CN105859676B - Compound with insect antifeedant activity and growth inhibitory activity and preparation method thereof - Google Patents
Compound with insect antifeedant activity and growth inhibitory activity and preparation method thereof Download PDFInfo
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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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 pharmaceutical technology field, the activity and structure of a variety of auspicious promise alkane diterpene-kind compounds of separation and Extraction from plant Chinese cassia tree are disclosed, there is provided the method for separating and preparing of Xin Ruinuo alkane diterpene compounds.Present invention is disclosed such compound to have immunosuppressive activity, insect antifeedant activity and growth inhibitory activity, wherein the compound with immunosuppressive activity shows as significantly inhibiting the T cell propagation of ConA inductions effect, and insect antifeedant activity and growth inhibitory activity show as having beet exigua larvae antifeedant activity, have cotton bollworm larvae antifeedant activity and having growth inhibition effect to cotton bollworm larvae.These compounds can be used for preparing immunosupress, have antifeedant activity and the medicine of growth inhibitory activity to insect.
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：Compound and its preparation with insect antifeedant activity and growth inhibitory activity
Method.
Technical field
The invention belongs to pharmaceutical technology field, it is related to auspicious promise alkane diterpene compound 1-11 method for separating and preparing and purposes.
More particularly to the process that isolates and purifies, structural identification, immunosupress, insect antifeedant and growth inhibition effect etc..
Background technology
Autoimmune disease is to be only second to the third-largest disease of angiocardiopathy and cancer, has been developed at present substantial amounts of
Immunosuppressive drug, the rejection for being mainly used in preventing in organ transplant and the progress for suppressing some autoimmune diseases
Deng.Though wherein many medicines have immunosuppressive action, toxic side effect is strong, easily causes systemic immunity suppression.Find simultaneously
The immunosupress lead compound for developing high-efficiency low-toxicity is a key subjects of medicine sector of the world.Newest research hair
Existing, autoimmune disease and T cell relation are especially close.ConA can stimulate the acceptor on T cell surface in vitro, and selectivity swashs
T cell hyper-proliferative living, therefore, immunosupress can be fast and efficiently screened using the multiplicative model of the ConA splenic t-cells established
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.Preventing and treating beet armyworm and bollworm still depend on chemical pesticide at present, but largely not
The pollution of soil, water, air is reasonably caused using chemical pesticide, the plant resistance to the action of a drug produces and harmful to human animal health
Etc. disastrous drawback.The thus study hotspot being developed into recent years of botanical pesticide, the insect killing substance in plant are mainly
Secondary metabolites, do not pollute the environment, it is comparatively safe to crops and ecological environment, and insect is not easy to develop immunity to drugs,
Therefore the development and application of botanical pesticide play more and more important effect in current " pollution-free food " production.
Cassia is canella xylocinnamomum (Cinnamomum cassia Presl (Lauraceae)) dry bark,
Basyleaves are the drying leaf of Chinese cassia tree.Chinese cassia tree can adjust body immunity, and Chinese cassia tree and its different auspicious promise alkane diterpene have anticomplement
Activity, Chinese cassia tree tool can expelling parasite, purification air, have the active component that can make insect antifeedant in Chinese cassia tree.
The content of the invention：
The task of the present invention is to provide compound and its method for separating and preparing and application in Chinese cassia tree with bioactivity.
Realize the technical scheme is that：
The method of isolated auspicious promise alkane diterpene-kind compound comprises the following steps from Chinese cassia tree：
Cassia will be dried to crush, extracted with ethanol room temperature, merge ethanol extract and be recovered under reduced pressure and be condensed into medicinal extract, obtain
To total cream, total cream is dispersed to suspension shape by hot water, is extracted successively with the incremental petroleum ether of polarity, chloroform, ethyl acetate, n-butanol
Take, recovery extract is concentrated under reduced pressure to obtain ethyl acetate extract, n-butanol portion, and petroleum ether and chloroform extract remove.
