CN104151323B - There is compound of insect antifeedant activity and growth inhibitory activity and preparation method thereof - Google Patents
There is compound of insect antifeedant activity and growth inhibitory activity and preparation method thereof Download PDFInfo
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- A01N43/08—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with oxygen as the ring hetero atom
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
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- C07D313/02—Seven-membered rings
- C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
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- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
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Abstract
The invention belongs to pharmaceutical technology field, disclose activity and the structure of the multiple auspicious promise alkane diterpene-kind compound of separation and Extraction from plant Cortex Cinnamomi, it is provided that the method for separating and preparing of Xin Ruinuo alkane diterpene compound.Present invention is disclosed this compounds and there is immunosuppressive activity, insect antifeedant activity and growth inhibitory activity, the compound wherein with immunosuppressive activity shows as the T cell propagation of ConA induction is significantly inhibited effect, and insect antifeedant activity and growth inhibitory activity show as to be had antifeedant activity, have antifeedant activity to cotton bollworm larvae and have growth inhibited effect to cotton bollworm larvae beet exigua larvae.These compounds can be used for preparation immunosuppressant, have the medicine of antifeedant activity and growth inhibitory activity to insecticide.
Description
Technical field
The invention belongs to pharmaceutical technology field, relate to method for separating and preparing and the purposes of auspicious promise alkane diterpene compound 1-11.
It is specifically related to isolated and purified process, structural identification, immunosuppressant, insect antifeedant and growth inhibited effect etc..
Background technology
Autoimmune disease is the third-largest disease being only second to cardiovascular disease and cancer, has been developed for substantial amounts of exempting from present
Epidemic disease suppression medicine, is mainly used in preventing the rejection in organ transplantation and the progress of some autoimmune disease of suppression
Deng.Though wherein many medicines have immunosuppressive action, but toxic and side effects is strong, easily causes systemic immunity suppression.Seek
The immunosuppressant lead compound looking for and developing high-efficiency low-toxicity is key subjects of medicine sector of the world.Up-to-date grinds
Study carefully discovery, autoimmune disease and T cell relation the closest.ConA can stimulate being subject to of T cell surface in vitro
Body, selectively activates T cell hyper-proliferative, therefore, utilize the splenic t-cell that ConA sets up multiplicative model can quickly,
Efficient screening immunosuppressant compound.
Beet armyworm and bollworm are all omnivorousness agricultural pests widely distributed in world wide, main harm Cotton Gossypii, jade
The crops such as rice, Semen sojae atricolor and vegetable.At present preventing and treating beet armyworm and bollworm still depend on chemical pesticide, but in a large number
Using chemical pesticide to cause the pollution of soil, water, air unreasonably, the Genes For Plant Tolerance property of medicine produces and harmful to human domestic animal
The disastrous drawbacks such as poultry is healthy.Thus the study hotspot being developed in recent years of botanical pesticide, the parasite killing thing in plant
Matter is mainly secondary metabolites, does not pollutes the environment, comparatively safe to crops and ecological environment, and insecticide is not easy to
Develop immunity to drugs, therefore the exploitation of botanical pesticide apply play in current " pollution-free food " produces the most important
Effect.
Cortex Cinnamomi is the dry bark of canella xylocinnamomum (Cinnamomum cassia Presl (Lauraceae)), Cortex Cinnamomi
Leaf is the dry leaves of Cortex Cinnamomi.Cortex Cinnamomi can regulate body immunity, Cortex Cinnamomi and different auspicious promise alkane diterpene thereof and have antialexic
Activity, Cortex Cinnamomi tool energy anthelmintic, purification air, Cortex Cinnamomi has the active component that can make insect antifeedant.
Summary of the invention:
The task of the present invention is to provide in Cortex Cinnamomi has bioactive compound and method for separating and preparing thereof and application.
