CN103588830A - New benzyl alcohol ester glycoside compound in gastrodia elata and application thereof - Google Patents

New benzyl alcohol ester glycoside compound in gastrodia elata and application thereof Download PDF

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Publication number
CN103588830A
CN103588830A CN201310224286.7A CN201310224286A CN103588830A CN 103588830 A CN103588830 A CN 103588830A CN 201310224286 A CN201310224286 A CN 201310224286A CN 103588830 A CN103588830 A CN 103588830A
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benzyl alcohol
alcohol ester
glycoside compound
ester glycoside
new benzyl
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Inventor
冯育林
李志峰
杨世林
张武岗
李俊
朱伟
范玫玫
王�琦
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Jiangxi Bencao Tiangong Technology Co Ltd
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Jiangxi Bencao Tiangong Technology Co Ltd
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Abstract

The invention relates to the field of medical technology, and discloses a new benzyl alcohol ester glycoside compound separated from gastrodia elata by extraction, and an application thereof in the aspect of preparation of medicines related to senile dementia, hypomnesis and the like caused by cerebral vessel ischemia. The new benzyl alcohol ester glycoside compound has the structure general formula as shown in the specification. Pharmacological research indicates that the new benzyl alcohol ester glycoside compound can obviously reduce reaction time, prolong latent time, decrease error count and reduce escape latent period and escape distance, and shows that the new benzyl alcohol ester glycoside compound can improve learning and memory ability of mice with vascular dementia caused by cerebral ischemia-reperfusion and has a certain improvement to vascular dementia. The new benzyl alcohol ester glycoside compound can obviously improve learning and memory ability (P is less than 0.05) of multi-infarct dementia rats, and can remarkably reduce brain tissue AchE (acetylcholinesterase) content of the multi-infarct dementia rats and increase CHAT (choline acetyl transferase), NE (norepinephrine), 5-HT (5-hydroxytryptamine) and GSH-Px (glutathione peroxidase) (P is less than 0.05-0.01) content of brain tissue.

