CN109265502A - Prenyl chromocor compound, derivative, pharmaceutical composition and its application - Google Patents
Prenyl chromocor compound, derivative, pharmaceutical composition and its application Download PDFInfo
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- CN109265502A CN109265502A CN201811271170.8A CN201811271170A CN109265502A CN 109265502 A CN109265502 A CN 109265502A CN 201811271170 A CN201811271170 A CN 201811271170A CN 109265502 A CN109265502 A CN 109265502A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
- C07H17/06—Benzopyran radicals
- C07H17/065—Benzo[b]pyrans
- C07H17/07—Benzo[b]pyran-4-ones
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P19/00—Drugs for skeletal disorders
- A61P19/08—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease
- A61P19/10—Drugs for skeletal disorders for bone diseases, e.g. rachitism, Paget's disease for osteoporosis
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P9/00—Drugs for disorders of the cardiovascular system
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H1/00—Processes for the preparation of sugar derivatives
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Abstract
Present disclose provides a kind of prenyl chromocor compound, derivative, pharmaceutical composition and its applications.The compound and derivant structure formula compound shown in formula I
Description
Technical field
The present invention relates to a kind of prenyl chromocor compounds and its derivative preparation method and such compound to exist
Prevention or treatment patient's diseases of cardiovascular and cerebrovascular systems, osteoporosis, cancer, the application in sex dysfunction.
Background technique
The single compound of the principle active component of natural products is as chemicals itself or the guideization of medicament research and development
Closing object is one of the important research method that medicament research and development personnel is engaged in chemicals research and development for many years, and flavonoid glycoside compound has
Free radical resisting, anti-oxidant, prevention and cure of cardiovascular disease, antibacterial, hormone adjusting and the effect for improving human immunity.
However, the price of icariin is high, the price of fractions per kilogram reaches 100,000 yuan, the price of raw material and source
Greatly limit the application of Herba Epimedii.
Summary of the invention
The price of the flavone glycoside of other plant origins is lower (most of to be not higher than 1000 yuan/kilogram), such as apiolin, Mongolian oak
Pi Su.Therefore the present invention is by synthesizing icariside I by catalyzed by biological enzyme using lower-cost chromocor compound
Class compound --- prenyl chromocor compound and its derivative has very high medical value and economic value.
Technical solution is as follows:
A kind of prenyl chromocor compound and its derivative, structural formula compound shown in formula I
Or it is the stereoisomer of compound shown in Formulas I, geometric isomer, tautomer, nitrogen oxides, hydrate, molten
Agent compound, metabolite, pharmaceutically acceptable salt or prodrug；Wherein,
1)R1Selected from H, OH, OCH3、CH3COO、NH2、CH3NH、(CH3)2N、CH3CONH or CN；
2)R2Selected from H, OH, OCH3、CH3COO、NH2、CH3NH、(CH3)2N、CH3CONH or CN；
3)R3Selected from H, OH, OCH3、CH3COO、NH2、CH3NH、(CH3)2N、CH3CONH or CN；
4)R4Selected from H, OH, OCH3、CH3COO、NH2、CH3NH、(CH3)2N、CH3CONH or CN；
5)R5Selected from H, OH, OCH3、CH3COO、NH2、CH3NH、(CH3)2N、CH3CONH or CN；
6)R6Selected from H or prenyl.
The functional group of preferred prenyl chromocor derivative is designated as: R1For OH or OCH3；R2For H, OH or
OCH3；R3For H, OH or OCH3；R4For H, OH or OCH3；R5For H, OH or OCH3；R6For
Further, by R1、R2、R3、R4、R5It is limited to OCH3；R6For
A kind of pharmaceutical composition, above-mentioned prenyl chromocor compound or derivative, also comprising pharmaceutically acceptable
Carrier, excipient, diluent, medium or their combination.
A kind of synthetic method of prenyl chromocor compound and its derivative, specifically: utilize catalyzed by biological enzyme
Prenyl is connect with chromocor compound, the chromocor compound includes Quercetin, apiolin, Kaempferol, baicalein, open country
Baicalein, Chrysin, Daidzein, genistein, Isorhamnetin, myricetin, luteolin, fisetin, icariine or
Naringenin.Using prenyltransferases in R6Upper connection prenyl；Using O- transmethylase in R1、R2、R3、R4、
R5Connect OCH3.It further include the derivative glycosylation isoamyl that prenyl chromocor compound is synthesized by UDP glycosyltransferase
Dialkylene flavones.
