Afendi FM, Okada T, Yamazaki M, Hirai-Morita A, Nakamura Y, Nakamura K, Ikeda S, Takahashi H, Altaf-Ul-Amin M, Darusman LK, Saito K, Kanaya S (2012) KNApSAcK family databases: integrated metabolite-plant species databases for multifaceted plant research. Plant Cell Physiol 53(2):e1. doi:10.1093/pcp/pcr165
Ahmed T, Javed S, Tariq A, Budzyńska B, D'Onofrio G, Daglia M, Nabavi SF, Nabavi SM (2017) Daidzein and its Effects on Brain. Curr Med Chem 24(4):365–375. doi:10.2174/0929867323666161101140214
Al-Shatti AH, Redha A, Suleman P, Al-Hasan R (2014) The allelopathic potential of Conocarpus lancifolius (Engl.) leaves on dicot (Vigna sinensis L.), Monocot (Zea mays L.) and soil-Borne pathogenic fungi. American Journal of Plant Sciences 5(19):2889–2903. doi:10.4236/ajps.2014.519304
Aulakh MS, Wassmann R, Bueno C, Kreuzwieser J, Rennenberg H (2001) Characterization of Root Exudates at Different Growth Stages of Ten Rice (Oryza sativa L.) Cultivars. Plant Biol 3(2):139–148. doi:10.1055/s-2001-12905
Ayaz M, Sadiq A, Junaid M, Ullah F, Ovais M, Ullah I, Ahmed J, Shahid M (2019) Flavonoids as Prospective Neuroprotectants and Their Therapeutic Propensity in Aging Associated Neurological Disorders. Frontiers in Aging Neuroscience 11 (155). doi:10.3389/fnagi.2019.00155
Brauchli J, Lüthy J, Zweifel U, Schlatter C (1982) Pyrrolizidine alkaloids fromSymphytum officinale L. and their percutaneous absorption in rats. Experientia 38(9):1085–1087. doi:10.1007/BF01955382
Brown AW, Stegelmeier BL, Colegate SM, Gardner DR, Panter KE, Knoppel EL, Hall JO (2016) The comparative toxicity of a reduced, crude comfrey (Symphytum officinale) alkaloid extract and the pure, comfrey-derived pyrrolizidine alkaloids, lycopsamine and intermedine in chicks (Gallus gallus domesticus). J Appl Toxicol 36(5):716–725. doi:10.1002/jat.3205
Clauson-Kaas F, Ramwell C, Hansen HCB, Strobel BW (2016) Ptaquiloside from bracken in stream water at base flow and during storm events. Water Res 106:155–162. doi:https://doi.org/10.1016/j.watres.2016.09.049
Derosa G, Maffioli P, Sahebkar A (2016) Piperine and Its Role in Chronic Diseases. Adv Exp Med Biol 928:173–184. doi:10.1007/978-3-319-41334-1_8
Ehmke A, von Borstel K, Hartmann T (1988) Alkaloid N-oxides as transport and vacuolar storage compounds of pyrrolizidine alkaloids in Senecio vulgaris L. Planta 176(1):83–90. doi:10.1007/bf00392483
Fletcher MT, Netzel G (2020) Food Safety and Natural Toxins. Toxins (Basel) 12(4):236. doi:10.3390/toxins12040236
Forsyth CS, Frank AA (1993) Evaluation of developmental toxicity of coniine to rats and rabbits. Teratology 48(1):59–64. doi:10.1002/tera.1420480110
Frank M, Weckman TJ, Wood T, Woods WE, Tai CL, Chang SL, Ewing A, Blake JW, Tobin T (1990) Hordenine: pharmacology, pharmacokinetics and behavioural effects in the horse. Equine Vet J 22(6):437–441. doi:10.1111/j.2042-3306.1990.tb04312.x
Gomez E, Ledbetter CA, Hartsell PL (1993) Volatile compounds in apricot, plum, and their interspecific hybrids. J Agric Food Chem 41(10):1669–1676. doi:10.1021/jf00034a029
Griffiths M, Strobel BW, Hama J, Cedergreen N (2020) Toxicity and Risk of Plant-Produced Alkaloids to Daphnia magna Environmental Sciences Europe (submitted)
Günthardt BF, Hollender J, Hungerbühler K, Scheringer M, Bucheli TD (2018) Comprehensive Toxic Plants-Phytotoxins Database and Its Application in Assessing Aquatic Micropollution Potential. J Agric Food Chem 66(29):7577–7588. doi:10.1021/acs.jafc.8b01639
