From Wikipedia, the free encyclopedia
Gramine
Names
Preferred IUPAC name
1-(1H -Indol-3-yl)-N ,N -dimethylmethanamine
Other names
donaxine
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.001.591
EC Number
KEGG
UNII
InChI=1S/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
Y Key: OCDGBSUVYYVKQZ-UHFFFAOYSA-N
Y InChI=1/C11H14N2/c1-13(2)8-9-7-12-11-6-4-3-5-10(9)11/h3-7,12H,8H2,1-2H3
Key: OCDGBSUVYYVKQZ-UHFFFAOYAK
Properties
C11 H14 N2
Molar mass
174.24 g/mol
Melting point
138 to 139 °C (280 to 282 °F; 411 to 412 K)
Hazards
NFPA 704 (fire diamond)
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Gramine (also called donaxine ) is a naturally occurring
indole
alkaloid present in several plant species. Gramine may play a defensive role in these plants, since it is toxic to many organisms.
[1]
Occurrence
Gramine has been found in the giant reed,
Arundo donax ,
[2]
[3]
Acer saccharinum (
Silver Maple ),
[4]
Hordeum ,
[1]
[3] (a grass genus that includes barley) and
Phalaris
[3] (another grass genus).
Effects and toxicity
Gramine has been found to act as an
agonist of the
adiponectin receptor 1 (AdipoR1).
[5]
The LD50 of gramine is 44.6 mg/ kg iv in mice and 62.9 mg/ kg iv in rats.
[6]
Numerous studies have been done on the toxicity of gramine to insects harmful to crops in order to assess its potential use as an insecticide.
[7]
References
^
a
b Corcuera, L. J. (1993). "Biochemical Basis of the Resistance of the Barley to Aphids".
Phytochemistry . 33 (4): 741–747.
doi :
10.1016/0031-9422(93)85267-U .
^ Orechoff, A.; Norkina, S. (1935). "Über die Alkaloide von Arundo Donax L.".
Berichte der Deutschen Chemischen Gesellschaft . 68 (3): 436–437.
doi :
10.1002/cber.19350680312 .
^
a
b
c Cheeke, P. R. (1989).
Toxicants of Plant Origin, Alkaloids . CRC Press. p. 172.
ISBN
0-8493-6990-8 .
^ Pachter, I. J.; Zacharias, D. E.; Ribeiro, O. (1959). "Indole Alkaloids of Acer saccharinum (the Silver Maple), Dictyoloma incanescens , Piptadenia colubrina , and Mimosa hostilis ".
Journal of Organic Chemistry . 24 (9): 1285–1287.
doi :
10.1021/jo01091a032 .
^ Sun Y, Zang Z, Zhong L, Wu M, Su Q, Gao X, Zan W, Lin D, Zhao Y, Zhang Z (2013).
"Identification of adiponectin receptor agonist utilizing a fluorescence polarization based high throughput assay" . PLOS ONE . 8 (5): e63354.
Bibcode :
2013PLoSO...863354S .
doi :
10.1371/journal.pone.0063354 .
PMC
3653934 .
PMID
23691032 .
^ Erspamer, V. (1954).
"Pharmacology of Indolealkylamines" . Pharmacological Reviews . 6 (4): 425–487.
PMID
13236482 .
^ Corcuera, L. J. (1984). "Effects of Indole Alkaloids from Gramineae on Aphids". Phytochemistry . 23 (3): 539–541.
doi :
10.1016/S0031-9422(00)80376-3 .