CN105859676A - Compound with insect antifeedant activity and growth inhibitory activity and preparing method thereof - Google Patents
Compound with insect antifeedant activity and growth inhibitory activity and preparing 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
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- 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
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
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- C07H15/26—Acyclic or carbocyclic radicals, substituted by hetero rings
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Abstract
The invention belongs to the technical field of medicine, discloses the activity and structure of multiple ryanoids diterpenoid compounds separated and extracted from cortex cinnamomi, and provides a method for separation and preparation of novel ryanoids diterpenoid compounds. The novel ryanoids diterpenoid compounds have immunosuppression activity, insect antifeedant activity and growth inhibitory activity. Immunosuppression activity is manifested in a remarkable suppression effect on ConA-induced T cell proliferation, and insect antifeedant activity and growth inhibitory activity are manifested in antifeedant activity to beet armyworm larvae and cotton bollworm larvae and growth inhibition in cotton bollworm larvae. The compounds can be used for preparing drugs with immunosuppression activity, insect antifeedant activity and growth inhibitory activity.
Description
The application is the divisional application of No. 2014103695394 patent applications.
The applying date of original application is: on July 30th, 2014.
The application number of original application is: 201410369539.4.
The invention and created name of original application is: have insect antifeedant activity and the compound of GIA and preparation thereof
Method.
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, immunosupress, insect antifeedant and growth inhibition effect etc..
Background technology
Autoimmune disease is the third-largest disease being only second to angiocardiopathy and cancer, has been developed for substantial amounts of at present
Immunosuppressive drug, is mainly used in preventing the rejection in organ transplant and the progress of some autoimmune disease of suppression
Deng.Though wherein many medicines have immunosuppressive action, but toxic and side effect is strong, easily causes systemic immunity suppression.Find also
The immunosupress lead compound developing high-efficiency low-toxicity is key subjects of medicine sector of the world.Up-to-date research is sent out
Existing, autoimmune disease and T cell relation are the closest.ConA can stimulate the acceptor on T cell surface in vitro, selectively swashs
Live T cell hyper-proliferative, therefore, utilize the multiplicative model of the splenic t-cell that ConA sets up can screen immunosupress fast and efficiently
Compound.
Beet armyworm and bollworm are all omnivorousness agricultural pests widely distributed in world wide, main harm cotton,
The crop such as corn and soybean and vegetables.At present preventing and treating beet armyworm and bollworm still depend on chemical pesticide, but a large amount of the most not
Reasonably using chemical pesticide to cause the pollution of soil, water, air, the Genes For Plant Tolerance property of medicine produces and harmful to human animal health
Etc. disastrous drawback.Thus the study hotspot being developed in recent years of botanical pesticide, the insect killing substance in plant is mainly
Secondary metabolites, does not pollutes the environment, comparatively safe to crops and ecological environment, and insect is not easy to develop immunity to drugs,
Therefore the exploitation of botanical pesticide is applied and is played the most important effect in current " pollution-free food " produces.
Cassia is the dry bark of canella xylocinnamomum (Cinnamomum cassia Presl (Lauraceae)),
Basyleaves are the dry leaf of Chinese cassia tree.Chinese cassia tree can regulate body immunity, Chinese cassia tree and different auspicious promise alkane diterpene thereof and have anticomplement
Activity, Chinese cassia tree tool can expelling parasite, purify air, Chinese cassia tree has the active component that can make insect antifeedant.
Summary of the invention:
The task of the present invention is to provide in Chinese cassia tree has bioactive compound and method for separating and preparing thereof and application.