Günthardt BF, Schönsee CD, Hollender J, Hungerbühler K, Scheringer M, Bucheli TD (2020) "Is there anybody else out there?" - First Insights from a Suspect Screening for Phytotoxins in Surface Water. Chimia 74(3):129–135. doi:10.2533/chimia.2020.129
Haas JS, Stolz ED, Betti AH, Stein AC, Schripsema J, Poser GL, Rates SM (2011) The anti-immobility effect of hyperoside on the forced swimming test in rats is mediated by the D2-like receptors activation. Planta Med 77(4):334–339. doi:10.1055/s-0030-1250386
Hama JR, Strobel BW (2019) Pyrrolizidine alkaloids quantified in soil and water using UPLC-MS/MS. RSC Advances 9(52):30350–30357. doi:10.1039/C9RA05301H
Hama JR, Strobel BW (2020) Occurrence of pyrrolizidine alkaloids in ragwort plants, soils and surface waters at the field scale in grassland. Science of The Total Environment:142822. doi:https://doi.org/10.1016/j.scitotenv.2020.142822
Harborne JB, Baxter H (1999) The Handbook of Natural Flavonoids. Wiley
Hernandez MF, Falé PLV, Araújo MEM, Serralheiro MLM (2010) Acetylcholinesterase inhibition and antioxidant activity of the water extracts of several Hypericum species. Food Chem 120(4):1076–1082. doi:https://doi.org/10.1016/j.foodchem.2009.11.055
Hoerger CC, Schenzel J, Strobel BW, Bucheli TD (2009a) Analysis of selected phytotoxins and mycotoxins in environmental samples. Anal Bioanal Chem 395(5):1261–1289. doi:10.1007/s00216-009-3088-y
Hoerger CC, Wettstein FE, Hungerbühler K, Bucheli TD (2009b) Occurrence and Origin of Estrogenic Isoflavones in Swiss River Waters. Environmental Science Technology 43(16):6151–6157. doi:10.1021/es901034u
Holman JD, Tabb DL, Mallick P (2014) Employing ProteoWizard to Convert Raw Mass Spectrometry Data. Curr Protoc Bioinformatics 46:13.24.11–19. doi:10.1002/0471250953.bi1324s46
Hostettmann K, Borloz A, Urbain A, Marston A (2006) Natural Product Inhibitors of Acetylcholinesterase. Curr Org Chem 10(8):825–847. doi:10.2174/138527206776894410
Hotti H, Rischer H (2017) The killer of Socrates: Coniine and Related Alkaloids in the Plant Kingdom. Molecules 22 (11). doi:10.3390/molecules22111962
Hotti H, Seppänen-Laakso T, Arvas M, Teeri TH, Rischer H (2015) Polyketide synthases from poison hemlock (Conium maculatum L.). Febs j 282(21):4141–4156. doi:10.1111/febs.13410
Hoult AH, Lovett JV (1993) Biologically active secondary metabolites of barley. III. A method for identification and quantification of hordenine and gramine in barley by high-performance liquid chromatography. J Chem Ecol 19(10):2245–2254. doi:10.1007/bf00979661
Huang J-L, Fu S-T, Jiang Y-Y, Cao Y-B, Guo M-L, Wang Y, Xu Z (2007) Protective effects of Nicotiflorin on reducing memory dysfunction, energy metabolism failure and oxidative stress in multi-infarct dementia model rats. Pharmacology Biochemistry Behavior 86(4):741–748. doi:https://doi.org/10.1016/j.pbb.2007.03.003
Isah T (2019) Stress and defense responses in plant secondary metabolites production. Biol Res 52(1):39. doi:10.1186/s40659-019-0246-3
Jensen PH, Pedersen RB, Svensmark B, Strobel BW, Jacobsen OS, Hansen HC (2009) Degradation of the potato glycoalkaloid alpha-solanine in three agricultural soils. Chemosphere 76(8):1150–1155. doi:10.1016/j.chemosphere.2009.04.008
Katajamaa M, Oresic M (2005) Processing methods for differential analysis of LC/MS profile data. BMC Bioinformatics 6:179. doi:10.1186/1471-2105-6-179
Khan H, Marya, Amin S, Kamal MA, Patel S (2018) Flavonoids as acetylcholinesterase inhibitors: Current therapeutic standing and future prospects. Biomed Pharmacother 101:860–870. doi:10.1016/j.biopha.2018.03.007
