{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,12]],"date-time":"2026-10-12T02:11:30Z","timestamp":1791771090495,"version":"4.3.4"},"reference-count":109,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2021,1,30]],"date-time":"2021-01-30T00:00:00Z","timestamp":1611964800000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Cyanogenic glycosides are an important and widespread class of plant natural products, which are however structurally less diverse than many other classes of natural products. So far, 112 naturally occurring cyanogenic glycosides have been described in the phytochemical literature. Currently, these unique compounds have been reported from more than 2500 plant species. Natural cyanogenic glycosides show variations regarding both the aglycone and the sugar part of the molecules. The predominant sugar moiety is glucose but many substitution patterns of this glucose moiety exist in nature. Regarding the aglycone moiety, four different basic classes can be distinguished, aliphatic, cyclic, aromatic, and heterocyclic aglycones. Our overview covers all cyanogenic glycosides isolated from plants and includes 33 compounds with a non-cyclic aglycone, 20 cyclopentane derivatives, 55 natural products with an aromatic aglycone, and four dihydropyridone derivatives. In the following sections, we will provide an overview about the chemical diversity known so far and mention the first source from which the respective compounds had been isolated. This review will serve as a first reference for researchers trying to find new cyanogenic glycosides and highlights some gaps in the knowledge about the exact structures of already described compounds.<\/jats:p>","DOI":"10.3390\/molecules26030719","type":"journal-article","created":{"date-parts":[[2021,1,30]],"date-time":"2021-01-30T06:22:20Z","timestamp":1611987740000},"page":"719","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":101,"title":["Chemical Diversity of Plant Cyanogenic Glycosides: An Overview of Reported Natural Products"],"prefix":"10.3390","volume":"26","author":[{"given":"Meri","family":"Yulvianti","sequence":"first","affiliation":[{"name":"Department of Pharmaceutical Biology, Christian-Albrechts-University of Kiel, 24118 Kiel, Germany"},{"name":"Department of Chemical Engineering, Faculty of Engineering, University of Sultan Ageng Tirtayasa, Serang 42124, Indonesia"},{"name":"Indonesia Center of Excellence for Food Security, University of Sultan Ageng Tirtayasa, Serang 42124, Indonesia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8956-9874","authenticated-orcid":false,"given":"Christian","family":"Zidorn","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical Biology, Christian-Albrechts-University of Kiel, 24118 Kiel, Germany"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,1,30]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"494","DOI":"10.1002\/andp.18300961115","article-title":"Neue Versuche \u00fcber die bitteren Mandeln und deren fl\u00fcchtiges Oel","volume":"96","author":"Robiquet","year":"1830","journal-title":"Ann. der Phys."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/S0041-0101(99)00128-2","article-title":"Plant cyanogenic glycosides","volume":"38","author":"Vetter","year":"2000","journal-title":"Toxicon"},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"3070","DOI":"10.1080\/14786419.2018.1517343","article-title":"Centaurea microcarpa Coss. & Dur. (Asteraceae) extracts: New cyanogenic glucoside and other constituents","volume":"33","author":"Baatouche","year":"2018","journal-title":"Nat. Prod. Res"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"155","DOI":"10.1146\/annurev-arplant-050213-040027","article-title":"Cyanogenic glycosides: Synthesis, physiology, and phenotypic plasticity","volume":"65","author":"Gleadow","year":"2014","journal-title":"Ann. Rev. Plant. Biol."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"568","DOI":"10.1098\/rspb.1905.0048","article-title":"On the probable existence of emulsin in yeast","volume":"76","author":"Henry","year":"1905","journal-title":"Proc. R. Soc. Lond. B."