Realization the technical scheme is that
From Cortex Cinnamomi, the method for isolated auspicious promise alkane diterpene-kind compound comprises the following steps:
Dry Cortex Cinnamomi is pulverized, extracts by ethanol room temperature, merge ethanol extract and recovered under reduced pressure is condensed into extractum,
To total cream, total cream is dispersed to suspendible shape by hot water, the petroleum ether that is incremented by by polarity successively, chloroform, ethyl acetate, positive fourth
Alcohol extracts, and reclaims extract concentrating under reduced pressure and obtains ethyl acetate extract, n-butanol portion, petroleum ether and chloroform extract removal.
Ethyl acetate extract is carried out silica gel column chromatography, chloroform to methanol elution gradient (chloroform/methanol 10:1-3:1), chlorine
Imitative/methanol 6:1 time obtain one section of Fr.1, Fr.1 through reversed-phase silica gel column chromatography (water/methanol 9:1) a position, this position
Compound 1 is obtained again through gel, preparation liquid phase purification；
N-butanol portion is carried out silica gel column chromatography, chloroform to methanol elution gradient (chloroform/methanol 10:1-3:1), chloroform/
Obtain Fr.2 during methanol 8:1, during chloroform/methanol 6:1, obtain Fr.3, obtain Fr.4 during chloroform/methanol 5:1, during chloroform/methanol 4:1
Obtain Fr.5；Fr.2 through reversed-phase silica gel column chromatography (water/methanol 9:1) a position, this position again through gel, prepare liquid
Phase purification obtains compound 4,5；Fr.3 obtains two positions through reversed-phase silica gel column chromatography (water/methanol 9:1-7:3) and is respectively
Fr.3.1、Fr.3.2.Fr.3.1 obtains compound 2,6,7 through silica gel, gel, preparation liquid phase purification；Fr.3.2 through gel,
Preparation liquid phase purification obtains compound 8,9；Fr.4 through reversed-phase silica gel column chromatography (water/methanol 9:1), then through silica gel,
Gel, preparation liquid phase purification obtain compound 3,11；Fr.5 obtains one through reversed-phase silica gel column chromatography (water/methanol 8:2)
Position, this position obtains compound 10 through silica gel, gel, preparation liquid phase purification again.The auspicious promise alkane of isolated of the present invention
The structural formula of diterpene-kind compound 1-11 and title are shown in Table 1, and separation process is shown in accompanying drawing 1.
Table 1. present invention is the auspicious promise alkane diterpene-kind compound 1-11 structural formula of isolated from Cortex Cinnamomi
Wherein compound Cortex Cinnamomi terpene F, Cortex Cinnamomi terpene G are New skeleton compound, 19-deoxidation Cortex Cinnamomi terpene G16-glucoside and
18-hydroxyperseanol is noval chemical compound.The single crystal diffraction structure chart of compound 1 is shown in accompanying drawing 2, the list of compound 2
Brilliant diffraction structure figure is shown in accompanying drawing 3.
The present invention, under the guidance that immunosuppressive activity is screened, has carried out systematic study to Cortex Cinnamomi active component.By this 11
The research of the T cell inhibited proliferation that ConA is induced by individual compound, present invention discover that compound Cortex Cinnamomi terpene G and
Cinnacaslo has significant inhibitory action to the T cell that ConA induces, and represents that it has significant immunosuppressive action.
By compound 1-7 being carried out the research of insect antifeedant and growth inhibitory activity, find compound Cortex Cinnamomi terpene F, Cortex Cinnamomi terpene
G and 18-hydroxyperseanol has an antifeedant activity to beet exigua larvae, compound Cortex Cinnamomi terpene F and
18-hydroxyperseanol has antifeedant activity to cotton bollworm larvae；Cotton bollworm larvae is had growth inhibited to make by compound 1-7
With.
