, Guo YW (2010) Sesquiterpenes from Chinese red alga Laurencia okamurai. Chin J Nat Med 8:321–325
  • Marete EN, Jacquier JC, O’Riordan D (2011) Feverfew as a source of bioactives for functional foods: storage stability in model beverages. J Funct Foods 3:38–43
  • Maries RJ, Pazos-Sanou L, Compadre CM, Pezzuto JM, Bloszyk E, Arnason JT (1995) Sesquiterpene lactones revisited. In: Amason JT, Mata JT, Romeo R (eds) Phytochemistry of medicinal plants. Springer, Boston, pp 333–356
  • Martin JD, Caballero P, Fernandez JJ, Norte M, Perez R, Rodriguez ML (1989) Metabolites from Laurencia obtusa. Phytochemistry 28:3365–3367
  • Maschek JA, Baker BJ (2008) The chemistry of algal secondary metabolism. In: Amsler CD (ed) Algal chemical ecology. Springer, Berlin/Heidelberg, pp 1–24
  • Matsuda H, Morikawa T, Ninomiya K, Yoshikawa M (2001) Absolute stereostructure of carabrane-type sesquiterpene and vasorelaxant-active sesquiterpenes from Zedoariae Rhizoma. Tetrahedron 57:8443–8453
  • Mattila P, Suonpää K, Piironen V (2000) Functional properties of edible mushrooms. Nutrition 16:694–696
  • Meding B (1983) Allergic contact dermatitis from artichoke, Cynara scolymus. Contact Dermat 9:314–314
  • Meng H, Yang Y, Li H (2018) Method for extracting volatile oil from fragrant scent for treating coronary heart disease. CN108379337A. Faming Zhuanli Shenqing
  • Meyer KD, Paul VJ (1995) Variation in secondary metabolite and aragonite concentrations in the tropical green seaweed Neomeris annulata: effects on herbivory by fishes. Mar Biol 122:537–545
  • Mizuno H, Usuki T (2018) Ionic liquid-assisted extraction and isolation of cynaropicrin and cnicin from artichoke and blessed thistle. Chem Sel 3:1781–1786
  • Montesano D, Rocchetti G, Putnik P, Lucini L (2018) Bioactive profile of pumpkin: an overview on terpenoids and their health-promoting properties. Curr Opin Food Sci 22:81–87
  • Morikawa T (2007) Search for bioactive constituents from several medicinal foods: hepatoprotective, antidiabetic, and antiallergic activities. J Nat Med 61:112–126
  • Morikawa T, Matsuda H, Ninomiya K, Yoshikawa M (2002) Medicinal Foodstuffs. XXIX. Potent protective effects of sesquiterpenes and curcumin from Zedoariae rhizoma on liver injury induced by D-Galactosamine/Lipopolysaccharide or tumor necrosis Factor-α. Biol Pharm Bull 25:627–631
  • Movahhedin N, Barar J, Azad FF, Barzegari A, Nazemiyeh H (2014) Phytochemistry and biologic activities of Caulerpa peltata native to Oman sea. Iran J Pharm Res 13:515–521
  • Muir AH, Robb R, McLaren M, Daly F, Belch JJ (2002) The use of Ginkgo biloba in Raynaud’s disease: a double-blind placebo-controlled trial. Vasc Med 7:265–267
  • Nabi N, Gaffar A, Lucchesi S, Afflitto JJ, Herles SM (1995) Oral compositions containing terpenoids for treatment of plaque and gingivitis. US5472684A. US Patent
  • Nagappan T, Vairappan CS (2014) Nutritional and bioactive properties of three edible species of green algae, genus Caulerpa (Caulerpaceae). J Appl Phycol 26:1019–1027
  • Nakatsu T, Lupo AT Jr, Chinn JW Jr, Kang RKL (2000) Biological activity of essential oils and their constituents. Stud Nat Prod Chem 21:571–631
  • Nakshatri H, Rice SE, Bhat-Nakshatri P (2004) Antitumor agent parthenolide reverses resistance of breast cancer cells to tumor necrosis factor-related apoptosis-inducing ligand through sustained activation of c-Jun N-terminal kinase. Oncogene 23:7330–7344
