CN104224797A - Application of oleanane type pentacyclic triterpene ester derivative for preparing anti-aging medicine - Google Patents
Application of oleanane type pentacyclic triterpene ester derivative for preparing anti-aging medicine Download PDFInfo
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Abstract
The invention provides an application of an oleanane type pentacyclic triterpene ester derivative in preparation of a medicine for delaying aging and treating aging disease, and the medicine is prepared by a pharmaceutical acceptable carrier or an excipient of the oleanane type pentacyclic triterpene ester derivative. The oleanane type pentacyclic triterpene ester derivative can obviously prolong the activity of yeast replicability life, and be used for preparing the medicine for delaying aging and treating aging disease. A structural formula of the oleanane type pentacyclic triterpene ester derivative is shown as following.
Description
Technical field
The invention belongs to medical art, be specifically related to Triterpenoids sapogenins class ester derivant and the application in the medicines such as slow down aging and treatment senile disease and health food thereof.
Background technology
According to statistics, China is that at present a unique old people makes a slip of the tongue the country of hundred million in the world.Data show, current global aging population are about 7.39 hundred million, Aged in China population was about 1.78 hundred million, accounts for 18% of global aging population, by 2025, aging population sum will more than 300,000,000, expect the year two thousand fifty, global aging population are about 20.16 hundred million, and China is about 4.37 hundred million, account for 21.6% of global aging population, China increases by 1,000 ten thousand aging population every year on average.The sharp increase of aging population, the thing followed is that Senile disease increases, and makes national healthcare system and economic system bear greatest pressure.
Therefore, prevent senilism, life lengthening, prevention or treatment senile disease have become the hot issue that medical circle is paid close attention to.It is not only a difficult medical problem, and will become an outstanding social problem.
Recently, the separation and purification from Chinese medicine Herba desmodii multifloi of this seminar obtains Triterpenoids sapogenins class ester compounds, and finds that it has significant prolongation yeast cells replicability life activities.Up to now, this compounds is not yet had to have the relevant report of similar activity.Using Triterpenoids sapogenins class ester compounds as primer, design and synthesize a series of derivant, extensively carry out the research of its external activity, find the structure activity relationship of such material.If can find, there is potential more excellent activity and/or more hypotoxic compound, for the new drug development of slow down aging and treatment senile disease aspect carries out basic research, will have important practical significance.
Summary of the invention
The object of this invention is to provide a kind of Triterpenoids sapogenins class ester derivant (
i) preparing the application in slow down aging and treatment senile disease medicine.
The structural formula of the Triterpenoids sapogenins class ester derivant that the present invention proposes is as follows:
In formula:
R
1and R
2difference, is selected from hydroxyl or R, in R: A respectively
1~ A
5hydrogen, hydroxyl, ester group, fluorine, chlorine, bromine, iodine, sulfydryl, amino, cyano group, nitro, sulfonic group, trifluoromethyl, acrylic, alkyl, alkoxyl, substituted-phenyl can be selected from respectively; A
6can be oxygen, sulfur, nitrogen; A
7oxygen, sulfur can be selected from; A
8-A
9can be the straight or branched saturated alkyl of carbon number from 1 to 20 or unsaturated alkyl.
R
3hydroxyl, ester group, fluorine, chlorine, bromine, iodine, sulfydryl, amino, cyano group, nitro, sulfonic group, trifluoromethyl, acrylic, alkyl, alkoxyl, substituted-phenyl can be selected from.
The present invention also provides the pharmaceutical composition of a kind of slow down aging and treatment senile disease further, and this pharmaceutical composition contains the (compound of physiology effective dose
i) shown in Triterpenoids sapogenins class ester compounds and derivant and pharmaceutically acceptable carrier or diluent.
