CN106279344A - A kind of native compound separated from Radix Saposhnikoviae and preparation method thereof, medical applications - Google Patents
A kind of native compound separated from Radix Saposhnikoviae and preparation method thereof, medical applications Download PDFInfo
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- CN106279344A CN106279344A CN201610663701.2A CN201610663701A CN106279344A CN 106279344 A CN106279344 A CN 106279344A CN 201610663701 A CN201610663701 A CN 201610663701A CN 106279344 A CN106279344 A CN 106279344A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07J—STEROIDS
- C07J63/00—Steroids in which the cyclopenta(a)hydrophenanthrene skeleton has been modified by expansion of only one ring by one or two atoms
- C07J63/008—Expansion of ring D by one atom, e.g. D homo steroids
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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
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/54—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame
- A61K31/542—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with at least one nitrogen and one sulfur as the ring hetero atoms, e.g. sulthiame ortho- or peri-condensed with heterocyclic ring systems
- A61K31/545—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine
- A61K31/546—Compounds containing 5-thia-1-azabicyclo [4.2.0] octane ring systems, i.e. compounds containing a ring system of the formula:, e.g. cephalosporins, cefaclor, or cephalexine containing further heterocyclic rings, e.g. cephalothin
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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
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K36/00—Medicinal preparations of undetermined constitution containing material from algae, lichens, fungi or plants, or derivatives thereof, e.g. traditional herbal medicines
- A61K36/18—Magnoliophyta (angiosperms)
- A61K36/185—Magnoliopsida (dicotyledons)
- A61K36/23—Apiaceae or Umbelliferae (Carrot family), e.g. dill, chervil, coriander or cumin
- A61K36/238—Saposhnikovia
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- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
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- Organic Chemistry (AREA)
- Steroid Compounds (AREA)
Abstract
The present invention relates to a kind of native compound separated from Radix Saposhnikoviae, and new medical use.The native compound separated first from Chinese herbal medicine Radix Saposhnikoviae that the present invention provides, this native compound (I) novel structure, compound (I), during this natural product independent role, alopecia is had therapeutical effect；This natural product can also and during other drug synergy, the medicine of hair growth can be developed into.
Description
Technical field
The invention belongs to biomedicine field, relate to a kind of native compound separated from Radix Saposhnikoviae, and the new use of medicine
On the way.
Background technology
Chinese herbal medicine Radix Saposhnikoviae is perennial herb, high 30-2000px.Root is sturdy, elongated cylindrical, has a branch, yellowish laurel color,
Root ramps up, the most isometric with stem, has thin rib.The month at florescence 8-9, really the phase 9-10 month.The nice and cool weather of its happiness, cold-resistant, drought-resistant.Preferably
Selecting sunny, soil layer is deep, loose sand loam fertile, well-drained cultivation, should not be big in acidity, the soil of viscosity weight
Middle plantation.The Gen Kesheng of Radix Saposhnikoviae uses.Acrid in the mouth, sweet, slightly warm in nature.There are expelling pathogenic wind from the body surface, removing dampness to relieve pain, effect of relieving convulsion.
Summary of the invention
It is an object of the invention to provide a kind of native compound separated first from Chinese herbal medicine Radix Saposhnikoviae, and this is natural
The preparation method of compound, also provides for the application of this native compound simultaneously, this native compound novel structure can individually or
Person works in coordination with other drug for hair growth.
The above-mentioned purpose of the present invention is achieved by techniques below scheme:
A kind of native compound separated from Radix Saposhnikoviae, described native compound is the compound with following structural formula
(I),
The preparation method of above-mentioned native compound, comprises following operating procedure: Radix Saposhnikoviae is pulverized by (a), with 75～85% second
Alcohol circumfluence distillation, united extraction liquid, it is concentrated into without alcohol taste, successively by petroleum ether, ethyl acetate and water saturated n-butyl alcohol extraction
Take, respectively obtain petroleum ether extract, acetic acid ethyl ester extract and n-butyl alcohol extract；B in () step (a), n-butyl alcohol takes thing use
Macroporous resin remove impurity, first with 8 column volumes of 25% ethanol elution, then with 12 column volumes of 70% ethanol elution, collects 70% and washes
De-liquid, concentrating under reduced pressure obtains 70% ethanol elution concentrate；C in () step (b), 70% ethanol elution concentrate purification on normal-phase silica gel is divided
From, obtain 4 components with the methylene chloride-methanol gradient elution that volume ratio is 85:1,45:1,25:1 and 15:1 successively；(d) step
Suddenly in (c), component 4 separates further by purification on normal-phase silica gel, is the methylene chloride-methanol of 20:1,15:1 and 1:1 by volume ratio successively
Gradient elution obtains 3 components；E reverse phase silica gel that in () step (d), component 2 is bonded by octadecylsilane separates, and uses volume
Percentage concentration is the methanol aqueous solution isocratic elution of 72%, collects 10～16 column volume eluents, and eluent concentrating under reduced pressure obtains
To compound (I).