On the other hand, this disclosure relates to which a kind of compound, derivative or composition are used to prepare the purposes of drug, the medicine
Object is used to preventing, mitigate or treating the purposes in diseases of cardiovascular and cerebrovascular systems.
It also relates to a kind of compound, derivative or composition be used to prepare the purposes of drug, the drug is for pre-
Purposes in anti-, mitigation or treatment osteoporosis.
And be related to the purposes that a kind of compound, derivative or composition are used to prepare drug, the drug for preventing,
Purposes in mitigation or treating cancer.
There is no prenyl flavones is synthesized by the natural flavones such as apiolin, Quercetin compound both at home and abroad at present
The report of compound and its derivative, and a series of Bioexperiment has been carried out to the compound of the present invention by inventor, it demonstrate,proves
The compound of the present invention-prenyl chromocor compound is illustrated, and there is prevention or treatment diseases of cardiovascular and cerebrovascular systems, sclerotin to dredge
Purposes in loose disease and treating cancer.Therefore, prenyl chromocor compound and its derivative of the present invention have fine
Application prospect.
Specific embodiment
The invention will be further described by the following examples, and the present invention illustrates structure of the present invention as example using Quercetin
Think, but be not limited to apiolin, also includes naringenin, Quercetin, Kaempferol, baicalein, scutellarin, Chrysin, soya bean
Aglycon, genistein, Isorhamnetin, myricetin, luteolin, fisetin, icariine etc..Example of the invention not office
It is limited to specific example, only a kind of synthesis thinking.
Embodiment 1: prenyl chromocor compound and its derivative are prepared by taking Quercetin as an example
The following steps are included:
(1) using Quercetin as substrate, by it with buffer at Quercetin solution；Quercetin (purity 98%)；It is slow
Fliud flushing is to contain (Mg containing 0.1mM2+(50%), Ba2+(11.3%), Ca2+(13.6%), Fe2+(5.8%), Co2+
(7.9%), Cu2+(7.6%), Zn2+(7.8%)) buffer salt solution, the buffer salt are sulfate, chlorate, nitrate or boron
Hydrochlorate etc. adjusts pH5 with hydrochloric acid；
(2) prenyltransferases and dimethylallyl diphosphate ester is first added, reacts 1h；The isoprene
The concentration of based transferase is 50 μ g/mL, and the concentration of dimethylallyl diphosphate ester is 100 μ g/mL, and the pH value of reaction is 5.0,
Dimethylallyl diphosphate ester is added in per half an hour before S-adenosylmethionine and O- transmethylase is added, and ties up concentration
It holds in 100 μ g/mL；
(3) after reacting 3 hours, S-adenosylmethionine and O- transmethylase is added, adjusts pH4.0, O- first with hydrochloric acid
The concentration of based transferase is 150 μ g/mL, and S-adenosylmethionine concentration is 600 μ g/mL, and the reaction was continued 3-7 hours；
(4) after boiling water bath heating 5min inactivator, product is obtained.
Embodiment 2: the preparation of glycosylation prenyl flavones (YCIA)
By embodiment 1 synthesizes 20 grams of compound phosphate-buffereds for being dissolved in pH6.8 it is molten in, fixation glucose base is added
It 10 grams of transferase, 18 grams of UDP glucose, at 60 DEG C, stirs lower reaction 12 hours, solid is collected by filtration in crystallization, recrystallizing methanol
Processing.Obtain 13.5 grams of glycosylation prenyl flavones (YCIA).
Embodiment 3: toxicological experiment
At 28 ± 1 DEG C of temperature, 70 ± 5% damp condition, 7~8 week old, healthy cleaning grade NIH mouse are chosen
20 half male and half females, weight is in 18~20g.By feed and water sterilization, before test and in the observation period of test, chow diet is pressed
Condition raising.
YCIA obtained in enzymatic clarification embodiment 2 is dissolved in 0.5%Tween80, concentration 300mg/ml, by this
Liquid oral administration mouse, dosage are 0.4ml/20g mouse weight.Observe Isosorbide-5-Nitrae after administration, 8,12 hours, later every 8h
Observation is primary.Death condition is observed, records mouse weight variation and other symptoms daily.10th day, the neck that breaks put to death mouse,
Each organ is taken to carry out pathologic finding.
