Gastrodin, 天麻素

Gastrodin is a phenolic glycoside that has been found in Gastrodia and has diverse biological activities. It reduces cell death of rat hippocampal neurons and BV-2 mouse microglia induced by amyloid-β (1-42) (Aβ42;) and improves learning and memory in various transgenic mouse models of Alzheimer's disease. It reduces motor deficits and loss of dopaminergic neurons in a rat model of Parkinson's disease induced by 6-OHDA. Gastrodin (50-200 mg/kg) reduces seizure duration and intensity in a rat model of pentylenetetrazole-kindling chronic epileptic seizures. In a mouse model of valproic acid-induced autistic-like phenotypes, gastrodin (100 mg/kg) increases social interaction and decreases marble burying and grooming behaviors, as well as restores inhibitory synaptic transmission and GAT1 and α5 subunit-containing GABAA expression in the basolateral amygdala. Gastrodin increases ultimate breaking force and bone stiffness, measures of biomechanical strength, in a rat model of osteoporosis induced by dexamethasone. It also inhibits ethanol-induced hepatocellular apoptosis and restores liver function in a rat model of alcoholic liver disease.

Gastrodin is a phenolic glycoside that can penetrate through the blood-brain barrier and has been suggested to have neuroprotective effects against hypoxia.

Gastrodin is a polysaccharide that has been extracted from the roots of Gastrodia elata. It has been shown to have neuroprotective activity in rat hippocampal neurons and is currently being studied for potential use as an experimental treatment for spinal cord injury. Gastrodin also has anti-inflammatory effects, inhibiting the production of pro-inflammatory cytokines such as IL-6 in response to injury. In vitro studies have shown that gastrodin inhibits the growth of tumor cells by binding to DNA topoisomerases and preventing DNA replication. This compound is also used as an ingredient in combination preparations with other herbs, such as black cohosh extract and dong quai, which are used for relief of menopause symptoms.

Title: Gastrodin

CAS Registry Number: 62499-27-8

CAS Name: 4-(Hydroxymethyl)phenyl-b-D-glucopyranoside

Additional Names: 4-(b-D-glucopyranosyloxy)benzyl alcohol

Molecular Formula: C13H18O7

Molecular Weight: 286.28

Percent Composition: C 54.54%, H 6.34%, O 39.12%

Literature References: Pharmacologically active constituent of the traditional medicinal plant, gastrodia, q.v. Prepn: B. Helferich et al., Ann. 508, 192 (1934); A. E. Pavlov et al., Russ. J. Gen. Chem. 71, 1811 (2001). Isoln from Gastrodia elata tuber: H. Taguchi et al., Chem. Pharm. Bull. 29, 55 (1981); H.-B. Li, F. Chen, J. Chromatogr. A 1052, 229 (2004). CE determn in medicinal formulations: Y. Zhao et al., ibid. 849, 277 (1999). Pharmacokinetics in rats: R. Wang et al., J. Liq. Chromatogr. Relat. Technol. 25, 857 (2002). Pharmacology in gerbils: S.-J. An et al., J. Neurosci. Res. 71, 534 (2003).

Properties: mp 169-170°. [a]D20 -17.5° (c = 1 in pyridine). pKa 9.10. uv max (aq soln): 249 nm (log e 4.140).

Melting point: mp 169-170°

pKa: pKa 9.10

Optical Rotation: [a]D20 -17.5° (c = 1 in pyridine)

Absorption maximum: uv max (aq soln): 249 nm (log e 4.140)

Derivative Type: Hemihydrate

Properties: Colorless needles from methanol + ethyl acetate, mp 156-157°. [a]D33 -62.1° (in ethanol). uv max (ethanol): 223, 273, 278 (log e 3.91, 2.88, sh 2.78).

Melting point: mp 156-157°

Optical Rotation: [a]D33 -62.1° (in ethanol)

Absorption maximum: uv max (ethanol): 223, 273, 278 (log e 3.91, 2.88, sh 2.78)

References:

1. Zhong yao tong bao, 1986, 11, p27