Further, described macroporous resin is D101 type macroporous adsorbent resin.
The application in the medicine preparing hair growth of the above-mentioned native compound.
Advantages of the present invention:
The natural product of a kind of novel structure that the present invention provides, during this natural product independent role, has alopecia and controls
Treatment effect；This natural product can also and during other drug synergy, the medicine of hair growth can be developed into.
Detailed description of the invention
Further illustrate the essentiality content of the present invention below in conjunction with embodiment, but do not limit the present invention with this and protect model
Enclose.Although the present invention being explained in detail with reference to preferred embodiment, it will be understood by those within the art that, can be right
Technical scheme is modified or equivalent, without deviating from the spirit and scope of technical solution of the present invention.
Embodiment 1: compound (I) separates preparation and structural identification
Separation method: Radix Saposhnikoviae (2kg) is pulverized by (a), extracts (15L × 3 time) with 80% alcohol heat reflux, united extraction
Liquid, is concentrated into without alcohol taste (3L), successively with petroleum ether (3L × 3 time), ethyl acetate (3L × 3 time) and water saturated n-butyl alcohol
(3L × 3 time) extract, and respectively obtain petroleum ether extract, acetic acid ethyl ester extract and n-butyl alcohol extract；In (b) step (a)
Acetic acid ethyl ester extract D101 type macroporous resin remove impurity, first with 8 column volumes of 25% ethanol elution, then uses 70% ethanol elution
12 column volumes, collect 70% eluent, and concentrating under reduced pressure obtains 70% ethanol elution concentrate；C in () step (b), 70% ethanol is washed
De-concentrate purification on normal-phase silica gel separates, successively with volume ratio be 85:1 (10 column volumes), 45:1 (8 column volumes), 25:1 (10
Individual column volume) and the methylene chloride-methanol gradient elution of 15:1 (8 column volumes) obtain 4 components；Component in (d) step (c)
4 separate further by purification on normal-phase silica gel, successively with volume ratio be 20:1 (10 column volumes), 15:1 (8 column volumes) and 1:1 (6
Column volume) methylene chloride-methanol gradient elution obtain 3 components；E in () step (d), component 2 is bonded by octadecylsilane
Reverse phase silica gel separate, with the methanol aqueous solution isocratic elution that concentration expressed in percentage by volume is 72%, collect 10～16 column volumes and wash
De-liquid, eluent is concentrated under reduced pressure to give compound (I) (HPLC normalization purity is more than 98%).
Structural identification: HR-ESI-MS shows [M+H]+For m/z 469.3238, can obtain molecular formula in conjunction with nuclear-magnetism feature is
C30H44O4, degree of unsaturation is 9.Hydrogen nuclear magnetic resonance modal data δH(ppm, CDCl3, 600MHz): H-1 (1.49, m), H-1 (2.87,
Ddd, J=13.3,7.0,4.2Hz), H-2 (2.41, ddd, J=15.4,6.8,4.2Hz), H-2 (2.65, ddd, J=15.4,
11.2,7.0Hz), and H-5 (1.37, d, J=11.2Hz), H-6 (1.68, m), H-6 (1.93, m), H-7 (1.73, m), H-7
(1.87, m), H-9 (1.60, d, J=9.4Hz), H-11 (4.17, d, J=9.1Hz), H-15 (5.43, d, J=10.3Hz), H-
16 (5.52, d, J=10.3Hz), and H-18 (2.46, d, J=8.4Hz), H-19 (1.41, m), H-20 (1.10, m), H-21
(1.28, m), H-21 (1.48, m), H-22 (1.36, m), H-22 (1.51, m), H-23 (1.32, s), H-24 (9.82, s), H-
25 (1.06, s), H-26 (1.17, s), H-27 (1.24, s), H-28 (0.87, s), H-29 (0.90, d, J=6.3Hz), H-30
(0.93, d, J=6.1Hz), and OH-11 (3.13, s), OH-12 (4.73, brs)；Carbon-13 nmr spectra data δC(ppm, CDCl3,
125MHz): 39.2 (CH2, 1-C), 22.3 (CH2, 2-C), 207.6 (C, 3-C), 34.5 (C, 4-C), 63.2 (CH, 5-C), 20.4
(CH2, 6-C), 40.9 (CH2, 7-C), 57.8 (C, 8-C), 51.6 (CH, 9-C), 38.2 (C, 10-C), 71.9 (CH, 11-C),
146.7 (C, 12-C), 119.2 (C, 13-C), 36.3 (C, 14-C), 128.9 (CH, 15-C), 139.5 (CH, 16-C), 41.4
