CN108794497A - A kind of new N- benzyls acridone type alkaloid and preparation method thereof and purposes - Google Patents
A kind of new N- benzyls acridone type alkaloid and preparation method thereof and purposes Download PDFInfo
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- CN108794497A CN108794497A CN201810743707.XA CN201810743707A CN108794497A CN 108794497 A CN108794497 A CN 108794497A CN 201810743707 A CN201810743707 A CN 201810743707A CN 108794497 A CN108794497 A CN 108794497A
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- 0 CC(C)(C=Cc1c(c2c3OC)N(Cc(cc4)ccc4O)c(cc4OC(C(*)(CO)CO)Oc4c4)c4C2=O)Oc1c3OC Chemical compound CC(C)(C=Cc1c(c2c3OC)N(Cc(cc4)ccc4O)c(cc4OC(C(*)(CO)CO)Oc4c4)c4C2=O)Oc1c3OC 0.000 description 1
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/12—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains three hetero rings
- C07D491/14—Ortho-condensed systems
- C07D491/153—Ortho-condensed systems the condensed system containing two rings with oxygen as ring hetero atom and one ring with nitrogen as ring hetero atom
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P3/00—Drugs for disorders of the metabolism
- A61P3/06—Antihyperlipidemics
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Abstract
The invention discloses a kind of N- benzyl acridone type alkaloids detached from curled mallow, as shown in formula I.N- benzyls acridone type alkaloid of the present invention has significant hypolipidemic activity, and therefore, the invention also discloses purposes of the N- benzyl acridone type alkaloids in preparing blood lipid-lowering medicine.
Description
Technical field
The invention belongs to pharmaceutical technology fields, and in particular to a kind of new N- benzyls acridone type alkaloid and preparation method thereof
With the purposes in preparing blood lipid-lowering medicine.
Background technology
Curled mallow (scientific name：Gynura cusimbua), leaf approximation agaric, it as a kind of vegetables of medicine-food two-purpose,
Civil very popular.Curled mallow is distributed widely in China's most area, and resource is very abundant, nutritive value pole
It is high.Ancient book is recorded, and curled mallow, which has, connects muscle symplectic bone, scattered stasis detumescence and other effects, cures mainly fracture, traumatic injury, rheumatic arthritis
Etc. illnesss.Modern pharmacological research finds that curled mallow has a variety of pharmacological activity such as anti-oxidant, antiviral and antibacterial anti-inflammatory.Together
Shi Faxian, containing there are many chemical compositions, including volatile oil, saponin(e, polysaccharide and various vitamins in curled mallow.Currently, invention
People's consulting literatures are found, have no correlative study report of the curled mallow in terms of reducing blood lipid.
Invention content
Present invention aims at medicine-food two-purpose vegetables-curled mallow is chosen as research object, is extracted using the modern times and detach skill
Art furthers investigate curled mallow chemical composition, and therefrom research finds novel natural blood lipid-lowering medicine, is from natural plants
Middle research finds that new drug establishes important material base.
The purpose of the present invention is what is be achieved through the following technical solutions：
A kind of new N- benzyls acridone type alkaloid (C detached from curled mallow31H31NO10), as shown in formula I：
Chemical name：3,4- dimethoxys -10- (5'- Hydroxy-benzvls) -14,15- dimethyl -1 "-(2 ", 3 ", 4 "-three hydroxyls
Base-propyl)-pyrans and acridine -5- ketone.
The preparation method of N- benzyls acridone type alkaloid of the present invention, steps are as follows：
Step (1) takes dry curled mallow to be placed in 90~100% ethyl alcohol, then soaking at room temperature 15~20 hours heats
Reflux 2~4 times 2~4 hours every time, stands filtering, and gained filtrate is concentrated into no alcohol taste, obtains the total thick paste of curled mallow；
Step (2), the total medicinal extract of curled mallow are suspended in 1.0~1.5%HCl solution, are stood 20~25 hours, are filtered
Clear liquid；
Step (3), with ammonium hydroxide adjust supernatant pH=10.0-12.0, successively use chloroform, ethyl acetate, n-butanol into
Row extraction, each extract liquor are concentrated and dried to obtain chloroform thick paste, ethyl acetate thick paste, n-butanol thick paste；
Step (4), chloroform thick paste petroleum ether dissolution, silicagel column in wet method；Using petroleum ether-ethyl acetate as eluant, eluent into
Row gradient elution obtains 3 fractions, respectively A fractions, B fractions, C fractions；
Step (5), B fraction petroleum ether dissolutions, silicagel column in wet method；It is carried out by eluant, eluent of n-hexane-ethyl acetate
Gradient elution obtains 3 fractions, respectively B-1 fractions, B-2 fractions, B-3 fractions；
Step (6), B-2 fractions are dissolved with methanol, upper Toyopearl HW-40 gel columns, are to wash with 90~100% methanol
De- agent carries out gradient elution, obtains B-2-1 fractions and B-2-2 fractions；
Step (7), B-2-2 fractions are isolated and purified using preparative liquid chromatography, obtain C-2-2-1 fractions；
Step (8), C-2-2-1 fractions are dissolved with methanol, upper Sephadex LH-20 gel columns, are eluted with 95% acetonitrile,
N- benzyls acridone type alkaloid shown in formula I.
