CN105801596A - Compound with insect antifeedant activity and growth inhibition activity and preparing method thereof - Google Patents
Compound with insect antifeedant activity and growth inhibition activity and preparing method thereof Download PDFInfo
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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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- 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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Abstract
The invention belongs to the technical field of medicine, discloses activity and structures of various ryanoids diterpene compounds separated and extracted from the plant cinnamon, and provides a method for separation and preparation of a novel ryanoids diterpene compound. The compound has immunity suppression activity, insect antifeedant activity and growth inhibition activity, wherein immunity suppression activity is realized through remarkable suppression of proliferation T cells induced by ConA, and insect antifeedant activity and growth inhibition activity are reflected in beet armyworm larva antifeedant activity, cotton bollworm larva antifeedant activity and cotton bollworm larva growth inhibition. The compounds can be used for preparing drugs which are capable of achieving immunity suppression and have insect antifeedant activity and growth inhibition 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 compound of insect antifeedant activity and growth inhibitory activity and preparation method thereof.
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 separate purge 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 immunosuppressive drug at present, is mainly used in preventing the progress etc. of rejection and some autoimmune disease of suppression in organ transplantation.Though wherein many medicines have immunosuppressive action, but toxic and side effects is strong, it is easy to cause systemic immunity to suppress.The immunosuppressant lead compound finding and developing high-efficiency low-toxicity is key subjects of medicine sector of the world.Up-to-date research finds, autoimmune disease and T cell relation are especially close.ConA can stimulate the receptor on T cell surface, selective activation T cell hyper-proliferative in vitro, therefore, utilizes the multiplicative model of the ConA splenic t-cell set up can screen immunosuppressant compound fast and efficiently.
Beet armyworm and bollworm are all the crops such as omnivorousness agricultural pests widely distributed in world wide, main harm Cotton Gossypii, corn and soybean and vegetable.Preventing and treating beet armyworm and bollworm still depend on chemical pesticide at present, but use chemical pesticide causes the disastrous drawbacks such as the pollution of soil, water, air, the generation of the Genes For Plant Tolerance property of medicine and harmful to human animal health unreasonably in a large number.Thus the study hotspot being developed in recent years of botanical pesticide, insect killing substance in plant is mainly secondary metabolites, do not pollute the environment, crops and ecological environment are comparatively safe, and insecticide is not easy to develop immunity to drugs, therefore the exploitation of botanical pesticide is applied in currently " pollution-free food " and plays more and more important effect in producing.
Cortex Cinnamomi is the dry bark of canella xylocinnamomum (CinnamomumcassiaPresl (Lauraceae)), and basyleaves are 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 prodigiosin anthelmintic, purification air, has the active component that can make insect antifeedant in Cortex Cinnamomi.
Summary of the invention:
The task of the present invention is to provide in Cortex Cinnamomi and has bioactive compound and method for separating and preparing thereof and application.
Realization the technical scheme is that
From Cortex Cinnamomi, separate the method obtaining auspicious promise alkane diterpene-kind compound comprise the following steps:
Dry Cortex Cinnamomi is pulverized, extract by ethanol room temperature, merge ethanol extract and recovered under reduced pressure is condensed into extractum, obtain total cream, total cream is dispersed to suspendible shape by hot water, successively with polarity be incremented by petroleum ether, chloroform, ethyl acetate, n-butanol extraction, reclaim extract concentrating under reduced pressure obtain ethyl acetate extract, n-butanol portion, petroleum ether and chloroform extract are removed.