(C, 17-C), 47.3 (CH, 18-C), 40.1 (CH, 19-C), 40.7 (CH, 20-C), 30.7 (CH2, 21-C), 39.2 (CH2, 22-
C), 22.3 (CH3, 23-C), 201.1 (CH, 24-C), 15.7 (CH3, 25-C), 19.4 (CH3, 26-C), 20.9 (CH3, 27-C),
19.1(CH3, 28-C), 17.2 (CH3, 29-C), 21.3 (CH3, 30-C).Infrared spectrum shows that this compound contains hydroxyl
(3478cm-1), carbonyl (1760cm-1), double bond (1663cm-1) and aldehyde radical (1641cm-1)。13In C-NMR, DEPT and hsqc spectrum
Show 30 carbon signals, including seven methyl, six methylene, nine methines (even oxygen carbon and two alkene carbon, one
Individual aldehyde radical), and eight quaternary carbons (ketone group, an oxygen-containing olefinic quaternary carbon, an olefinic quaternary carbon), function above structure is tied again
Close insatiable hunger sum and show that this compound is pentacyclic triterpene structure.1H-NMR spectrum combines five tertiary methyl proton letters that hsqc spectrum shows
Number δH1.32 (3H, s), 1.06 (3H, s), 1.17 (3H, s), 1.24 (3H, s) He 0.87 (3H, s), two secondary methyl proton letters
Number δH0.90 (3H, d, J=6.3Hz), 0.93 (3H, d, J=6.1Hz) and1H-NMR data show that this compound is ursane
Type triterpenoid compound.H-5 and H in HMBC spectrum3The dependency of-23 and C-24 shows that C-4 position is connected with an aldehyde radical, and NOESY composes
Middle H-24 and H3The coherent signal hint aldehyde radical of-25 is in β position.Understand containing hydroxyl in structure from ultrared spectrum, and from1H-NMR
Data understand containing two hydroxyls.H-9 and H-18 and C-12, H-18 and H in HMBC spectrum3-27 and C-13, OH-12 and C-12 phase
OFF signal and their carbon chemical shifts show that this compound exists enol-type structure, hydroxyl be connected to C-12 position and C-12 and
The double bond that C-13 is formed constitutes enol-type structure, the coherent signal of OH-11 Yu C-11 and chemical potential in composing further according to HMBC
Move and confirm that another-OH is connected in C-11 position.Another C-15 Yu C-16 also forms double bond structure, and C-3 position forms ketone group.In HMBC spectrum
H3The dependency of-23 and H-24 Yu C-3 and their carbon chemical shifts are confirmed C-3 position further and are formed ketone group.Comprehensive hydrogen spectrum,
Carbon spectrum, HMBC spectrum and NOESY spectrum, and document is about correlation type nuclear magnetic data, can substantially determine that this compound is as follows,
Spatial configuration is determined by ECD test further, and theoretical value is basically identical with experiment value.
This compound chemical formula and carbon atoms numbered are as follows:
Embodiment 2: pharmacological action
Alopecia is a kind of most common dermatosis.For a long time, people are devoted to find and research and develop hair growth always
Medicine, such as glucocorticoid, minoxidil etc..But up to the present, still do not have a kind of medicine can cure alopecia completely, and deposit
In bigger untoward reaction.Therefore, the medicine of the preventing and treating alopecia develop determined curative effect, having no adverse reaction has important society's meaning
Justice and economic implications.The present embodiment uses cyclophosphamide (Cyclophosphamide, CTX) to set up mice depilation model, observes
The medicine effect to improving depilation mouse hair growth.
1, materials and methods
1.1 animal
SPF level, male C57BL/6 mice, weight 18～20g, Shanghai Slac Experimental Animal Co., Ltd..Raise ring
Border: room temperature controls at 24～26 DEG C, light every 12h light and shade alternately, ad lib, the next day change bedding and padding.
1.2 reagent and sample
CEFUROXIME AXETIL is purchased from Nat'l Pharmaceutical & Biological Products Control Institute.Compound (I) is made by oneself, and preparation method is shown in embodiment 1.
Cyclophosphamide (Hengrui Medicine Co., Ltd., Jiangsu Prov.).CBA detection kit (U.S., BD company), CD4 detection kit
(Shanghai Ying Xin laboratory equlpment company limited), CD8 detection kit (Shanghai Ying Xin laboratory equlpment company limited).
