MMSL 2016, 85(4):171-181 | DOI: 10.31482/mmsl.2016.029

TOXIC ALCOHOLS: ALIPHATIC UNSATURATED ALCOHOLSReview article

Jiří Patočka ORCID...1,2*, Eugenie Nepovímová2,4, Kamil Kuča ORCID...2,3
1 Institute of Radiology, Toxicology and Civil Protection, Faculty of Health and Social Studies, University of South Bohemia, Ceske Budejovice, Czech Republic
2 Biomedical Research Centre, University Hospital, Hradec Kralove, Czech Republic
3 Center of Advanced Studies, Faculty of Military Health Sciences, University of Defence, Hradec Králové, Czech Republic
4 Department of Toxicology and Military Pharmacy, Faculty of Military Health Sciences, University of Defence, Hradec Králové, Czech Republic

Short-chain unsaturated aliphatic alcohols exist as volatile liquids, some of them are used in both industrial and non-industrial environments, and some of them are natural products of different organisms. These alcohols very often work as semiochemicals, including acting as pheromones, attractants, repellents, etc.. Long-chain poly-unsaturated alcohols are often toxic principals of certain plants, thereby presenting a risk to humans.

Keywords: unsaturated alcohols; alkenols; alkynols; semiochemicals; plant toxins; cicutoxin; oenanthotoxin

Received: June 27, 2016; Revised: September 10, 2016; Published: December 16, 2016  Show citation

ACS AIP APA ASA Harvard Chicago Chicago Notes IEEE ISO690 MLA NLM Turabian Vancouver
Patočka, J., Nepovímová, E., & Kuča, K. (2016). TOXIC ALCOHOLS: ALIPHATIC UNSATURATED ALCOHOLS. MMSL, 85(4), 171-181. doi: 10.31482/mmsl.2016.029
Share...
Download citation
  • BibTeX (.bib)
  • Bookends (.ris)
  • EasyBib (.ris)
  • EndNote (.enw)
  • EndNote 8 (.xml)
  • ISI WoS (.isi)
  • Medlars (.medlars)
  • Mendeley (.ris)
  • MODS (.xml)
  • Papers (.ris)
  • RefWorks (.txt)
  • RefManager (.ris)
  • RIS (.ris)
  • MS Word (.xml)
  • Zotero (.ris)
    • Open full article

    References

    1. Abdel-Rahman FH, Alaniz NM, Saleh MA. Nematicidal activity of terpenoids. J Environ Sci Health B. 2013, 48(1), 16-22. Go to original source... Go to PubMed...
    2. Anet EFLJ, Lythgoe B, Silk MH, Tripplett S. Oenanthotoxin and Cicutoxin. Isolation and Structures. J Chem Soc. 1953, 309-322. Go to original source...
    3. Anet EFLJ, Lythgoe B, Silk MH, Tripplett S. (1952). The Chemistry of Oenanthotoxin and Cicutoxin. Chem Ind. 1952, 31, 757-758.
    4. Anonymous. 3-phenyl-2-propen-1-ol. Vopr Pitaniya. Probl Nutr. 1974, 33(5), 48.
    5. Anonymous. Citronellol. Food Cosmet Toxicko. 1975, 13(6), 757-758. Go to original source...
    6. Aoki S, Matsui K, Takata T, Hong W, Kobayashi M. Lembehyne A, a spongean polyacetylene, induces neuronal differentiation in neuroblastoma cell. Biochem Biophys Res Commun. 2001, 289(2), 558-563. Go to original source... Go to PubMed...
    7. Aoki S, Matsui K, Takata T, Kobayashi M. In situ photoaffinity labeling of the target protein for lembehyne A, a neuronal differentiation inducer. FEBS Lett. 2003, 544(1-3), 223-227. Go to original source... Go to PubMed...