At the 10th day, the YCIA of whole mouse survivals, 2.2g/kg dosage had no toxic reaction.Each organ pathology inspection of mouse
It looks into normally, does not find lesion, mouse weight has no mitigation in 10 days.Therefore, illustrate YCIA drug of the invention take orally to
Toxicity is had no when medicine animal.
Purposes of the embodiment 4:YCIA in protection, processing, treatment, diseases of cardiovascular and cerebrovascular systems drug
The pharmacodynamics test of the therapeutic effect of cerebral infarction is caused to rat " rabbit brain powder-macromolecule glucan ".
Material: animal: rat, 250~350g of weight, half male and half female.Equipment: cone and plate viscometer, centrifuge, scale from
The heart, test tube, eye scissors, ophthalmic tweezers and common surgical instrument, No. 0 operation silk thread, blood vessel clip etc..
Drug and reagent: test group 1: icariside I；Test group 2:YCIA contrast groups 1: apiolin；Contrast groups 2: Mongolian oak
Pi Su.The above drug is prepared into test sample using conventional method.
It is compareed by positive drug of commercially available Breviscapini injection；Rabbit brain powder (rabbit brain powder thromboplastin powder).Take sub-sieve 120
Rabbit brain powder between~150 mesh, particle are 100~120 μm.Macromolecule glucan: molecular weight 5,000,000.The preparation of suppository: will
25mg rabbit brain powder is mixed in 10% macromolecule dextran solution 100mL, is placed in 37 DEG C of water-baths 40 minutes.Then, -18 DEG C are put in
Refrigerator is spare.Rapid Medical ZT glue.Balf serum albumin, ringer solution.Heparin sodium: by 20u/mL blood dosage be added test tube, 40
DEG C or less be dried for standby.
Test method: 1, prepared by rat cerebral infarction model: rat etherization, fixation of lying on the back, skin cropping disinfection, neck
It cuts, separation left side neck always beats one's brains, neck is interior, external carotid artery.Folder closes external carotid artery, arteria carotis communis proximal part respectively.In distal end
Place presss from both sides a blood vessel clip again.After suppository is shaken up, neck is lunged by 0.03mL/100g rat dosage with 0.25mL syringe and is always moved
Arteries and veins opens distal end blood vessel clip, suppository is injected.Then, folder closes arteria carotis communis distal end, extracts syringe needle, uses medical adhesive dressing
Close pin hole.The blood vessel clip of arteria carotis communis distal end, proximal part, external carotid artery is successively decontroled after 1 minute, restores blood flow, cleaning wound
Mouthful, skin suture.
Drug influences the hemorheology of different time after cerebral infarction: rat is divided into (1~3 group of test group of administration group
Or 1~3 group+animal model of reference examples group), physiological saline group (physiological saline+animal model group), sham-operation group (control group),
Every group of 12 rats.Administration group, physiological saline group impose surgical procedure, the complete phase of sham-operation group surgical procedure according to the above method
Together, but not injected plug agent, suppository is replaced with physiological saline, is injected in internal carotid.Administration group is in operation consent oral medicine in 3 days
Object (test group, reference examples) 1.42g/Kg.Positive drug is in 1 hour intraperitoneal injection of drugs 1.0mg/Kg of operation consent.Physiological saline group
Inject same amount physiological saline.Sham-operation group does not inject any drug.Later every morning is administered once, for three days on end.
By rat anesthesia (25% urethane 0.3mL/100g weight, intraperitoneal injection), right common carotid artery is put within the 3rd day after surgery
Blood measures the whole blood viscosity under different shear rates with cone and plate viscometer in 2 hours in heparin test tube.Again by whole blood with
1500rpm centrifugation, sucks upper plasma.Then three times with 0.25% bovine serum albumin(BSA)-ringer solution rinsing red blood cell, every time
1500rpm is centrifuged 10 minutes.Finally, preparing erythroblast in scale test tube: albumen ringer solution=6:4 red blood cell protein is appointed
Family name's liquid measured its viscosity under 1 shear rate at 20 seconds.Using red blood cell protein ringer solution viscosity as red cell deformability.It is all
Experiment carries out under 25 DEG C of constant temperature, carries out statistical test to experimental result.Specific value and it the results are shown in Table 1.
