CN105801596B - 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 PDF

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CN105801596B
CN105801596B CN201610242147.0A CN201610242147A CN105801596B CN 105801596 B CN105801596 B CN 105801596B CN 201610242147 A CN201610242147 A CN 201610242147A CN 105801596 B CN105801596 B CN 105801596B
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methanol
chloroform
silica gel
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CN105801596A (en
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张勇慧
姚广民
曾俊芬
张锦文
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Huazhong University of Science and Technology
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C07D493/02—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system in which the condensed system contains two hetero rings
    • C07D493/08—Bridged systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • 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
    • A01N43/06—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
    • 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
    • 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
    • A01N43/22—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 rings with more than six members
    • 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
    • A01N43/90—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D307/93—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 condensed with a ring other than six-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D313/00—Heterocyclic compounds containing rings of more than six members having one oxygen atom as the only ring hetero atom
    • C07D313/02—Seven-membered rings
    • C07D313/06—Seven-membered rings condensed with carbocyclic rings or ring systems
    • C07D313/08—Seven-membered rings condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H1/00—Processes for the preparation of sugar derivatives
    • C07H1/06—Separation; Purification
    • C07H1/08—Separation; Purification from natural products
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
    • 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

Compound with insect antifeedant activity and growth inhibitory activity and preparation method thereof
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 the method for separating and preparing and purposes of auspicious promise alkane diterpene compound 1-11. 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 for 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, be easy to cause 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.Prevention 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 research hotspot being developed into recent years of botanical pesticide, the insect killing substance in plant are mainly Secondary metabolites, does not pollute the environment, 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 the dry bark of canella xylocinnamomum (Cinnamomum cassia Presl (Lauraceae)), 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 ingredient that can make insect antifeedant in Chinese cassia tree.
The content of the invention：
The task of the present invention is provide biologically active compound and its method for separating and preparing and application in Chinese cassia tree.
Realize the technical scheme is that：
The method of isolated auspicious promise alkane diterpene-kind compound comprises the following steps from Chinese cassia tree：
Dry cassia is crushed, is extracted with ethanol room temperature, merges ethanol extract and is recovered under reduced pressure and be condensed into medicinal extract, is obtained 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, recycling 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 is purified 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 structural formula of the isolated auspicious promise alkane diterpene-kind compound 1-11 of the present invention and Title is shown in Table 1, and separation process is shown in attached 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 attached drawing 2, and the monocrystalline of compound 2 spreads out Penetrate structure chart and see attached drawing 3.
The present invention has carried out system research under the guidance of immunosuppressive activity screening to Chinese cassia tree active ingredient.Pass through this The research for the T cell inhibited proliferation that 11 compounds induce 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 beet exigua larvae an antifeedant activity, 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 present invention provides the plant origin of compound 1-11, isolation and purification method, immunosuppressive activity, insect antifeedant and Growth inhibitory activity and application.The present invention immunosuppressive activity screening guidance under, to Chinese cassia tree immunosuppressive activity component into 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：
1,2,3,4 method for separating and preparing of the compounds of this invention 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. 1：1 flow chart of embodiment；
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 drying cassias crush, and are extracted 3 times with ethanol room temperature, 7 days every time, merge 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, recycling 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 that HRESIMS is provided [M+H]+M/z 383.2066, determines that its molecular formula is C with reference to hydrogen spectrum and carbon modal data20H30O7(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.
1 compound 1-4's of Table1H 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 lures 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 3 compounds of Table induce ConA
Experiment conclusion：Compound 2 has the ConA mouse T cells induced the inhibitory action of highly significant, its inhibitory action 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 is seen Influence of the compound (50 μ g/ml) to cotton bollworm larvae 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.
4. compounds of Table are to concentration and growth inhibition ratio in the food refusal of larva
Experiment conclusion：Except 5 most diterpene of compound has beet armyworm or bollworm different degrees of food refusal to live 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 has cotton bollworm larvae growth inhibition effect, and compound 2 even makes the cotton boll in the growth stage Worm weight loss.

Claims (1)

1. one or more methods from Chinese cassia tree in isolated following auspicious promise alkane diterpene-kind compound 4-10, including it is following Step：
Step 1：Dry cassia is crushed, is extracted with ethanol room temperature, merges ethanol extract and is recovered under reduced pressure and be condensed into leaching Cream, obtains total cream, and 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 recycling 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 and methyl alcohol mixed liquor gradient elution, Gradient is chloroform/methanol 10:1-3:1, chloroform/methanol 8:Fr.2, chloroform/methanol 6 are obtained when 1:Fr.3, chloroform/first are obtained when 1 Alcohol 4:Fr.5 is obtained when 1；
Step 3：Fr.2 is passed through into water/methanol 9:1 reversed-phase silica gel column chromatography obtains a position, this position is again through gel, preparation liquid phase Purifying obtains compound 4,5；Or
Fr.3 is passed through into water/methanol 9:1-7:It is respectively Fr.3.1, Fr.3.2 that 3 reversed-phase silica gel column chromatographies, which obtain two positions,；Fr.3.1 Purify to obtain compound 6,7 through silica gel, gel, preparation liquid phase；Or Fr.3.2 through gel, prepare liquid phase purify to obtain compound 8, 9；Or
Fr.5 is passed through into water/methanol 8:2 reversed-phase silica gel column chromatographies obtain a position, this position is again through silica gel, gel, preparation liquid-phase pure Change obtains compound 10.
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