    8. Appendino G, Pollastro F, Verotta L, Ballero M, Romano A, Wyrembek P, Czcuraszek K, Mozrzymas JW, Taglialatela-Scafati O. Polyacetylenes from Sardinian Oenanthe fistulosa: A molecular clue to risus sardonicus. J Nat Prod. 2009, 72(5), 962-965. Go to original source... Go to PubMed...
    9. Arnone A, Nasini G, Vajna de Pava O. Structure and absolute configuration of new acetylenic compounds isolated from cultures of Clitocybe catinus. Phytochemistry. 2000, 53(8), 1087-1090. Go to original source... Go to PubMed...
    10. Belinsky SA, Bradford BU, Forman DT, Glassman EB, Felder MR, Thurman RG. Hepatotoxicity due to allyl alcohol in deermice depends on alcohol dehydrogenase. Hepatology. 1985, 5(6), 1179-1182. Go to original source... Go to PubMed...
    11. Berger RS. Isolation, identification, and synthesis of the sex attractant of the cabbage looper, Trichoplusia ni. Ann Entomol Soc Am. 1966, 59, 767-771. Go to original source...
    12. Beroza M, Bierl BA, Moffitt HR. Sex Pheromones: (E,E)-8,10-Dodecadien-1-ol in the Codling Moth. Science. 1974; 183(4120): 89-90. Go to original source... Go to PubMed...
    13. Bohlmann F, Niedballa U, Rode KM: Polyacetylene compounds. CXVIII. New polyynes with a C17-chain, Chem Ber. 1966, 99, 3552-3558. Go to original source...
    14. Bråred Christensson J, Forsström P, Wennberg AM, Karlberg AT, Matura M. Air oxidation increases skin irritation from fragrance terpenes. Contact Dermatitis. 2009, 60(1), 32-40. Go to original source... Go to PubMed...
    15. Brito RG, Guimarães AG, Quintans JS, Santos MR, De Sousa DP, Badaue-Passos D Jr, de Lucca W Jr, Brito FA, Barreto EO, Oliveira AP, Quintans LJ Jr. Citronellol, a monoterpene alcohol, reduces nociceptive and inflammatory activities in rodents. J Nat Med. 2012, 66(4), 637-644. Go to original source... Go to PubMed...
    16. Brodmann J, Twele R, Francke W, Yi-bo L, Xi-qiang S, Ayasse M. Orchid mimics honey bee alarm pheromone in order to attract hornets for pollination. Curr Biol. 2009, 19(16), 1368-1372. Go to original source... Go to PubMed...
    17. Bruneton J. Toxic Plants Dangerous to Humans and Animals; Lavoisier Publishing: Paris, 1999; pp.105-107.
    18. Butenandt., Beckmann R, Stamm D, Hecker E. Uber den Sexual-lockstoff des Seidenspinners Bomvyx mori. Reindarstelling und Konstitution. Z Naturforsch. 1959, 14(4), 283-284.
    19. Chiang LC, Chiang W, Chang MY, Ng LT, Lin CC. Antileukemic activity of selected natural products in Taiwan. Am J Chin Med. 2003, 31(1), 37-46. Go to original source... Go to PubMed...
    20. Christensen LP. Aliphatic C(17)-polyacetylenes of the falcarinol type as potential health promoting compounds in food plants of the Apiaceae family. Recent Pat Food Nutr Agric. 2011, 3(1), 64-77. Go to original source... Go to PubMed...
    21. Cohen JL, Lee W, Lien EJ. Dependence of toxicity on molecular structure: group theory analysis. J Pharm Sci. 1974, 63(7), 1068-1072. Go to original source... Go to PubMed...
    22. Farrar JJ, Yen LM, Cook T, Fairweather N, Binh N, Parry J, Parry CM. Tetanus. J Neurol Neurosurg Psychiatry. 2000, 69(3), 292-301. Go to original source... Go to PubMed...
    23. Fontaine FR, Dunlop RA, Petersen DP, Burcham PC. Oxidative bioactivation of crotyl alcohol to the toxic endogenous aldehyde crotonaldehyde: association of protein carbonylation with toxicity in mouse hepatocytes. Chem Res Toxicol. 2002, 15(8), 1051-1058. Go to original source... Go to PubMed...