The invention provides the plant origin of compound 1-11, isolation and purification method, immunosuppressive activity, insect antifeedant and
Growth inhibitory activity and application.Cortex Cinnamomi immunosuppressive activity, under the guidance that immunosuppressive activity is screened, is become by the present invention
Point having carried out systematic study, isolated compound 1-11, wherein compound 1,2 is New skeleton compound, chemical combination
Thing 3 and 4 is noval chemical compound.Structural formula is as shown in table 1.T cell ConA induced by this 11 compounds
The research of inhibited proliferation, finds that the T cell of compound 2 and 11 pairs of ConA inductions has significant inhibitory action,
Represent that it has significant immunosuppressive action.By compound 1,2,4,5,6,8,9 is carried out insect antifeedant and life
The research of long inhibitory activity, finds that 1,2 and 4 pairs of beet exigua larvaes of compound have antifeedant activity, compound 2 and 4
Cotton bollworm larvae there is antifeedant activity；1,2,4,5,6,8,9 pairs of cotton bollworm larvaes of compound have growth inhibited effect.
Immunosuppressive activity provided by the present invention, insect antifeedant activity and growth inhibitory activity compound 1,2,3,4
As follows with the structural formula of 5:
The compounds of this invention 1,2,3,4 method for separating and preparing is: by equal to Cortex Cinnamomi ethyl acetate extract and n-butanol portion
Section is drawn by normal phase silicagel column (flowing phase: chloroform/methanol 10:1-3:1 gradient elution)；Then the equal warp of part that will obtain
Cross reverse phase silica gel (flowing phase: water/methanol 10:0-7:3 gradient elution) again to carry out drawing section；By the fragment of isolated
Further across the isolated compound such as gel, HPLC 1,2,3,4.
Present patent application embodiment 1 set forth the concrete side of present invention isolated from Cortex Cinnamomi auspicious promise alkane diterpene-kind compound
Method.
Accompanying drawing explanation
Fig. 1: embodiment 1 flow chart；
The single crystal diffraction structure chart of Fig. 2: compound 1；
The single crystal diffraction structure chart of Fig. 3: compound 2.
Detailed description of the invention
Embodiment 1: prepared by the separation of compound.
50Kg is dried Cortex Cinnamomi and pulverizes, and extracts 3 times by ethanol room temperature, each 7 days, merges ethanol extract and reduce pressure
Recovery is condensed into extractum, obtains total cream 5.1Kg, and total cream is dispersed to suspendible shape, the oil being incremented by successively by polarity by hot water
Ether, chloroform, ethyl acetate, n-butanol extraction, reclaim extract concentrating under reduced pressure and obtain ethyl acetate extract 70g, n-butyl alcohol
Position 320g, petroleum ether and chloroform extract are removed.
Compound 1 (22mg): ethyl acetate extract 70g carries out silica gel column chromatography, chloroform to methanol elution gradient (chloroform/
Methanol 10:1-3:1), obtain one section of Fr.1, Fr.1 during chloroform/methanol 6:1 through reversed-phase silica gel column chromatography (water/methanol 9:1)
Obtaining a position, this position obtains compound 1 through gel, preparation liquid phase purification again.
Compound 4 (3mg), 5 (6mg): n-butanol portion 320g carries out silica gel column chromatography, and chloroform is to methanol elution gradient
(chloroform/methanol 10:1-3:1), obtains Fr.2 during chloroform/methanol 8:1, obtain Fr.3, chloroform/methanol 5:1 during chloroform/methanol 6:1
Time obtain Fr.4, obtain Fr.5 during chloroform/methanol 4:1.Fr.2 obtains a position through reversed-phase silica gel column chromatography (water/methanol 9:1),
This position obtains compound 4,5 through gel, preparation liquid phase purification again.
Compound 2 (4mg), 6 (21mg), 7 (42mg): Fr.3 are through reversed-phase silica gel column chromatography (water/methanol 9:1-7:3)
Obtain two positions and be respectively Fr.3.1, Fr.3.2.Fr.3.1 obtains compound 2,6,7 through silica gel, gel, preparation liquid phase purification.