  • Nam JH, Nam D-Y, Lee D-U (2016) Valencene from the rhizomes of Cyperus rotundus inhibits skin photoaging-related ion channels and UV-induced melanogenesis in B16F10 melanoma cells. J Nat Prod 79:1091–1096
  • Nielsen PG, Carlé JS, Christophersen C (1982) Final structure of caulerpicin, a toxin mixture from the green alga Caulerpa racemosa. Phytochemistry 21:1643–1645
  • Nishimura H, Kondo Y, Nagasaka T, Satoh A (2000) Allelochemicals in chicory and utilization in processed foods. J Chem Ecol 26:2233–2241
  • Noldin VF, Cechinel Filho V, Monache FD, Benassi JC, Christmann IL, Pedrosa RC, Yunes RA (2003) Composição química e atividades biológicas das folhas de Cynara scolymus L. (alcachofra) cultivada no Brasil. Quim Nova 26:331–334
  • Noori S, Mahboob T (2009) Ameliorative effect of ethanolic extract of Cichorium intybus on cisplatin–induced nephrotoxicity in rats. Pak J Sci Ind Res 52:208–216
  • Okamoto Y, Nitanda N, Ojika M, Sakagami Y (2001) Aplysiallene, a new bromoallene as an Na, K-ATPase inhibitor from the sea hare, Aplysia kurodai. Biosci Biotechnol Biochem 65:474–476
  • Okuno Y, Marumoto S, Miyazawa M (2017) Comparison of essential oils from three kinds of Cryptotaenia japonica Hassk (kirimitsuba, nemitsuba, and itomitsuba) used in Japanese food. J Oleo Sci 66:1273–1276
  • Okwu DE, Emenike IN (2006) Evaluation of phytonutrients and vitamins content citrus fruits. Int J Molecular Med Adv Sci 2:1–6
  • Pallela R, Kim SK (2011) Impact of marine micro- and macroalgal consumption on photoprotection. In: Kim SK (ed) Advances in food and nutrition research. Academic, Waltham, pp 287–295
  • Paul VJ, Cronan JM Jr, Cardellina JH II. (1993) Isolation of new brominated sesquiterpene feeding deterrents from tropical green alga Neomeris annulata (Dasycladaceae: Chlorophyta). J Chem Ecol 19:1847–1860
  • Paulsen E (2017) Systemic allergic dermatitis caused by sesquiterpene lactones. Contact Dermatitis 76:1–10
  • Pechous SW, Whitaker BD (2004) Cloning and functional expression of an (E,E)-α-farnesene synthase cDNA from peel tissue of apple fruit. Planta 219:84–94
  • Peet RC, Justice B (2015) Low bitter chicory products. US9700070B2. US Patent
  • Peña-Espinoza M, Thamsborg SM, Desrues O, Hansen TVA, Enemark HL (2016) Anthelmintic effects of forage chicory (Cichorium intybus) against gastrointestinal nematode parasites in experimentally infected cattle. Parasitology 143:1279–1293
  • Pereira L (2015) Seaweed flora of the european north atlantic and mediterranean. In: Kim S (ed) Springer handbook of marine biotechnology. Springer, Heidelberg, pp 65–178
  • Pereira L (2016) Edible seaweeds of the world, 1st edn. CRC Press, Boca Raton
  • Perestrelo R, Silva C, Pereira J, Camara JS (2014) Healthy effects of bioactive metabolites from Vitis vinifera L. grapes: a review. In: Grapes. Nova Science Technology, New York, pp 305–338
  • Peters AM, Van Amerongen A (1996) Sesquiterpene lactones in chicory (Cichorium intybus L.): distribution in chicons and effect of storage. Food Res Int 29:439–444
  • Peters AM, Haagsma N, Van Amerongen A (1996) Monoclonal antibodies against the bitter sesquiterpene lactones, lactucin and lactucopicrin, from chicory (Cichorium intybus L.). Food Agric Immunol 8:147–156
  • Peters AM, Haagsma N, van Amerongen A (1997) A pilot study on the effects of cultivation conditions of chicory (Cichorium intybus L.) roots on the levels of sesquiterpene lactones in chicons. Z Lebensmittelunters Forschung A 205:143–147