Kim SC, Lee JH, Kim MH, Lee JA, Kim YB, Jung E, Kim YS, Lee J, Park D (2013) Hordenine, a single compound produced during barley germination, inhibits melanogenesis in human melanocytes. Food Chem 141(1):174–181. doi:10.1016/j.foodchem.2013.03.017
Kolpin DW, Hoerger CC, Meyer MT, Wettstein FE, Hubbard LE, Bucheli TD (2010) Phytoestrogens and Mycotoxins in Iowa Streams: An Examination of Underinvestigated Compounds in Agricultural Basins. J Environ Qual 39(6):2089–2099. doi:10.2134/jeq2010.0121
König M, Escher BI, Neale PA, Krauss M, Hilscherová K, Novák J, Teodorović I, Schulze T, Seidensticker S, Kamal Hashmi MA, Ahlheim J, Brack W (2017) Impact of untreated wastewater on a major European river evaluated with a combination of in vitro bioassays and chemical analysis. Environmental Pollution 220 Part B:1220–1230. doi:http://dx.doi.org/10.1016/j.envpol.2016.11.011
Lake BG (1999) Coumarin Metabolism, Toxicity and Carcinogenicity: Relevance for Human Risk Assessment. Food Chem Toxicol 37(4):423–453. doi:https://doi.org/10.1016/S0278-6915(99)00010-1
Lamartiniere CA, Wang J, Smith-Johnson M, Eltoum IE (2002) Daidzein: bioavailability, potential for reproductive toxicity, and breast cancer chemoprevention in female rats. Toxicol Sci 65(2):228–238. doi:10.1093/toxsci/65.2.228
Liu M, Yanagihara N, Toyohira Y, Tsutsui M, Ueno S, Shinohara Y (2007) Dual effects of daidzein, a soy isoflavone, on catecholamine synthesis and secretion in cultured bovine adrenal medullary cells. Endocrinology 148(11):5348–5354. doi:10.1210/en.2007-0073
López TA, Cid MS, Bianchini ML (1999) Biochemistry of hemlock (Conium maculatum L.) alkaloids and their acute and chronic toxicity in livestock. A review. Toxicon 37(6):841–865. doi:https://doi.org/10.1016/S0041-0101(98)00204-9
Mei N, Guo L, Fu PP, Fuscoe JC, Luan Y, Chen T (2010) Metabolism, genotoxicity, and carcinogenicity of comfrey. J Toxicol Environ Health B Crit Rev 13(7–8):509–526. doi:10.1080/10937404.2010.509013
Miean KH, Mohamed S (2001) Flavonoid (Myricetin, Quercetin, Kaempferol, Luteolin, and Apigenin) Content of Edible Tropical Plants. J Agric Food Chem 49(6):3106–3112. doi:10.1021/jf000892m
Miyazawa M, Kawata J (2006) Identification of the main aroma compounds in dried seeds of Brassica hirta. J Nat Med 60(1):89–92. doi:10.1007/s11418-005-0009-z
Müller E, Huber C, Beckers LM, Brack W, Krauss M, Schulze T (2020) A Data Set of 255,000 Randomly Selected and Manually Classified Extracted Ion Chromatograms for Evaluation of Peak Detection Methods. Metabolites 10 (4). doi:10.3390/metabo10040162
Nakamura K, Shimura N, Otabe Y, Hirai-Morita A, Nakamura Y, Ono N, Ul-Amin MA, Kanaya S (2013) KNApSAcK-3D: a three-dimensional structure database of plant metabolites. Plant Cell Physiol 54(2):e4. doi:10.1093/pcp/pcs186
Nanusha MY, Krauss M, Brack W (2020a) Non-target screening for detecting the occurrence of plant metabolites in river waters. Environmental Sciences Europe 32(1):130. doi:10.1186/s12302-020-00415-5
Nanusha MY, Krauss M, Schönsee CD, Günthardt BF, Bucheli TD, Brack W (2020b) Target screening of plant secondary metabolites in river waters by liquid chromatography coupled to high-resolution mass spectrometry (LC–HRMS). Environmental Sciences Europe 32(1):142. doi:10.1186/s12302-020-00399-2
Neuman MG, Cohen L, Opris M, Nanau RM, Hyunjin J (2015) Hepatotoxicity of Pyrrolizidine Alkaloids. J Pharm Pharm Sci 18(4):825–843. doi:10.18433/j3bg7j