    24. Fujimoto Y, Satoh M, Takeuchi N, Kirisawa M. Synthesis and absolute configurations of the cytotoxic polyacetylenes isolatér from the callus of Panax ginseng. Chem Pharm Bull (Tokyo). 1990, 38(6), 1447-1450. Go to original source... Go to PubMed...
    25. Fukuyama N, Shibuya M, Orihara Y. Antimicrobial polyacetylenes from Panax ginseng hairy root culture. Chem Pharm Bull (Tokyo). 2012, 60(3), 377-380. Go to original source... Go to PubMed...
    26. Gilpin S, Maibach H. Allergic contact dermatitis caused by farnesol: clinical relevance. Cutan Ocul Toxicol. 2010, 29(4), 278-287. Go to original source... Go to PubMed...
    27. Graeve M, Lundberg M, Böer M, Kattner G, Hop H, Petersen SF. The fate of dietary lipids in the Arctic ctenophore Mertensia ovum (Fabricius 1780). Mar Biol. 2008, 153, 643-651. Go to original source...
    28. Hall DR, Beevor PS, Cork A, Nesbitt BN, Vale GA. 1-Octen-3-ol. A potent olfacrory stimulant and attractant for tsetse isolated feom cattle odours. Int J Tropical Insct. 1984, 5(5), 335-339. Go to original source...
    29. Heath KB. A fatal case of apparent water hemlock poisoning. Vet Hum Toxicol. 2001, 43(1), 35-36.
    30. Izumi M, Yogosawa S, Aoki S, Watanabe H, Kamiyama J, Takahara Y, Sowa Y, Kobayashi M, Hosoi H, Sugimoto T, Sakai T. A novel synthetic drug, LB-18, closely related to lembehyne-A derived from a marine sponge, induces caspase-independent cell death to human neuroblastoma cells. Int J Oncol. 2006, 29(1), 169-173. Go to original source...
    31. Jin HR, Zhao J, Zhang Z, Liao Y, Wang CZ, Huang WH, Li SP, He TC, Yuan CS, Du W. The antitumor natural compound falcarindiol promotes cancer cell death by inducing endoplasmic reticulum stress. Cell Death Dis. 2012, 3, e376. Go to original source... Go to PubMed...
    32. Joglekar GV, Balwani JH. Allyl alcohol induced hepatotoxicity in rats and its protection by Liv. 52. J Exp Med Sci. 1967 Jun, 11(1), 7-9.
    33. Joo JH, Jetten AM. Molecular mechanisms involved in farnesol-induced apoptosis. Cancer Lett. 2009, 287(2), 123-35.
    34. Kirkham JED, Courtney TDL, Lee V, Baldwin JE. Asymmetric synthesi of cytotoxic sponge metabolites R-strongylodiols A and B. Tetrahedron Lett. 2004, 45(29), 5645-5647. Go to original source...
    35. Kromidas L, Perrier E, Flanagan J, Rivero R, Bonnet I. Release of antimicrobial actives from microcapsules by the action of axillary bacteria. Int J Cosmet Sci. 2006, 28(2), 103-108. Go to original source... Go to PubMed...
    36. Lantz TC, Swerhun K, Turner NJ. Devil's Club (Oplopanax horridus): An Ethnobotanical Review. HerbalGram. 2004, 62, 33-48.
    37. Lapczynski A, Bhatia SP, Letizia CS, Api AM. Fragrance material review on farnesol. Food Chem Toxicol. 2008, 46 Suppl 11, S149-S156. Go to original source... Go to PubMed...
    38. Larue JP, Barbier M. The track pheromone of the termite Schedorhinotermes lamanianus (Sjöstedt). [Article in French] C R Acad Sci Hebd Seances Acad Sci D. 1976, 282(21), 1897-1900.