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"609","DOI":"10.1002\/ardp.19813140707","article-title":"A structural investigation by 13C-NMR of the cyanogenic glycosides","volume":"314","author":"Nahrstedt","year":"1981","journal-title":"Arch. Pharm."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"2650","DOI":"10.1021\/jo00008a015","article-title":"Structure determination of natural epoxycyclopentanes by X-ray crystallography and NMR spectroscopy","volume":"56","author":"Olafsdottir","year":"1991","journal-title":"J. Org. Chem."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"35","DOI":"10.1007\/BF00985566","article-title":"Cyanogenic compounds as protecting agents for organisms","volume":"150","author":"Nahrstedt","year":"1985","journal-title":"Plant Syst. Evol."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1111\/aab.12464","article-title":"Cassava wastewater as a natural pesticide: Current knowledge and challenges for broader utilization","volume":"173","author":"Zevallos","year":"2018","journal-title":"Ann. Appl. Biol."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"223","DOI":"10.1016\/j.fitote.2011.10.019","article-title":"Neuroprotective activity of galloylated cyanogenic glucosides and hydrolysable tannins isolated from leaves of Phyllagathis rotundifolia","volume":"83","author":"Tan","year":"2012","journal-title":"Fitoterapia"},{"key":"ref_11","first-page":"529","article-title":"La Linamarine. Nouveau glucoside fournissant de l\u2019acide cyanhydrique par dedoublement, et retire du Linum usitatissimum","volume":"21","author":"Jorissen","year":"1891","journal-title":"Bull. Acad. Roy. Sci. Belg."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"102","DOI":"10.1016\/j.fitote.2016.03.015","article-title":"Leucine-derived cyanoglucosides from the aerial parts of Sorbaria sorbifolia (L.) A. Braun","volume":"111","author":"Qu","year":"2016","journal-title":"Fitoterapia"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"507","DOI":"10.1021\/jo01291a027","article-title":"Linustatin and neolinustatin: Cyanogenic glycosides of linseed meal that protect animals against selenium toxicity","volume":"45","author":"Smith","year":"1980","journal-title":"J. Org. Chem."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1016\/j.fitote.2015.08.008","article-title":"Cyanogenetic glycosides and simple glycosides from the linseed meal","volume":"106","author":"Yang","year":"2015","journal-title":"Fitoterapia"},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1016\/j.fitote.2013.02.006","article-title":"Antioxidative polyphenols from Nigerian mistletoe Loranthus micranthus (Linn.) parasitizing on Hevea brasiliensis","volume":"86","author":"Agbo","year":"2013","journal-title":"Fitoterapia"},{"key":"ref_16","first-page":"162","article-title":"The cyanogenetic constituents of Australian and other plants. VII","volume":"57","author":"Finnemore","year":"1938","journal-title":"J. Soc. Chem. Ind. Lond."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"489","DOI":"10.1080\/14786410802364168","article-title":"New acylated flavone and cyanogenic glycosides from Linum grandiflorum","volume":"23","author":"Mohammed","year":"2009","journal-title":"Nat. Prod. Res."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"840","DOI":"10.1248\/cpb.57.840","article-title":"Supinaionosides A and B: Megastigmane glucosides and supinanitrilosides A\u2014F: Hydroxynitrile glucosides from the whole plants of Euphorbia supina Rafinesque","volume":"57","author":"Cai","year":"2009","journal-title":"Chem. Pharm. Bull."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"388","DOI":"10.1055\/s-2007-969745","article-title":"Cyanogene Glykoside aus Triticum monococcum","volume":"50","author":"Pitsch","year":"1984","journal-title":"Planta Med."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"1167","DOI":"10.1016\/0031-9422(95)00398-Q","article-title":"Cyanogenic and non-cyanogenic glycosides from Manihot esculenta","volume":"40","author":"Prawat","year":"1995","journal-title":"Phytochemistry"},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1505","DOI":"10.1248\/cpb.55.1505","article-title":"Bioactive constituents from Chinese natural medicines. XXVI. Chemical structures and hepatoprotective effects of constituents from roots of Rhodiola sachalinensis","volume":"55","author":"Nakamura","year":"2007","journal-title":"Chem. Pharm. Bull."