| Identification | More | [Name]
Gastrodin | [CAS]
62499-27-8 | [Synonyms]
(2R,3S,4S,5R,6S)-2-HYDROXYMETHYL-6-(4-HYDROXYMETHYL-PHENOXY)-TETRAHYDRO-PYRAN-3,4,5-TRIOL
4-hydroxybenzyl alcohol 4-o-bata-d-glucoside
4-O-BETA-D-GLUCOPYRANOSYLOXYBENZYL ALCOHOL
GASTRODIN
Gastro enterical
Gastrodin ,98%
4-(Hydroxymethyl)phenyl β-D-glucopyranoside
4-(β-D-Glucopyranosyloxy)benzyl alcohol
p-(Hydroxymethyl)phenyl β-D-glucopyranoside | [EINECS(EC#)]
683-202-7 | [Molecular Formula]
C13H18O7 | [MDL Number]
MFCD00272169 | [Molecular Weight]
286.28 | [MOL File]
62499-27-8.mol |
| Chemical Properties | Back Directory | [Melting point ]
169-170° | [alpha ]
D20 -17.5° (c = 1 in pyridine) | [Boiling point ]
563.2±50.0 °C(Predicted) | [density ]
1.504±0.06 g/cm3(Predicted) | [storage temp. ]
Sealed in dry,2-8°C | [solubility ]
DMSO (Slightly, Sonicated), Methanol (Slightly), Water (Slightly, Sonicated) | [form ]
Solid | [pka]
9.10(at 25℃) | [color ]
White to Off-White | [λmax]
272nm(MeOH)(lit.) | [Detection Methods]
HPLC,NMR | [Merck ]
14,4375 | [InChI]
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-/s3 | [InChIKey]
PUQSUZTXKPLAPR-SYDLEIBONA-N | [SMILES]
[C@@H]1([C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O)OC1C=CC(CO)=CC=1 |&1:0,1,3,4,6,r| | [LogP]
-1.939 (est) | [CAS DataBase Reference]
62499-27-8(CAS DataBase Reference) |
| Hazard Information | Back Directory | [Description]
Gastrodin is extracted from the dry root of the orchid plant, Gastrodia elata. The
source of raw materials is Yunnan Province. Traditional Chinese medicine Gastrodia
elata (Gastrodia elata Bl.) is also known as Chi Jian, Ding Feng Cao, Shui Yang Yu,
and so on, belonging to special symbiosis perennial herb of Orchidaceae and
Armillaria mellea. The medicinal part is its tubers. It has sweet flavor and liver
channel tropism and is neutral in nature. Traditional Chinese medicine believes that
its main functions are to expel wind and relieve convulsion, calm the liver and suppress liver-yang, and expel wind evil and channel. There are 23 chemical ingredients extracted from Gastrodia elata, including gastrodin, gastrodia glycosides,
vanilla alcohol, vanilla aldehyde, beta steroid valley alcohol, p-hydroxybenzoic
acid, carrot glycosides, and so on, among which the highest content of single active
ingredient is Gastrodia glycosides, namely, gastrodin | [Chemical Properties]
White solid | [Physical properties]
Appearance: white prismatic crystal, odorless, and bitter; little hygroscopicity.
Solubility: soluble in water, methanol, ethanol, acetone, and acetonyl acetate, insoluble in chloroform, and poorly soluble in ethyl ether. Melting point: ?153 to 156?°C.
Specific optical rotation: ?68 to ?72° . | [History]
It has been more than 30?years since the chemical composition of Gastrodia elata
was analyzed. It includes phenols, organic acids, sterols, and so on. At present, the
studies of the composition of Gastrodia elata focus on the fingerprint, but the studies of gastrodin were centered on the activity. The studies showed that gastrodin has
many pharmacological effects with safety and few side effects; moreover, it is not easy to accumulate in the body. Based on traditional medicinal experience of
Gastrodia elata, gastrodin has been developed as a medicine for the treatment of
insomnia, headaches, and other symptoms related to the functions and indications
of Gastrodia elata. At present, many pharmaceutical factories in China have produced active pharmaceutical ingredients (API) and general preparation of gastrodin,
such as Gastrodia tablet, Gastrodia capsule, and Gastrodia injection. To reduce the
frequency of administration, the fluctuations of blood drug concentration, as well as
side effects, some new dosage forms have been developed in recent years, such as
Gastrodia dispersible tablets, Gastrodia sustained-release tablet, sustained-release
pellets and osmotic pump tablets, etc. . Although gastrodin has been applied
clinically, a lot of studies still need to be done to confirm the pharmacological
effects of gastrodin. Recent studies found that other compositions of Gastrodia
elata also showed rather excellent biological activity, suggesting that the study of
Gastrodia elata and gastrodin needs further investigation. | [Uses]
Gastrodin up regulates heme oxygenase-1 expression through activation of p38 MAPK/Nrf2 signaling pathway thus protecting the SH-SY5Y cells from MPP+-induced oxidative cell death. | [Definition]
ChEBI: Gastrodin is a glycoside. | [Indications]
Gastrodin is included in the International Pharmacopoeia (5th ed.).
The dosage forms include injections, tablets, and capsules. They are widely used
for the treatment of vertigo (Meniere’s disease, medicinal dizziness, traumatic vertigo, sudden deafness, vestibular neuronitis, vertebrobasilar insufficiency, etc.),
headache (vascular headache, migraine, etc.), neuralgia (trigeminal neuralgia, sciatica, etc.), neurasthenia syndrome, and brain traumatic syndrome . | [Pharmacology]
Gastrodin has the pharmacological effects of hypnosis, sedation, and anticonvulsive. The pentobarbital sodium-induced sleep time test and sodium barbital-induced
sleep onset latency test demonstrated that gastrodin can prolong the sleeping time
and shorten the sleep onset latency in mouse, suggesting that gastrodin has the sedative and hypnotic effects .
Gastrodin also has antiepileptic effect. It suggested that gastrodin may inhibit the
hippocampal excitatory neurotransmitter receptors of amino acid glutamate, activate hippocampal inhibitory neurotransmitter receptor of GABA, reduce the excitability of the cerebral cortex, and thus attenuate the development of epilepsy to play
a role of antiepileptic effect .
Additionally, research has shown that gastrodin has certain pharmacological
effect on scavenging free radicals and inhibiting the central nerve cell apoptosis,
etc., which may be related to antiaging and neural protection . According to the
available references, the researches of pharmacology and clinical efficacy of gastrodin are very preliminary; more research evidences still need to confirm whether
gastrodin is the active constituent of rhizoma gastrodiae. | [Clinical Use]
Gastrodin has sedative and hypnotic, analgesia, and immune enhancement function
and is used for the treatment of tension headache to relieve pain and intense sentiment and thus further relieve the related symptoms . Clinical usage of gastrodin
acupoint injection to treat insomnia also achieves certain effect . Moreover, gastrodin agents have been used for the treatment of cardiovascular diseases and microcirculation system, such as hypertension and coronary heart disease without
obvious side effects .
It is also reported that gastrodin can treat epilepsy, vascular dementia, deafness,
tinnitus, herpes zoster, osteoarthritis, cognitive impairment, and so on but still needs
further investigation. |
|
|