Table 1: (unit: mPa.s) is influenced on the whole blood viscosity of different time after rat cerebral infarction
Note: * * P < 0.05***P < 0.01 is compared with physiological saline group.
By 1 test result of table it is found that infraction 3 days when, physiological saline group compared with sham-operation group, whole blood viscosity rise (P <
0.05), illustrate animal model modeling success, each administration group can reduce whole blood viscosity to some extent, wherein with the application medicine
Object effect preferably (P < 0.01), take second place, and control drug effect is poor by Herba Epimedii effect.With physiological saline group ratio, under whole blood viscosity
Drop, statistical procedures have significant.
The protection of embodiment 5:YCIA, processing, the purposes in treating cancer drug
1) it cultivates cell: selecting prostate gland cancer cell as experimental subjects.By cell inoculation in the culture that diameter is 10cm
After ware, using 10% fetal calf serum DMEM culture medium, 37 DEG C, 5%CO2It is cultivated in environment.
2) inoculating cell: by cell inoculation in the culture dish of 96 orifice plates, cell density is about 2000/ml, then 37
DEG C, 5%CO215h is cultivated in environment.
3) the aerial culture solution of plate is siphoned away, the compounds of this invention solution for preparing concentration is added.The compounds of this invention DMSO
Solution is prepared, and concentration for the treatment of is respectively 0 μM, 0.1%DMSO, 5 μM, 10 μM, 20 μM, 30 μM, 40 μM, 50 μM.At each concentration
Reason is three times.
4) 96 orifice plates after drug-treated are placed at 5%CO2, cultivate in 37 DEG C of incubators respectively for 24 hours, 48h and
72h。
5) culture solution is drawn, the MTT, 20 μ l of 5mg/ml are added into every hole.It is placed again into incubator and stands 4h.
6) after forming methanol crystallization, extra MTT solution is siphoned away, in every 100 μ lDMSO solution of Kong Zhongjia and fullys shake, makes
Yellow crystal dissolution.
7) light absorption value being detected with microplate reader and being read, record reads result and calculates the inhibiting rate of cell with software.Finally,
To result table for statistical analysis 2.
Table 2: inhibiting rate of the compounds of this invention various concentration to prostate gland cancer cell
| Sample | Concentration | Cell survival rate |
| Blank control | 0.1%DMSO | 94.2% |
| Example 1 | 5μM | 100.7% |
| Example 2 | 10μM | 93.6% |
| Example 3 | 20μM | 75.4% |
| Example 4 | 30μM | 61.5% |
| Example 5 | 40μM | 42.8% |
| Example 6 | 50μM | 32.3% |
From Table 2, it can be seen that YCIA of the invention has good inhibiting effect to prostate gland cancer cell, can be used as
The selection of anticancer drug.
Purposes in the protection of embodiment 6:YCIA, processing, treatment fracture and osteoporosis agents
The compounds of this invention is to the proliferation of osteoclast and the activity experiment of differentiation
Principle: the osteoclastic precursor of monokaryon can gradually melt under the noble cells factor (such as RANKL, M-CSF) induction
Close the mature osteoclast for being divided into multicore.Osteoclastic precursor does not have the ability of bone resorption, and only differentiation and maturation is osteoclastic thin
The ability that born of the same parents just have dissolution stubborn, therefore, the level of differentiation of osteoclast can react its bone resorption ability.
Method: osteoclastic neural progenitor cell line or the primary osteoclastic precursor of mouse being separately cultured are inoculated into 12 well culture plates
In, 10000 cells/wells.Control group, single dosing group 1 (YCIA), single dosing group 2 (RANKL) and double dosing group (YCIA+ are set
RANKL).After cell is adherent overnight, the compounds of this invention of various dose and/or the RANKL of 50ng/ml is added, it is lasting to train
It supports 3~5 days.Deng single plus RANKL cell fusion it is complete after, it is primary with the 37 degree distillation preheated washing cells, methanol is added and consolidates
Determine 30 seconds, the distillations washing cells of 37 degree of preheatings three times, then carry out TRAP dyeing, count the more of the TRAP positive under the microscope
Nucleus number.
As a result with evaluation: the results are shown in Table shown in 3.Compared with the control group, after the compounds of this invention is added, no matter osteoclastic
In neural progenitor cell line or the primary osteoclastic precursor of mouse being separately cultured, the amount of osteoclast by RANKL induction differentiation is bright
Aobvious to reduce, this result proves: the compounds of this invention can effectively inhibit the differentiation of the osteoclast of RANKL induction.