},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"314","DOI":"10.1016\/S0031-9422(00)94174-8","article-title":"Die cyanogenen Verbindungen von Heterodendron oleaefolium","volume":"17","author":"Nahrstedt","year":"1978","journal-title":"Phytochemistry"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1419","DOI":"10.1016\/S0031-9422(00)98641-2","article-title":"Dihydroacacipetalin-a new cyanogenic glucoside from Acacia sieberiana var. woodii","volume":"14","author":"Seigler","year":"1975","journal-title":"Phytochemistry"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"2221","DOI":"10.1016\/0031-9422(81)80117-3","article-title":"Structural elucidation and partial synthesis of 3-hydroxyheterodendrin, A cyanogenic glucoside from Acacia sieberiana var. woodii","volume":"20","author":"Brimer","year":"1981","journal-title":"Phytochemistry"},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"2330","DOI":"10.1016\/0031-9422(74)85058-2","article-title":"A new cyanogenic glycoside from Cardiospermum hirsutum","volume":"13","author":"Seigler","year":"1974","journal-title":"Phytochemistry"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"4395","DOI":"10.1016\/S0040-4039(01)86597-7","article-title":"Cardiosperminsulfate\u2014A sulphur containing cyanogenic glucoside from Cardiospermum grandiflorum","volume":"20","author":"Nahrstedt","year":"1979","journal-title":"Tetrahedron Lett."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1309","DOI":"10.1016\/0031-9422(81)80028-3","article-title":"Leusine-derived cyanogenic glucosides in the Rosaceae-Spiraeoideae","volume":"20","author":"Nahrstedt","year":"1981","journal-title":"Phytochemistry"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"397","DOI":"10.1515\/znc-1976-7-809","article-title":"Ein neues cyanogenes Glykosid aus der Rosacee Sorbaria arborea: A new cyanogenic glycoside from Sorbaria arborea (Rosaceae)","volume":"31c","author":"Nahrstedt","year":"1976","journal-title":"Z. Naturforsch. C"},{"key":"ref_29","first-page":"51","article-title":"The occurrence of cyanogenetic glucosides in South African species of Acacia I","volume":"4","author":"Steyn","year":"1935","journal-title":"Onderstepoort J. Vet. Sci. Anim. Ind."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"952","DOI":"10.1039\/c39770000952","article-title":"Proacacipetalin and acacipetalin","volume":"24","author":"Ettlinger","year":"1977","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/0305-1978(83)90023-6","article-title":"Cyanogenic glycosides from four Latin American species of Acacia","volume":"11","author":"Seigler","year":"1983","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"1081","DOI":"10.1002\/cbdv.201200103","article-title":"A new phenolic constituent and a cyanogenic glycoside from Balanophora involucrata (Balanophoraceae)","volume":"10","author":"She","year":"2013","journal-title":"Chem. Biodivers."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"1311","DOI":"10.1016\/0031-9422(81)80029-5","article-title":"Proacaciberin, A cyanogenic glycoside from Acacia sieberiana var. woodii","volume":"20","author":"Nartey","year":"1981","journal-title":"Phytochemistry"},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"845","DOI":"10.1016\/S0031-9422(00)85191-2","article-title":"Isolation and structure determination of triglochinin, a new cyanogenic glucoside from Triglochin maritimum","volume":"9","year":"1970","journal-title":"Phytochemistry"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1339","DOI":"10.1016\/S0031-9422(00)98621-7","article-title":"Cyanogenese der Araceen","volume":"14","author":"Nahrstedt","year":"1975","journal-title":"Phytochemistry"},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3069","DOI":"10.1016\/0031-9422(72)80108-0","article-title":"The major cyanogenic glycoside in Thalictrum aquilegifolium","volume":"11","author":"Shawles","year":"1972","journal-title":"Phytochemistry"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"349","DOI":"10.1039\/CT9058700349","article-title":"XLII.