In step (1), 90~100% ethyl alcohol is generally required to submerge 2~4 centimetres of medicinal material.
In step (2), the volume ratio of the total thick paste of the curled mallow and 1.0~1.5%HCl solution is 1:1.5.
In step (3), obtained thick paste carries out Lipid-lowering activities screening respectively using the phagocytosis experiment of DiI-LDL cells, as a result
Show that chloroform thick paste position has significant hypolipidemic activity.
In step (4), the silica gel used is 100-200 mesh silica gel；The volume ratio of petroleum ether and ethyl acetate is 15:1~
5:1。
Using the method for bioactivity guidance separation, determine that B fractions are hypolipidemic activity fraction.
In step (5), the silica gel used is 200-300 mesh silica gel；The volume ratio of n-hexane and ethyl acetate is 12:1~
7:1。
In step (7), preparative liquid chromatography uses C18 columns, mobile phase：90~100% methanol, absorbing wavelength：225nm,
Flow velocity：5~7mL/min.
Another object of the present invention is to provide the N- benzyl acridone type alkaloids to prepare blood lipid-lowering medicine
In purposes.
Beneficial effects of the present invention：
N- benzyls acridone type alkaloid structure of the present invention is novel, and has significant hypolipidemic activity, preparation method
It is simple and easy to do, convenient for carrying out further pharmacology and clinical research to it.
Specific implementation mode
Technical scheme of the present invention is described further below by specific implementation mode.
The preparation of embodiment 1N- benzyl acridone type alkaloids
Step (1) takes dry curled mallow (9 kilograms) to be placed in 95% ethyl alcohol, submerges 2-4 centimetres of medicinal material, soaking at room temperature
18 hours；Then it is heated to reflux 3 hours, stands filtering, gained filtrate is concentrated into no alcohol taste, obtain the total thick paste of curled mallow (850
Gram)；
Step (2), according to volume ratio 1:1.5 are uniformly suspended in curled mallow total thick paste in 1.3%HCl solution, stand 22
Hour, filter to obtain supernatant；
Step (3) adjusts supernatant pH=11 with ammonium hydroxide, is extracted successively with chloroform, ethyl acetate, n-butanol, respectively
Extract liquor is concentrated and dried to obtain chloroform thick paste (36.8 grams), ethyl acetate thick paste (258.5 grams), n-butanol thick paste (364.0 grams)；
Lipid-lowering activities screening is carried out to above-mentioned thick paste using DiI-LDL cells phagocytosis experiment respectively, the selection result shows that chloroform thick paste has
There is significant hypolipidemic activity；
Step (4), hypolipidemic activity position (chloroform thick paste) use petroleum ether dissolution, silica gel (100-200 mesh) column in wet method；
With petroleum ether-ethyl acetate (15:1→9:1→5:1) elution system carries out gradient elution, obtains A fractions (8.5 grams), B fractions
(15.6 grams), C fractions (10.2 grams)；Using the method for bioactivity guidance separation, determine that B fractions are hypolipidemic activity fraction；
Step (5), B fraction petroleum ether dissolutions, silica gel (200-300 mesh) column in wet method；Use n-hexane-ethyl acetate
(12:1→10:1→7:1) gradient elution is carried out, B-1 fractions (3.6 grams), B-2 fractions (6.4 grams), B-3 fractions (4.5 are obtained
Gram)；
Step (6), B-2 fractions are dissolved with methanol, upper Toyopearl HW-40 gel columns, with 95% methanol and 100% first
Alcohol gradient elution respectively obtains B-2-1 (2.2 grams) fractions and B-2-2 (3.6 grams) fraction；
Step (7), B-2-2 fractions are isolated and purified using preparative liquid chromatography, C18 columns, mobile phase：90-100% methanol,
Absorbing wavelength：225nm, flow velocity：5-7mL/min obtains B-2-2-1 fractions (1.8 grams) through preparation, purifying repeatedly；
Step (8), B-2-2-1 fractions are dissolved with methanol, upper Sephadex LH-20 gel columns, are eluted with 95% acetonitrile,
Finally obtain monomeric compound I (9.36 milligrams).