Realization the technical scheme is that
From Chinese cassia tree, the method for isolated auspicious promise alkane diterpene-kind compound comprises the following steps:
Dry cassia is pulverized, extracts by ethanol room temperature, merge ethanol extract and recovered under reduced pressure is condensed into medicinal extract,
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, n-butanol extraction
Take, reclaim extract reduced pressure concentration and obtain 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/methyl alcohol 6:1 time obtain one section of Fr.1, Fr.1 through reversed-phase silica gel column chromatography (water/methyl alcohol 9:1) a position, this position warp again
Gel, preparation liquid phase purify and obtain compound 1；
N-butanol portion is carried out silica gel column chromatography, chloroform to methanol elution gradient (chloroform/methanol 10:1-3:1), chlorine
Imitative/methyl alcohol 8:1 time obtain Fr.2, obtain Fr.3 during chloroform/methanol 6:1, obtain Fr.4 during chloroform/methanol 5:1, obtain during chloroform/methanol 4:1
Fr.5；Fr.2 obtains a position through reversed-phase silica gel column chromatography (water/methyl alcohol 9:1), and this position purifies through gel, preparation liquid phase again
To compound 4,5；Fr.3 through reversed-phase silica gel column chromatography (water/methyl alcohol 9:1-7:3) two positions be respectively Fr.3.1,
Fr.3.2.Fr.3.1 purifies obtain compound 2,6,7 through silica gel, gel, preparation liquid phase；Fr.3.2 is through gel, preparation liquid-phase pure
Change and obtain compound 8,9；Fr.4 is through reversed-phase silica gel column chromatography (water/methyl alcohol 9:1), then purifies through silica gel, gel, preparation liquid phase
Obtain compound 3,11；Fr.5 through reversed-phase silica gel column chromatography (water/methyl alcohol 8:2) a position, this position is again through silica gel, solidifying
Glue, preparation liquid phase purify and obtain compound 10.The structural formula of the auspicious promise alkane diterpene-kind compound 1-11 of isolated of the present invention and
Title is 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 Chinese cassia tree
Wherein compound Chinese cassia tree terpene F, Chinese cassia tree terpene G are New skeleton compound, 19-deoxidation Chinese cassia tree terpene G 16-glucoside and
18-hydroxyperseanol is noval chemical compound.The single crystal diffraction structure chart of compound 1 is shown in that accompanying drawing 2, the monocrystalline of compound 2 spread out
Penetrate structure chart and see accompanying drawing 3.
The present invention, under the guidance that immunosuppressive activity is screened, has carried out system research to Chinese cassia tree active component.By this
The research of the T cell inhibited proliferation that ConA is induced by 11 compounds, present invention discover that compound Chinese cassia tree terpene G and
Cinnacaslo has significant inhibitory action to the T cell that ConA induces, and represents that it has significant immunosuppressive action.By right
Compound 1-7 carries out the research of insect antifeedant and GIA, finds compound Chinese cassia tree terpene F, Chinese cassia tree terpene G and 18-
Hydroxyperseanol has antifeedant activity, compound Chinese cassia tree terpene F and 18-hydroxyperseanol pair to beet exigua larvae
Cotton bollworm larvae has antifeedant activity；Compound 1-7 has growth inhibition effect to cotton bollworm larvae.
The invention provides the plant origin of compound 1-11, isolation and purification method, immunosuppressive activity, insect antifeedant and
GIA and application.Chinese cassia tree immunosuppressive activity composition, under the guidance that immunosuppressive activity is screened, is entered by the present invention
Having gone system research, isolated compound 1-11, wherein compound 1,2 is New skeleton compound, and compound 3 and 4 is new
Compound.Structural formula is as shown in table 1.By the research of the T cell inhibited proliferation that ConA is induced by these 11 compounds, send out
The T cell of existing compound 2 and 11 pairs of ConA inductions has significant inhibitory action, represents that it has significant immunosuppressive action.Logical
Cross the research that compound 1,2,4,5,6,8,9 is carried out insect antifeedant and GIA, find that compound 1,2 and 4 is to sweet
Dish exigua larvae has antifeedant activity, compound 2 and 4 pairs of cotton bollworm larvaes to have antifeedant activity；Compound 1,2,4,5,6,8,9 is to cotton
Earworm larva has growth inhibition effect.
Immunosuppressive activity provided by the present invention, insect antifeedant activity and GIA compound 1,2,3,4 and 5
Structural formula as follows:
The compounds of this invention 1,2,3,4 method for separating and preparing is: by Chinese cassia tree ethyl acetate extract and n-butanol portion by
Normal phase silicagel column (flowing phase: chloroform/methanol 10:1-3:1 gradient elution) draws section；Then by the part that obtains all through anti-phase silicon
Glue (flowing phase: water/methyl alcohol 10:0-7:3 gradient elution) carries out drawing section again；By the fragment of isolated further across solidifying
The isolated compound such as glue, HPLC 1,2,3,4.