The influence that 3 YCIA of table breaks up the marrow BMMs cell of originally culture to osteoclast
| Compound | Concentration | Appreciation rate (%) |
| Blank control | -/- | 0.00 |
| Single dosing group 1 | 0.5μM | 28.6% |
| Single dosing group 2 | 1.0μM | 22.5% |
| Double dosing groups | 1.0μM | 20.1% |
From table 3 it can be seen that compared with the control group, after YCIA is added, no matter in osteoclastic neural progenitor cell line or primary point
From in the osteoclastic precursor of the mouse of culture, significantly reduced by the amount of osteoclast of RANKL induction differentiation, this result card
Bright: YCIA can effectively inhibit the differentiation of the osteoclast of RANKL induction.
Claims (10)
1. a kind of prenyl chromocor compound and its derivative, it is characterised in that: its structural formula compound shown in formula I
Or the stereoisomer of compound shown in Formulas I, geometric isomer, tautomer, nitrogen oxides, hydrate, solvation
Object, metabolite, pharmaceutically acceptable salt or prodrug；Wherein,
1)R1Selected from H, OH, OCH3、CH3COO、NH2、CH3NH、(CH3)2N、CH3CONH or CN；
2)R2Selected from H, OH, OCH3、CH3COO、NH2、CH3NH、(CH3)2N、CH3CONH or CN；
3)R3Selected from H, OH, OCH3、CH3COO、NH2、CH3NH、(CH3)2N、CH3CONH or CN；
4)R4Selected from H, OH, OCH3、CH3COO、NH2、CH3NH、(CH3)2N、CH3CONH or CN；
5)R5Selected from H, OH, OCH3、CH3COO、NH2、CH3NH、(CH3)2N、CH3CONH or CN；
6)R6Selected from H or prenyl.
2. prenyl chromocor compound according to claim 1 and its derivative, it is characterised in that: R1For OH or
OCH3；R2For H, OH or OCH3；R3For H, OH or OCH3；R4For H, OH or OCH3；R5For H, OH or OCH3；
R6For
3. prenyl chromocor compound according to claim 2 and its derivative, it is characterised in that: R1、R2、R3、R4、
R5It is OCH3；R6For
4. a kind of pharmaceutical composition, it is characterised in that: include the described in any item prenyl flavones of claims 1 to 3
Object or derivative are closed, also includes pharmaceutically acceptable carrier, excipient, diluent, medium or their combination.
5. the synthetic method of a kind of prenyl chromocor compound and its derivative, it is characterised in that: utilize biological enzyme
Prenyl is connect by method with chromocor compound, the chromocor compound include Quercetin, apiolin, Kaempferol, baicalein,
Scutellarin, Chrysin, Daidzein, genistein, Isorhamnetin, myricetin, luteolin, fisetin, icariine
Or naringenin.
6. synthetic method according to claim 5, it is characterised in that: using prenyltransferases in R6Upper connection is different
Pentadienyl；Using O- transmethylase in R1、R2、R3、R4、R5Connect OCH3。
7. synthetic method according to claim 6, it is characterised in that: further include different by the synthesis of UDP glycosyltransferase
The derivative of pentadienyl chromocor compound glycosylates prenyl flavones.
8. Claims 1 to 4 any one compound, derivative or composition are used to prepare the purposes of drug, which is used for
Prevention mitigates or treats the purposes in diseases of cardiovascular and cerebrovascular systems.
9. Claims 1 to 4 any one compound, derivative or composition are used to prepare the purposes of drug, which is used for
Prevention mitigates or treats the purposes in osteoporosis.
10. Claims 1 to 4 any one compound, derivative or composition are used to prepare the purposes of drug, which is used for
Purposes in prevention, mitigation or treating cancer.
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| CN110042112A (en) * | 2019-04-23 | 2019-07-23 | 上海辰山植物园 | Skullcapflavone Phenylpropanoid Glycosides and flavonoids O- methyl transferase gene and its vector construction and application |
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| CN101148444A (en) * | 2006-09-20 | 2008-03-26 | 上海特化医药科技有限公司 | Flavone derivative, preparation method and application |
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Application publication date: 20190125 |