Chemical compounds I is white powder (acetone), HR-ESI-MS m/z 600.1637 [M+Na]+(calcd.for
C31H31NO10Na, 600.1689).UV(MeOH)λmax:202,230,285,302nm；IRνmax:3387,2913,1622,1509,
1346cm-1；1H-NMR(CDCl3, 400MHz) and13C-NMR(CDCl3, 100MHz) and data are shown in Table 1.?1H-NMR(CDCl3,
In 400MHz) composing, a 5'- Hydroxy-benzvl signals [δ is providedH5.52 (2H, s, H-1 '), δH6.95 (2H, d, J=8.2Hz,
H-3′/7′]；One trihydroxy-propyl signal [δH5.65 (1H, s, H-1 "), δH 3.58(4H,s,3″/4″-CH2]；Two first
Oxygroup signal [δH 3.72(3H,s,3-OCH3),δH 3.88(3H,s,4-OCH3)]；One 14,15- dimethyl pyranoid rings [δH
6.86 (1H, d, J=9.9Hz, H-11), δH5.64 (1H, d, J=9.9Hz, H-12), δH 1.42(6H,s,14,15-CH3]。
HMBC, NOESY of binding compounds I,1H-1The coupling such as H COSY is related, determines compound structure as shown in formula I, and chemistry is entitled：
(2 ", 3 ", 4 "-trihydroxies-propyl)-pyrans is simultaneously for 3,4- dimethoxys -10- (5'- Hydroxy-benzvls) -14,15- dimethyl -1 " -
Acridine -5- ketone.It is retrieved through SciFinder, determines that chemical compounds I is a new N- benzyls acridone type alkaloid.
1 chemical compounds I of table1H NMR、13C NMR and HMBC related datas
The hypolipidemic activity of 2 chemical compounds I of embodiment
Experimental method
(1) DiI-LDL is prepared
DiI (Sheng Ruitai Science and Technology Ltd.s in Beijing) is dissolved in DMSO, the DiI mother liquors of 15mg/mL are configured to.It will
DiI mother liquors are added to LDL/LPDS (V/V=1:2) in mixed liquor, make the final concentration of 300 μ g/mg LDL of DiI.In 37 DEG C
Water-bath 18h.Mixture density is adjusted to 1.063g/mL with sodium bromide, ultracentrifugation is for 24 hours.It is label in gradient liquid top layer
LDL is opened with free DiI points.Upper layer DiI-LDL is collected, dialysis is transferred to afterwards for 24 hours in PBS buffer solution (3L) dialyses for 24 hours again.
By 0.22 μm of filter filtration sterilizations of the DiI-LDL to have dialysed, survey after its protein content for use.
(2) HepG2 cells are marked with DiI-LDL
HepG2 cells (Shanghai Ji Ning Industrial Co., Ltd.s) are seeded on 24 orifice plates, 10% fetal calf serum (FBS) is placed in
DMEM in cultivate for 24 hours, shifted in the DMEM containing 2% degreasing serum according to experiment purpose, chemical compounds I be then dissolved in DMSO
Being added to afterwards in the DMEM containing 2% degreasing serum makes its final concentration of 5 μM, makes its starvation for 24 hours to promote the expression of LDLR, discards
300 holes μ L/ of serum-free medium containing DiI-LDL (20 μ g/mL) are added in old culture solution, and 2-3h is cultivated at 37 DEG C, measure total thin
Born of the same parents' correlation LDL intakes.
(3) fluorescent value is measured
It is carefully rinsed 2 times with the PBS buffer solution containing 0.4% bovine serum albumin(BSA) (BSA), removes the culture in 24 orifice plates
Base, PBS are rinsed 3 times, are washed away the cell of excess dyestuff, add isopropanol (the every 24 orifice plate single holes of 0.5mL/).After shaking table 20min, receive
Collect isopropanol, ultracentrifugation 15min (3000rpm), 200 μ L of Aspirate supernatant are placed in black fluorescent plate, in exciting light 520nm
Fluorescence intensity is measured at transmitting light 570nm.
Experimental result
Experiment is swallowed using DiI-LDL cells to measure the hypolipidemic activity of chemical compounds I, a concentration of 5 μM of compound, with
Phagocytic rate is shown with the ratio of blank control (DMSO), when phagocytic rate is more than 1.36, is considered to have significant reducing blood lipid
Activity, shown in table 2.
The lipid phagocytic rate result of 2 chemical compounds I of table
| Compound | Phagocytic rate |
| Chloroform thick paste | 1.96±0.09 |
| B fractions | 1.75±0.11 |
| Chemical compounds I | 1.51±0.04 |
As shown in Table 2, N- benzyls acridone type alkaloid has significant hypolipidemic activity.
