CN104398523B - Application of (22-trans)-3beta-hydroxyl-cholester-5,22-diene-24-ketone in neuroprotection medicine - Google Patents
Application of (22-trans)-3beta-hydroxyl-cholester-5,22-diene-24-ketone in neuroprotection medicine Download PDFInfo
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/56—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids
- A61K31/575—Compounds containing cyclopenta[a]hydrophenanthrene ring systems; Derivatives thereof, e.g. steroids substituted in position 17 beta by a chain of three or more carbon atoms, e.g. cholane, cholestane, ergosterol, sitosterol
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J9/00—Normal steroids containing carbon, hydrogen, halogen or oxygen substituted in position 17 beta by a chain of more than two carbon atoms, e.g. cholane, cholestane, coprostane
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Abstract
The invention relates to a compound (22-trans)-3beta-hydroxyl-cholester-5,22-diene-24-ketone, a preparation method and an application thereof. The compound is obtained through extraction from Caulerpa racemosa, pressure reduction and concentration, extraction, silica gel column chromatography and gel column chromatography purification; which has the structure which is measured via a rationalize constant and defined via a spectrum data analysis. Multiple in-vitro SH-SY5Y cell injury neuroprotection experiments prove that the compound has obvious protection effect to beta-amyloid protein 25-35(Abeta-25-35)injury-SY5Y cell, and can be used for preparing the neuroprotectants and medicines to prevent and treat Alzheimer's disease.
Description
Technical field
The present invention relates to one kind extract from Caulerpa racemosa (Forssk) Web V. Boss (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone and
Preparation Method And The Use；The invention still further relates to this compound is to a β25-35The sh-sy5y cell damaging has protective effect
Active component, thus it can be used for preparing nerve protection medicine and prevents Alzheimer disease drug.
Background technology
Alzheimer's disease (alzheimer ' s disease, ad) is a kind of central nervous system's constitutional degeneration disease
Disease, this disease is suffered from more than 35,000,000 people in the whole world.Its clinical manifestation is progressive dysmnesia, the dyskinesia, cognitive disorder etc.
(prince, m. er al,world alzheimer report 2013; alzheimer’s disease
international: london, uk, 2013;Pp 1 92).The existing ad patient of China there are about as many as 8,000,000.Due to evening
Phase ad, minimal invasive treatment can not take care of oneself, and is often accompanied by serious spirit, nervous symptoms, not only seriously reduces the life matter of old people
Amount, returns family and society brings heavy spirit and financial burden.Ad, as the main Types of senile dementia, is the heart that continues
The 4th cause of the death after disease of ZANG-organs, cancer, apoplexy.Therefore, the preventing and treating of ad has been caused with the extensive of medicine sector or even the whole society
Concern.The discovery of pilot compound carrying out for ad and its research of the mechanism of action, it has also become Chinese and western medicine pharmacy works
Person endeavours the important topic studied.
Caulerpa racemosa (Forssk) Web V. Bosscaulerpa racemosa(forssk l) j. agardh system Chlorophyta (chlorophyta)
Chlorophyceae (chlorophyceae) Siphonales (siphonales) Caulerpaceae (caulerpaceae) Caulerpa belongs to
(caulerpa) sea-plant, it is distributed mainly on Perenniporia martius marine site, be grown in the rock of below Intertidal zone, on coral reef
Or in, on the sand ground of low tide band.Also have in China marine site widely distributed, focus primarily upon Dongshan, Fujian, Taiwan, Hainan, west
Husky, Coast of Guangdong Province.Research shows both at home and abroad, contains sesquiterpenoidss, Diterpeneses, steroid, glyceride type, fragrance in Caulerpa racemosa (Forssk) Web V. Boss
The compositions such as class, amide-type and alkaloidss (alarif, w. m. et al,clean: soil, air, water,
2010, 38(5-6), 548–557；wang, h. et al,botanica marina, 2007, 50(3), 185–190;
ayyad, s.-e. n. et al,alexandria journal of pharmaceutical sciences, 1994, 8
(3), 217–219; anjaneyulu, a. s. r. et al,journal of natural products, 1992,
55(4), 496–499).Wherein most terpenoids contain rare 1,4- diacetoxy (aldehyde radical) butadiene of nature
Structure fragment, and alkaloidss are then the peculiar bis-indole compounds of structure.Modern pharmacology research shows, from Caulerpa racemosa (Forssk) Web V. Boss
It is various that the secondary metabolite of middle discovery often shows very strong antibacterial, antiinflammatory, antiviral, parasite killing, antitumor and malicious fish etc.