  • Pharmacopeia US (2014) United States pharmacopoeia and national formulary (USP37-NF32). United States Pharmacopeial Convention, Inc., Rockville
  • Pinheiro BG, Silva ASB, Souza GEP, Figueiredo JG, Cunha FQ, Lahlou S, da Silva JKR, Maia JGS, Sousa PJC (2011) Chemical composition, antinociceptive and anti-inflammatory effects in rodents of the essential oil of Peperomia serpens. J Ethnopharmacol 138:479–486
  • Poli F, Sacchetti G, Tosi B, Fogagnolo M, Chillemi G, Lazzarin R, Bruni A (2002) Variation in the content of the main guaianolides and sugars in Cichorium intybus var. “Rosso di Chioggia” selections during cultivation. Food Chem 76:139–147
  • Rahman A, Al-Reza SM, Kang SC (2011) Antifungal activity of essential oil and extracts of Piper chaba hunter against phytopathogenic fungi. J Am Oil Chem Soc 88:573–579
  • Raj G, Chandrasekaran M, Jegan S, Venkatesalu V (2016) Phytochemical analysis and antifungal activity of Ulva species from the Kanniyakumari Gulf of Mannar, South Coast India. Nat Prod 12:1–17
  • Rajasree RS, Sibi PI, Francis F, William H (2016) Phytochemicals of cucurbitaceae family–a review. Int J Pharmacogn Phytochem Res 8:113–123
  • Rao YK, Wu ATH, Geethangili M, Huang MT, Chao WJ, Wu CH, Deng WP, Yeh CT, Tzeng YM (2011) Identification of antrocin from Antrodia camphorata as a selective and novel class of small molecule inhibitor of Akt/mTOR signaling in metastatic breast cancer MDA-MB-231 cells. Chem Res Toxicol 24:238–245
  • Rapparini F, Baraldi R, Facini O (2001) Seasonal variation of monoterpene emission from Malus domestica and Prunus avium. Phytochemistry 57:681–687
  • Rial C, Novaes P, Varela RM, Molinillo JMG, Macias FA (2014) Phytotoxicity of cardoon (Cynara cardunculus) allelochemicals on Standard Target Species and weeds. J Agric Food Chem 62:6699–6706
  • Rial C, García BF, Varela RM, Torres A, Molinillo JMG, Macías FA (2016) The joint action of sesquiterpene lactones from leaves as an explanation for the activity of Cynara cardunculus. J Agric Food Chem 64:6416–6424
  • Roeder E (1995) Medicinal-plants in europe containing pyrrolizidine alkaloids. Pharmazie 50:83–98
  • Rouphael Y, Bernardi J, Cardarelli M, Bernardo L, Kane D, Colla G, Lucini L (2016) Phenolic compounds and sesquiterpene lactones profile in leaves of nineteen artichoke cultivars. J Agric Food Chem 64:8540–8548
  • Sádecká J, Polovka M, Kolek E, Belajová E, Tobolková B, Daško ĽU, Durec JÁN (2014) Orange juice with pulp: impact of pasteurization and storage on flavour, polyphenols, ascorbic acid and antioxidant activity. J Food Nut Res 53:371–388
  • Santhanasabapathy R, Sudhandiran G, (2015) Farnesol attenuates lipopolysaccharide-induced neurodegeneration in Swiss albino mice by regulating intrinsic apoptotic cascade. Brain Research 1620:42–56
  • Sayyah M, Hadidi N, Kamalinejad M (2004) Analgesic and anti-inflammatory activity of Lactuca sativa seed extract in rats. J Ethnopharmacol 92:325–329
  • Scavo A, Restuccia A, Pandino G, Onofri A, Mauromicale G (2018) Allelopathic effects of Cynara cardunculus L. leaf aqueous extracts on seed germination of some Mediterranean weed species. Ital J Agron 11:119–125
  • Schapowal A (2002) Randomised controlled trial of butterbur and cetirizine for treating seasonal allergic rhinitis. Br Med J 324:1–4