Claims (8)
1. the N- benzyls acridone type alkaloid as shown in formula I：
2. the preparation method of N- benzyls acridone type alkaloid described in claim 1, it is characterised in that steps are as follows：
Step (1) takes dry curled mallow to be placed in 90~100% ethyl alcohol, then soaking at room temperature 15~20 hours is heated to reflux
2~4 times, 2~4 hours every time, filtering is stood, gained filtrate is concentrated into no alcohol taste, obtains the total thick paste of curled mallow；
Step (2), the total medicinal extract of curled mallow are suspended in 1.0~1.5%HCl solution, are stood 20~25 hours, are filtered to obtain supernatant
Liquid；
Step (3), the pH=10.0-12.0 that supernatant is adjusted with ammonium hydroxide, are extracted with chloroform, ethyl acetate, n-butanol successively
It takes, each extract liquor is concentrated and dried to obtain chloroform thick paste, ethyl acetate thick paste, n-butanol thick paste；
Step (4), chloroform thick paste petroleum ether dissolution, silicagel column in wet method；Ladder is carried out by eluant, eluent of petroleum ether-ethyl acetate
Degree elution, obtains 3 fractions, respectively A fractions, B fractions, C fractions；
Step (5), B fraction petroleum ether dissolutions, silicagel column in wet method；Gradient is carried out by eluant, eluent of n-hexane-ethyl acetate
Elution, obtains 3 fractions, respectively B-1 fractions, B-2 fractions, B-3 fractions；
Step (6), B-2 fractions are dissolved with methanol, upper Toyopearl HW-40 gel columns, using 90~100% methanol as eluant, eluent
Gradient elution is carried out, B-2-1 fractions and B-2-2 fractions are obtained；
Step (7), B-2-2 fractions are isolated and purified using preparative liquid chromatography, obtain C-2-2-1 fractions；
Step (8), C-2-2-1 fractions are dissolved with methanol, upper Sephadex LH-20 gel columns, are eluted, are obtained with 95% acetonitrile
N- benzyls acridone type alkaloid shown in formula I.
3. the preparation method of N- benzyls acridone type alkaloid according to claim 2, it is characterised in that in step (1),
90~100% ethyl alcohol submerge 2~4 centimetres of medicinal material.
4. the preparation method of N- benzyls acridone type alkaloid according to claim 2, it is characterised in that in step (2),
The volume ratio of the total thick paste of the curled mallow and 1.0~1.5%HCl solution is 1:1.5.
5. the preparation method of N- benzyls acridone type alkaloid according to claim 2, it is characterised in that in step (4),
The silica gel used is 100-200 mesh silica gel；The volume ratio of petroleum ether and ethyl acetate is 15:1~5:1.
6. the preparation method of N- benzyls acridone type alkaloid according to claim 2, it is characterised in that in step (5),
The silica gel used is 200-300 mesh silica gel；The volume ratio of n-hexane and ethyl acetate is 12:1~7:1.
7. the preparation method of N- benzyls acridone type alkaloid according to claim 2, it is characterised in that in step (7),
Preparative liquid chromatography uses C18 columns, mobile phase：90~100% methanol, absorbing wavelength：225nm, flow velocity：5~7mL/min.
8. purposes of the N- benzyls acridone type alkaloid described in claim 1 in preparing blood lipid-lowering medicine.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS203756B1 (en) * | 1979-04-06 | 1981-03-31 | Bohumil Proksa | Tetracyclic compounds derived from narceonic acid and process for preparing thereof |
| CN104610271A (en) * | 2015-01-09 | 2015-05-13 | 新乡学院 | 12-(2-fluorophenyl)-benzo [h][1,3] methylenedioxy [4,5-b] acridine-10,11-diketone and synthesis method thereof |
-
2018
- 2018-07-09 CN CN201810743707.XA patent/CN108794497B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CS203756B1 (en) * | 1979-04-06 | 1981-03-31 | Bohumil Proksa | Tetracyclic compounds derived from narceonic acid and process for preparing thereof |
| CN104610271A (en) * | 2015-01-09 | 2015-05-13 | 新乡学院 | 12-(2-fluorophenyl)-benzo [h][1,3] methylenedioxy [4,5-b] acridine-10,11-diketone and synthesis method thereof |
Non-Patent Citations (2)
| Title |
|---|
| MARK R. SPALLER，等: "Combinatorial Synthetic Design. Solution and Polymer-Supported Synthesis of Heterocycles via Intramolecular Aza Diels-Alder and Imino Alcohol Cyclizations", 《J. COMB. CHEM.》 * |
| 周杨晶，等: "民族药木耳菜挥发油成分和脂溶性成分GC-MS分析", 《天然产物研究与开发》 * |
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