\u2014Gynocardin, a new cyanogenetic glucoside","volume":"87","author":"Power","year":"1905","journal-title":"J. Chem. Soc. Trans."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"501","DOI":"10.1016\/S0031-9422(01)00485-X","article-title":"Cyanohydrin glycosides of Passiflora: Distribution pattern, a saturated cyclopentane derivative from P. guatemalensis, and formation of pseudocyanogenic \u03b1-hydroxyamides as isolation artefacts","volume":"59","author":"Jaroszewski","year":"2002","journal-title":"Phytochemistry"},{"key":"ref_39","doi-asserted-by":"crossref","unstructured":"Clapp, R.C., Ettlinger, M.G., and Long, L. (1970). Deidaclin. A natural glucoside of cyclopentenone cyanhydrin. J. Am. Chem. Soc., 6378\u20136379.","DOI":"10.1021\/ja00724a068"},{"key":"ref_40","first-page":"1341","article-title":"Die Verbreitung der Blaus\u00e4ure bei den Cormophyten. Mitteilung: \u00dcber cyanogene Verbindungen bei den Parietales und bei einigen weiteren Sippen","volume":"104","author":"Tantisewie","year":"1969","journal-title":"Pharm. Weekbl."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"1373","DOI":"10.1016\/S0031-9422(00)84345-9","article-title":"The structure of tetraphyllin A and B, two new cyanoglucosides from Tetrapathea tetrandra","volume":"10","author":"Russel","year":"1971","journal-title":"Phytochemistry"},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"271","DOI":"10.1016\/S0031-9422(00)94162-1","article-title":"Two cyanogenic glucosides, tetraphyllin B and epi-tetraphyllin B from Adenia volkensii","volume":"17","author":"Gondwe","year":"1978","journal-title":"Phytochemistry"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"5297","DOI":"10.1016\/S0040-4039(00)85195-3","article-title":"Natural glycosides of cyclopentenone cyanohydrins. Part II. Revised structure of so-called epitetraphyllin B","volume":"27","author":"Jaroszewski","year":"1986","journal-title":"Tetrahedron Lett."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2277","DOI":"10.1016\/0031-9422(82)85191-1","article-title":"Tetraphyllin B and epitetraphyllin B sulfate: Novel cyanogenic glucosides from Passiflora caerulea and P. alato-caerulea","volume":"21","author":"Seigler","year":"1982","journal-title":"Phytochemistry"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"1661","DOI":"10.1016\/S0031-9422(00)82265-7","article-title":"Passicoriacin and epipassicoriacin: C-4 epimers of tetraphyllin B and epitetraphyllin B from Passiflora coriacea","volume":"26","author":"Spencer","year":"1987","journal-title":"Phytochemistry"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1055\/s-2006-962449","article-title":"Novel cyclopentenoid cyanohydrin rhamnoglucosides from Flacourtiaceae","volume":"54","author":"Jaroszewski","year":"1988","journal-title":"Planta Med."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"981","DOI":"10.1016\/S0031-9422(00)83166-0","article-title":"Passibiflorin, epipassibiflorin and passitrifasciatin: Cyclopentenoid cyanogenic glycoside from Passiflora","volume":"24","author":"Spencer","year":"1985","journal-title":"Phytochemistry"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"867","DOI":"10.1016\/0031-9422(91)85268-5","article-title":"Cyanohydrin glycosides with unusual sugar residues: Revised structure of passitrifasciatin","volume":"30","author":"Olafsdottir","year":"1991","journal-title":"Phytochemistry"},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"51","DOI":"10.3891\/acta.chem.scand.43-0051","article-title":"Cyclopentenoid cyanohydrin glycosides with unusual sugar residues","volume":"43","author":"Olafsdottir","year":"1989","journal-title":"Acta Chem. Scand."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"42","DOI":"10.1055\/s-2007-971239","article-title":"Cyanogenesis in Passifloraceae: Cyanogenic compounds from Passiflora capsularis, P. warmingii and P. Perfoliata","volume":"45","author":"Fischer","year":"1982","journal-title":"Planta Med."