Pharmaceutically acceptable carrier described here refers to the pharmaceutical carrier of pharmaceutical field routine, and in this way etc., filler is as starch, sucrose, microcrystalline Cellulose etc. for such as diluent, excipient; Binding agent is as starch slurry, hyprolose, gelatin, Polyethylene Glycol etc.; Wetting agent is as magnesium stearate, micropowder silica gel, polyethylene glycols etc.; Absorption enhancer gathers Pyrusussuriensis fat, lecithin etc., and smooth, poly-Pyrusussuriensis fat of surfactant poloxamer, fatty acid Pyrusussuriensis etc., can also add other adjuvant in addition in the composition as flavouring agent, sweeting agent etc.
Triterpenoids sapogenins class ester compounds of the present invention and derivant thereof can administrations in a unit, and route of administration can be intestinal and non-bowel, comprises oral, muscle, subcutaneous and nasal cavity.
Compound administration approach of the present invention can be intravenously administrable.Injection comprises intravenous injection, intramuscular injection, subcutaneous injection and acupoint injection therapy.
The various dosage forms of pharmaceutical composition of the present invention can be prepared according to the conventional production process of pharmaceutical field, such as, make active component mix with one or more carriers, be then made into required dosage form.
Form of administration can be tablet, capsule, dispersible tablet, oral liquid, infusion solutions, little pin, freeze-dried powder, ointment, liniment or suppository.
Triterpenoids sapogenins class ester derivant of the present invention has the activity in significant prolongation yeast replicability life-span, can in slow down aging and treatment senile disease etc. in obtain application.
Accompanying drawing explanation
Fig. 1 is compound
i-1a ~ I-1cextend the yeast cells replicability life-span.
Fig. 2 is compound
i-2aextend the yeast cells replicability life-span
.
detailed description of the invention
The present invention is described in further detail by embodiment and accompanying drawing, but this should be interpreted as that the scope of the above-mentioned theme of the present invention is only limitted to following example, and all technology realized based on foregoing of the present invention all belong to scope of the present invention.
embodiment 1
Compound
i-1awith
i-1bpreparation method:
With 2 ml dichloromethane and 2 ml pyridinium dissolution compounds (1) [3 in 25 ml eggplant type bottles
, 23,28-trihydroxy-12-oleanene-3
-caffeic acid ester (3
, 23,28-trihydroxy-12-oleanene-3
-caffeate)] (10 mg), add 0.5 mg DMAP(4-dimethylamino naphthyridine), stir, add 100 μ l acetic anhydrides, be spin-dried for reactant liquor, carry out solvent distribution by water and ethyl acetate, reclaim ester layer, and purify ester layer sample with PTLC and HPLC, obtain compound
i-1awith
i-1b.
Compound
i-1aphysicochemical property: white solid, it is C that high resolution mass spectrum demonstrates its molecular formula
47h
64o
10(HR ESI-TOF-MS
m/z(M+Na)
+calcd. for C
47h
64o
10na:811.4392, Found:811.4422);
1h NMR (500 MHz, CDCl
3)
7.57 (d,
j=16.0 Hz, 1H), 7.39 (dd,
j=1.88,8.34 Hz, 1H), 7.35 (d,
j=1.8 Hz, 1H), 7.21 (d,
j=8.4 Hz, 1H), 6.34 (d,
j=16.0 Hz, 1H), 5.21 (brt, 1H), 4.94 (dd,
j=11.7,4.7 Hz, 1H), 4.00 (dd,
j=25.5,11.3 Hz, 2H), 3.68 (dd,
j=11.3,8.3 Hz, 2H), 2.30 (s, 3H), 2.30 (s, 3H), 2.07 (s, 6H), 2.06 (s, 6H), 1.15 (s, 3H), 1.01 (s, 3H), 0.95 (s, 3H), 0.91 (s, 3H), 0.89 (s, 3H), 0.87 (s, 3H).
?13C?NMR?(125?MHz,?CDCl
3)?