Biological activity (anjaneyulu, a. s. r. et al,phytochemistry, 1991, 30(9), 3041-
3042; anjaneyulu, a. s. r. et al,journal of the indian chemical society,
1991, 68(8), 480; capon, r. j.phytochemistry, 1983, 22(6), 1465-1467;
nielsen, p. g. et al,phytochemistry, 1982, 21(7), 1643–1645; doty, m. s. et
al,nature, 1966,211 (5052), 990).
(22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone, English entitled (22e)-3β-hydroxy-
Cholesta-5,22-dien-24-one, molecular formula is c27h42o2.(22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24-
Ketone is a kind of white powder, 114 ~ 116 DEG C of fusing point.In view of the specificity of this steroidal compounds side chain, synthesis chemist is not using
With synthetic method it has been carried out complete synthesis (koch, p. et al,bulletin de la societe chimique de france, 1983, (7-8, pt. 2), 189–194; khripach, v. a. et al,zhurnal organicheskoi khimii, 1993, 29(7), 1368–1371;Cui Jianguo etc.,Zhongshan University's journal (natural science Version), 2000, 39(2), 46–50; litvinovskaya, r. p. et al,russian journal of organic chemistry (translation of zhurnal organicheskoi khimii), 2002, 38(3),
355–360; morisaki, n. et al,chemical & pharmaceutical bulletin, 2002, 50(7),
935–940; cui, j.-g. et al,steroids, 2002,67 (13-14), 1,015 1019).This is first in sea
Separate in foreign algae and obtain (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone.And, so far, there is not yet
The research report of the biological activity of related compounds (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone.
Content of the invention
The invention reside in providing a kind of compound (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone and its preparation
Method and purposes.This compound is using extraction, concentrating under reduced pressure, extraction, silica gel column chromatography and gel from Caulerpa racemosa (Forssk) Web V. Boss
(22 is trans) -3 beta-hydroxies-cholesteric -5 obtained from column chromatography eluting, 22- diene -24- ketone, its structure is by physicochemical constant
Measure and spectral data analysis and determine.Show, this compound is to a β through pharmacological testing research25-35The sh-sy5y damaging is thin
Born of the same parents have significant protective effect.
Therefore, it is an object of the present invention to provide one kind prepare compound (22 is trans) -3 β-hydroxyl from Caulerpa racemosa (Forssk) Web V. Boss
The method of base-cholesteric -5,22- diene -24- ketone.
It is a further object to provide compound (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone
Purposes.Specifically, this compound is to a β25-35The sh-sy5y cell damaging has significant protective effect, can be used for preparation god
Through protective agent and the medicine preventing Alzheimer's disease.
