The GABA system is an important site of action by a variety of chemicals, including alcohols, heavy metals, and insecticides.[5] A study conducted on frog spinal cords and rat brains indicated that anisatin was a strong non-competitive GABA antagonist.[5] Anisatin was shown to suppress GABA-induced signals but when anisatin was added without GABA, there was no change in the signal.[5] Anisatin was also found to share the same binding site as picrotoxinin, and did not cause additional suppression of GABA-induced signals in the presence of high concentrations of picrotoxinin.[5]
Anisatin poisoning has been shown to cause epilepsy, hallucinations, nausea, and convulsions.[6][7] Diazepam has been studied as an anti-convulsive on the GABA system, and has been shown to be an effective treatment for anisatin-induced convulsions.[7]
Synthesis[edit]
A total synthesis of (-)-anisatin was reported in 1990.[8]
References[edit]
^"Anisatin". PubChem, National Library of Medicine, US National Institutes of Health. 11 May 2019. Retrieved 17 May 2019.
^Lane JF, Koch WT, Leeds NS, Gorin G (1952). "The toxin of Illicium anisatum. I. The isolation and characterization of a convulsant principle: anisatin". Journal of the American Chemical Society. 74 (13): 3211–3215. doi:10.1021/ja01133a002.
^Kouno I, Kawano N, Yang C (1988). "New pseudoanisatin-like sesquiterpene lactones from the bark of Illicium dunnianum". Journal of the Chemical Society, Perkin Transactions 1 (6): 1537. doi:10.1039/P19880001537.
^Naoru.com:シキミ(Japanese)
^ a b c dIkeda T, Ozoe Y, Okuyama E, Nagata K, Honda H, Shono T, Narahashi T (August 1999). "Anisatin modulation of the gamma-aminobutyric acid receptor-channel in rat dorsal root ganglion neurons". British Journal of Pharmacology. 127 (7): 1567–76. doi:10.1038/sj.bjp.0702700. PMC 1566146. PMID 10455311.
^Li P, Wei DD, Wang JS, Yang MH, Kong LY (January 2016). "(1)H NMR metabolomics to study the effects of diazepam on anisatin induced convulsive seizures". Journal of Pharmaceutical and Biomedical Analysis. 117: 184–94. doi:10.1016/j.jpba.2015.08.029. PMID 26361344.
^ a bShen Y, van Beek TA, Claassen FW, Zuilhof H, Chen B, Nielen MW (October 2012). "Rapid control of Chinese star anise fruits and teas for neurotoxic anisatin by Direct Analysis in Real Time high resolution mass spectrometry". Journal of Chromatography A. 1259: 179–86. doi:10.1016/j.chroma.2012.03.058. PMID 22484123.
^Niwa H, Nisiwaki M, Tsukada I, Ishigaki T, Ito S, Wakamatsu K, Mori T, Ikagawa M, Yamada K (November 1990). "Stereocontrolled total synthesis of (-)-anisatin: a neurotoxic sesquiterpenoid possessing a novel spiro .beta.-lactone". Journal of the American Chemical Society. 112 (24): 9001–9003. doi:10.1021/ja00180a067. ISSN 0002-7863.
vteGABA receptor modulators
Ionotropic
GABAA
Agonists: (+)-Catechin
Bamaluzole
Barbiturates (e.g., phenobarbital)
Beta-Alanine
BL-1020
DAVA
Dihydromuscimol
GABA
Gabamide
GABOB
Gaboxadol (THIP)
Homotaurine (tramiprosate, 3-APS)
Ibotenic acid
iso-THAZ
iso-THIP
Isoguvacine
Isomuscimol
Isonipecotic acid
Kojic amine
L-838,417
Lignans (e.g., honokiol)
Methylglyoxal
Monastrol
Muscimol
Nefiracetam
Neuroactive steroids (e.g., allopregnanolone)
Org 20599
PF-6372865
Phenibut
Picamilon
P4S
Progabide
Propofol
Quisqualamine
SL-75102
Taurine
TACA
TAMP
Terpenoids (e.g., borneol)
Thiomuscimol
Tolgabide
ZAPA
Positive modulators (abridged; see here for a full list): α-EMTBL