Description

A kind of new benzylalcohol ester glycosides compound and uses thereof in rhizoma Gastrodiae
Technical field
The present invention relates to medical technical field, is from rhizoma Gastrodiae, to extract separatedly to obtain a kind of new benzylalcohol ester glycosides compound and the application in medicine aspect preparing the hypomnesis that cerebrovascular trauma causes.
Background technology
Rhizoma Gastrodiae be China's rare traditional Chinese medicine this, have another name called rhizoma gastrodiae, rhizoma gastrodiae sesame, solely shake sesame, DINGFENGCAO, from female, close from grass.For orchid rhizoma Gastrodiae ( gastrodia elata BI.) dry tuber, be perennial phytoparasite, its host is honey mushroom Armillaria mellea (Vahl.eX Fr) Quel, take the mycelia of honey mushroom or the secretory product of mycelia is source of nutrition, so as to growing.Be born in moistening sylvan life and fertile soil.Be distributed in the ground such as Sichuan, Yunnan, Guizhou, Tibet, existing widely cultivation.According to < < Compendium of Materia Medica > >, record, pungent, warm, nontoxic, cure mainly the diseases such as all rheumatism numbness, spasm of the limbs, paralysis are unsuccessful, dizziness and headache.Its relevant kind, the clinical application that is used for the relative disease that cerebrovascular trauma causes, then, at present in rhizoma Gastrodiae, main active ingredient Gastrodine is mainly to act as master with tranquilizing soporific etc., the working substance of its encephalopathy is still unclear, this seminar tests in conjunction with Chemistry for Chinese Traditional Medicine research method with cerebral ischemia, thereby separation is studied in its related substances basis, obtains this compound.
Summary of the invention
The invention provides a kind of from orchid rhizoma Gastrodiae ( gastrodia elata BI.) in separation obtain a kind ofly there is the new compound that improves the hypomnesis that cerebrovascular ischemia causes, and adopt the spectroscopic techniques such as UV, IR, MS, NMR to identify its structure.Called after: the gloomy glycosides I(parishin of Bali I).Its chemical structure is as follows:
Figure 2013102242867100002DEST_PATH_IMAGE002
The preparation method of the compounds of this invention is as follows:
1, extract and prepare general extractive: will be dried after Rhizoma Gastrodiae pulverizing, by 50% ethanolic soln heating and refluxing extraction, each 2 hours, totally 3 times, united extraction liquid, the concentrated general extractive that to obtain.
2, the preparation of crude extract: by said extracted gained general extractive, press 1:1 sample and resin ratio, upper AB-8 type macroporous adsorbent resin, respectively with water, 20% ethanolic soln, 70% ethanolic soln, 95% ethanolic soln gradient elution, collect 70% ethanolic soln wash-out position, concentrate to obtain crude extract.
3, the above-mentioned crude extract that obtains, again with silica gel column chromatography, eluent is with the methylene chloride/methanol mixing solutions gradient elution of volume ratio 9:1-1:1, collect methylene dichloride: methyl alcohol (7:3) wash-out position, concentrate, mesolow liquid phase chromatography again, adopt 20% methyl alcohol, 30% methyl alcohol, 40% methyl alcohol, 50% methyl alcohol, 70% methyl alcohol, 100% methyl alcohol carries out gradient elution, 20% methyl alcohol wherein, 30% methyl alcohol position is identical through high-efficient liquid phase analysis, after merging again through preparative high performance liquid chromatography, the methanol-water (24:76) of take is moving phase, detect wavelength 230nm, flow velocity 10ml/min, retention time 45min place is prepared into this compound 20mg.
Pharmacological research shows, this compound can significantly shorten its reaction times, extends latent period, reduces errors number, shortens escape latency and escape distance, illustrate that it can improve the learning and memory function of vascular dementia due to Cerebral Ischemia-reperfusion in Mice, has some improvement to vascular dementia.It can significantly improve multi-infarct dementia learning and memory in rats ability (P < 0.05); Significantly reduce the AchE of multi-infarct dementia rat cerebral tissue content, rising cerebral tissue CHAT, NE, 5-HT and GSH-Px content (P < 0.05-0.01).
The preparation method of the compounds of this invention is simple, and pharmacological action is obvious.For researching and developing the new drug of the neurological disorder treatment aspect that new cerebrovascular trauma causes, provide a new lead compound.And provide scientific basis for the deep development of rhizoma Gastrodiae.
