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Novel iridoids compound and neuroprotective effect thereof

A technology of compounds and drugs, which is applied in the field of preparing drugs for the treatment and prevention of central nervous system diseases, and can solve problems such as compounds that have not yet been seen

Inactive Publication Date: 2013-06-12
SOUTHWEST JIAOTONG UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

At present, there is no report similar to the chemical structure of the compound described in the present invention and its derivatives

Method used

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  • Novel iridoids compound and neuroprotective effect thereof
  • Novel iridoids compound and neuroprotective effect thereof
  • Novel iridoids compound and neuroprotective effect thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation of structural formula I compound

[0030] The dry rhizome powder (20kg) of spider incense (Valeriana jatamansi Jones) was used as raw material, extracted by cold soaking with 95% industrial ethanol for 4 times, 24h each time, and the extract was concentrated under reduced pressure to obtain 2.8kg brown viscous extract. The extract was dissolved in distilled water, extracted successively with petroleum ether, ethyl acetate, and n-butanol to obtain 450 g of ethyl acetate extract. Take 400g of ethyl acetate extract, go through silica gel (100-200 mesh) column chromatography, elution with chloroform-methanol system gradient (100:1-1:1), and thin-layer chromatography to detect and combine similar parts, collect and combine into Fractions 1, 2, 3, and 4, the second fraction (130g) was chromatographed on a silica gel (100-200 mesh) column again, and eluted with petroleum ether-acetone system gradient (30:1-1:1), Thin-layer chromatographic detection combined si...

Embodiment 2

[0032] Identification of Compounds of Structural Formula I

[0033] Compound of structural formula Ⅰ, yellow oil, high resolution mass spectrometry HRESIMS (see figure 1 ) gives an m / z of 390.5, confirming its molecular formula as C 17 h 23 ClO 7 , with an unsaturation of 6.

[0034] according to 1 H NMR (see figure 2 )with 13 C NMR (see image 3 ) can be judged as the iridoid compound skeleton, combined with the molecular weight, its molecular formula is determined to be C 17 h 23 ClO 7 . Through two-dimensional NMR HMBC (see Figure 4 ) and COZY (see Figure 5 ) spectrum can see that H-3 is related to C-1 / C-4 / C-11 / C-8 / C-5, and it can be judged that the 3 and 8 positions are connected by epoxy bonds, and H-10 and C- 7 / C-8 / C-9 are correlated, H-1 / H-9 and H-6 / H-7 are COZY correlated. δ H1 6.41(d, 3.4) and δ H9 The coupling constants of 2.65(d, 3.4) are both 3.4. According to the literature, H-1 / H-9 should be trans.

[0035] Based on the analysis of the above d...

Embodiment 3

[0041] Tablet preparation

[0042]

[0043] Take prescription amount of compound of structural formula Ⅰ and mix evenly with prescription amount of lactose, add 3% povidone ethanol solution to make soft material, pass through 18 mesh sieve to make granules, dry at 50°C for 30-45 minutes, granulate, add magnesium stearate, mix Evenly, press into tablets. Each tablet contains 20mg of the compound.

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Abstract

The invention discloses a novel iridoids compound with a structure shown in formula I and a neuroprotective effect thereof, a preparation method of the compound I and an application of a pharmaceutically acceptable salt of the compound in the preparing of medicines for treating and preventing central nervous system diseases, and an application of the compound or the pharmaceutically acceptable salt thereof in the preparing of medicines with nerve cell protection effects. The cell survival rate of a 18mg / L group of the compound with the structure shown in formula I is obviously higher than a glutamic acid group (P(0.01)), so that the compound with the structure shown in formula I has an obvious protection effect on PC12 (pheochromocytoma-12) cells damaged by glutamic acid and can be used for preventing and treating central nervous system diseases such as cerebral infarction, Alzheimer disease, Parkinson disease, anxiety disorder and the like.

Description

technical field [0001] The present invention relates to extracting and isolating compounds from natural plants, more specifically, the present invention relates to extracting and isolating a new compound and its derivatives from the rhizome of spider incense (Valeriana jatamansi Jones); the present invention also relates to the use of the compound in the preparation of medicines The application, especially in the field of preparation of medicines for treating and preventing central nervous system diseases. Background technique: [0002] Spider incense is the dried rhizome of Valeriana jatamansi Jones, a plant of Valerianaceae (Valerianaceae). Its medicinal properties are pungent, slightly bitter, and warm. It can be used to regulate qi and balance, dispel cold and dampness, promote blood circulation and reduce swelling. It is mainly used to treat abdominal distension and pain, vomiting and diarrhea, malnutrition in children, wind-cold-damp arthralgia, beriberi edema, and ir...

Claims

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Application Information

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IPC IPC(8): C07D493/08A61K31/357A61P25/00A61P25/28A61P25/16A61P25/22A61P9/10A61P39/00
Inventor 闫智勇左长英林玉兰明李少华陈朝勇陈冲张瑞桐张天娥
Owner SOUTHWEST JIAOTONG UNIV
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