According to first purpose of the present invention, the present invention provides one kind using extraction, concentrating under reduced pressure, extraction from Caulerpa racemosa (Forssk) Web V. Boss
Take, silica gel column chromatography and gel column chromatography prepare compound (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24-
The method of ketone, specifically comprises the following steps that
1) prepare extract extractum
By freezing Caulerpa racemosa (Forssk) Web V. Boss (c. racemosa) thaw under room temperature, with ethanol routinely seepage pressure effects three times, every time
Percolation 1 day, obtains extracting solution, extracting solution concentrating under reduced pressure is reclaimed ethanol, obtains crude extract；
2) isolate and purify
(1) above-mentioned crude extract is dispersed in water into suspension, suspension is used successively petroleum ether, ethyl acetate and just
Butanol extracts three times respectively, gained extract concentrating under reduced pressure respectively obtain Petroleum ether extraction extractum, ethyl acetate extract extractum and
N-butanol extraction extractum；
(2) ethyl acetate extract is carried out silica gel column chromatography, with petroleum ether/acetone gradient elution, the separation component of collection
Using silica gel thin-layer chromatography detection, after the merging of composition identical separation component, concentration, obtain five separation components of a, b, c, d, e；
Wherein component c be petroleum ether/acetone volume ratio 8:2 and 7:3 elution fraction through sephadex lh-20 gel filtration chromatography with dichloro
Methane/methanol-eluted fractions, silica gel column chromatography is with petroleum ether/dichloromethane gradient volume ratio for 7:3 eluting, reversed-phase high-performance liquid chromatography
Method uses c18Post (10 μm, 250 × 10 mm), using methanol: water=83:17(v/v) as eluent gradient eluting, flow velocity is
Detect under 3ml/min, 210nm wavelength], obtain compound (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone, change
Learning structural formula is:
In above-mentioned preparation method, in preparing extract extractum step, the described ethanol adopting that extracts is 95% ethanol.
In above-mentioned preparation method, in purification procedures, in described sephadex lh-20 gel filtration chromatography
Methylene chloride/methanol wash-out concentration is volume ratio 1:1.
According to second object of the present invention, the invention provides (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -
The purposes of 24- ketone.
The present invention tests (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone antagonism a β using mtt method25-35Draw
The activity that the neuroblastoma sh-sy5y cell survival rate rising declines.It is experimentally confirmed that (22 is trans) -3 beta-hydroxies-cholesteric -5,
22- diene -24- ketone has significant protective effect to the sh-sy5y cell injury in above-mentioned model.
Therefore, (22 is trans) -3 beta-hydroxies-cholesteric -5 of the present invention, 22- diene -24- ketone can be used as preparation protection nerve
Cell is (for example, through a β25-35The sh-sy5y cell damaging) medicine, and then can be used as preparing nerve protection medicine and prevent
Alzheimer disease drug.
Brief description
Fig. 1: (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone is under variable concentrations to a β25-35The sh- of induction
The cell survival rate block diagram of sy5y cell injury.
Specific embodiment
Embodiment 1 (22 is trans) -3 β-The preparation of hydroxyl-cholesteric -5,22- diene -24- ketone
(1) by freezing Chinese Caulerpa racemosa (Forssk) Web V. Boss (c. racemosa) (picking up from Zhanjiang coastal) 5 kg(dry weight) often
Temperature is lower to thaw, respectively with 30 l, 95% ethanol percolate extraction three times, each percolation 24 hours, and united extraction liquid；
(2) said extracted liquid is reclaimed ethanol in temperature≤45 DEG C concentrating under reduced pressure, obtain crude extract 350g；By this crude extract
It is dispersed in water into suspension, suspension is used petroleum ether (1.5l), ethyl acetate (1.5l) and n-butyl alcohol (1l) respectively successively
Extraction three times, gained extract concentrating under reduced pressure respectively obtains Petroleum ether extraction extractum (38g), ethyl acetate extracts extractum (160g)
With n-butanol extraction extractum (120g)；
(3) ethyl acetate extract is carried out silica gel column chromatography, with petroleum ether/acetone gradient elution, the separation component of collection
Using silica gel thin-layer chromatography detection, after the merging of composition identical separation component, concentration, obtain five separation components of a, b, c, d, e；
Wherein component c be petroleum ether/acetone volume ratio 8:2 and 7:3 elution fraction successively through sephadex lh-20 gel filtration chromatography (with
Methylene chloride/methanol eluting), silica gel column chromatography (with petroleum ether/dichloromethane gradient volume ratio for 7:3 eluting), reversed phase high efficiency
Liquid chromatography is [using c18Post (10 μm, 250 × 10 mm), using methanol: water=83:17(v/v) wash as eluent gradient
De-, flow velocity is 3ml/min, detects under 210nm wavelength], obtain compound (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -
24- ketone.