Embodiment:
Now in conjunction with example, content of the present invention is described in detail
Embodiment 1: prepare benzylalcohol ester glycoside compound of the present invention
Get dried Rhizoma Gastrodiae, after pulverizing, use respectively 50% ethanolic soln, heating and refluxing extraction 3 times, each 2 hours, united extraction liquid, extracting solution obtains medicinal extract in 60 ℃ of concentrating under reduced pressure, medicinal extract is with after water dissolution, press medicinal material with resin than the upper AB-8 type of 1:1 macroporous adsorptive resins, then water, 20% ethanolic soln, 70% ethanolic soln, 95% ethanolic soln gradient elution, four retention volume of each gradient elution, collect 70% ethanolic soln wash-out position, in 60 ℃ of concentrating under reduced pressure, obtain medicinal extract.
Aforesaid method is prepared into medicinal extract, again through silica gel column chromatography, first with silica gel: sample (1:1) ratio is mixed sample, then with dry method upper prop method filling silicagel column, again with methylene dichloride: methanol mixed solution carries out gradient elution, each retention volume is collected two cuts, then with sample difference in each cut of thin-layer chromatography discriminatory analysis, after identical cut is merged, again through silica gel column chromatography, with methylene dichloride: methyl alcohol 9:1-1:1 carries out gradient elution, collect methylene dichloride: methyl alcohol (7:3) wash-out position, concentrate to obtain sample, cross quick mesolow liquid chromatography, with 20%, 30%, 40%, 50%, 70%, 100% methanol solution gradient elution, through high-efficient liquid phase analysis 20%, 30% position ingredient is basic identical, after merging again with preparative high performance liquid chromatography, with methanol-water (24:76), with 230nm wavelength place, detect, flow velocity 10ml/min, retention time 45min place preparation is separated must this compound, and under similarity condition, high performance liquid chromatography purifying and obtaining.
Through physico-chemical property and spectral data result, identify its structure, its spectral data is as follows:
(1) the gloomy glycosides I(parishin of Bali I): white amorphous powder, ESI-MS:741[M-H] -, 473[M-268] -. 1h NMR (600MHz, DMSO): 6 2.73,2.89 (each 1H, d, J=15.7 Hz ,-CH 2-), 2.80,2.95 (each 1H, d, J=15.4Hz ,-CH 2-), 3.51 (2H, dd, J=4.9,12.1Hz, 2 * Glc H-6), 3.68 (2H, d, J=12.1Hz, 2 * Glc H-6), 4.88,4.89 (each 1H, d, J=7.5 Hz, 2 * anomeric H), 4.98,5.02 (each 2H, s, 2 * H-7'), 7.02 (4H, d, J=8.1 Hz, 2 x H-3', 5'), 7.27 (4H, d, J=8.1 Hz, 2 * H-2', 6'). 13cNMR (150MHz, DMSO): δ 44.3,44.4 (C-l, 3), 61.2 (2C, 2 * Glc C-6), 65.9,66.6 (2 * C-7'), 73.5 (C-1'), 70.2,73.6,77.1,77.5 (each 2C, 2 * Glc C-2,3,4,5), 100.8 (2C, 2 * Glc C-l), 116.6 (4C, 2 * C-3', 5'), 129.5 (2C, 2 x C-1'), 130.1 (4C, 2 x C-2', 6'), 157.7 (2C, 2 * C-4'), 169.6 (COO-), 170.1 (COO-), 172.9 (COO-), 51.9 (OCH 3).
Effect experiment:
[the effect research of the gloomy glycosides I of Bali to vascular dementia]
1. the impact on fourth ventricle in mice with vascular dementia learning and memory
Mouse vascular dementia model copies: animal first 1 day in modeling, and water 12h is can't help in fasting, according to the method for document, (the 350mg.kg of Chloral Hydrate for mouse -1) intraperitoneal anesthesia, anesthesia layback position is fixed on operating table, after the routine disinfection of the positive middle part of neck, cut skin of neck, under stereoscopic microscope, separated Bilateral Cervical is always moving, overlap No. 4 four cableties standby, fastening screw thread, bilateral common carotid arteries blocking blood flow 15min, 7 of tail tip bloodletting (about 0.3ml) simultaneously, heat setting hemostasis.Unclamp screw thread and pour into after 10min again, blocking blood flow 15min, unclamps screw thread again, skin suture, in otch local injection gentamicin 0.2 ten thousand U, and surveys mouse temperature and respiration rate before blocking blood flow and during the 2nd blocking blood flow, the sign of cerebral ischemia is that body temperature reduces, respiration inhibition.Postoperative intramuscular injection every day penicillin 0.2 ten thousand U, continuous 2 days.Sham operated rats separated arteria carotis communis only wherein, blocking blood flow not, not tail point bloodletting, observing time is identical with other groups.Postoperative 48h, carries out learning and memory test.