Ethyl acetate extract is subjected to silica gel column chromatography, chloroform to methanol elution gradient (chloroform/methanol 10:1-3:1), chlorine
Imitative/methanol 6:One section of Fr.1 is obtained when 1, Fr.1 passes through reversed-phase silica gel column chromatography (water/methanol 9:1) position is obtained, this position passes through again
Gel, preparation liquid phase purify to obtain compound 1；
N-butanol portion is subjected to silica gel column chromatography, chloroform to methanol elution gradient (chloroform/methanol 10:1-3:1), chlorine
Imitative/methanol 8:Fr.2, chloroform/methanol 6 are obtained when 1:Fr.3, chloroform/methanol 5 are obtained when 1:Fr.4, chloroform/methanol 4 are obtained when 1:Obtained when 1
Fr.5；Fr.2 passes through reversed-phase silica gel column chromatography (water/methanol 9:1) position is obtained, this position purifies through gel, preparation liquid phase again
To compound 4,5；Fr.3 passes through reversed-phase silica gel column chromatography (water/methanol 9:1-7:3) two positions be respectively Fr.3.1,
Fr.3.2.Fr.3.1 purifies to obtain compound 2,6,7 through silica gel, gel, preparation liquid phase；Fr.3.2 is through gel, preparation liquid-phase pure
Change obtains compound 8,9；Fr.4 passes through reversed-phase silica gel column chromatography (water/methanol 9:1), then through silica gel, gel, preparation liquid phase purifying
Obtain compound 3,11；Fr.5 passes through reversed-phase silica gel column chromatography (water/methanol 8:2) a position, this position is again through silica gel, solidifying
Glue, preparation liquid phase purify to obtain compound 10.The isolated auspicious promise alkane diterpene-kind compound 1-11 of present invention structural formula and
Title is shown in Table 1, and separation process is shown in accompanying drawing 1.
The present invention of table 1. auspicious promise alkane diterpene-kind compound 1-11 structural formulas isolated from Chinese cassia tree
Wherein compound Chinese cassia tree terpene F, Chinese cassia tree terpene G are New skeleton compound, 19- deoxidations Chinese cassia tree terpene G 16- glucosides and
18-hydroxyperseanol is noval chemical compound.The single crystal diffraction structure chart of compound 1 is shown in accompanying drawing 2, and the monocrystalline of compound 2 spreads out
Penetrate structure chart and see accompanying drawing 3.
The present invention has carried out system research under the guidance of immunosuppressive activity screening to Chinese cassia tree active component.Pass through this
The research for the T cell inhibited proliferation that 11 compounds are induced ConA, present invention discover that compound Chinese cassia tree terpene G and
Cinnacaslo has significant inhibitory action to the ConA T cells induced, represents that it has significant immunosuppressive action.By right
Compound 1-7 carries out the research of insect antifeedant and growth inhibitory activity, finds compound Chinese cassia tree terpene F, Chinese cassia tree terpene G and 18-
Hydroxyperseanol has antifeedant activity to beet exigua larvae, compound Chinese cassia tree terpene F and 18-hydroxyperseanol pairs
Cotton bollworm larvae has antifeedant activity；Compound 1-7 has growth inhibition effect to cotton bollworm larvae.
The invention provides compound 1-11 plant origin, isolation and purification method, immunosuppressive activity, insect antifeedant and
Growth inhibitory activity and application.The present invention enters under the guidance of immunosuppressive activity screening to Chinese cassia tree immunosuppressive activity composition
System research is gone, 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.The research of the T cell inhibited proliferation induced by this 11 compounds ConA, hair
Existing compound 2 and the T cell of 11 pairs of ConA inductions have significant inhibitory action, represent that it has significant immunosuppressive action.It is logical
The research that insect antifeedant and growth inhibitory activity are carried out to compound 1,2,4,5,6,8,9 is crossed, finds 1,2 and 4 pair of sweet tea of compound
Dish exigua larvae has antifeedant activity, and compound 2 and 4 pairs of cotton bollworm larvaes have antifeedant activity；Compound 1,2,4,5,6,8,9 pairs of cottons
Earworm larva has growth inhibition effect.
Immunosuppressive activity provided by the present invention, insect antifeedant activity and growth inhibitory activity compound 1,2,3,4 and 5
Structural formula it is as follows：
The method for separating and preparing of the compounds of this invention 1,2,3,4 is：By Chinese cassia tree ethyl acetate extract and n-butanol portion by
Normal phase silicagel column (mobile phase：Chloroform/methanol 10:1-3:1 gradient elution) draw section；Then anti-phase silicon is passed through into obtained part
Glue (mobile phase：Water/methanol 10:0-7:3 gradient elutions) carry out drawing section again；By isolated fragment further across solidifying
The isolated compound 1,2,3,4 such as glue, HPLC.
Present patent application embodiment 1 set forth the specific of the present invention auspicious promise alkane diterpene-kind compound isolated from Chinese cassia tree
Method.
Brief description of the drawings
Fig. 1：The flow chart of embodiment 1；
Fig. 2：The single crystal diffraction structure chart of compound 1；
Fig. 3：The single crystal diffraction structure chart of compound 2.
Embodiment
Embodiment 1：It is prepared by the separation of compound.