Ethyl acetate extract is carried out silica gel column chromatography, chloroform is to methanol elution gradient (chloroform/methanol 10:1-3:1), one section of Fr.1 is obtained during chloroform/methanol 6:1, Fr.1 obtains a position through reversed-phase silica gel column chromatography (water/methanol 9:1), and this position obtains compound 1 then through gel, preparation liquid phase purification;
N-butanol portion is carried out silica gel column chromatography, and chloroform, to methanol elution gradient (chloroform/methanol 10:1-3:1), obtains Fr.2 during chloroform/methanol 8:1, obtain Fr.3 during chloroform/methanol 6:1, obtains Fr.4 during chloroform/methanol 5:1, obtains Fr.5 during chloroform/methanol 4:1;Fr.2 obtains a position through reversed-phase silica gel column chromatography (water/methanol 9:1), and this position obtains compound 4,5 then through gel, preparation liquid phase purification;Fr.3 obtains two positions respectively Fr.3.1, Fr.3.2 through reversed-phase silica gel column chromatography (water/methanol 9:1-7:3).Fr.3.1 obtains compound 2,6,7 through silica gel, gel, preparation liquid phase purification;Fr.3.2 obtains compound 8,9 through gel, preparation liquid phase purification;Fr.4, through reversed-phase silica gel column chromatography (water/methanol 9:1), obtains compound 3,11 then through silica gel, gel, preparation liquid phase purification;Fr.5 obtains a position through reversed-phase silica gel column chromatography (water/methanol 8:2), and this position obtains compound 10 then through silica gel, gel, preparation liquid phase purification.The structural formula of the auspicious promise alkane diterpene-kind compound 1-11 that present invention separation obtains and title are in Table 1, and separation process is shown in accompanying drawing 1.
Table 1. present invention separates the auspicious promise alkane diterpene-kind compound 1-11 structural formula obtained from Cortex Cinnamomi
Wherein compound Cortex Cinnamomi terpene F, Cortex Cinnamomi terpene G are New skeleton compound, and 19-deoxidation Cortex Cinnamomi terpene G16-glucoside and 18-hydroxyperseanol are noval chemical compound.Accompanying drawing 2 is shown in by the single crystal diffraction structure chart of compound 1, and accompanying drawing 3 is shown in by the single crystal diffraction structure chart of compound 2.
Cortex Cinnamomi active component, under the guidance that immunosuppressive activity is screened, has been carried out systematic study by the present invention.By the research of the T cell inhibited proliferation that ConA is induced by these 11 compounds, present invention discover that the ConA T cell induced is had significant inhibitory action by compound Cortex Cinnamomi terpene G and cinnacaslo, represent that it has significant immunosuppressive action.By compound 1-7 being carried out the research of insect antifeedant and growth inhibitory activity, finding that beet exigua larvae is had antifeedant activity by compound Cortex Cinnamomi terpene F, Cortex Cinnamomi terpene G and 18-hydroxyperseanol, cotton bollworm larvae is had antifeedant activity by compound Cortex Cinnamomi terpene F and 18-hydroxyperseanol;Cotton bollworm larvae is had growth inhibited effect by compound 1-7.
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 composition, under the guidance that immunosuppressive activity is screened, has been carried out systematic study by the present invention, separates and obtains compound 1-11, and wherein compound 1,2 is New skeleton compound, and compound 3 and 4 is noval chemical 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, it has been found that the T cell of compound 2 and 11 pairs of ConA inductions has significant inhibitory action, represents that it has significant immunosuppressive action.By compound 1,2,4,5,6,8,9 being carried out the research of insect antifeedant and growth inhibitory activity, it has been found that 1,2 and 4 pairs of beet exigua larvaes of compound have antifeedant activity, compound 2 and 4 pairs of cotton bollworm larvaes to have 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, the structural formula of insect antifeedant activity and growth inhibitory activity compound 1,2,3,4 and 5 is as follows:
The compounds of this invention 1,2,3,4 method for separating and preparing is: by normal phase silicagel column (mobile phase: chloroform/methanol 10:1-3:1 gradient elution), Cortex Cinnamomi ethyl acetate extract and n-butanol portion are drawn section;Then all again carry out drawing section through reverse phase silica gel (mobile phase: water/methanol 10:0-7:3 gradient elution) by the part obtained;Compound 1,2,3,4 is obtained further across the separation such as gel, HPLC by separating the fragment obtained.
