Gastrodin

Gastrodin
Chemical structure of 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-[4-(hydroxymethyl)phenoxy]oxane-3,4,5-triol
Other names
Gastrodine
4-(β-D-glucopyranosyloxy)benzyl alcohol
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.208.712 Edit this at Wikidata
UNII
  • 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/s1 ☒N
    Key: PUQSUZTXKPLAPR-UJPOAAIJSA-N ☒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/s1
    Key: PUQSUZTXKPLAPR-UJPOAAIJBX
  • O(c1ccc(cc1)CO)[C@@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2O)CO
Properties
C13H18O7
Molar mass 286.280 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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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.[1] It can also be produced by biotransformation of 4-hydroxybenzaldehyde by Datura tatula cell cultures.[2]

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.[3] 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.[4] 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.[5]

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.