  • Schmidt TJ (1999) Quantitative structure-cytotoxicity relationships within a series of helenanolide type sesquiterpene lactones. Pharmaceutical Pharmacol Lett 9:9–13
  • Schmidt TJ, Heilmann J (2002) Quantitative structure-cytotoxicity relationships of sesquiterpene lactones derived from partial charge (Q)-based fractional accessible surface area descriptors (Q_frASAs). Quant Struct Act Relat 21:276–287
  • Schmidt TJ, Lyß G, Pahl HL, Merfort I (1999) Helenanolide type sesquiterpene lactones. Part 5: the role of glutathione addition under physiological conditions. Bioorg Med Chem 7:2849–2855
  • Schmidt BM, Ilic N, Poulev A, Raskin I (2007) Toxicological evaluation of a chicory root extract. Food Chem Toxicol 45:1131–1139
  • Sessa RA, Bennett MH, Lewis MJ, Mansfield JW, Beale MH (2000) Metabolite profiling of sesquiterpene lactones from Lactuca species major latex components are novel oxalate and sulfate conjugates of lactucin and its derivatives. J Biol Chem 275:26877–26884
  • Sharon-asa L, Shalit M, Frydman A, Bar E, Holland D, Or E, Lavi U, Lewinsohn E, Eyai J (2003) Citrus fruit flavor and aroma biosynthesis: isolation, functional characterization, and developmental regulation of Cstps1, a key gene in the production of the sesquiterpene aroma compound valencene. Plant J 36:664–674
  • Shaza M (2014) Phytochemical and biological properties of sesquiterpene constituents from the marine red seaweed Laurencia: a Review. Nat Prod Chem Res 2:1–13
  • Shim HC (2001) Hair treatment composition containing loess, artemesia, brown algae and pine juices. US6254858B1. United States Patent
  • Shimoda H, Tanaka J, Yamada E, Morikawa T, Kasajima N, Yoshikawa M (2006) Anti type I allergic property of Japanese butterbur extract and its mast cell degranulation inhibitory ingredients. J Agric Food Chem 54:2915–2920
  • Si L, Chen Y, Han X, Zhan Z, Tian S, Cui Q, Wang Y (2012) Chemical composition of essential oils of Litsea cubeba harvested from its distribution areas in China. Molecules 17:7057–7066
  • Siah Ku C, Pham TX, Park Y, Kim B, Shin M, Kang I, Jiyoung L (2013) Edible blue-green algae reduce the production of pro-inflammatory cytokines by inhibiting NF-κB pathway in macrophages and splenocytes. Biochim Biophys Acta 1830:2981–2988
  • Siedle B, Gustavsson L, Johansson S, Murillo R, Castro V, Bohlin L, Merfort I (2003) The effect of sesquiterpene lactones on the release of human neutrophil elastase. Biochem Pharmacol 65:897–903
  • Sims JJ, Donnell MS, Leary JV, Lacy GH (1975) Antimicrobial agents from marine algae. Antimicrob Agents Chemother 7:320–321
  • Singh NP, Panwar VK (2006) Case report of a pituitary macroadenoma treated with artemether. Integr Cancer Ther 5:391–394
  • Singh NP, Verma KB (2002) Case report of a laryngeal squamous cell carcinoma treated with artesunate. Arch Oncol 10:279–280
  • Smit AJ (2004) Medicinal and pharmaceutical uses of seaweed natural products: a review. J Appl Phycol 16:245–262
  • Sowden RJ, Yasmin S, Rees NH, Bell SG, Wong L (2005) Biotransformation of the sesquiterpene (+)-valencene by cytochrome P450. Org Biomol Chem 3:57–64
  • ŠpicákovᡠA, Szotáková B, Dimunová D, Myslivecková Z, Ambrož M (2017) Nerolidol and farnesol inhibit some cytochrome P450 activities but did not affect other xenobiotic-metabolizing enzymes in rat and human hepatic subcellular fractions. Molecules 22:1–11
