CN110256276A - There is in solanum rostratum to bollworm the benzene acryloyl aminated compounds and its purification methods and uses of Antifeedant Effects - Google Patents
There is in solanum rostratum to bollworm the benzene acryloyl aminated compounds and its purification methods and uses of Antifeedant Effects 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
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- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/16—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms
- C07C233/17—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/22—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by singly-bound oxygen atoms with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to an acyclic carbon atom of a carbon skeleton containing six-membered aromatic rings
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Abstract
The invention belongs to agricultural technology fields, and in particular to benzene acryloyl aminated compounds.Extraction separation method is as follows: being concentrated under reduced pressure to extract medicinal extract after taking dry solanum rostratum cold soaking to mention；It after distilled water is suspended, is extracted respectively with petroleum ether and ethyl acetate, extraction medicinal extract is concentrated under reduced pressure to obtain；It using silica gel column chromatography, is eluted, collects fraction through silica gel thin-layer chromatography and obtain tetra- parts Fr.A~Fr.D；Fr.B uses silica gel column chromatography, is eluted, and collects fraction through silica gel thin-layer chromatography and obtains six parts Fr.B-1~Fr.B-6；Fr.B-2 uses MCI column chromatography, is eluted, obtains fraction, by silica gel thin-layer chromatography, obtains five parts Fr.B-2-1~Fr.B-2-5；Using high performance liquid chromatography, the isolated target product in Fr.B-2-2~Fr.B-2-4.Extraction separation method of the present invention is simple, favorable reproducibility, and DNA purity is high.The compound of acquisition has preferable antifeedant activity effect to bollworm.
Description
Technical field
The invention belongs to agricultural technology field, it is related to benzene acryloyl aminated compounds in solanum rostratum and its extracts separation side
Method, the invention further relates to application of such compound in terms of inhibiting bollworm feeding activity.
Background technique
In recent years, the serious ecological and economic problems caused by exotic plant invasion has received much attention.Adventitious plant is new
The successful invasion in habitat should also have some distinctive invasion mechanisms other than having some basic biological properties.For a long time
Since, people have conducted extensive research the invasion mechanism of adventitious plant in terms of Ecology, however often ignore
Or without paying attention to instruction plant to the chemical defence problem of plant-feed insect.In fact, instruction plant under newborn environment
In plant-feed insect evolutionary process, there is the chemical actions for by secondary metabolite being medium, in face of plant-feed insect
Feeding, instruction plant, which can induce synthesis and discharge specific secondary metabolite, resists infringement, this chemical defence relationship by
It illustrates.
Solanum rostratum (Solanum rostrat-um Duna.) also known as Yellow calla, Kansas Ji are Solanaceae Solanum
A kind of extremely strong annual malignant weed of invasive.The plant origin in North America, at present Spreading and diffusion to Europe, Asia,
16 countries and regions such as Africa and Oceania.At home, solanum rostratum in 1981 is found in Liaoning for the first time, has been spread to
The ground such as Jilin, Hebei, Shanxi, Beijing, Xinjiang and the Inner Mongol, and the trend for spreading diffusion is also constantly expanding, and the Ministry of Agriculture is
It is classified as the pernicious quarantine weeds of exotic invasive.Species breeding is rapid, adaptable, diffusion velocity is fast, with eciophyte
Sunlight, nutrition, moisture and living space are fought for, the harm of exclusion property is caused to crops, it has also become that urgently prevents and kill off is external pernicious
Weeds.Solanum rostratum is as most higher plants, secondary metabolite rich in, so far domestic and foreign scholars
The secondary metabolite for separating and identifying from solanum rostratum is mainly alkaloids, and in addition there are flavones, steroid etc. are secondary
Metabolite.Studies have shown that alkaloid compound is mostly defensive substance in plant, there is protection plant, resist phytophagous
The effect of the natural enemies such as insect invasion is the natural protection substance of plant, and solanum rostratum is rich in alkaloid compound, therefore this kind of
Secondary metabolite may be it to the potential defensive substance of plant-feed insect.Therefore it finds from solanum rostratum to agricultural pests
The good compound of antifeedant activity will be helpful to that angle is chemically defendd to disclose its invasion mechanism, and it is expected to obtain anti-with plant source
Guide's active material of worm pesticides application prospect, while also scientific basis is provided for the development and utilization of solanum rostratum.
Summary of the invention
The purpose of the present invention is intended to find guide's active material with antifeedant activity from the aerial part of solanum rostratum,
Extraction, the extraction separation method of benzene acryloyl aminated compounds are provided, and study their antifeedant activities to bollworm.This hair
Bright another is designed to provide the Structural Identification method of such compound.