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"2615","DOI":"10.1016\/S0031-9422(00)80680-9","article-title":"Passicoccin: A sulfated cyanogenic glycoside Passiflora coccinea","volume":"24","author":"Spencer","year":"1985","journal-title":"Phytochemistry"},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1665","DOI":"10.1016\/S0031-9422(00)82266-9","article-title":"Passisuberosin and epipassisuberosin: Two cyclopentenoid cyanogenic glycosides from Passiflora suberosa","volume":"26","author":"Spencer","year":"1987","journal-title":"Phytochemistry"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1508","DOI":"10.1002\/cber.18950280261","article-title":"Ueber ein neues dem amygdalin \u00e4hhnliches glucosid","volume":"28","author":"Fischer","year":"1895","journal-title":"Ber. Dtsch. Chem. Ges."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"359","DOI":"10.1098\/rspb.1912.0058","article-title":"Studies on enzyme action. XVI. The enzymes of emulsin. (I) Prunase, the correlate of prunasin","volume":"85","author":"Armstrong","year":"1912","journal-title":"Proc. R. Soc. Lond. B."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"0641","DOI":"10.1002\/ardp.19072450168","article-title":"Ueber das vorkommen von amygdonitrilglykosid in Cerasus padus Delarb","volume":"245","author":"Bourquelot","year":"1907","journal-title":"Arch. Pharm. Pharm. Med. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"243","DOI":"10.1039\/CT9099500243","article-title":"XXXII.The constituents of the bark of Prunus serotina. Isolation of l-mandelonitrile glucoside","volume":"95","author":"Power","year":"1909","journal-title":"J. Chem. Soc. Trans"},{"key":"ref_57","first-page":"598","article-title":"Sur la sambunigrine, glucoside cyanhydrique nouveau, retir\u00e9 des feuilles de Sureau noir","volume":"141","author":"Bourquelot","year":"1905","journal-title":"Compt. Rend. Hebd. S\u00e9ances Acad. Sci."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2193","DOI":"10.1021\/ol016044+","article-title":"Natural glycosides containing allopyranose from the passion fruit plant and circular dichroism of benzaldehyde cyanohydrin glycosides","volume":"3","author":"Christensen","year":"2001","journal-title":"Org. Lett."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"873","DOI":"10.1016\/S0031-9422(02)00170-X","article-title":"Cyanogenic allosides and glucosides from Passiflora edulis and Carica papaya","volume":"60","author":"Seigler","year":"2002","journal-title":"Phytochemistry"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"757","DOI":"10.1016\/S0031-9422(98)00130-7","article-title":"A cyanogenic glycoside from Passiflora edulis fruits","volume":"49","author":"Chassacne","year":"1998","journal-title":"Phytochemistry"},{"key":"ref_61","first-page":"1091","article-title":"A set of two diastereomers of cyanogenic glycosides from Passiflora quadrangularis","volume":"6","author":"Saeki","year":"2011","journal-title":"Nat. Prod. Commun."},{"key":"ref_62","first-page":"832","article-title":"Vicianin, a new glucoside containing hydrocyanic acid, found in the seeds of vetch","volume":"143","author":"Bertrand","year":"1906","journal-title":"Compt. Rend. Acad. Sci."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"1898","DOI":"10.3891\/acta.chem.scand.25-1898","article-title":"Constitution and stereochemistry of lucumin, a cyanogenic glycoside from Lucuma mammosa Gaertn","volume":"25","year":"1971","journal-title":"Acta Chem. Scand."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"143","DOI":"10.1055\/s-2007-969835","article-title":"New acylated cyanogenic diglycosides from fruits of Anthemis cairica","volume":"49","author":"Nahrstedt","year":"1983","journal-title":"Planta Med."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"567","DOI":"10.1016\/0031-9422(92)90039-S","article-title":"Cyanogenic glycosides from Psydrax and Oxyanthus species","volume":"31","author":"Rockenbach","year":"1992","journal-title":"Phytochemistry"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1080\/10575630008041228","article-title":"Cyanogenic glycosides from Sambucus nigra","volume":"14","author":"Dellagreca","year":"2000","journal-title":"Nat. Prod. Lett."