Present patent application embodiment 1 set forth the concrete of present invention isolated from Chinese cassia tree 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 cassia and pulverizes, and extracts 3 times by ethanol room temperature, each 7 days, merges ethanol extract recovered under reduced pressure
Being condensed into medicinal extract, obtain total cream 5.1Kg, total cream is dispersed to suspendible shape by hot water, the petroleum ether that is incremented by by polarity successively, chloroform,
Ethyl acetate, extracting n-butyl alcohol, reclaim extract reduced pressure concentration and obtain ethyl acetate extract 70g, n-butanol portion 320g, petroleum ether
And chloroform extract removal.
Compound 1 (22mg): ethyl acetate extract 70g carries out silica gel column chromatography, chloroform to methanol elution gradient (chloroform/
Methyl alcohol 10:1-3:1), obtain one section of Fr.1, Fr.1 during chloroform/methanol 6:1 and obtain one through reversed-phase silica gel column chromatography (water/methyl alcohol 9:1)
Position, this position purifies obtain compound 1 through gel, preparation liquid phase 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, during chloroform/methanol 5:1 during chloroform/methanol 6:1
Obtain Fr.4, during chloroform/methanol 4:1, obtain Fr.5.Fr.2 obtains a position, this position through reversed-phase silica gel column chromatography (water/methyl alcohol 9:1)
Purify obtain compound 4,5 through gel, preparation liquid phase again.
Compound 2 (4mg), 6 (21mg), 7 (42mg): Fr.3 obtain through reversed-phase silica gel column chromatography (water/methyl alcohol 9:1-7:3)
Two positions are respectively Fr.3.1, Fr.3.2.Fr.3.1 purifies obtain compound 2,6,7 through silica gel, gel, preparation liquid phase.
Compound 8 (12mg), 9 (28mg): Fr.3.2 purify obtain compound 8,9 through gel, preparation liquid phases.
Compound 3,11:Fr.4 are through reversed-phase silica gel column chromatography (water/methyl alcohol 9:1), then through silica gel, gel, preparation liquid phase
Purifying obtains compound 3 (3mg), 11 (57mg).
Compound 10:Fr.5 through reversed-phase silica gel column chromatography (water/methyl alcohol 8:2) a position, this position is again through silica gel, solidifying
Glue, preparation liquid phase purify and 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, Chinese cassia tree terpene F (cinncassiol F) is colorless prismatic crystal,UV
(MeOH)λmax(logε):204(3.78)nm；IR(KBr)Vmax 3394,2968,2881,1709,1445,1388,1367,
1331,1257,1086,1039,999,851,787,758,683cm–1；The quasi-molecular ion peak [M+Na] that HRESIMS is given+m/
z 421.1822.Its1H NMR and13C NMR spectra data are shown in Table 1 and Table 2.
Compound 2, Chinese cassia tree terpene G (cinncassiol G) is water white transparency column crystal,
UV(MeOH)λmax(log ε)=202 (3.7) nm；IR(KBr)Vmax 3418,2969,2886,2115,1641,1581,1412,
1388,1269,1103,1026,833cm–1；The quasi-molecular ion peak [M+H] that HRESIMS is given+M/z 383.2066, in conjunction with hydrogen
Spectrum and carbon modal data determine that its molecular formula is C20H30O7(calculated value 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 Chinese cassia tree terpene G 16-glucoside (19-deoxycinncassiol G 16-O-β-D-
Glucopyranoside) it is colourless oil liquid,UV(MeOH)λmax(log ε)=204
(3.7)nm；IR(KBr)Vmax 3391,2960,2931,1716,1629,1459,1376,1240,1214,1165,1081,
1027,943,869,774,693cm–1；The quasi-molecular ion peak [M+Na] that HRESIMS is given+(calculated value is m/z 567.2385
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/z423.1979 (calculates
Value 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
Table2 compound 1-4's13C NMR data
Embodiment 2
The T cell propagation of compound 2 and 11 pairs of ConA inductions significantly inhibits effect, compound 1-11 nothing equal to splenocyte
Toxic and side effect, splenocyte survival rate is all higher than 90%.ConA is lured by compound 1-11 ion vitro immunization inhibitory activity by CCK-8 method
The impact of the T cell propagation led is evaluated, and result is as shown in following table Table 3:
The inhibiting rate of the T cell propagation that ConA is induced by Table 3 compound
Experiment conclusion: compound 2 has the inhibitory action of highly significant, its inhibitory action to the mouse T cell that ConA induces
Relevant in concentration, the inhibiting rate of its variable concentrations is all higher than 85%, and inhibition can be compared with positive control CsA.Compound 11
Mouse boosting cell to ConA induction also has the inhibitory action of the strongest highly significant, and under experimental concentration, its inhibiting rate 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；Table
In 7 compounds cotton bollworm larvae is had growth inhibition effect.Antifeedant activity is by compound in table 4 in leaf dish method observation 24h
Beet armyworm and cotton bollworm larvae are taken food blade area and evaluates its antifeedant activity.GIA is seen by feed mixed poison method
Examine the compound (the 50 μ g/ml) impact on cotton bollworm larvae body weight in following table in 24h, evaluate it and growth inhibition of larva is lived
Property.Result is as shown in following table Table 4.