To achieve the goals above, the technical solution adopted by the present invention is as follows, has food refusal to bollworm in solanum rostratum
The benzene acryloyl aminated compounds of effect, structure is as follows,
Wherein, R1For one of methoxyl group, hydroxyl, hydrogen；R2For hydroxyl or hydrogen；
Wherein, R3For one of methoxyl group, hydroxyl, hydrogen.
There is in above-mentioned solanum rostratum to bollworm the extraction separation side of the benzene acryloyl aminated compounds of Antifeedant Effects
Method includes the following steps:
1) aerial part of dry solanum rostratum is taken to extract 2-5 times with 60~80% ethyl alcohol cold soaking, every time 5~10
It, combined extract is concentrated under reduced pressure to extract medicinal extract；
2) it after medicinal extract and distilled water suspension will be extracted, is extracted respectively with petroleum ether and ethyl acetate, extract liquor is concentrated under reduced pressure
Medicinal extract must be extracted；
3) extraction medicinal extract uses silica gel column chromatography, is gradually eluted with methylene chloride, methanol system, collects 20-30 altogether and evaporates
Point, through silica gel thin-layer chromatography, merge into tetra- parts Fr.A~Fr.D；
4) Fr.B uses silica gel column chromatography, and with methylene chloride: methanol system gradually elutes, and collects 20-30 fraction, warp altogether
Silica gel thin-layer chromatography merges into six parts Fr.B-1~Fr.B-6；
5) Fr.B-2 uses MCI column chromatography, and with methanol: water system gradually elutes, and there are 15~25 fractions, passes through silica gel
Thin layer plate layer chromatography merges into five parts Fr.B-2-1~Fr.B-2-5；
6) high performance liquid chromatography, it is isolated in Fr.B-2-2~Fr.B-2-4 as mobile phase using methanol, water system
Target product.
Preferably, above-mentioned extraction separation method, in step 1), by solid-to-liquid ratio, the aerial part of solanum rostratum: 60~
80% ethyl alcohol=1kg:5-7L.
Preferably, above-mentioned extraction separation method in step 2), by solid-to-liquid ratio, extracts medicinal extract: water: petroleum ether: acetic acid second
Ester=1:2-3:2- 5:2-5.
Preferably, above-mentioned extraction separation method, in step 3), by volume, methylene chloride: methanol is 100:1~1:
1。
Preferably, above-mentioned extraction separation method, in step 4), by volume, methylene chloride: methanol is 50:1~5:1.
Preferably, above-mentioned extraction separation method, in step 5), by volume, methanol: water is 20:80~70:30.
Preferably, above-mentioned extraction separation method, in step 6), by volume, mobile phase, methanol: water be 10:90~
30:70。
There is the benzene acryloyl aminated compounds of Antifeedant Effects to inhibit bollworm bollworm in above-mentioned solanum rostratum
Application in feeding effect.
The invention has the following advantages: finding the propenyl benzene good to bollworm antifeedant activity for the first time from solanum rostratum
Amides compound facilitates the invasion mechanism for defending angle to disclose the noxious plant from food refusal, these compounds promise to be
Guide's active material with the pest-resistant pesticides application prospect of plant source, at the same also for the development and utilization of solanum rostratum provide science according to
According to realizing turning waste into wealth truly.
Detailed description of the invention
Fig. 1 is the ultraviolet spectrogram of compound 1.
Fig. 2 is the infrared spectrogram of compound 1.
Fig. 3 is the high-resolution electrospray ionization mass spectrometry figure of compound 1.
Fig. 4 is compound 11H-NMR spectrum.
Fig. 5 is compound 113C-NMR spectrogram.
Fig. 6 is the heteronuclear list quantum relation spectrogram of compound 1.
Fig. 7 is the heteronuclear Multiple-quantum relation spectrum of compound 1.
Fig. 8 is compound 11H-1H COSY spectrogram.
Fig. 9 is the key that compound 11H-1H COSY and HMBC signal graph.
Figure 10 is calculating and the actual measurement ECD spectrogram of compound 1.
Figure 11 is the ultraviolet spectrogram of compound 2.
Figure 12 is the infrared spectrogram of compound 2.
Figure 13 is the high-resolution electrospray ionization mass spectrometry figure of compound 2.
Figure 14 is compound 21H-NMR spectrum.
Figure 15 is compound 213C-NMR spectrogram.
Figure 16 is the ultraviolet spectrogram of compound 3.
Figure 17 is the infrared spectrogram of compound 3.
Figure 18 is the high-resolution electrospray ionization mass spectrometry figure of compound 3.
Figure 19 is compound 31H-NMR spectrum.
Figure 20 is compound 313C-NMR spectrogram.
Figure 21 is the ultraviolet spectrogram of compound 4.
Figure 22 is the infrared spectrogram of compound 4.
Figure 23 is the high-resolution electrospray ionization mass spectrometry figure of compound 4.