171.56,?171.12,?168.23,?168.16,?166.21,?143.76,?143.53,?142.81,?142.50,?133.42,?126.54,?124.02,?122.83,?122.81,?119.77,?77.41,?77.36,?77.16,?76.91,?75.04,?70.90,?65.82,?51.04,?47.97,?47.77,?46.27,?42.63,?41.68,?40.82,?39.85,?38.00,?36.74,?35.88,?34.07,?33.28,?32.27,?31.49,?31.02,?25.97,?25.60,?23.66,?23.20,?22.24,?22.14,?21.15,?21.12,?20.82,?20.78,?18.09,?16.81,?16.10,?13.37。
Compound
i-1bphysicochemical property: white solid, it is C that high resolution mass spectrum demonstrates its molecular formula
43h
60o
8(HR ESI-TOF-MS
m/z(M+Na)
+calcd. for C
39h
61o
6na:727.4195, Found:727.4212);
1h NMR (500 MHz, CDCl
3)
7.49 (d,
j=15.9 Hz, 1H), 7.04 (s, 1H), 6.90 (d,
j=8.2 Hz, 1H), 6.82 (d,
j=8.2 Hz, 1H), 6.18 (d,
j=15.9 Hz, 1H), 5.20 (s, 1H), 4.93 (dd,
j=11.3,5.0 Hz, 1H), 3.98 (dd,
j=11.6,57.7 Hz, 2H), 3.72 (dd,
j=23.5,11.3 Hz, 2H), 2.08 (s, 3H), 2.07 (s, 3H), (1.15 s, 3H), 1.00 (s, 3H), 0.94 (s, 3H), 0.91 (s, 3H), 0.89 (s, 3H), 0.87 (s, 3H).
13C?NMR?(125?MHz,?CDCl
3)?
171.87,?171.81,?167.43,?146.76,?145.21,?144.34,?143.72,?127.35,?122.84,?122.41,?115.58,?115.46,?114.29,?74.65,?71.06,?66.02,?51.01,?47.96,?47.76,?46.27,?42.63,?41.68,?40.88,?39.86,?38.01,?36.77,?35.88,?34.07,?33.28,?32.26,?31.50,?31.02,?25.99,?25.62,?23.66,?23.28,?22.24,?21.17,?18.05,?16.81,?16.12,?14.28,?13.39。
Compound
i-1cpreparation method:
By 10 mg compounds (
1), 5 mg lithium carbonate are dissolved in the DMF (DMF) of 2 mL dryings, stir lower dropping 0.6 mL iodomethane.Room temperature reaction 4 days.Reactant liquor is poured in 5 mL water, add 10% hydrochloric acid solution neutralization, absolute ether extraction (3 × 4 mL).Merge organic facies, use water (2 × 5 mL), saturated aqueous common salt (5 mL) to wash successively, anhydrous sodium sulfate drying, concentrated, be separated by Preparative TLC and high performance liquid chromatography and obtain compound
i-1c.
Compound
i-1cphysicochemical property: white solid, it is C that high resolution mass spectrum demonstrates its molecular formula
40h
58o
6(HR ESI-TOF-MS
m/z(M+Na)
+calcd. for C
40h
59o
6: 635.4306, Found:635.4307).
1H?NMR?(500?MHz,?CDCl
3)?
7.61?(d,?
J?=?15.9?Hz,?1H),?7.15?(s,?1H),?7.04?(d,?
J?=?9.4?Hz,?1H),?6.85?(d,?
J?=?8.4?Hz,?1H),?6.29?(d,?
J?=?15.9?Hz,?1H),?5.19?(s,?1H),?5.01?(dd,?
J?=?12.1,?4.5?Hz,?1H),?3.93?(s,?3H),?3.55?(d,?
J?=?11.0?Hz,?1H),?3.40?(d,?
J?=?12.6?Hz,?1H),?3.22?(d,?
J?=?11.0?Hz,?1H),?2.94?(d,?
J?=?12.7?Hz,?1H),?1.18?(s,?3H),?1.02?(s,?3H),?0.95?(s,?3H),?0.89?(s,?