Piyachaturawat P, Glinsukon T, Toskulkao C (1983) Acute and subacute toxicity of piperine in mice, rats and hamsters. Toxicol Lett 16(3–4):351–359. doi:10.1016/0378-4274(83)90198-4
Pluskal T, Castillo S, Villar-Briones A, Orešič M (2010) MZmine 2: Modular framework for processing, visualizing, and analyzing mass spectrometry-based molecular profile data. BMC Bioinformatics 11(1):395. doi:10.1186/1471-2105-11-395
Puri B, Hall A, Baxter H, Harborne JB, Moss GP (1998) Phytochemical Dictionary: A Handbook of Bioactive Compounds from Plants, Second Edition. CRC Press
Rosenmeier L, Kjær ED, Nielsen LR (2013) The Scotch broom, Cytisus scoparius (Fabaceae), a paradox in Denmark – an invasive plant or endangered native species? Bot J Linn Soc 171(2):429–440. doi:10.1111/j.1095-8339.2012.01319.x
Salehi B, Sharopov F, Boyunegmez Tumer T, Ozleyen A, Rodríguez-Pérez C, Ezzat SM, Azzini E, Hosseinabadi T, Butnariu M, Sarac I, Bostan C, Acharya K, Sen S, Nur Kasapoglu K, Daşkaya-Dikmen C, Özçelik B, Baghalpour N, Sharifi-Rad J, Fokou VT, Cho P, Martins WC N (2019) Symphytum Species: A Comprehensive Review on Chemical Composition, Food Applications and Phytopharmacology. Molecules 24(12):2272. doi:10.3390/molecules24122272
Schlatter J, Zimmerli B, Dick R, Panizzon R, Schlatter C (1991a) Dietary intake and risk assessment of phototoxic furocoumarins in humans. Food Chem Toxicol 29(8):523–530. doi:https://doi.org/10.1016/0278-6915(91)90044-8
Schlatter J, Zimmerli B, Dick R, Panizzon R, Schlatter C (1991b) Dietary intake and risk assessment of phototoxic furocoumarins in humans. Food Chem Toxicol 29(8):523–530. doi:10.1016/0278-6915(91)90044-8
Schmeller T, Sauerwein M, Sporer F, Wink M, Müller WE (1994) Binding of Quinolizidine Alkaloids to Nicotinic and Muscarinic Acetylcholine Receptors. J Nat Prod 57(9):1316–1319. doi:10.1021/np50111a026
Schnabel A, Cotinguiba F, Athmer B, Yang C, Westermann B, Schaks A, Porzel A, Brandt W, Schumacher F, Vogt T (2020) A piperic acid CoA ligase produces a putative precursor of piperine, the pungent principle from black pepper fruits. Plant J 102(3):569–581. doi:10.1111/tpj.14652
Schönsee CD, Bucheli TD (2020) Experimental Determination of Octanol–Water Partition Coefficients of Selected Natural Toxins. Journal of Chemical Engineering Data 65(4):1946–1953. doi:10.1021/acs.jced.9b01129
Schulze T, Ahel M, Ahlheim J, Aït-Aïssa S, Brion F, Di Paolo C, Froment J, Hidasi AO, Hollender J, Hollert H, Hu M, Kloß A, Koprivica S, Krauss M, Muz M, Oswald P, Petre M, Schollée JE, Seiler T-B, Shao Y, Slobodnik J, Sonavane M, Suter MJF, Tollefsen KE, Tousova Z, Walz K-H, Brack W (2017) Assessment of a novel device for onsite integrative large-volume solid phase extraction of water samples to enable a comprehensive chemical and effect-based analysis. Science of The Total Environment 581–582:350–358. doi:https://doi.org/10.1016/j.scitotenv.2016.12.140
Shinbo Y, Nakamura Y, Altaf-Ul-Amin M, Asahi H, Kurokawa K, Arita M, Saito K, Ohta D, Shibata D, Kanaya S (2006) KNApSAcK: A Comprehensive Species-Metabolite Relationship Database. In: Saito K, Dixon RA, Willmitzer L (eds) Plant Metabolomics. Springer Berlin Heidelberg, Berlin, pp 165–181. doi:10.1007/3-540-29782-0_13
Shoba G, Joy D, Joseph T, Majeed M, Rajendran R, Srinivas PSSR (1998) Influence of Piperine on the Pharmacokinetics of Curcumin in Animals and Human Volunteers. Planta Med 64(04):353–356. doi:10.1055/s-2006-957450
Tahirovic I, Rimpapa Z, Cavar S, Huseinovic S, Muradic S, Salihovic M, Sofic E (2010) Content of some phenolic acids and rutin in the leaves and roots of Symphytum officinale L. Planta Med 76(12):P293. doi:10.1055/s-0030-1264591