Figure 24 is compound 41H-NMR spectrum.
Figure 25 is compound 413C-NMR spectrogram.
Figure 26 is the ultraviolet spectrogram of compound 5.
Figure 27 is the infrared spectrogram of compound 5.
Figure 28 is the high-resolution electrospray ionization mass spectrometry figure of compound 5.
Figure 29 is compound 51H-NMR spectrum.
Figure 30 is compound 513C-NMR spectrogram.
Figure 31 is the ultraviolet spectrogram of compound 6.
Figure 32 is the infrared spectrogram of compound 6.
Figure 33 is the high-resolution electrospray ionization mass spectrometry figure of compound 6.
Figure 34 is compound 61H-NMR spectrum.
Figure 35 is compound 613C-NMR spectrogram.
Figure 36 is the ultraviolet spectrogram of compound 7.
Figure 37 is the infrared spectrogram of compound 7.
Figure 38 is the high-resolution electrospray ionization mass spectrometry figure of compound 7.
Figure 39 is compound 71H-NMR spectrum.
Figure 40 is compound 713C-NMR spectrogram.
Figure 41 is the ultraviolet spectrogram of compound 8.
Figure 42 is the infrared spectrogram of compound 8.
Figure 43 is the high-resolution electrospray ionization mass spectrometry figure of compound 8.
Figure 44 is compound 81H-NMR spectrum.
Figure 45 is compound 813C-NMR spectrogram.
Figure 46 is histogram of the compound 1-8 to the antifeedant activity of bollworm.
AI (antifeedant index) is food refusal index in figure, and Azadirachtin A is positive control nimbin A, a
Significant difference between b c representation compound various concentration.
Specific embodiment
There is in 1 solanum rostratum of embodiment to bollworm the extraction of the benzene acryloyl amine of Antifeedant Effects to separate
1) take the aerial part 15kg of dry solanum rostratum with the extraction of ethyl alcohol cold soaking 3 times of 100L 70%, every time 6 days,
Combined extract is concentrated under reduced pressure to extract medicinal extract 1.2kg.
2) it after medicinal extract 1.2kg and the suspension of 3L distilled water will be extracted, is extracted respectively with 3.2L petroleum ether and 3.2L ethyl acetate,
Extraction medicinal extract 220g is concentrated under reduced pressure to obtain in extract liquor.
3) extraction medicinal extract uses silica gel column chromatography, is repeatedly eluted with methylene chloride, methanol system, volume ratio is successively
For 100:1,50:1,30:1,20:1,10:1,5:1,2:1,1:1, every 500mL are a fraction, collect 25 fractions, warp altogether
Silica gel thin-layer chromatography inspection is known, and tetra- parts Fr.A~Fr.D are merged into.
4) Fr.B (43g) uses silica gel column chromatography, is repeatedly eluted with methylene chloride, methanol system, volume ratio, according to
Secondary to be, 50:1,30:1,20:1,10:1,5:1 collect 20 fractions altogether, examine and know through silica gel thin-layer chromatography, merge into Fr.B-1
Six parts~Fr.B-6.
5) Fr.B-2 (6.3g) uses MCI column chromatography, is repeatedly eluted with methanol, water system, volume ratio, successively
For 20:80,30:70,50:50,70:30 elution there are 19 fractions, examined and known by silica gel thin-layer plate layer chromatography, merged into
Five parts Fr.B-2-1~Fr.B-2-5.
6) high performance liquid chromatography is utilized, using methanol, water as mobile phase, volume ratio 15:85 divides in Fr.B-2-2
From compound 1 and 3 is obtained, using high performance liquid chromatography, using methanol, water as mobile phase, volume ratio 20:80,
Isolated compound 4 in Fr.B-2-3,5,7,8, utilize high performance liquid chromatography, using methanol, water as mobile phase, volume
Than for 23:77, the isolated compound 2 and 6 in Fr.B-2-4.
There is in 2 solanum rostratum of embodiment to bollworm the extraction of the benzene acryloyl amine of Antifeedant Effects to separate
1) take the aerial part 22kg of dry solanum rostratum with the extraction of ethyl alcohol cold soaking 4 times of 120L 70%, every time 7 days,
Combined extract is concentrated under reduced pressure to extract medicinal extract 1.4kg.
2) it after medicinal extract 1.4kg and the suspension of 4L distilled water will be extracted, is extracted respectively with 5.0L petroleum ether and 5.0L ethyl acetate,
Extraction medicinal extract 260g is concentrated under reduced pressure to obtain in extract liquor.