Present patent application embodiment 1 set forth the present invention and separates the concrete grammar obtaining auspicious promise alkane diterpene-kind compound from Cortex Cinnamomi.
Accompanying drawing explanation
Fig. 1: embodiment 1 flow chart;
Fig. 2: the single crystal diffraction structure chart of compound 1;
Fig. 3: the single crystal diffraction structure chart of compound 2.
Detailed description of the invention
Embodiment 1: prepared by the separation of compound.
50Kg is dry, and Cortex Cinnamomi is pulverized, extract 3 times by ethanol room temperature, each 7 days, merging ethanol extract and recovered under reduced pressure is condensed into extractum, obtain total cream 5.1Kg, total cream is dispersed to suspendible shape by hot water, successively with polarity be incremented by petroleum ether, chloroform, ethyl acetate, n-butanol extraction, reclaim extract concentrating under reduced pressure 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 is to methanol elution gradient (chloroform/methanol 10:1-3:1), one section of Fr.1 is obtained during chloroform/methanol 6:1, Fr.1 obtains a position through reversed-phase silica gel column chromatography (water/methanol 9:1), and this position obtains compound 1 then through gel, preparation liquid phase purification.
Compound 4 (3mg), 5 (6mg): n-butanol portion 320g carries out silica gel column chromatography, chloroform is to methanol elution gradient (chloroform/methanol 10:1-3:1), Fr.2 is obtained during chloroform/methanol 8:1, Fr.3 is obtained during chloroform/methanol 6:1, obtain Fr.4 during chloroform/methanol 5:1, during chloroform/methanol 4:1, obtain Fr.5.Fr.2 obtains a position through reversed-phase silica gel column chromatography (water/methanol 9:1), and this position obtains compound 4,5 then through gel, preparation liquid phase purification.
Compound 2 (4mg), 6 (21mg), 7 (42mg): Fr.3 obtain two positions respectively Fr.3.1, Fr.3.2 through reversed-phase silica gel column chromatography (water/methanol 9:1-7:3).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), obtain compound 3 (3mg), 11 (57mg) then through silica gel, gel, preparation liquid phase purification.
Compound 10:Fr.5 obtains a position through reversed-phase silica gel column chromatography (water/methanol 8:2), and this position obtains compound 10 then through silica gel, gel, preparation liquid phase purification.
Separate preparation flow figure and see Fig. 1.
Test through NMR, X-Ray and chemical reaction and resolve the absolute configuration obtaining compound 1,2,3,4.
Compound 1, Cortex Cinnamomi terpene F (cinncassiolF) 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 peak [M+Na] that HRESIMS provides+m/z421.1822.Its1HNMR and13CNMR spectral data is shown in Table1 and Table2.
Compound 2, Cortex Cinnamomi terpene G (cinncassiolG) 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 provides+In conjunction with hydrogen spectrum and carbon modal data, m/z383.2066, determines that its molecular formula is C20H30O7(value of calculation C20H32O7H[M+H]+, 383.2065), fusing point 195 196 DEG C.Its1HNMR and13CNMR spectral data is shown in Table1 and Table2.
Compound 3,19-deoxidation Cortex Cinnamomi terpene G16-glucoside (19-deoxycinncassiolG16-O-β-D-glucopyranoside) 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 provides+(value of calculation is C to m/z567.238526H40O12[M+Na]+,567.2412).Its1HNMR and13CNMR spectral data is shown in Table1 and Table2.
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 provides+(value of calculation is C to m/z423.197920H32O8H[M+Na]+,423.1989).Its1HNMR and13CNMR spectral data is shown in Table1 and Table2.