US-EPA (2011) 40 CFR Part 136, Appendix B to Part 136 - Definition and Procedure for the Determination of the Method Detection Limit-Revision 1.11. 40
USA-ATSDR (2018) Toxicological profile for isophorone.. Agency for Toxic Substances and Disease Registry (ATSDR), Atlanta, GA
Välitalo P, Massei R, Heiskanen I, Behnisch P, Brack W, Tindall AJ, Du Pasquier D, Küster E, Mikola A, Schulze T, Sillanpää M (2017) Effect-based assessment of toxicity removal during wastewater treatment. Water Res 126:153–163. doi:https://doi.org/10.1016/j.watres.2017.09.014
van Egmond HP (2004) Natural toxins: risks, regulations and the analytical situation in Europe. Anal Bioanal Chem 378(5):1152–1160. doi:10.1007/s00216-003-2373-4
Vila-Nova NS, Morais SM, Falcão MJC, Bevilaqua CML, Rondon FCM, Wilson ME, Vieira IGP, Andrade HF (2012) Leishmanicidal and cholinesterase inhibiting activities of phenolic compounds of Dimorphandra gardneriana and Platymiscium floribundum, native plants from Caatinga biome. Pesquisa Veterinária Brasileira 32:1164–1168
Villalpando-Vargas F, Medina-Ceja L (2016) Sparteine as an anticonvulsant drug: Evidence and possible mechanism of action. Seizure 39:49–55. doi:https://doi.org/10.1016/j.seizure.2016.05.010
Walter JF, Gange RW, Mendelson IR (1982) Psoralen-containing sunscreen induces phototoxicity and epidermal ornithine decarboxylase activity. J Am Acad Dermatol 6(6):1022–1027. doi:10.1016/s0190-9622(82)70086-6
Wang L, Yue Z, Guo M, Fang L, Bai L, Li X, Tao Y, Wang S, Liu Q, Zhi D, Zhao H (2016) Dietary Flavonoid Hyperoside Induces Apoptosis of Activated Human LX-2 Hepatic Stellate Cell by Suppressing Canonical NF-κB Signaling. Biomed Res Int 2016:1068528. doi:10.1155/2016/1068528
Wang X, Liu Y, Xiao L, Li L, Zhao X, Yang L, Chen N, Gao L, Zhang J (2018) Hyperoside Protects Against Pressure Overload-Induced Cardiac Remodeling via the AKT Signaling Pathway. Cell Physiol Biochem 51(2):827–841. doi:10.1159/000495368
Whang WK, Park HS, Ham I, Oh M, Namkoong H, Kim HK, Hwang DW, Hur SY, Kim TE, Park YG, Kim JR, Kim JW (2005) Natural compounds, fraxin and chemicals structurally related to fraxin protect cells from oxidative stress. Exp Mol Med 37(5):436–446. doi:DOI 10.1038/emm.2005.54
Wiedenfeld H (2011) Plants containing pyrrolizidine alkaloids: toxicity and problems. Food Additives Contaminants: Part A 28:282–292
Witaicenis A, Seito LN, Di Stasi LC (2010) Intestinal anti-inflammatory activity of esculetin and 4-methylesculetin in the trinitrobenzenesulphonic acid model of rat colitis. Chem Biol Interact 186(2):211–218. doi:10.1016/j.cbi.2010.03.045
Yaber Grass MA, Leicach SR (2012) Changes in Senecio grisebachii pyrrolizidine alkaloids abundances and profiles as response to soil quality. J Plant Interact 7(2):175–182. doi:10.1080/17429145.2011.591504
Yang L, Wen K-S, Ruan X, Zhao Y-X, Wei F, Wang Q (2018) Response of Plant Secondary Metabolites to Environmental Factors. Molecules 23(4):762. doi:10.3390/molecules23040762
Zhang N, Liu J, Chen Z, Dou W (2019) In vitro inhibitory effects of kaempferitrin on human liver cytochrome P450 enzymes. Pharm Biol 57(1):571–576. doi:10.1080/13880209.2019.1656257
Zwart N, Nio SL, Houtman CJ, de Boer J, Kool J, Hamers T, Lamoree MH (2018) High-Throughput Effect-Directed Analysis Using Downscaled in Vitro Reporter Gene Assays To Identify Endocrine Disruptors in Surface Water. Environ Sci Technol 52(7):4367–4377. doi:10.1021/acs.est.7b06604