1.3 instrument
JEM-1010 type Electronic Speculum (Japan, NEC company), C6 type flow cytometer (U.S., BD company), MK3 type enzyme
Mark instrument (U.S., Thermo company).
Prepared by 1.4 mice group and model
C57BL/6 mice anesthetic machine is anaesthetized.After anesthesia, Colophonium and paraffin are melted in the ratio Hybrid Heating of 1: 1, and
Uniform application in item back, solidify hardening after throw off, induced growth phase hair, every mice depilation area be about 2.0cm ×
2.0cm.It is careful not to burned mouse skin.Lose hair or feathers latter 9 days (generation of mouse back skin induced growth phase hair follicle), according at random
Numeral table, is divided into 5 groups by mice, and often group 20, is blank group, model control group, CEFUROXIME AXETIL group respectively
(280mg·kg-1), compound (I) group (280mg kg-1), CEFUROXIME AXETIL and compound (I) compositions group [140mg kg-1CEFUROXIME AXETIL+140mg kg-1Compound (I)].After all mices depilation district subcutaneous injection CTX150mg/kg, model group
Giving free rein to growth, blank group gives the treatment of normal saline (100mg/kg) gavage, other group medicine gavage treatments, continues
8 weeks.
1.5 tissue sampling
1,2,4,8 weeks the most upon administration, often group randomly selected each 5 of mice, and row eye socket is taken a blood sample, every 1～2mL.With
Detecting in ELISA: often group takes 2 blood samples, add EDTA anticoagulant, 3000r/min is centrifuged 30min and takes supernatant, in-20 DEG C of preservations
Standby.For Flow cytometry: often group takes 3 blood samples, separate serum, save backup in-70 DEG C.After all animals take blood
Put to death immediately, take its epilating area skin histology.Fixing through 10% formalin, routine paraffin wax embeds, paraffin section, slice thick
4～5 μm, save backup at-80 DEG C.
1.6ELISA detects peripheral blood CD4+、CD8+Expression
20min is balanced under sample room temperature.Standard sample wells, sample aperture and blank well are set.What is all not added with blank well, standard
Sample wells respectively adds the standard substance 50 μ L of variable concentrations.Sample to be tested first adds Sample dilution 40 μ L, then adds sample to be tested 10 μ L, subsequently
Standard sample wells and sample aperture (blank well is not added with) add the detection antibody 100 μ L of horseradish peroxidase-labeled, seal with shrouding film
Living reacting hole, 37 DEG C of calorstats hatch 60min.Discarding liquid, absorbent paper pats dry, every hole adds cleaning mixture, stands 1min, gets rid of
Cleaning mixture, absorbent paper pats dry, and is repeated 5 times.The each 50 μ L of porose addition substrate A, B, 37 DEG C of lucifuges hatch 15min.Add termination
Liquid 50 μ L, in 15min, measures each hole OD value at 450nm wavelength.Statistics CD4 and CD8 OD value, using CD4/CD8 average as
Result carries out statistical analysis.
1.7 statistical method
Result is with mean ± standard deviationRepresent.Using SPSS17.0 statistical software analytical data, comparing between group should
Use one factor analysis of variance.
2, experimental result
2.1 changes of body mass and hair growth situation
Mice is terminated to experiment through CTX induction depilation, each group Mice Body quality no significant difference (P ＞ 0.05).Lose hair or feathers little
Mus after CEFUROXIME AXETIL, compound (I), CEFUROXIME AXETIL and compound (I) compositions are administered 1～2 week, each group mice loses hair or feathers
District's local skin is gradually transformed into grey black by pink colour, and mice depilation skin grey black region, district is substantially than model group and physiology salt
Water group wants big；Being administered to 4～8 weeks, each group mice depilation district is black, and has hair gradually to grow, extends.Administration group hair phase
For model group and normal saline group, hair is the finest and close.
2.2 couples of depilation mouse peripheral blood CD4+/CD8+The impact of ratio expression
CEFUROXIME AXETIL group, compound (I) group, CEFUROXIME AXETIL group and compound (I) compositions group peripheral blood CD4+/
CD8+Ratio prolongation over time, on a declining curve.1,2,3,4 weeks, with model control group ratio, CEFUROXIME AXETIL group and chemical combination
Thing (I) compositions group peripheral blood CD4+/CD8+Ratio is remarkably decreased (P ＜ 0.01)；With model control group ratio, CEFUROXIME AXETIL group,
Compound (I) group peripheral blood CD4+/CD8+Ratio declines (P ＜ 0.05).Result of the test is shown in Table 1.