Compound 8 (12mg), 9 (28mg): Fr.3.2 obtain compound 8,9 through gel, preparation liquid phase purification.
Compound 3,11:Fr.4 through reversed-phase silica gel column chromatography (water/methanol 9:1), then through silica gel, gel, prepare liquid
Phase purification obtains compound 3 (3mg), 11 (57mg).
Compound 10:Fr.5 through reversed-phase silica gel column chromatography (water/methanol 8:2) a position, this position again through silica gel,
Gel, preparation liquid phase purification obtain compound 10.
Separate preparation flow figure and see Fig. 1.
Test parsing through NMR, X-Ray and chemical reaction and obtain the absolute configuration of compound 1,2,3,4.
Compound 1, Cortex Cinnamomi terpene F (cinncassiol F) is colorless prismatic crystal,UV
(MeOH)λmax(logε):204(3.78)nm；IR(KBr)Vmax3394,2968,2881,1709,1445,1388,
1367,1331,1257,1086,1039,999,851,787,758,683cm–1；The quasi-molecular ion that HRESIMS is given
Peak [M+Na]+m/z421.1822.Its1H NMR and13C NMR spectra data are shown in Table 1 and Table 2.
Compound 2, Cortex Cinnamomi terpene G (cinncassiol G) is water white transparency column crystal,
UV(MeOH)λmax(log ε)=202 (3.7) nm；IR(KBr)Vmax3418,2969,2886,2115,1641,1581,
1412,1388,1269,1103,1026,833cm–1；The quasi-molecular ion peak [M+H] that HRESIMS is given+m/z
383.2066, determine that its molecular formula is C in conjunction with hydrogen spectrum and carbon modal data20H30O7(value of calculation C20H32O7H[M+H]+,
383.2065), fusing point 195 196 DEG C.Its1H NMR and13C NMR spectra data are shown in Table 1 and Table 2.
Compound 3,19-deoxidation Cortex Cinnamomi terpene G16-glucoside (19-deoxycinncassiol G16-O-β-D-
Glucopyranoside) it is colourless oil liquid,UV(MeOH)λmax(log ε)=
204(3.7)nm；IR(KBr)Vmax3391,2960,2931,1716,1629,1459,1376,1240,1214,1165,
1081,1027,943,869,774,693cm–1；The quasi-molecular ion peak [M+Na] that HRESIMS is given+m/z
567.2385 (value of calculation is C26H40O12[M+Na]+,567.2412).Its1H NMR and13C NMR spectra data are shown in
Table 1 and Table 2.
Compound 4,18-hydroxyperseanol is colourless oil liquid,UV
(MeOH)λmax(log ε)=206 (3.4) nm；IR(KBr)Vmax3388,2963,2879,1602,1465,1387,1177,
1110,1029,962,892,829,699cm–1；The quasi-molecular ion peak [M+Na] that HRESIMS is given+m/z
423.1979 (value of calculation is C20H32O8H[M+Na]+,423.1989).Its1H NMR and13C NMR spectra data are shown in
Table 1 and Table 2.
Table 1 compound 1-4's1H NMR data
Table 2 compound 1413C NMR data
Embodiment 2
The T cell propagation of compound 2 and 11 pairs of ConA inductions significantly inhibits effect, and compound 1-11 is to splenocyte
All having no side effect, splenocyte survival rate is all higher than 90%.Compound 1-11 ion vitro immunization inhibitory activity passes through CCK-8
The impact of the T cell propagation that ConA is induced by method is evaluated, and result is as shown in following table Table 3:
The suppression ratio of the T cell propagation that ConA is induced by Table 3 compound
Experiment conclusion: compound 2 has the inhibitory action of highly significant to the mouse T cell that ConA induces, it suppresses to make
With relevant in concentration, the suppression ratio of its variable concentrations is all higher than 85%, and inhibition can be compared with positive control CsA.
Compound 11 also has the inhibitory action of the strongest highly significant to the mouse boosting cell that ConA induces, under experimental concentration its
Suppression ratio is all higher than 50%.
