サイカシン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/08/04 11:52:31」(JST)
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Cycasin
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Names |
Systematic IUPAC name
[(E)-Methyl-ONN-azoxy]methyl β-D-glucopyranoside[1]
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Other names
β-D-Glucosyloxyazoxymethane; Methylazoxymethanol β-D-glucoside; Cycas revoluta glucoside
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Identifiers |
CAS Registry Number
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14901-08-7 |
ChEBI |
CHEBI:CHEBI:17074 |
ChemSpider |
4573631 |
InChI
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InChI=1S/C8H16N2O7/c1-10(15)9-3-16-8-7(14)6(13)5(12)4(2-11)17-8/h4-8,11-14H,2-3H2,1H3/b10-9+/t4-,5-,6+,7-,8-/m1/s1
Key: YHLRMABUJXBLCK-IRCVIWNGSA-N
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InChI=1/C8H16N2O7/c1-10(15)9-3-16-8-7(14)6(13)5(12)4(2-11)17-8/h4-8,11-14H,2-3H2,1H3/b10-9+/t4-,5-,6+,7-,8-/m1/s1
Key: YHLRMABUJXBLCK-IRCVIWNGBN
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Jmol-3D images |
Image |
KEGG |
C01418 |
MeSH |
D003492 |
PubChem |
5459896 |
SMILES
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[O-]/[N+](=N/CO[C@@H]1O[C@@H]([C@@H](O)[C@H](O)[C@H]1O)CO)C
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Properties |
Chemical formula
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C8H16N2O7 |
Molar mass |
252.22 g·mol−1 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references |
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Cycasin is a phytotoxin found in cycads such as Cycas revoluta and Zamia pumila. Both plants are used to produce sago. The butterfly Eumaeus atala, whose larvae feed on Z. pumila, also contains the compound. The seeds of C. revoluta contain the highest level of the toxin.
It induces hepatotoxicity and Zamia staggers, a fatal nervous disease affecting cattle where they browse on the leaves or fruit of cycads.
The enzyme methyl-ONN-azoxymethanol beta-D-glucosyltransferase uses the two substrates UDP-glucose and methyl-ONN-azoxymethanol to produce UDP and cycasin.[2]
See also
- List of IARC Group 2B carcinogens
- List of MeSH codes (D02)
References
- ^ b-D-Glucosyloxyazoxymethane, ChemSpider
- ^ Tadera K, Yagi F, Arima M and Kobayashi A (1985). "Formation of cycasin from methylazoxymethanol by UDP-glucosyltransferase from leaves of Japanese cycad". Agric. Biol. Chem. 49 (9): 2827–2828. doi:10.1271/bbb1961.49.2827.
English Journal
- Toxic phytochemicals and their potential risks for human cancer.
- Bode AM1, Dong Z2.
- Cancer prevention research (Philadelphia, Pa.).Cancer Prev Res (Phila).2015 Jan;8(1):1-8. doi: 10.1158/1940-6207.CAPR-14-0160. Epub 2014 Oct 27.
- Consuming plants for their presumed health benefits has occurred since early civilizations. Phytochemicals are found in various plants that are frequently included in the human diet and are generally thought to be safe for consumption because they are produced naturally. However, this is not always
- PMID 25348854
- Cycads and their association with certain neurodegenerative diseases.
- Rivadeneyra-Domínguez E1, Rodríguez-Landa JF2.
- Neurología (Barcelona, Spain).Neurologia.2014 Nov-Dec;29(9):517-22. doi: 10.1016/j.nrl.2013.03.005. Epub 2013 May 30.
- INTRODUCTION: Cycads are ornamental plants that in some parts of the world are used as fresh food or raw material for producing flour with a high nutritional value. However, they also contain active compounds, including methylazoxymethanol, β-methylamino-L-alanine, β-alanine-L-oxalylamino and cyca
- PMID 23725821
- Relative seed and fruit toxicity of the Australian cycads Macrozamia miquelii and Cycas ophiolitica: further evidence for a megafaunal seed dispersal syndrome in cycads, and its possible antiquity.
- Hall JA1, Walter GH.
- Journal of chemical ecology.J Chem Ecol.2014 Aug;40(8):860-8. doi: 10.1007/s10886-014-0490-5. Epub 2014 Aug 30.
- An apparent contradiction in the ecology of cycad plants is that their seeds are known to be highly poisonous, and yet they seem well adapted for seed dispersal by animals, as shown by their visually conspicuous seed cones and large seeds presented within a brightly colored fleshy "fruit" of sarcote
- PMID 25172315
Japanese Journal
- 琉球大学農学部学術報告 = THE SCIENCE BULLETIN OF THE FACULTY OF AGRICULTURE UNIVERSITY OF THE RYUKYUS (61), 1-9, 2014-12-27
- NAID 120005649617
- サイカシン投与山羊における第一胃内容物の揮発性脂肪酸の動態 : サイカシン投与法に対する一考察
- ソテツ葉ならびにサイカシン投与山羊における第一胃内容物内の揮発性脂肪酸の動態に関する研究
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