3) extraction medicinal extract uses silica gel column chromatography, is repeatedly eluted with methylene chloride, methanol system, volume ratio is successively
For 100:1,50:1,30:1,20:1,10:1,5:1,1:1, every 500mL are a fraction, 27 fractions are collected altogether, through silica gel
Thin-layer chromatography inspection is known, and tetra- parts Fr.A~Fr.D are merged into.
4) Fr.B (54g) use silica gel column chromatography, repeatedly eluted with methylene chloride, methanol system, volume ratio according to
It is secondary to be, 50:1,20:1,10:1,5:1, altogether collect 20 fractions, through silica gel thin-layer chromatography examine know, merge into Fr.B-1~
Six parts Fr.B-6.
5) Fr.B-2 (7.2g) uses MCI column chromatography, is repeatedly eluted with methanol, water system, and volume ratio is followed successively by,
20:80,30:70,40:60,50:50,70:30 elution, there are 22 fractions, are examined and are known by silica gel thin-layer plate layer chromatography, merged into
Five parts Fr.B-2-1~Fr.B-2-5.
6) high performance liquid chromatography is utilized, using methanol, water as mobile phase, volume ratio 12:88 divides in Fr.B-2-2
From compound 1 is obtained, high performance liquid chromatography, using methanol, water as mobile phase, volume ratio 25:75, in Fr.B-2- are utilized
Isolated compound 4 in 3,5,7,8, utilize high performance liquid chromatography, using methanol, water as mobile phase, volume ratio 30:
70, the isolated compound 2,3,6 in Fr.B-2-4.
There is in 3 solanum rostratum of embodiment to bollworm the extraction of the benzene acryloyl amine of Antifeedant Effects to separate
1) take the aerial part 24kg of dry solanum rostratum with the extraction of ethyl alcohol cold soaking 3 times of 120L 75%, every time 5 days,
Combined extract is concentrated under reduced pressure to extract medicinal extract 1.6kg.
2) it after medicinal extract 1.6kg and the suspension of 5L distilled water will be extracted, is extracted respectively with 7.5L petroleum ether and 7.5L ethyl acetate,
Extraction medicinal extract 270g is concentrated under reduced pressure to obtain in extract liquor.
3) extraction medicinal extract uses silica gel column chromatography, is repeatedly eluted with methylene chloride, methanol system, volume ratio is successively
For 100:1,50:1,20:1,10:1,8:1,5:1,2:1,1:1, every 500mL are a fraction, collect 25 fractions, warp altogether
Silica gel thin-layer chromatography inspection is known, and tetra- parts Fr.A~Fr.D are merged into.
4) Fr.B (58g) uses silica gel column chromatography, is eluted with methylene chloride, methanol system, and volume ratio is followed successively by,
50:1,40:1,20:1,8:1,5:1 collect 25 fractions altogether, examine and know through silica gel thin-layer chromatography, merge into Fr.B-1~Fr.B-
6 six parts.
5) Fr.B-2 (8.8g) uses MCI column chromatography, is eluted with methanol, water system, and volume ratio is followed successively by, and 20:
80,30:70,40:60,50:50,60:40 are eluted, and there are 26 fractions, are examined and are known by silica gel thin-layer plate layer chromatography, merged into
Five parts Fr.B-2-1~Fr.B-2-5.
6) high performance liquid chromatography is utilized, using methanol, water as mobile phase, volume ratio 10:90 divides in Fr.B-2-2
From obtaining compound Isosorbide-5-Nitrae, 5, using high performance liquid chromatography, using methanol, water as mobile phase, volume ratio 25:75,
Isolated compound 2 in Fr.B-2-3,3,7,8, utilize high performance liquid chromatography, using methanol, water as mobile phase, volume
Than for 28:72, the isolated compound 6 in Fr.B-2-4.
The 8 of the present invention benzene acryloyl aminated compounds with antifeedant activity, wherein compound 1 is new chemical combination
Object, other are the compound separated from the plant for the first time.Title is respectively as follows: phenylethylamine A, 3- (4-
hydroxyphenyl)-N-[2-(4-hydroxyphenyl)- 2-methoxyethyl]-acrylamide(2),N-trans-
p-coumaroyl octopamine(3),N-trans-p-coumaroyl-3',4'-
dihydroxyphenylethylamine(4),trans-N-coumaroyltyramine(5),N-cis-p-
coumaroyloctopamine(6),cis-N- phydroxycinnamoyl-7'-methoxyltyramine(7),cis-N-
coumaroyltyramine(8)。
Embodiment 4
The compound 1 that embodiment 1 extracts separation is faint yellow unformed powder,
10% ethanol solution of sulfuric acid displaing yellow.