    39. Lee HS, Lee JH, Won H, Park SK, Kim HM, Shin HJ, Park HS, Sim CJ, Kim HK. Identification of Novel Acetylenic Alcohols and a New Dihydrothiopyranone from the Tropical Sponge Reniochalina sp. Lipids. 2009, 44(1), 71-75. Go to original source... Go to PubMed...
    40. Li AA, Fowles J, Banton MI, Picut C, Kirkpatrick DT. Acute inhalation study of allyl alcohol for derivation of acute exposure guideline levels. Inhal Toxicol. 2012, 24(4), 213-226. Go to original source... Go to PubMed...
    41. Loizzo MR, Tundis R, Menichini F, Saab AM, Statti GA, Menichini F. Antiproliferative effects of essential oils and their major constituents in human renal adenocarcinoma and amelanotic melanoma cells. Cell Prolif. 2008, 41(6), 1002-1012. Go to original source... Go to PubMed...
    42. Lu YC, Chang HS, Peng CF, Lin CH, Chen IS. Secondary metabolites from the unripe pulp of Persea americana and their antimycobacterial activities. Food Chem. 2012, 135(4), 2904-2909. Go to original source... Go to PubMed...
    43. Machado S, Silva E, Massa A. Occupational allergic contact dermatitis from falcarinol. Contact Dermatitis. 2002, 47(2), 113-114. Go to PubMed...
    44. Maddox JF, Roth RA, Ganey PE. Allyl alcohol activation of protein kinase C delta leads to cytotoxicity of rat hepatocytes. Chem Res Toxicol. 2003 May, 16(5), 609-615. Go to original source... Go to PubMed...
    45. Marhold J. Přehled průmyslove toxikologie: Organické látky. Avicenum Praha. 1986, Pg. 202.
    46. Matsunaga H, Katano M, Yamamoto H, Fujito H, Mori M, Takata K. Cytotoxic activity of polyacetylene compounds in Panax ginseng C. A. Meyer. Chem Pharm Bull (Tokyo). 1990, 38(12), 3480-3482. Go to original source... Go to PubMed...
    47. McMahon DM, Winstead S, Weant KA. Toxic alcohol ingestions: focus on ethylene glycol and methanol. Adv Emerg Nurs J. 2009, 31(3), 206-213. Go to original source... Go to PubMed...
    48. Molaison LJ, O'Connor RT, Spadalo JJ. Long-chain unsaturated alcohols from jojoba oil by sodium reduction. J Am Oil Chem Soc. 1959, 36(9), 379-382. Go to original source...
    49. Ohnuma T, Anan E, Hoashi R, Takeda Y, Nishiyama T, Ogura K, Hiratsuka A. Dietary diacetylene falcarindiol induces phase 2 drug-metabolizing enzymes and blocks carbon tetrachloride-induced hepatotoxicity in mice through suppression of lipid peroxidation. Biol Pharm Bull. 2011, 34(3), 371-378. Go to original source... Go to PubMed...
    50. Olivera JE, Dossb RP, Williamson RT, Carneyd JR, DeVilbissa ED. Bruchins-Mitogenic 3-(Hydroxypropanoyl) esters of long chain diols from Weevils of the Bruchidae. Tetrahedron. 2000, 56(39), 7633-7641. Go to original source...
    51. Panter KE, Gardner DR, Stegelmeier BL, Welch KD, Holstege D. Water hemlock poisoning in cattle: Ingestion of immature Cicuta maculata seed as the probable cause. Toxicon. 2011, 57(1), 157-161. Go to original source... Go to PubMed...
    52. Patočka J, Kuča K. Toxic alcohols: aliphatic saturated alcohols. Mil Med Sci Lett. (Voj Zdrav Listy) 2012, 81(4), 141-162. Go to original source...
    53. Pohlit AM, Lopes NP, Gama RA, Tadei WP, Neto VF. Patent literature on mosquito repellent inventions which contain plant essential oils - a review. Planta Med. 2011, 77(6), 598-617. Go to original source... Go to PubMed...