50Kg dries cassia and crushed, and is extracted 3 times with ethanol room temperature, 7 days every time, merges ethanol extract and be recovered under reduced pressure
Be condensed into medicinal extract, obtain total cream 5.1Kg, total cream is dispersed to suspension shape by hot water, successively with the incremental petroleum ether of polarity, chloroform,
Ethyl acetate, extracting n-butyl alcohol, recovery extract are concentrated under reduced pressure to obtain ethyl acetate extract 70g, n-butanol portion 320g, petroleum ether
And chloroform extract removes.
Compound 1 (22mg)：Ethyl acetate extract 70g progress silica gel column chromatographies, chloroform to methanol elution gradient (chloroform/
Methanol 10:1-3:1), chloroform/methanol 6:One section of Fr.1 is obtained when 1, Fr.1 passes through reversed-phase silica gel column chromatography (water/methanol 9:1) one is obtained
Position, this position purify to obtain compound 1 through gel, preparation liquid phase again.
Compound 4 (3mg), 5 (6mg)：N-butanol portion 320g carries out silica gel column chromatography, chloroform to methanol elution gradient
(chloroform/methanol 10:1-3:1), chloroform/methanol 8:Fr.2, chloroform/methanol 6 are obtained when 1:Fr.3, chloroform/methanol 5 are obtained when 1:When 1
Obtain Fr.4, chloroform/methanol 4:Fr.5 is obtained when 1.Fr.2 passes through reversed-phase silica gel column chromatography (water/methanol 9:1) position, this position are obtained
Purify to obtain compound 4,5 through gel, preparation liquid phase again.
Compound 2 (4mg), 6 (21mg), 7 (42mg)：Fr.3 passes through reversed-phase silica gel column chromatography (water/methanol 9:1-7:3)
Two positions are respectively Fr.3.1, Fr.3.2.Fr.3.1 purifies to obtain compound 2,6,7 through silica gel, gel, preparation liquid phase.
Compound 8 (12mg), 9 (28mg)：Fr.3.2 purifies to obtain compound 8,9 through gel, preparation liquid phase.
Compound 3,11：Fr.4 passes through reversed-phase silica gel column chromatography (water/methanol 9:1), then through silica gel, gel, preparation liquid phase
Purifying obtains compound 3 (3mg), 11 (57mg).
Compound 10：Fr.5 passes through reversed-phase silica gel column chromatography (water/methanol 8:2) a position, this position is again through silica gel, solidifying
Glue, preparation liquid phase purify to obtain compound 10.
Separation preparation flow figure is shown in Fig. 1.
By NMR, X-Ray and chemical reaction test parsing have obtained the absolute configuration of compound 1,2,3,4.
Compound 1, Chinese cassia tree terpene F (cinncassiol F) are 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 provided+m/
z 421.1822.Its1H NMR and13C H NMR spectroscopy diagram datas are shown in Table 1 and Table 2.
Compound 2, Chinese cassia tree terpene G (cinncassiol G) are water white transparency column crystal,
UV(MeOH)λmax(3.7) nm of (log ε)=202；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 provided+M/z 383.2066, with reference to hydrogen
Spectrum and carbon modal data determine that its molecular formula is C20H30O7(calculated value C20H32O7H[M+H]+, 383.2065), 195-196 DEG C of fusing point.
Its1H NMR and13C H NMR spectroscopy diagram datas are shown in Table 1 and Table 2.
Compound 3,19- deoxidation Chinese cassia tree terpene G 16- glucosides (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 provided+(calculated value is m/z 567.2385
C26H40O12[M+Na]+,567.2412).Its1H NMR and13C H NMR spectroscopy diagram datas are shown in Table 1 and Table 2.
Compound 4,18-hydroxyperseanol are colourless oil liquid,UV
(MeOH)λmax(3.4) nm of (log ε)=206；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 provided+M/z423.1979 (is calculated
It is worth for C20H32O8H[M+Na]+,423.1989).Its1H NMR and13C H NMR spectroscopy diagram datas are shown in Table 1 and Table 2.
The compound 1-4's of Table 11H NMR datas
Table2 compounds 1-4's13C NMR datas
Embodiment 2
Compound 2 and the T cell propagation of 11 pairs of ConA inductions significantly inhibit effect, and compound 1-11 is to the equal nothing of splenocyte
Toxic side effect, splenocyte survival rate are all higher than 90%.Compound 1-11 ion vitro immunizations inhibitory activity is lured ConA by CCK-8 methods
The influence for the T cell propagation led is evaluated, as a result as shown in following table Table 3：
The inhibiting rate for the T cell propagation that the compounds of Table 3 are induced ConA
Experiment conclusion：Compound 2 has the inhibitory action of highly significant, its inhibitory action to the ConA mouse T cells induced
Related in concentration, the inhibiting rate of its various concentrations is all higher than 85%, and inhibition can compare with positive control CsA.Compound 11
Also there is the inhibitory action of very strong highly significant to the mouse boosting cell of ConA inductions, its inhibiting rate is all higher than under experimental concentration
50%.