The gloomy glycosides I of table 1 Bali on the impact of mouse vascular dementia learning and memory (diving tower) (
Figure 2013102242867100002DEST_PATH_IMAGE004
± s)
Group N Escape latency (s)
Sham operated rats 10 18.26±8.64
Model group 10 105.59±36.17 △△
Low dose group 10 72.61±29.43*
Middle dosage group 10 65.56±34.43*
High dose group 10 50.25±30.63**
Positive group 10 35.34±30.67**
Note: △represent and sham operated rats comparison, P < 0.05, △ △represent to compare P < 0.01 with sham operated rats
* represent and model group comparison, P < 0.05, * * represents and model group comparison, same under P < 0.01()
The gloomy glycosides I of table 2 Bali on the impact of mouse vascular dementia learning and memory (Morris water maze) (
Figure 2013102242867100002DEST_PATH_IMAGE006
± s)
Group N Escape latency (s) Escape total distance (cm)
Blank group 10 40.05±17.54 756.14±171.25
Model group 10 111.51±20.34 △△ 1,378.87±199.32 △△
Low dose group 10 69.67±23.34* 1,023.54±245.23*
Middle dosage group 10 63.34±25.67** 993.43±185.75*
High dose group 10 52.45±27.97** 892.32±171.43**
Results suggest: the gloomy glycosides I of Bali can significantly shorten its reaction times, extends latent period, reduces errors number, shortens escape latency and escape distance, explanation can improve the learning and memory function of vascular dementia due to Cerebral Ischemia-reperfusion in Mice, and vascular dementia is had some improvement.
2. the impact on rat multi-infarct dementia
The gloomy glycosides I of Bali can significantly improve multi-infarct dementia learning and memory in rats ability (P < 0.05); Significantly reduce the AchE of multi-infarct dementia rat cerebral tissue content, rising cerebral tissue CHAT, NE, 5-HT and GSH-Px content (P < 0.05-0.01).
A, the impact on learning and memory
The gloomy glycosides I of table 3 Bali on the impact of multiple cerebral learning and memory in rats (Morris water maze) (
Figure 593594DEST_PATH_IMAGE006
± s)
Group N Escape latency (s) Escape total distance (s)
Sham operated rats 10 19.53±16.35 280.76±109.53
Model group 10 81.22±27.16 △△ 1090.04±272.67 △△
Low dose group 10 69.15±20.64 895.28±139.09
Middle dosage group 10 51.63±21.95* 502.74±206.69**
High dose group 10 39.22±17.75** 432.55±190.74**
Positive group 10 38.54±17.34* 369.48±208.71**
B, the impact on monoamine neurotransmitter
The gloomy glycosides I of table 4 Bali on the impact of the NE of multiple cerebral rat cerebral tissue, 5-HT content (
Figure 510734DEST_PATH_IMAGE004
± s)
Group N NE content (pg/mL) 5-HT（ng/ml）
Sham operated rats 10 362.27±55.43 486.45±54.71
Model group 10 167.45±43.17 △△ 360.28±40.21 △△
Low dose group 10 235.34±55.78* 380.43±30.89
Middle dosage group 10 254.99±68.19 * 409.24±51.18*
High dose group 10 314.03±58.37** 431.42±40.38**
Positive group 10 289.41±38.26* 412.30±38.81*
C, the impact on central cholinergic system
The gloomy glycosides I of table 5 Bali on the impact of the AchE of multiple cerebral rat cerebral tissue, CHAT content (
Figure 290471DEST_PATH_IMAGE004
± s)
Group N AchE（U/mgprot） CHAT（U/g）
Sham operated rats 10 6.88±1.53 207.64±60.80
Model group 10 8.68±1.72 △ 115.34±42.05 △△
Low dose group 10 7.32±1.18* 186.24±36.27**
Middle dosage group 10 7.15±0.70* 188.28±35.26**
High dose group 10 6.98±0.89* 190.06±56.08**
Positive group 10 6.96±1.60* 195.42±46.36**
D, the impact on GSH-PX
The gloomy glycosides I of table 6 Bali on the impact of the GSH-PX of multiple cerebral rat cerebral tissue content (
Figure 747998DEST_PATH_IMAGE006
± s)
Group N GSH-PX (U/L）
Sham operated rats 10 687.43±69.30
Model group 10 388.42±47.35 △△
Low dose group 10 498.98±40.93*
Middle dosage group 10 527.62±58.34*
High dose group 10 599.34±67.84**
Positive group 10 568.44±65.63**

Claims (1)

1. a benzylalcohol ester glycosides compound, its general structure is as follows:
Figure 134849DEST_PATH_IMAGE001
。
CN201310224286.7A 2013-06-07 2013-06-07 New benzyl alcohol ester glycoside compound in gastrodia elata and application thereof Pending CN103588830A (en)

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CN109160928A (en) * 2017-09-21 2019-01-08 暨南大学 New phenol glycosides compound and its application in moringa seeds

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109160928A (en) * 2017-09-21 2019-01-08 暨南大学 New phenol glycosides compound and its application in moringa seeds
CN109160928B (en) * 2017-09-21 2020-07-21 暨南大学 Novel phenolic glycoside compound in moringa seeds and application thereof

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Application publication date: 20140219