    54. Ravizza R, Gariboldi MB, Molteni R, Monti E. Linalool, a plant-derived monoterpene alcohol, reverses doxorubicin resistance in human breast adenocarcinoma cells. Oncol Rep. 2008, 20(3), 625-630. Go to PubMed...
    55. Regnier FE, Law JH. Insect pheromones. J Lipid Res. 1968; 9, 541-551. Go to original source...
    56. Rhazi L, Grillas P, Saber ER, Rhazi M, Brendock L, Waterkeyn A. Vegetation of Mediterranean tempotary pools: a fading jewel. Hydrobiologia. 2012; 689(1), 23-36. Go to original source...
    57. Ribichini S. Il Riso Sardonico. Storia di un Proverbio Antico; Carlo Delfino Editore: Sassari, Italy, 2000.
    58. Robert A, Peppuy A, Sémon E, Boyer FD, Lacey MJ, Bordereau C. A new C12 alcohol identified as a sex pheromone and a trail-following pheromone in termites: the diene (Z,Z)-dodeca-3,6-dien-1-ol. Naturwissenschaften. 2004, 91(1), 34-39. Go to original source... Go to PubMed...
    59. Rooney F, Capon RJ. Callyspongines A and B: new polyacetylenic lipids from a southern Australian marine sponge, Callyspongia sp. Lipids. 1998, 33(6), 639-642. Go to original source... Go to PubMed...
    60. Schep LJ, Slaughter RJ, Becket G, Beasley DM. Poisoning due to water hemlock. Clin Toxicol (Phila). 2009, 47(4), 270-278. Go to original source... Go to PubMed...
    61. Sekul AA, Sparks AN. Sex pheromone of the fall armyworm: isolation, identification, and synthesis. J Econ Entomol. 1967, 60, 1270-1272. Go to original source...
    62. Shoeb M, Jaspars M. Chlorinated C12 fatty acid metabolites from the red alga Gracilaria verrucosa. J Nat Prod. 2003, 66(11), 1509-1511. Go to original source... Go to PubMed...
    63. Smyth HF Jr, Carpenter CP, Weil CS, Pozzani UC, Striegel JA. Range-finding toxicity data: List VI. Am Ind Hyg Assoc J. 1962, 23, 95-107. Go to original source... Go to PubMed...
    64. Starreveld E, Hope E. Cicutoxin poisoning (water hemlock). Neurology. 1975, 25(8), 730-734. Go to original source... Go to PubMed...
    65. Strauss U, Wittstock U, Schubert R, Teuscher E, Jung S, Mix E. Cicutoxin from Cicuta virosa - a new and potent potassium channel blocker in T lymphocytes. Biochem Biophys Res Commun. 1996, 219(2), 332-336. Go to original source... Go to PubMed...
    66. Taylor WG, Schreck CE. Chiral-phase capillary gas chromatography and mosquito repellent activity of some oxazolidine derivatives of (+)- and (-)-citronellol. J Pharm Sci. 1985, 74(5), 534-539. Go to original source... Go to PubMed...
    67. Vanhaelen M, Vanhaelen-Fastré R, Geeraerts J, Wirthlin T. Cis- and trans-octa-1,5-dien-3-ol, new attractants to the cheese mite Tyrophagus putrescentiae (Schrank) (Acarina, Acaridae) idintified in Trichothecium roseum (Fungi Imperfecti). Microbios. 1978, 23(93-94), 199-212. Go to PubMed...
    68. Veith GD, Lipnick RL, Russom CL. The Toxicity of Acetylenic Alcohols to the Fathead Minnow, Pimephales Promelas: Narcosis and Proelectrophile Activation. Xenobiotica. 1989, 19 No(5), 555-565. Go to original source... Go to PubMed...
    69. Vinothkumar V, Manoharan S. Chemopreventive efficacy of geraniol against 7,12-dimethylbenz[a]anthracene-induced hamster buccal pouch carcinogenesis. Redox Rep. 2011, 16(3), 91-100. Go to original source... Go to PubMed...