  • Stegelmeier BL, Edgar JA, Colegate SM, Gardner DR, Schoch TK, Coulombe RA, Molyneux RJ (1999) Pyrrolizidine alkaloid plants, metabolism and toxicity. J Nat Toxins 8:95–116
  • Stoessl A, Stothers J, Ward EW (1975) The structures of some stress metabolites from Solanum melongena. Can J Chem 53:3351–3358
  • Summer H, Salan U, Knight DW, Hoult JRS (1992) Inhibition of 5-lipoxygenase and cyclo-oxygenase in leukocytes by feverfew: involvement of sesquiterpene lactones and other components. Biochem Pharmacol 43:2313–2320
  • Sun J, Shi D, Ma M, Li S, Wang S, Han L, Yang Y, Fan X, Shi Y, He L (2005) Sesquiterpenes from the red alga Laurencia tristicha. J Nat Prod 68:915–919
  • Sutherland A, Sweet BV (2010) Butterbur: an alternative therapy for migraine prevention. Am J Health Syst Pharm 67:705–711
  • Sweeney B, Vora M, Ulbricht C, Basch E (2005) Evidence-based systematic review of dandelion (Taraxacum officinale) by natural standard research collaboration. J Herb Pharmacother 5:79–93
  • Thomet OA, Wiesmann UN, Schapowal A, Bizer C, Simon H-U (2001) Role of petasin in the potential anti-inflammatory activity of a plant extract of Petasites hybridus. Biochem Pharmacol 61:1041–1047
  • Tracanna M, Catalan CA, Bach H (2012) Chemical composition, antimicrobial and antioxidant properties of the volatile oil and methanol extract of Xenophyllum poposum. Nat Prod Commun 7:1663–1666
  • Tzeng YM, Yang TS, Yeh CT (2012) Antrocin containing pharmaceutical compositions for inhibiting cancer cells. US 2012/0100175 A1. US Patent
  • Usami A, Ono T, Kashima Y, Nakahashi H, Marumoto S, Nosaka S, Watanabe S, Miyazawa M (2014) Comparison of Agitake (Pleurotus eryngii var. ferulae) volatile components with characteristic odors extracted by hydrodistillation and solvent-assisted flavor evaporation. J Oleo Sci 63:83–92
  • Vairappan CS (2003) Potent antibacterial activity of halogenated metabolites from Malaysian red algae, Laurencia majuscula (Rhodomelaceae, Ceramiales). Biomol Eng 20:255–259
  • Vairappan CS, Suzuki M, Abe T, Masuda M (2001) Halogenated metabolites with antibacterial activity from the Okinawan Laurencia species. Phytochemistry 58:517–523
  • van der Hoeven RS (2000) Genetic control and evolution of sesquiterpene biosynthesis in Lycopersicon esculentum and L. hirsutum. Plant Cell Online 12:2283–2294
  • van Hulssen CJ, Koolhaas DR (2010) The essential oils from Litsea Cubeba Pers. Recueil Des Travaux Chimiques Des Pays-Bas 59:105–110
  • Vidal JP, Laurent D, Kabore SA, Rechencq E, Boucard M, Girard JP, Escale JC, Rossi JC (1984) Caulerpin, Caulerpicin, Caulerpa scalpelliformis: comparative acute toxicity study. Bot Mar 27:533–537
  • Wagner S, Kratz F, Merfort I (2004) In vitro Behaviour of sesquiterpene lactones and sesquiterpene lactone-containing plant preparations in human blood, plasma and human serum albumin solutions. Planta Med 70:227–233
  • Wang Q, Cui J (2011) Perspectives and utilization technologies of chicory (Cichorium intybus L.): a review. Afr J Biotechnol 10:1966–1977
  • Wang H, Liu Y (2010) Chemical composition and antibacterial activity of essential oils from different parts of Litsea cubeba. Chem Biodivers 7:229–235
  • Wang Y, Wang M, Xu M, Li T, Fan K, Yan T, Xiao F (2018) Nootkatone, a neuroprotective agent from Alpiniae Oxyphyllae Fructus, improves cognitive impairment in lipopolysaccharide-induced mouse model of Alzheimer’s disease. Int Immunopharmacol 62:77–85
