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Gastrodin

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Gastrodin
Chemical structure of gastrodin
Names
IUPAC name 4-(Hydroxymethyl)phenyl β-D-glucopyranoside
Systematic IUPAC name (2R,3S,4S,5R,6S)-2-(Hydroxymethyl)-6-oxane-3,4,5-triol
Other names Gastrodine
4-(β-D-glucopyranosyloxy)benzyl alcohol
Identifiers
CAS Number
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.208.712 Edit this at Wikidata
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • InChI=1S/C13H18O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1Key: PUQSUZTXKPLAPR-UJPOAAIJSA-N
  • InChI=1/C13H18O7/c14-5-7-1-3-8(4-2-7)19-13-12(18)11(17)10(16)9(6-15)20-13/h1-4,9-18H,5-6H2/t9-,10-,11+,12-,13-/m1/s1Key: PUQSUZTXKPLAPR-UJPOAAIJBX
SMILES
  • O(c1ccc(cc1)CO)2O((O)(O)2O)CO
Properties
Chemical formula C13H18O7
Molar mass 286.280 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

Gastrodin is a chemical compound which is the glucoside of gastrodigenin. It has been isolated from the orchid Gastrodia elata and from the rhizome of Galeola faberi. It can also be produced by biotransformation of 4-hydroxybenzaldehyde by Datura tatula cell cultures.

G. elata is a herb used in traditional Chinese medicine to treat headache, and it is standardized in the Chinese Pharmacopoeia by gastrodin and gastrodigenin content. In line with this traditional use, gastrodin and its acetyl derivative are used in China as an over-the-counter drug to treat neurasthenia, headache, and migraine. It is available as a dietary supplement in other countries.

A Chinese literature review considers it useful for a range of central nervous system disorders, with the evidence coming from mostly Chinese researches.

References

  1. Li, Y. M.; Zhou, Z. L.; Hong, Y. F. (1993). "Studies on the phenolic derivatives from Galeola faberi Rolfe". Yao Xue Xue Bao = Acta Pharmaceutica Sinica. 28 (10): 766–71. PMID 8009989.
  2. Gong, J.; Ma, W.; Pu, J.; Xu, S.; Zheng, S.; Xiao, C. (2006). "Production of Gastrodin Through Biotransformation of p-hydroxybenzaldehyde Using Cell Suspension Cultures of Datura tatula L". Chinese Journal of Biotechnology. 22 (5): 800–804. doi:10.1016/S1872-2075(06)60056-3. PMID 17037205.
  3. 国家药典委员会 (2015). "天麻 / GASTRODIAE RHIZOMA". 中国药典 (in Chinese). Vol. 1. p. 58. ISBN 978-7-5067-7337-9.
  4. "Gastrodin Tablets (天麻素片) Monograph". drugs.dxy.cn.
  5. Liu, Y; Gao, J; Peng, M; Meng, H; Ma, H; Cai, P; Xu, Y; Zhao, Q; Si, G (2018). "A Review on Central Nervous System Effects of Gastrodin". Frontiers in Pharmacology. 9: 24. doi:10.3389/fphar.2018.00024. PMC 5801292. PMID 29456504.
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