Embodiment 3：1,2 and 4 pair of beet exigua larvae of compound has the antifeedant activity of antifeedant activity and cotton bollworm larvae；Table
In 7 compounds have growth inhibition effect to cotton bollworm larvae.Antifeedant activity passes through compound in table 4 in leaf dish method observation 24h
Its antifeedant activity is evaluated to beet armyworm and cotton bollworm larvae feeding blade area.Growth inhibitory activity is mixed malicious method by feed and seen
Influence of the compound (50 μ g/ml) to cotton bollworm larvae body weight in following table in 24h is examined, its growth inhibition to larva is evaluated and lives
Property.As a result as shown in following table Table 4.
The compounds of Table 4. are to concentration and growth inhibition ratio in the food refusal of larva
Experiment conclusion：Except 5 most diterpene of compound has different degrees of food refusal to live to beet armyworm or bollworm
Property.1,2 and 4 pair of beet exigua larvae of compound has notable antifeedant activity, and compound 1 and 4 pairs of cotton bollworm larvaes 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 weight loss.
Claims (7)
1. the compound with structure shown in following compound 2, compound 3：
2. the method for isolated following auspicious promise alkane diterpene-kind compound 2 or 3, comprises the following steps from Chinese cassia tree：
Step 1：Cassia will be dried to crush, extracted with ethanol room temperature, merge ethanol extract and be recovered under reduced pressure and be condensed into leaching
Cream, total cream is obtained, total cream is dispersed to suspension shape by hot water, successively with the incremental petroleum ether of polarity, chloroform, ethyl acetate, positive fourth
Alcohol extracts, and recovery extract is concentrated under reduced pressure to obtain ethyl acetate extract, n-butanol portion, petroleum ether part and chloroform extract；
Step 2：The n-butanol portion obtained in step 1 is subjected to silica gel column chromatography, chloroform to methanol elution gradient, it is eluted
Gradient is：Chloroform/methanol 10:1-3:1, chloroform/methanol 6:Fr.3, chloroform/methanol 5 are obtained when 1:Fr.4 is obtained when 1；
Fr.3 is passed through into reversed-phase silica gel column chromatography, its mobile phase is：Water/methanol 9:1-7:3, obtain two positions be respectively Fr.3.1,
Fr.3.2；Fr.3.1 purifies to obtain compound 2 through silica gel, gel, preparation liquid phase；Or
Fr.4 is passed through into reversed-phase silica gel column chromatography, its mobile phase is：Water/methanol 9:1, then through silica gel, gel, preparation liquid phase purifying
Obtain compound 3.
3. application of the compound with structure shown in following compound 2 in immunosupress is prepared：
4. following compounds 2 or 3 are preparing the application in having antifeedant activity and/or growth inhibitory activity medicine to insect：
5. application according to claim 4, it is characterised in that described insect is bollworm or beet armyworm.
6. application according to claim 4, it is characterised in that described insect is cotton bollworm larvae or beet armyworm children
Worm.
7. following compounds 2 are preparing the application in having antifeedant activity medicine to beet exigua larvae,
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| CN201610238948.XA CN105859676B (en) | 2014-07-30 | 2014-07-30 | Compound with insect antifeedant activity and growth inhibitory activity and preparation method thereof |
| 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 |
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| CN201410369539.4A Active CN104151323B (en) | 2014-07-30 | 2014-07-30 | There is compound of insect antifeedant activity and growth inhibitory activity and preparation method thereof |
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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 |
| 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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| JPS55136283A (en) * | 1979-03-29 | 1980-10-23 | Itsuo Nishioka | Novel diterpene derivative |
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Non-Patent Citations (2)
| Title |
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| Insect Antifeedant Isoryanodane Diterpenes from Persea indica;Braulio M. Fraga,et al.;《Journal of Natural Products》;19971231;880-883 * |
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| Publication number | Publication date |
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| CN105801596B (en) | 2018-04-24 |
| CN105801596A (en) | 2016-07-27 |
| CN104151323A (en) | 2014-11-19 |
| CN104151323B (en) | 2016-09-28 |
| CN105859676A (en) | 2016-08-17 |
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