Embodiment 3: 1,2 and 4 pairs of beet exigua larvaes of compound have the antifeedant activity of antifeedant activity and cotton bollworm larvae；
In table, 7 compounds have growth inhibited effect to cotton bollworm larvae.Antifeedant activity is by table 4 in leaf dish method observation 24h
Compound takes food blade area to beet armyworm and cotton bollworm larvae and evaluates its antifeedant activity.Growth inhibitory activity passes through feedstuff
In mixed poison method observation 24h, the compound (the 50 μ g/ml) impact on cotton bollworm larvae body weight in following table, evaluates it to larva
Growth inhibitory activity.Result is as shown in following table Table 4.
Table 4. compound is to concentration and growth inhibition ratio in the refusing to eat of larva
Experiment conclusion: except the most diterpene of compound 5 all has antifeedant activity in various degree to beet armyworm or bollworm.
1,2 and 4 pairs of beet exigua larvaes of compound have notable antifeedant activity, compound 1 and 4 pairs of cotton bollworm larvaes to have significantly
Antifeedant activity；Compound is chosen in all experiments growth inhibited effect to cotton bollworm larvae, and compound 2 even makes the growth stage
In bollworm lose weight.
Claims (4)
1. there is the compound of structure shown in following compound 1:
2. the method for structural compounds shown in isolated following compounds 1 from Cortex Cinnamomi, comprises the following steps:
Step one: pulverized by dry Cortex Cinnamomi, extracts by ethanol room temperature, merges ethanol extract and recovered under reduced pressure is condensed into extractum,
Obtaining total cream, total cream is dispersed to suspendible shape by hot water, the petroleum ether that is incremented by by polarity successively, chloroform, ethyl acetate, n-butyl alcohol extraction
Take, reclaim extract concentrating under reduced pressure and obtain ethyl acetate extract, n-butanol portion, petroleum ether and chloroform extract removal；
Step 2: ethyl acetate extract is carried out silica gel column chromatography, carries out chloroform to methanol gradient with chloroform/methanol for 10:1-3:1
Eluting, obtains one section of Fr.1, Fr.1 under the conditions of eluent is water/methanol 9:1 through reversed-phase silica gel column chromatography during chloroform/methanol 6:1
Obtaining a position, this position obtains compound 1 through gel, preparation liquid phase purification again.
3. beet exigua larvae is had in antifeedant activity and/or growth inhibitory activity medicine by following compounds 1 (Cortex Cinnamomi terpene F) in preparation
Application,
4. cotton bollworm larvae is had in antifeedant activity and/or growth inhibitory activity medicine by following compounds 1 (Cortex Cinnamomi terpene F) in preparation
Application,
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| CN201410369539.4A CN104151323B (en) | 2014-07-30 | 2014-07-30 | There is compound of insect antifeedant activity and growth inhibitory activity and preparation method thereof |
| CN201610242147.0A CN105801596B (en) | 2014-07-30 | 2014-07-30 | Compound with insect antifeedant activity and growth inhibitory activity and preparation method thereof |
| CN201610238948.XA CN105859676B (en) | 2014-07-30 | 2014-07-30 | Compound with insect antifeedant activity and growth inhibitory activity and preparation method thereof |
| CN201610238969.1A CN105777772B (en) | 2014-07-30 | 2014-07-30 | Compound with insect antifeedant activity and growth inhibitory activity and preparation method thereof |
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| CN108935473B (en) * | 2018-09-28 | 2021-01-05 | 广东省农业科学院果树研究所 | Application of eurycollactone in antifeedant activity and inhibition of growth and development of insects |
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|---|---|
| CN105859676B (en) | 2018-03-09 |
| CN105859676A (en) | 2016-08-17 |
| CN105801596B (en) | 2018-04-24 |
| CN104151323A (en) | 2014-11-19 |
| CN105801596A (en) | 2016-07-27 |
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