Table 4. compound is to concentration and growth inhibition ratio in the food refusal of larva
Experiment conclusion: all have food refusal in various degree to live except the most diterpene of compound 5 to beet armyworm or bollworm
Property.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 notable food refusal
Activity；Compound is chosen in all experiments growth inhibition effect to cotton bollworm larvae, and compound 2 even makes the cotton boll in the growth stage
Worm loses weight.
Claims (7)
1. there is the compound of structure shown in following compound 2, compound 3:
2. the method for the following auspicious promise alkane diterpene-kind compound 2 or 3 of isolated from Chinese cassia tree, comprises the following steps:
Step one: pulverized by dry cassia, extracts by ethanol room temperature, merges ethanol extract and recovered under reduced pressure is condensed into leaching
Cream, obtains total cream, and 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 reduced pressure concentration and obtains ethyl acetate extract, n-butanol portion, petroleum ether part and chloroform extract；
Step 2: the n-butanol portion obtained in step one is carried out silica gel column chromatography, chloroform to methanol elution gradient (chloroform/
Methyl alcohol 10:1-3:1), obtain Fr.3 during chloroform/methanol 6:1, during chloroform/methanol 5:1, obtain Fr.4；
Fr.3 is obtained two positions through reversed-phase silica gel column chromatography (water/methyl alcohol 9:1-7:3) and is respectively Fr.3.1, Fr.3.2；
Fr.3.1 purifies obtain compound 2 through silica gel, gel, preparation liquid phase；Or
By Fr.4 through reversed-phase silica gel column chromatography (water/methyl alcohol 9:1), then purify obtain compound through silica gel, gel, preparation liquid phase
3。
3. have the compound of structure shown in following compound 2 preparation immunosupress in application:
4. following compounds 2 or 3 has an application in antifeedant activity and/or GIA medicine in preparation to insect:
Application the most according to claim 4, it is characterised in that described insect is bollworm or beet armyworm.
Application the most according to claim 4, it is characterised in that described insect is cotton bollworm larvae or beet armyworm children
Worm.
7. following compounds 2 (Chinese cassia tree terpene G) has the application in antifeedant activity medicine in preparation to beet exigua larvae,
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| CN108935473A (en) * | 2018-09-28 | 2018-12-07 | 广东省农业科学院果树研究所 | Eurycomalactone is in insect antifeedant activity and the application for inhibiting insect growth to develop |
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| CN104478832B (en) * | 2015-01-05 | 2016-04-20 | 项敬来 | Diterpene compound, containing its pharmaceutical composition and its preparation method and application |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55136283A (en) * | 1979-03-29 | 1980-10-23 | Itsuo Nishioka | Novel diterpene derivative |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS55136283A (en) * | 1979-03-29 | 1980-10-23 | Itsuo Nishioka | Novel diterpene derivative |
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| Title |
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| AKIRA YAGI, ET AL.: "The Constituents of Cinnamomi Cortex.I.Structrues of Cinncassiol A and Its Glucoside", 《CHEM.PHAR.BULL.》 * |
| BRAULIO M. FRAGA,ET AL.: "Insect Antifeedant Isoryanodane Diterpenes from Persea indica", 《JOURNAL OF NATURAL PRODUCTS》 * |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108935473A (en) * | 2018-09-28 | 2018-12-07 | 广东省农业科学院果树研究所 | Eurycomalactone is in insect antifeedant activity and the application for inhibiting insect growth to develop |
| 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 |
Also Published As
| Publication number | Publication date |
|---|---|
| CN104151323A (en) | 2014-11-19 |
| CN104151323B (en) | 2016-09-28 |
| CN105801596B (en) | 2018-04-24 |
| CN105859676B (en) | 2018-03-09 |
| CN105801596A (en) | 2016-07-27 |
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