The detection of 1 ultraviolet spectra of compound, infrared spectroscopy detection, HR-ESIMS Mass Spectrometer Method, proton magnetic resonance (PMR) are detected,
Nuclear magnetic resonance of carbon detection, HSQC detect, HMBC is detected,1H-1H COSY detection.Figure it is seen that the IR spectrum of compound 1 is aobvious
It is shown with hydroxyl (3309cm-1), amide (1650cm-1) and phenyl ring (1515,1224 and 829cm-1).From figure 3, it can be seen that such as
Shown in Fig. 3, HR- ESIMS spectrogram provides quasi-molecular ion peak m/z 352.1183 [M+Na]+(calcd for
C27H31NO12Na, 352.1161), determine that the molecular weight of the compound is 329, molecular formula C27H31NO12, calculate its unsaturation
Degree is 10.
Compound 11H-NMR(600MHz,Methanol-d4) compose as shown in table 1, δ 7.40 (2H, d, J=8.2Hz, H-
2, H-6) and 6.78 (2H, d, J=8.2Hz, H-3, H-5) prompt for the proton signal on one group of contraposition substituted benzene ring.δ6.78
(1H, br s, H-2'), δ 6.76 (1H, d, J=7.9 Hz, H-5') and δ 6.66 (1H, dd, J=7.9,1.3Hz, H-6') prompt
For the proton signal on one group of 1,3,4 substituted benzene ring.δ 7.45 (1H, d, J=15.6Hz, H-7) and 6.44 (1H, d, J=
15.6Hz, H-8) prompt for proton signal in one group of trans double bond.δ 3.21 (3H, s, H-9') is prompted on one group of methoxyl group
Proton signal.
Compound 113C-NMR(150MHz,Methanol-d4) compose as shown in table 1, δ 169.2 (C-9), 141.9 (C-7)
There are one group of alpha, beta unsaturated ketone carbon signals with 118.3 (C-8) prompt.δ160.5(C-4),130.5(C-2,C-6),127.7(C-
1), there are the carbon signals on one group of contraposition substituted benzene ring for 116.7 (C-3, C-5) prompt.δ146.5(C-4'),146.3(C-3'),
133.2 (C-1'), 119.6 (C-6'), there are on one group of neighbour's dioxy substituted benzene ring for 114.7 (C-2'), 116.2 (C-5') prompt
Carbon signal.δ 56.7 (C-9') prompts for the carbon signal on one group of methoxyl group.As shown in figure 44, in HMBC spectrum, H-7 and C2,
C6, C9 are related, and H-8 ' is related to C-9, H-7 ' and C-2 ', C-6 ', C-8 ', and C-9 ' is related.Simultaneously in Figure 441H-1H COSY
Spectrum, H-2 is related to H-3, and H-5 is related to H-6, and H-7 is related to H-8, and H-5 ' is related to H-6 ', and H-7 ' is related to H-8 ', above
Information has determined the planar structure of compound 1.
1 compound 1 of table1H(600MHz)and 13C (150MHz) NMR data
The absolute configuration of compound 1 is the method by comparing optical value with similar compound and calculating ECD to determine,
The optical value of 7 ' S benzene acryloyl aminated compounds of similar structures is negative value, and the optical value of 7 ' R benzene acryloyl aminated compounds is equal
For positive value, and it is also negative value that compound 1, which surveys optical value, therefore speculates that the absolute configuration of 17 ' position of compound is S.Compound simultaneously
The absolute configuration of 17 ' position is determined by calculating the method for ECD, using TD-DFT theory, calculates 2 enantiomerisms
Body (A:7 ' S；B:7 ' R) ECD spectrogram.The results show that actual measurement ECD curve and the ECD spectrogram trend of 7 ' S are almost the same, explanation
1 and 7 ' S of compound absolute configuration having the same, i.e. 7 ' S, as shown in figure 45.
In conclusion the compound structure has finally been determined, retrieved through Scifinder scholar, has no document for one
The noval chemical compound of report is named as phenylethylamine A.The structural formula of compound 1 is as follows:
Embodiment 5
The compound 2 that embodiment 1 extracts separation is faint yellow unformed powder,
10% ethanol solution of sulfuric acid displaing yellow.
The detection of 2 ultraviolet spectra of compound, infrared spectroscopy detection, HR-ESIMS Mass Spectrometer Method, proton magnetic resonance (PMR) are detected,
Nuclear magnetic resonance of carbon detection.From fig. 10 it can be seen that the IR spectrum of compound 2 shows hydroxyl (3289cm-1), amide (1650cm-1)
With phenyl ring (1515,1224 and 829cm-1).As shown in figure 11, HR-ESIMS provides quasi-molecular ion peak m/z 336.1261
[M+Na]+(calcd for C18H19NO4Na, 336.1212), determine that the molecular weight of the compound is 313, molecular formula is
C18H19NO4, calculating its degree of unsaturation is 10.