Table1 compound 1-4's1HNMR data
Table2 compound 1-4's13CNMR data
Embodiment 2
The T cell propagation of compound 2 and 11 pairs of ConA inductions significantly inhibits effect, and splenocyte is all had no side effect by compound 1-11, and splenocyte survival rate is all higher than 90%.The impact that the ConA T cell induced is bred by compound 1-11 ion vitro immunization inhibitory activity by CCK-8 method is evaluated, and result is such as shown in following table Table3:
The suppression ratio that the ConA T cell induced is bred by Table3 compound
Experiment conclusion: the ConA mouse T cell induced is had the inhibitory action of highly significant by compound 2, its inhibitory action is that concentration is correlated with, and the suppression ratio of its variable concentrations is all higher than 85%, it is suppressed that effect can be compared with positive control CsA.The ConA mouse boosting cell induced also is had the inhibitory action of very strong highly significant by compound 11, and 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, cotton bollworm larvae is had growth inhibited effect by 7 compounds.Beet armyworm and cotton bollworm larvae are taken food blade area by compound in table 4 in leaf dish method observation 24h and evaluate its antifeedant activity by antifeedant activity.Growth inhibitory activity observes the compound (the 50 μ g/ml) impact on cotton bollworm larvae body weight in following table in 24h by feedstuff mixed poison method, evaluates its growth inhibitory activity to larva.Result is such as shown in following table Table4.
Table4. compound is to concentration and growth inhibition ratio in the refusing to eat of larva
Experiment conclusion: except beet armyworm or bollworm are all had antifeedant activity in various degree by the most diterpene of compound 5.1,2 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 antifeedant activity;Compound is chosen in all experiments growth inhibited effect to cotton bollworm larvae, and compound 2 even makes the bollworm in the growth stage lose weight.
Claims (7)
1. there is the compound of structure shown in following compound 4:
2. from Cortex Cinnamomi, separate one or more the method obtaining in following auspicious promise alkane diterpene-kind compound 4-10, comprise the following steps:
Step one: dry Cortex Cinnamomi is pulverized, extract by ethanol room temperature, merge ethanol extract and recovered under reduced pressure is condensed into extractum, obtain total cream, total cream is dispersed to suspendible shape by hot water, successively with polarity be incremented by petroleum ether, chloroform, ethyl acetate, n-butanol extraction, reclaim extract concentrating under reduced pressure obtain 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/methanol 10:1-3:1), obtains Fr.2 during chloroform/methanol 8:1, obtain Fr.3 during chloroform/methanol 6:1, obtains Fr.5 during chloroform/methanol 4:1;
Step 3: through reversed-phase silica gel column chromatography (water/methanol 9:1), Fr.2 is obtained a position, this position obtains compound 4,5 then through gel, preparation liquid phase purification;Or
Fr.3 is obtained two positions respectively Fr.3.1, Fr.3.2 through reversed-phase silica gel column chromatography (water/methanol 9:1-7:3);Fr.3.1 obtains compound 6,7 through silica gel, gel, preparation liquid phase purification;Or Fr.3.2 obtains compound 8,9 through gel, preparation liquid phase purification;Or
Through reversed-phase silica gel column chromatography (water/methanol 8:2), Fr.5 is obtained a position, and this position obtains compound 10 then through silica gel, gel, preparation liquid phase purification.
3. any one compound in following compounds 4 to compound 7 is preparing application insecticide being had in antifeedant activity and/or growth inhibitory activity medicine:
4. application according to claim 3, it is characterised in that described insecticide is bollworm or beet armyworm.
5. application according to claim 3, it is characterised in that described insecticide is cotton bollworm larvae or beet exigua larvae.
6. following compounds 4 (18-hydroxyperseanol) is preparing application beet exigua larvae being had in antifeedant activity medicine,
7. following compounds 4 (18-hydroxyperseanol) is preparing application cotton bollworm larvae being had in antifeedant activity medicine,
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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 |
Citations (1)
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JPS55136283A (en) * | 1979-03-29 | 1980-10-23 | Itsuo Nishioka | Novel diterpene derivative |
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JPS55136283A (en) * | 1979-03-29 | 1980-10-23 | Itsuo Nishioka | Novel diterpene derivative |
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CN104151323A (en) | 2014-11-19 |
CN105859676A (en) | 2016-08-17 |
CN105859676B (en) | 2018-03-09 |
CN105801596B (en) | 2018-04-24 |
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