3H),?0.87?(s,?3H),?0.73?(s,?3H)。
13C?NMR?(125?MHz,?CDCl
3)?
168.52,?148.79,?146.04,?145.49,?144.51,?128.07,?122.35,?122.16,?116.04,?113.20,?110.65,?74.68,?69.90,?64.64,?56.16,?47.60,?46.81,?46.58,?42.83,?42.48,?41.94,?39.95,?38.41,?37.09,?36.80,?34.22,?33.33,?32.35,?31.17,?31.11,?26.20,?25.67,?23.74,?22.17,?21.21,?17.84,?16.88,?16.39,?14.35,?13.11。
Compound
i-2apreparation method:
With 2 mL dichloromethane and 2 mL pyridinium dissolution compounds (2) [3 in 25 mL eggplant type bottles
, 23,28-trihydroxy-12-oleanene-23-caffeic acid ester (3
, 23,28-trihydroxy-12-oleanene-23-caffeate)] (10 mg), add 0.5 mg DMAP(4-dimethylamino naphthyridine), stir, add 100
acetic anhydride, is spin-dried for reactant liquor, carries out solvent distribution by water and ethyl acetate, reclaims ester layer, and purifies ester layer sample with PTLC and HPLC, obtains compound
i-2a.
Compound
i-2aphysicochemical property: white solid, it is C that high resolution mass spectrum demonstrates its molecular formula
43h
60o
8(HR ESI-TOF-MS
m/z(M+Na)
+calcd. for C
43h
60o
8na:727.4195, Found:727.4201);
1h NMR (500 MHz, CDCl
3)
7.51 (d,
j=15.8 Hz, 1H), 7.04 (d,
j=4.4 Hz, 1H), 6.85 (d,
j=15.2 Hz, 2H), 6.21 (d,
j=15.8 Hz, 1H), 5.20 (s, 1H), 4.85 (s, 1H), 4.00 (dd,
j=19.0,11.4 Hz, 2H), 3.88 (d,
j=11.3 Hz, 1H), 3.68 (d,
j=14.6 Hz, 1H), 2.08 (s, 3H), 2.05 (s, 3H), 1.14 (s, 3H), 1.00 (s, 3H), 0.95 (s, 3H), 0.91 – 0.85 (m, 9H).
13C?NMR?(125?MHz,?CDCl
3)?
171.83,?171.65,?167.46,?146.61,?145.28,?144.22,?143.82,?127.51,?122.78,?122.62,?115.57,?115.30,?114.44,?75.25,?70.96,?65.32,?48.07,?47.86,?46.30,?42.67,?41.73,?40.98,?39.89,?38.10,?36.79,?35.91,?34.08,?33.28,?32.31,?31.51,?31.02,?26.04,?25.59,?23.68,?23.12,?22.27,?21.51,?21.14,?18.11,?16.84,?16.16,?13.31,?13.27。
embodiment 2
Saccharomyces cerevisiae be all Eukaryotic animal and plant cell there is much identical structure, easily cultivate again, yeast is used as studying Eukaryotic model organism, is also understood one of maximum biology by people at present.Protein important in human body is much all first found its congener in yeast, comprising the albumen in cells involved cycle, signal protein and protein processive enzyme.Its Asymmetric division is usually used to study its replicability life-span, but needs before blast cell fragmentation, with micromanipulation bar, daughter cell is removed.Stefanie, the mutant strain (K6001) of the saccharomyces cerevisiae that the people such as Jarolim find is in dextrose culture-medium, only have blast cell can divide generation daughter cell, and daughter cell can not produce offspring, as long as so the number counting daughter cell under the microscope just can determine the replicability life-span of K6001 yeast cells.Therefore, K6001 yeast cells is suitable as the model organism of screening anti-senescence compounds very much.And resveratrol is the most effective micromolecular compound in current long-life research field, it can not only extend yeast, nematicide, the life-span of fruit bat and mice, and the effect being had to prolongation the life-span of Rhesus Macacus.Using resveratrol as positive control, screen the reactive compound obtained, to further research on anti-senescence, there is very large realistic meaning.