  • Wani BA, Bodha RH, Wani AH (2010) Nutritional and medicinal importance of mushrooms. J Med Plant Res 4:2598–2604
  • Wattenberg LW (1991) Inhibition of azoxymethane-induced neoplasia of the large bowel by 3-hydroxy-3,7,11-trimethyl-1,6,10-dodecatriene (nerolidol). Carcinogenesis 12:151–152
  • Weng-Keong C, Loh Teng-Hern T, Kok-Gan C, Learn-Han L, Bey-Hing G (2016) Nerolidol: a sesquiterpene alcohol with multi-faceted pharmacological and biological activities. Molecules 21:529
  • Willeman H, Hance P, Fertin A, Voedts N, Duhal N, Goossens J-F, Hilbert J-L (2014) A method for the simultaneous determination of chlorogenic acid and sesquiterpene lactone content in industrial chicory root foodstuffs. Sci World J 2014:1–11
  • Wirngo FE, Lambert MN, Jeppesen PB (2016) The physiological effects of dandelion (Taraxacum Officinale) in type 2 diabetes. Rev Diabet Stud 13:113–131
  • Won Y-K, Ong C-N, Shi X, Shen H-M (2004) Chemopreventive activity of parthenolide against UVB-induced skin cancer and its mechanisms. Carcinogenesis 25:1449–1458
  • Wulfkuehler S, Gras C, Carle R (2013) Sesquiterpene lactone content and overall quality of fresh-cut witloof chicory (Cichorium intybus L. Var. foliosum hegi) as affected by different washing procedures. J Agric Food Chem 61:7705–7714
  • Wulfkuehler S, Dietz J, Schmidt H, Weiss A, Carle R (2015) Quality of fresh-cut radicchio cv. Rosso di Chioggia (Cichorium intybus L. var. foliosum Hegi) as affected by water jet cutting and different washing procedures. Eur Food Res Technol 240:159–172
  • Yan F, Bengtsson M, Makranczy G, Löfqvist J (2003) Roles of α-farnesene in the behaviors of codling moth females. Z Zeitschrift Naturforschung C 58:113–118
  • Yang T-S, Liou M-L, Hu T-F, Peng C-W, Liu T-T (2013) Antimicrobial activity of the essential oil of Litsea cubeba on cariogenic bacteria. J Essent Oil Res 25:120–128
  • Yang C, Chen H, Chen H, Zhong B, Luo X, Chun J (2017) Antioxidant and anticancer activities of essential oil from Gannan navel orange peel. Molecules 22:1391
  • Yoshikawa M, Morikawa T, Junji Tanaka HS (2006) Medicinal foodstuffs. XXXII. Novel sesquiterpene glycoside sulfate, fukinoside A, with antiallergic activity from Japanese Butterbur (Petasites japonicus). Heterocycles 68:2335–2342
  • Yu F, Utsumi R (2009) Diversity, regulation, and genetic manipulation of plant mono- and sesquiterpenoid biosynthesis. Cell Mol Life Sci 66:3043–3052
  • Zeng Q, Ma C, Zhou L (2016) Method for synthesizing trans, trans-farnesol. CN105859524A. Faming Zhuanli Shenqing
  • Zengion AH, Yarnell E (2011) Herbal and nutritional supplements for painful conditions. Pain Proced Clin Pract 20:187–204
  • Zhang ZY, Yu SQ, Miao LY, Huang XY, Zhang XP, Zhu YP, Xia XH, Li DQ (2008) Artesunate combined with vinorelbine plus cisplatin in treatment of advanced non-small cell lung cancer: a randomized controlled trial. J Chin Integr Med 6:134–138
  • Zhao M, Matter K, Laissue JA, Zimmermann A (1996) Copper/zinc and manganese superoxide dismutase in alcoholic liver disease: immunohistochemical quantitation. Histol Histopathol 11:899–907
  • Zouari N, Abid M, Fakhfakh N, Ayadi MA, Zorgui L, Ayadi M, Attia H (2011) Blue-green algae (Arthrospira platensis) as an ingredient in pasta: free radical scavenging activity, sensory and cooking characteristics evaluation. Int J Food Sci Nutr 62:811–813