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"1379","DOI":"10.1016\/j.bmcl.2012.12.077","article-title":"Five new phenolic glycosides from Hedyotis scandens","volume":"23","author":"Wang","year":"2013","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"633","DOI":"10.1016\/0031-9422(96)00018-0","article-title":"A cyanogenic glycoside from Canthium schimperianum","volume":"42","author":"Schwarz","year":"1996","journal-title":"Phytochemistry"},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"472","DOI":"10.1039\/CT9038300472","article-title":"The catalytic racemisation of amygdalin","volume":"83","author":"Walker","year":"1903","journal-title":"J. Chem. Soc. Trans."},{"key":"ref_70","first-page":"447","article-title":"Biologically active cyanogenetic, iridoid and lignan glycosides from Eremophila maculata","volume":"67","author":"Syah","year":"1996","journal-title":"Fitoterapia"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"2325","DOI":"10.1016\/j.phytochem.2011.08.022","article-title":"Phenylalanine derived cyanogenic diglucosides from Eucalyptus camphora and their abundances in relation to ontogeny and tissue type","volume":"72","author":"Neilson","year":"2011","journal-title":"Phytochemistry"},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"1179","DOI":"10.1016\/0031-9422(90)85424-E","article-title":"Amygdalin acyl derivatives, cyanogenic glycosides from the seeds of Merremia dissecta","volume":"29","author":"Nahrstedt","year":"1990","journal-title":"Phytochemistry"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"207","DOI":"10.1248\/cpb.57.207","article-title":"New flavonoid glycosides and cyanogenic glycosides from Dracocephalum peregrinum","volume":"57","author":"Fu","year":"2009","journal-title":"Chem. Pharm. Bull."},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"3507","DOI":"10.1016\/0031-9422(92)83717-D","article-title":"Polyoxygenated terpenes and cyanogenic glucosides from Centaurea aspera var. subinermis","volume":"31","author":"Cardona","year":"1992","journal-title":"Phytochemistry"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"623","DOI":"10.1016\/0031-9422(89)80064-0","article-title":"Prunasin-6\u2032-malonate, a cyanogenic glucoside from Merremia dissecta","volume":"28","author":"Nahrstedt","year":"1989","journal-title":"Phytochemistry"},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"607","DOI":"10.1016\/S0305-1978(98)00121-5","article-title":"Prunasin 6\u2032-malonate from Lotononis fruticoides and Lotononis aff. falcata (Fabaceae)","volume":"27","author":"Lechtenberg","year":"1999","journal-title":"Biochem. Syst. Ecol."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1021\/np010393v","article-title":"New cyanogenic and alkyl glycoside constituents from Phyllagathis rotundifolia","volume":"65","author":"Ling","year":"2002","journal-title":"J. Nat. Prod."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"1365","DOI":"10.1016\/j.phytochem.2006.03.022","article-title":"A galloylated cyanogenic glycoside from the Australian endemic rainforest tree Elaeocarpus sericopetalus (Elaeocarpaceae)","volume":"67","author":"Miller","year":"2006","journal-title":"Phytochemistry"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"2363","DOI":"10.1016\/S0031-9422(00)84720-2","article-title":"Cyanogenic and phenylpropanoid glucosides from Prunus grayana","volume":"26","author":"Shimomura","year":"1987","journal-title":"Phytochemistry"},{"key":"ref_80","first-page":"69","article-title":"Two new cyanogenic glycosides from Microlepia strigose","volume":"51","author":"Wada","year":"1997","journal-title":"Nat. Med."},{"key":"ref_81","first-page":"257","article-title":"Cyanogenetic glucosides in Australian plants. Part 5. Phyllanthus gastroemii","volume":"70","author":"Finnemore","year":"1937","journal-title":"J. Proc. R. Soc. N.S.W."