1) experimental technique:
(1) the K6001 yeast strain that-30 degree are preserved is washed three times with 5 mL sterilized water, removing glycerol wherein.Add 1 mL sterilized water, piping and druming makes it suspend, and joins in 10 mL fluid mediums (yeast powder of 1%, the peptone of 2%, the galactose of 3%).Put it into shaking table, 28 degree of joltings cultivate 48 hours, make its restoration ecosystem ability.
(2) from shaking table, take out cultured yeast, wash three times with 5 mL sterilized water, removing fluid medium wherein, counts with blood counting chamber.
(3) in culture dish, add the solid medium (yeast powder of 1% of 5 mL, the peptone of 2%, the glucose of 2%, the agar powder of 2%), after culture medium solidifying, add the sample dissolved wherein, then add 4000 yeast, put into constant incubator 28 degree of constant temperature culture 48 hours.
(4) the daughter cell number that blast cell produces is counted under microscope, mapping analysis.Positive control is wherein resveratrol.
2) experimental result:
Compare with negative control, all have under synthesized derivant finite concentration the significant prolongation yeast cells replicability life-span (
p<0.05) activity, with positive control 10
resveratrol (Res) quite (see Fig. 1 and Fig. 2).
Claims (3)
1. Triterpenoids sapogenins class ester derivant is preparing the application in slow down aging and treatment senile disease medicine, the structural formula of described Triterpenoids sapogenins class ester derivant:
In formula:
R
1and R
2difference, is selected from hydroxyl or R, in R: A respectively
1~ A
5hydrogen, hydroxyl, ester group, fluorine, chlorine, bromine, iodine, sulfydryl, amino, cyano group, nitro, sulfonic group, trifluoromethyl, acrylic, alkyl, alkoxyl, substituted-phenyl can be selected from respectively; A
6can be oxygen, sulfur, nitrogen; A
7oxygen, sulfur can be selected from; A
8-A
9can be the straight or branched saturated alkyl of carbon number from 1 to 20 or unsaturated alkyl;
R
3hydroxyl, ester group, fluorine, chlorine, bromine, iodine, sulfydryl, amino, cyano group, nitro, sulfonic group, trifluoromethyl, acrylic, alkyl, alkoxyl, substituted-phenyl can be selected from.
2. a kind of Triterpenoids sapogenins class ester derivant according to claim 1 is preparing the application in slow down aging and treatment senile disease medicine, it is characterized in that, described medicine is made up of the pharmaceutically acceptable carrier of Triterpenoids sapogenins class ester derivant or excipient.
3. application according to claim 2, is characterized in that, the dosage form of described medicine is liquid preparation or solid preparation, and route of administration is intestinal and non-bowel.
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Cited By (2)
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| WO2017171404A1 (en) * | 2016-03-31 | 2017-10-05 | (주)아모레퍼시픽 | Composition for skin moisturization or skin whitening, containing pentacyclic triterpene caffeic acid esters |
| CN116693591A (en) * | 2022-11-25 | 2023-09-05 | 大理大学 | Preparation and antitumor application of ursane triterpene caffeic acid ester compound |
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| WO2017171404A1 (en) * | 2016-03-31 | 2017-10-05 | (주)아모레퍼시픽 | Composition for skin moisturization or skin whitening, containing pentacyclic triterpene caffeic acid esters |
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| CN109789073B (en) * | 2016-03-31 | 2022-04-01 | 株式会社爱茉莉太平洋 | Composition containing pentacyclic triterpene caffeate for moisturizing or whitening skin |
| CN116693591A (en) * | 2022-11-25 | 2023-09-05 | 大理大学 | Preparation and antitumor application of ursane triterpene caffeic acid ester compound |
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