Compound 21H-NMR(600MHz,Methanol-d4) compose as shown in table 2, δ 7.40 (2H, d, J=8.5Hz, H-
2, H-6), 6.78 (2H, d, J=8.5Hz, H-3, H-5) and δ 7.16 (2H, d, J=8.2Hz, H-2', H-6'), 6.78 (2H,
D, J=8.2Hz, H-3', H-5') prompt for proton signal on two groups of contraposition substituted benzene rings.δ 7.45 (1H, d, J=15.8Hz,
H-7) and 6.43 (1H, d, J=15.8Hz, H-8) prompt for the proton signal in one group of trans double bond.δ3.21(3H,s,H-9')
Prompt for the proton signal on one group of methoxyl group.Compound 213C-NMR (150MHz,Methanol-d4) compose as shown in table 2,
There are one group of alpha, beta unsaturated ketone carbon signals for δ 169.2 (C-9), 141.9 (C-7) and 118.3 (C-8) prompt.δ160.5(C-4),
129.2 (C-2, C-6), 127.7 (C-1), 116.7 (C-3, C-5) and δ 158.5 (C-4'), 130.6 (C-2', C-6'),
There are the carbon signals on two groups of contraposition substituted benzene rings for 131.4 (C-1'), 116.3 (C-3', C-5') prompt.δ 56.7 (C-9') is mentioned
The carbon signal being shown as on one group of methoxyl group.
2 compound 2 of table1H(600MHz)and 13C (150MHz) NMR data
By the NMR data of compound 2 and 3- reported in the literature (4-hydroxyphenyl)-N- [2- (4-
Hydroxyphenyl) -2-methoxyethyl]-acrylamide compares, and data are consistent, therefore authenticating compound 2 is 3-
(4-hydroxyphenyl)-N-[2-(4-hydroxyphenyl)-2- methoxyethyl]-acrylamide.Structure is such as
Under:
Embodiment 6
The compound 3 that embodiment 1 extracts separation is faint yellow unformed powder,
10% ethanol solution of sulfuric acid displaing yellow.
The detection of 3 ultraviolet spectra of compound, infrared spectroscopy detection, HR-ESIMS Mass Spectrometer Method, proton magnetic resonance (PMR) are detected,
Nuclear magnetic resonance of carbon detection.It can be seen from fig. 15 that the IR spectrum of compound 3 shows hydroxyl (3309cm-1), amide (1650cm-1)
With phenyl ring (1515,1224 and 829cm-1).As shown in figure 16, HR-ESIMS provides quasi-molecular ion peak m/z 322.1058
[M+Na]+(calcd for C17H17NO4Na, 322.1055), determine that the molecular weight of the compound is 299, molecular formula is
C17H17NO4, calculating its degree of unsaturation is 10.
Compound 31H-NMR(600MHz,Methanol-d4) compose as shown in table 3, δ 7.39 (2H, d, J=8.3Hz, H-
2, H-6), 6.78 (2H, d, J=8.3Hz, H-3, H-5) and δ 7.21 (2H, d, J=8.5Hz, H-2', H-6'), 6.78 (2H,
D, J=8.5Hz, H-3', H-5') prompt for proton signal on two groups of contraposition substituted benzene rings.δ 7.45 (1H, d, J=15.7Hz,
H-7) and 6.43 (1H, d, J=15.7Hz, H-8) prompt for the proton signal in one group of trans double bond.Compound 313C-NMR
(150MHz,Methanol-d4) compose as shown in table 3, there are one for δ 169.5 (C-9), 142.0 (C-7) and 118.2 (C-8) prompt
Group alpha, beta unsaturated ketone carbon signal.δ 158.1 (C-4), 130.6 (C-2, C-6), 127.6 (C-1), 116.7 (C-3, C-5) and δ
160.6 (C-4'), 128.4 (C-2', C-6'), there are two groups of contrapositions to replace for 134.7 (C-1'), 116.1 (C-3', C-5') prompt
Carbon signal on phenyl ring.
3 compound 3 of table1H(600MHz)and 13C (150MHz) NMR data
The NMR data of compound 3 and N-trans-p-coumaroyl octopamine reported in the literature are carried out pair
Than data are consistent, therefore authenticating compound 3 is N-trans-p-coumaroyl octopamine.Structure is as follows:
Embodiment 7
The compound 4 that embodiment 1 extracts separation is faint yellow unformed powder,
10% ethanol solution of sulfuric acid displaing yellow.
The detection of 4 ultraviolet spectra of compound, infrared spectroscopy detection, HR-ESIMS Mass Spectrometer Method, proton magnetic resonance (PMR) are detected,
Nuclear magnetic resonance of carbon detection.From fig. 10 it can be seen that the IR spectrum of compound shows hydroxyl (3293cm-1), amide (1650cm-1)
With phenyl ring (1514,1224and 830cm-1).As shown in figure 21, HR-ESIMS provides 322.1023 [M of quasi-molecular ion peak m/z
+Na]+(calcd for C17H17NO4Na, 322.1055), determine that the molecular weight of the compound is 299, molecular formula is
C17H17NO4, calculating its degree of unsaturation is 10.