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1016\/S0040-4020(01)98398-X","article-title":"The absolute configurations of the phenolic cyanogenetic glucosides taxyphillin and dhurrin","volume":"20","author":"Towers","year":"1964","journal-title":"Tetrahedron"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"399","DOI":"10.1098\/rsta.1902.0018","article-title":"VII. Cyanogenesis in Plants. Part II. The great millet, Sorghum vulgare","volume":"199","author":"Dunstan","year":"1902","journal-title":"Phil. Trans. R. Soc. Lond. A"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"569","DOI":"10.1016\/0031-9422(96)00297-X","article-title":"Dhurrin-6\u2032-glucoside, a cyanogenic diglucoside from Sorghum bicolor","volume":"43","author":"Selmar","year":"1996","journal-title":"Phytochemistry"},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"210","DOI":"10.1016\/j.phytochem.2013.03.004","article-title":"The rare cyanogen proteacin and dhurrin, from foliage of Polyscias australiana, a tropical Araliaceae","volume":"93","author":"Miller","year":"2013","journal-title":"Phytochemistry"},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"1013","DOI":"10.1248\/cpb.c14-00352","article-title":"Taxiphyllin 6\u2019 O-gallate, Actinidioionoside 6\u2032-O-gallate and Myricetrin 2\u2033-O-sulfate from the leaves of Syzygium samarangense and their biological activities","volume":"62","author":"Mamdouh","year":"2014","journal-title":"Chem. Pharm. Bull."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"591","DOI":"10.1248\/cpb.52.591","article-title":"Glochidiolide, isoglochidiolide, acuminaminoside, and glochidacuminosides A-D from the leaves of Glochidion acuminatum Muell","volume":"52","author":"Otsuka","year":"2004","journal-title":"Chem. Pharm. Bull."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"597","DOI":"10.1016\/S0031-9422(00)85406-0","article-title":"Identification and biosynthesis of two cyanogenic glycosides in Thalictrum aquilegifolium","volume":"8","author":"Sharples","year":"1969","journal-title":"Phytochemistry"},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"457","DOI":"10.1016\/0031-9422(73)80040-8","article-title":"Holocalin: Ein neues cyanogenes Glykosid aus Holocalyx balansae","volume":"12","author":"Gmelin","year":"1973","journal-title":"Phytochemistry"},{"key":"ref_90","first-page":"175","article-title":"Cyanogenetic glucosides in Australian plants. Part 4. Zieria l\u00e6vigata","volume":"70","author":"Finnemore","year":"1937","journal-title":"J. Proc. R. Soc. N.S.W."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"178","DOI":"10.1055\/s-2007-971435","article-title":"Zierinxylosid, ein neues cyanogenes Glykosid aus Xeranthemum cylindraceum","volume":"44","author":"Nahrstedt","year":"1982","journal-title":"Planta Med."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"1903","DOI":"10.1016\/0031-9422(90)85038-H","article-title":"Structure elucidation of an acylated cyanogenic triglycoside, and further cyanogenic constituents from Xeranthemum cylindraceum","volume":"29","author":"Schwind","year":"1990","journal-title":"Phytochemistry"},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"4639","DOI":"10.1016\/j.tetlet.2009.05.111","article-title":"The absolute stereostructures of cyanogenic glycosides, hydracyanosides A, B, and C, from the leaves and stems of Hydrangea macrophylla","volume":"50","author":"Nakamura","year":"2009","journal-title":"Tetrahedron Lett."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"909","DOI":"10.3987\/COM-09-11886","article-title":"New cyanoglycosides, hydracyanosides D, E, and F, from the leaves of Hydrangea macrophylla","volume":"81","author":"Wang","year":"2010","journal-title":"Heterocycles"},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"5396","DOI":"10.3390\/molecules17055396","article-title":"Two new cyanogenic glucosides from the leaves of Hydrangea macrophylla","volume":"17","author":"Yang","year":"2012","journal-title":"Molecules"},{"key":"ref_96","first-page":"193","article-title":"Chemical investigation of the plant Acalypha indica. Isolation of triacetonamine, a cyanogenetic glucoside and quebrachite","volume":"9","author":"Rimington","year":"1937","journal-title":"Onderstepoort J. Vet. Sci. Anim. Ind."