    70. Vite JP, Gara RI, R. Kliefoth RA. Collection and bioassay of a volatile fraction attractive to Ips confusus (LeC) (coleoptera: Scolytidae). Boyce Thompson Institute for Plant Research, Contributions 1963, 22, 39-50.
    71. Watanabe K, Tsuda Y, Ymane Y, Takahashi H, Iguchi K, Naoki H, Fujita T, Vaan Soest RWM. Strongylodiols A, B and C, new cytotoxic acetylenic alcohols isolatér from the okinawan marine sponge of the genus Strongylophora as each enantiomeric mixture with a different ratio. Tetrahedron Lett. 2000, 41(48), 9271-9276. Go to original source...
    72. Watanabe K, Tsuda Y, Hamada M, Omori M, Mori G, Iguchi K, Naoki H, Fujita T, Vaan Soest RWM. Acetylenic strongylodiols from a Petrosia (Strongylophora) Okinawan marine sponge. J Nat Prod. 2005, 68(7), 1001-1005. Go to original source... Go to PubMed...
    73. Wiberg GS, Trenholm HL, Coldwell BB. Increased ethanol toxicity in old rats: changes in LD50, in vivo and in vitro metabolism, and liver alcohol dehydrogenase activity. Toxicol Appl Pharmacol. 1970, 16, 718-727. Go to original source... Go to PubMed...
    74. Wittstock U, Lichtnow KH, Teuscher E. Effects of cicutoxin and related polyacetylenes from Cicuta virosa on neuronal action potentials: a comparative study on the mechanism of the convulsive action. Planta Med. 1997, 63(2), 120-124. Go to original source... Go to PubMed...
    75. Wnuk S, Kinastowski S, Kamiński E. Synthesis and analysis of 1-octen-3-ol, the main flavour component of mushrooms. Nahrung. 1983, 27(5), 479-486. Go to original source... Go to PubMed...
    76. Wyrembek P, Negri R, Kaczor P, Czyżewska M, Appendino G, Mozrzymas JW. Falcarindiol allosterically modulates GABAergic currents in cultured rat hippocampal neurons. J Nat Prod. 2012, 75(4), 610-616. Go to original source... Go to PubMed...
    77. Yadav JS, Boyapelly K, Alugubelli SR, Pabbaraja S, Vangala JR, Kalivendi SV. Stereoselective total synthesis of (+)-oploxyne A, (-)-oploxyne B, and their C-10 epimers and structure revision of natural oploxyne B. J Org Chem. 2011, 76(8), 2568-2576. Go to original source... Go to PubMed...
    78. Yamawakit T. Pharmacological effects of geraniol. [Article in Japanese] Nihon Yakurigaku Zasshi. 1962, 58, 394-400. Go to original source... Go to PubMed...
    79. Yang MC, Kwon HC, Kim YJ, Lee KR, Yang HO. Oploxynes A and B, polyacetylenes from the stems of Oplopanax elatus. J Nat Prod. 2010, May 73(5), 801-805. Go to original source... Go to PubMed...
    80. Youssef DT, van Soest RW, Fusetani N. Callyspongenols A-C, new cytotoxic C22-polyacetylenic alcohols from a red sea sponge, Callyspongia species. J Nat Prod. 2003, 66(5), 679-681. Go to original source... Go to PubMed...
    81. Zawirska-Wojtasiak R. Optical purity of (R)-(-)-1-octen-3-ol in the aroma of various species of edible mushrooms. Food Chem. 2004, 86(1), 113-118. Go to original source...
    82. Zidorn C, Jöhrer K, Ganzera M, Schubert B, Sigmund EM, Mader J, Greil R, Ellmerer EP, Stuppner H. Polyacetylenes from the Apiaceae vegetables carrot, celery, fennel, parsley, and parsnip and their cytotoxic activities. J Agric Food Chem. 2005, 53(7), 2518-2523. Go to original source... Go to PubMed...

    Return to the content