Compound 41H-NMR(600MHz,Methanol-d4) compose as shown in table 4, δ 7.38 (2H, d, J=8.3Hz, H-
2, H-6) and 6.77 (2H, d, J=8.3Hz, H-3, H-5) prompt for the proton signal on one group of contraposition substituted benzene ring.δ6.67
(1H, br s, H-2'), δ 6.70 (1H, d, J=8.0Hz, H-5') and δ 6.54 (1H, dd, J=8.0,1.5Hz, H-6') prompt
For the proton signal on one group of 1,3,4 substituted benzene ring.δ 7.44 (1H, d, J=15.7Hz, H-7) and 6.38 (1H, d, J=
15.7Hz, H-8) prompt for proton signal in one group of trans double bond.Compound 413C- NMR(150MHz,Methanol-
d4) compose as shown in table 4, there are one group of α, beta unsaturated ketone carbon letters for δ 169.2 (C-9), 141.7 (C-7) and 118.4 (C-8) prompt
Number.δ 160.4 (C-4), 130.5 (C-2, C-6), there are one group of contraposition substituted benzenes for 127.6 (C-1), 116.6 (C-3, C-5) prompt
Carbon signal on ring.δ146.2(C-3'),144.7(C-4'),132.0(C-1'),121.0(C-6'),116.8(C-2'),
There are the carbon signals on one group of neighbour's dioxy substituted benzene ring for 116.3 (C-5') prompt.
4 compound 4 of table1H(600MHz)and 13C (150MHz) NMR data
By the NMR data of compound 4 and N-trans-p-coumaroyl-3' reported in the literature, 4'-
Dihydroxyphenylethylamine is compared, and data are consistent, therefore authenticating compound 4 is N-trans-p-
coumaroyl-3',4'-dihydroxyphenylethylamine.Structure is as follows:
Embodiment 8
The compound 5 that embodiment 1 extracts separation is faint yellow unformed powder,
10% ethanol solution of sulfuric acid displaing yellow.
The detection of 5 ultraviolet spectra of compound, infrared spectroscopy detection, HR-ESIMS Mass Spectrometer Method, proton magnetic resonance (PMR) are detected,
Nuclear magnetic resonance of carbon detection.As can be seen from Figure 25, the IR spectrum of compound 5 shows hydroxyl (3306cm-1), amide (1650cm-1)
With phenyl ring (1514,1224 and 829cm-1).As shown in figure 26, HR-ESIMS provides quasi-molecular ion peak m/z 306.1104
[M+Na]+(calcd for C17H17NO3Na, 306.1106), determine that the molecular weight of the compound is 283, molecular formula is
C17H17NO3, calculating its degree of unsaturation is 10.
Compound 51H-NMR(600MHz,Methanol-d4) compose as shown in table 5, δ 7.39 (2H, d, J=8.5Hz, H-
2, H-6), 6.78 (2H, d, J=8.5Hz, H-3, H-5) and δ 7.05 (2H, d, J=8.2Hz, H-2', H-6'), 6.71 (2H,
D, J=8.2Hz, H-3', H-5') prompt for proton signal on two groups of contraposition substituted benzene rings.δ 7.43 (1H, d, J=15.7Hz,
H-7) and 6.37 (1H, d, J=15.7Hz, H-8) prompt for the proton signal in one group of trans double bond.Compound 513C-NMR
(150MHz,Methanol-d4) compose as shown in table 5, there are one for δ 169.2 (C-9), 141.7 (C-7) and 118.3 (C-8) prompt
Group alpha, beta unsaturated ketone carbon signal.δ 160.5 (C-4), 130.5 (C-2, C-6), 127.6 (C-1), 116.2 (C-3, C-5) and δ
156.9 (C-4'), 130.7 (C-2', C-6'), there are two groups of contrapositions to replace for 131.3 (C-1'), 116.7 (C-3', C-5') prompt
Carbon signal on phenyl ring.
5 compound 5 of table1H(600MHz)and 13C (150MHz) NMR data
The NMR data of compound 5 and trans-N-coumaroyltyramine reported in the literature are compared, number
According to consistent, therefore authenticating compound 5 is trans-N-coumaroyltyramine.
Structure is as follows:
Embodiment 9
The compound 6 that embodiment 1 extracts separation is faint yellow unformed powder,
10% ethanol solution of sulfuric acid displaing yellow.