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1016\/0031-9422(82)80022-8","article-title":"Acalyphin, a cyanogenic glucoside from Acalypha indica","volume":"21","author":"Nahrstedt","year":"1982","journal-title":"Phytochemistry"},{"key":"ref_98","first-page":"104","article-title":"Bioactivity and chemical characterization of Acalypha fruticosa Forssk. growing in Saudi Arabia","volume":"25","author":"Fawzy","year":"2017","journal-title":"SPJ"},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"270","DOI":"10.1016\/j.phytochem.2008.12.011","article-title":"Cyanogenic and non-cyanogenic pyridone glucosides from Acalypha indica (Euphorbiaceae)","volume":"70","author":"Hungeling","year":"2009","journal-title":"Phytochemistry"},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"88","DOI":"10.3923\/rjphyto.2015.88.115","article-title":"Bioactive principles from medicinal plants","volume":"9","author":"Chikezie","year":"2015","journal-title":"Res. J. Phytochem."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"112717","DOI":"10.1016\/j.jep.2020.112717","article-title":"Amygdalin\u2014A pharmacological and toxicological review","volume":"254","author":"He","year":"2020","journal-title":"J. Ethnopharmacol."},{"key":"ref_102","doi-asserted-by":"crossref","unstructured":"Barakat, H. (2020). Amygdalin as a plant-based bioactive constituent. A mini-review on intervention with gut microbiota, anticancer mechanisms, bioavailability, and microencapsulation. Proceedings, 61.","DOI":"10.3390\/IECN2020-06984"},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"122841","DOI":"10.1016\/j.matchemphys.2020.122841","article-title":"An update on the toxicity of cyanogenic glycosides bioactive compounds. Possible clinical application in targeted cancer therapy","volume":"246","author":"Mosayyebi","year":"2020","journal-title":"Mat. Chem. Phys."},{"key":"ref_104","first-page":"1","article-title":"An exploration on the toxicity mechanisms of phytotoxins and their potential utilities","volume":"21","author":"Chen","year":"2020","journal-title":"Crit. Rev. Env. Sci. Tech."},{"key":"ref_105","unstructured":"Sun, S., Qu, G., Wu, C., Zhang, H., Sun, Y., Liu, J., Yi, P., and Jing, J. (2017). CN106974921 A 20170725: Preparation of (2R)-cardiospermin-5-p-hydroxybenzoate and application thereof in preparation of medicine for treating rheumatoid arthritis. Faming Zhuanli Shenqing, 1\u20134."},{"key":"ref_106","unstructured":"Qu, G., Zhang, H., Wu, C., Sun, S., Sun, Y., Liu, J., Cao, Q., and Jing, J. (2017). CN106974922 A 20170725: Preparation of (2S)-cardiospermin-5-cis-p-coumarate and application thereof in preparation of medicine for treating rheumatoid arthritis. Faming Zhuanli Shenqing, 1\u201312."},{"key":"ref_107","unstructured":"Qu, G., Wu, C., Sun, S., Sun, Y., Liu, J., Cao, Q., and Jing, J. (2017). CN106977560 A 20170725: Preparation of (2S)-cardiospermin-5-benzoate and application thereof in preparation of medicine for treating rheumatoid arthritis. Faming Zhuanli Shenqing, 1\u201310."},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"1507","DOI":"10.1016\/j.phytochem.2008.01.022","article-title":"Diversification of an ancient theme. Hydroxynitrile glucosides","volume":"69","author":"Bjarnholt","year":"2008","journal-title":"Phytochemistry"},{"key":"ref_109","doi-asserted-by":"crossref","unstructured":"Kadereit, J.W., K\u00f6rner, C., Kost, B., and Sonnewald, U. (2014). Stoffwechselphysiologie. Strasburger\u2014Lehrbuch der Pflanzenwissenschaften, Springer Spektrum.","DOI":"10.1007\/978-3-642-54435-4"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/3\/719\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:17:30Z","timestamp":1760159850000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/3\/719"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,1,30]]},"references-count":109,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2021,2]]}},"alternative-id":["molecules26030719"],"URL":"https:\/\/doi.org\/10.3390\/molecules26030719","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,1,30]]}}}