Table 1 is to depilation mouse peripheral blood CD4+/CD8+The impact of ratio expression
| Group | 1 week | 2 weeks | 3 weeks | 4 weeks |
| Model control group | 5.48±0.06 | 5.37±0.05 | 4.99±0.09 | 4.83±0.11 |
| CEFUROXIME AXETIL group | 5.15±0.05 | 4.76±0.06 | 4.40±0.17 | 4.12±0.08 |
| Compound (I) group | 4.87±0.02 | 4.34±0.13 | 4.16±0.06 | 3.65±0.27 |
| CEFUROXIME AXETIL and compound (I) compositions group | 3.94±0.04 | 3.67±0.02 | 3.29±0.25 | 2.94±0.08 |
The depilation the most frequently used laboratory animal of model is C57BL/6 mice, and owing to it is coloured kind, skin color is with hair follicle
Grow and show different colors, be research hair follicle development and a kind of well laboratory animal of regeneration.
At present the pathophysiological mechanism about alopecia is not yet clear and definite, possible reason is main and local infection, neurotoxic substance,
The factor such as spirit depressing, endocrine factors is correlated with.Recently as heredity, gene, the development of molecular level, the most all
Many scholars think that alopecia is mainly a kind of autoimmune inflammation disease immune-mediated by T cell, expose owing to hair follicle is abnormal
In potential immunocompetent immune system, then activating powerful immune system by the antigenic substance of hair follicle, induction release is a large amount of
Inflammation, causes alopecia then.CD4+And CD8+T cell in hair loss patient hair follicle and around infiltration cause alopecia
Key, CD8+T cell is considered the hair follicle direct cytotoxicity of performance always, and CD4+T cell plays auxiliary cytosis,
In the pathogenic process of alopecia, both play a role jointly.
CEFUROXIME AXETIL, compound (I), CEFUROXIME AXETIL group and compound (I) compositions maintaining treatment are to depilation mice
There is obvious curative effects, significantly improve the hair growth situation in mice depilation district, by lowering peripheral blood CD4+/CD8+Ratio comes
Playing a role, the Drug therapy for clinical alopecia provides new therapeutic scheme.When compound (I) individually acts on, it is right to have
The improvement result of hair growth is significantly acted on, when compound (I) is equipped with CEFUROXIME AXETIL synergy, to hair growth
Improvement result effect is notable, and is better than CEFUROXIME AXETIL or compound (I) individually action effect, can develop into preventing and treating and take off
The medicine sent out.
The effect of above-described embodiment indicates that the essentiality content of the present invention, but does not limit the protection of the present invention with this
Scope.It will be understood by those within the art that, technical scheme can be modified or equivalent,
Essence and protection domain without deviating from technical solution of the present invention.
Claims (4)
1. the native compound separated from Radix Saposhnikoviae, it is characterised in that described native compound is to have following structural formula
Compound (I),
2. the preparation method of the native compound described in claim 1, it is characterised in that comprise following operating procedure: (a) will be anti-
Wind pulverize, with 75～85% alcohol heat reflux extract, united extraction liquid, be concentrated into without alcohol taste, successively use petroleum ether, ethyl acetate
With water saturated n-butanol extraction, respectively obtain petroleum ether extract, acetic acid ethyl ester extract and n-butyl alcohol extract；(b) step
Suddenly in (a), n-butyl alcohol takes thing macroporous resin remove impurity, first with 8 column volumes of 25% ethanol elution, then with 70% ethanol elution 12
Individual column volume, collects 70% eluent, and concentrating under reduced pressure obtains 70% ethanol elution concentrate；70% ethanol elution in (c) step (b)
Concentrate purification on normal-phase silica gel separates, and washes by the methylene chloride-methanol gradient that volume ratio is 85:1,45:1,25:1 and 15:1 successively
Take off and obtain 4 components；D in () step (c), component 4 separates further by purification on normal-phase silica gel, successively with volume ratio be 20:1,15:1 and
The methylene chloride-methanol gradient elution of 1:1 obtains 3 components；In (e) step (d) component 2 with octadecylsilane be bonded anti-
Phase silica gel separates, and with the methanol aqueous solution isocratic elution that concentration expressed in percentage by volume is 72%, collects 10～16 column volume eluents,
Eluent is concentrated under reduced pressure to give compound (I).
The preparation method of compound the most according to claim 2 (I), it is characterised in that: described macroporous resin is D101 type
Macroporous adsorbent resin.
4. the application in the medicine preparing hair growth of the native compound described in claim 1.
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