Embodiment 2 (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone is to a β25-35Induction sh-sy5y cellular damage
Protective effect
1st, laboratory sample and experimental technique
The preparation of sample solution: test sample is the sterling compound (22 is trans) -3 of preparation in above-described embodiment 1
Beta-hydroxy-cholesteric -5,22- diene -24- ketone.Accurately weigh appropriate amount of sample, be configured to the solution of desired concn with dmso, for medicine
Reason active testing.
Cell line and the successive transfer culture of cell: active testing adopts sh-sy5y cell line (purchased from U.S. atcc
(american type culture collection)).With the dmem culture medium containing 10% fbs, it is passed through 5% at 37 DEG C
Successive transfer culture in the incubator of carbon dioxide.
Cytoactive method of testing (mtt method): the present invention adopts mtt method, and the tested sample of test evaluation is to a
β25-35Lead to the protective effect that sh-sy5y cell viability declines.In living cells mitochondria, dehydrogenase metabolism can reduce yellow
Bromination 3- (4,5- dimethylthiazole) -2,5- diphenyltetrazolium bromide is that hepatic water-fast first wears in one's hair (formazan),
First hairpin number its trap can be measured by microplate reader and try to achieve.Amount due to formazan is directly proportional to living cells, so can
Obtain the number of living cells according to trap, thus understanding the impact to cell for the sample.
During active testing, the sh-sy5y cell of trophophase of taking the logarithm, being configured to density with fresh dmem culture medium is
Every milliliter 5 × 104The cell suspension of individual cell, is inoculated in 96 orifice plates by every hole 100 μ l, adds medicinal liquid 10 μ after culture 24h
L/ hole, is all provided with six multiple holes, separately sets blank and model group to each concentration.Cell is under 37 DEG C, 5% carbon dioxide conditions
After culture 2h, in addition to blank control group, every hole adds a β25-35(ultimate density is 1 μm) damaging cells, 37 DEG C, 5%co2Bar
After culture 24h under part, every hole adds mtt solution 10 μ l (5mg/ml), after continuing culture 4h, carefully removes supernatant, adds
Dmso100 μ l/ hole, then surveys od with microplate reader570/630Value.Calculate the protective effect to cell for the measured object by following equation: deposit
Motility rate %=100 × administration group od/ matched group od
Evaluation of result: the survival rate of sample group is higher, test sample is stronger to the protective effect of cell.
2nd, experimental result
(22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone is to a β25-35The protection of induction sh-sy5y cellular damage is made
See Fig. 1 with Activity Results.(##P ＜ 0.01 compared to blank control group,**P ＜ 0.01 is compared to model group): (22 is anti-
Formula) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone in 10 μm of concentration to a β25-35The sh-sy5y cell injury causing has bright
Aobvious protective effect.
3rd, conclusion
(22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone has to neuroblastoma cell at low concentrations
Significant protective effect, thus can be used as preparing nerve protection medicine and preventing Alzheimer disease drug.
Embodiment 3
Example 1 gained compound, adds common drug adjuvant, makes the dosage forms such as tablet, capsule, oral agents.
Claims (3)
1. (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone is protected through a β in preparation25-35The sh-sy5y cell damaging
Medicine in purposes.
2. (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone is preparing the purposes of nerve protection medicine.
3. (22 is trans) -3 beta-hydroxies-cholesteric -5,22- diene -24- ketone prevents the purposes of Alzheimer disease drug in preparation.
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| WO2013071282A1 (en) * | 2011-11-13 | 2013-05-16 | Blanchette Rockefeller Neurosciences Institute | Pkc activators and combinations thereof |
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