The detection of 6 ultraviolet spectra of compound, infrared spectroscopy detection, HR-ESIMS Mass Spectrometer Method, proton magnetic resonance (PMR) are detected,
Nuclear magnetic resonance of carbon detection.As can be seen from Figure 30, the IR spectrum of compound 6 shows hydroxyl (3335cm-1), amide (1650cm-1)
With phenyl ring (1514,1223 and 829cm-1).As can be seen from Figure 31, HR-ESIMS provides quasi-molecular ion peak m/z
322.1026[M+Na]+(calcd for C17H17NO4Na, 322.1055), determine that the molecular weight of the compound is 299, molecule
Formula is C17H17NO4, calculating its degree of unsaturation is 10.
Compound 61H-NMR(600MHz,Methanol-d4) compose as shown in table 6, δ 7.18 (2H, d, J=8.4Hz, H-
2, H-6), 6.71 (2H, d, J=8.4Hz, H-3, H-5) and δ 7.38 (2H, d, J=8.5Hz, H-2', H-6'), 6.75 (2H,
D, J=8.5Hz, H-3', H-5') prompt for proton signal on two groups of contraposition substituted benzene rings.δ 5.80 (1H, d, J=12.6Hz,
H-7) and 6.61 (1H, d, J=12.6Hz, H-8) prompt for the proton signal on one group of cis-double bonds.Compound 613C-NMR
(150MHz,Methanol-d4) compose as shown in table 6, there are one for δ 170.4 (C-9), 138.6 (C-7) and 121.0 (C-8) prompt
Group alpha, beta unsaturated ketone carbon signal.δ 159.5 (C-4), 132.4 (C-2, C-6), 127.8 (C-1), 116.1 (C-3, C-5) and δ
158.1 (C-4'), 128.5 (C-2', C-6'), there are two groups of contrapositions to replace for 134.5 (C-1'), 116.0 (C-3', C-5') prompt
Carbon signal on phenyl ring.
6 compound 6 of table1H(600MHz)and 13C (150MHz) NMR data
The NMR data of compound 6 and N-cis-p-coumaroyloctopamine reported in the literature are compared,
It is almost the same, therefore authenticating compound 6 is N-cis-p-coumaroyloctopamine.Structure is as follows:
Embodiment 10
The compound 7 that embodiment 1 extracts separation is faint yellow unformed powder,
10% ethanol solution of sulfuric acid displaing yellow.
The detection of 7 ultraviolet spectra of compound, infrared spectroscopy detection, HR-ESIMS Mass Spectrometer Method, proton magnetic resonance (PMR) are detected,
Nuclear magnetic resonance of carbon detection.As can be seen from Figure 35, the IR spectrum of compound 7 shows hydroxyl (3310cm-1), amide (1650cm-1)
With phenyl ring (1515,1224 and 829cm-1).As can be seen from Figure 36, HR-ESIMS provides quasi-molecular ion peak m/z
336.1214[M+Na]+(calcd for C18H19NO4Na, 336.1212), determine that the molecular weight of the compound is 313, molecule
Formula is C18H19NO4, calculating its degree of unsaturation is 10.
Compound 71H-NMR(600MHz,Methanol-d4) compose as shown in chart 7, δ 7.13 (2H, d, J=8.4Hz,
H-2, H-6), 6.72 (2H, d, J=8.4Hz, H-3, H-5) and δ 7.38 (2H, d, J=8.4Hz, H-2', H-6'), 6.76
(2H, d, J=8.4Hz, H-3', H-5') prompts for the proton signal on two groups of contraposition substituted benzene rings.δ 5.81 (1H, d, J=
12.6Hz, H-7) and 6.62 (1H, d, J=12.6Hz, H-8) prompt for the proton signal on one group of cis-double bonds.δ2.85(3H,
S) proton signal on one group of methoxyl group is prompted for.Compound 713C-NMR(150 MHz,Methanol-d4) compose such as 7 institute of table
Show, δ 170.2 (C-9), there are one group of α, beta unsaturated ketone carbon signals for 138.3 (C-7) and 121.3 (C-8) prompt.δ159.2(C-
4), 132.3 (C-2, C-6), 127.9 (C-1), 116.3 (C-3, C-5) and δ 158.5 (C-4'), 129.2 (C-2', C-6'),
There are the carbon signals on two groups of contraposition substituted benzene rings for 131.3 (C- 1'), 115.9 (C-3', C-5') prompt.
7 compound 7 of table1H(600MHz)and 13C (150MHz) NMR data
By the NMR data of compound 7 and cis-N-phydroxycinnamoyl-7'- reported in the literature
Methoxyltyramine is compared, almost the same, therefore authenticating compound 7 is cis-N-phydroxycinnamoyl-7'-
methoxyltyramine.Structure is as follows:
Embodiment 11
The compound 8 that embodiment 1 extracts separation is faint yellow unformed powder,
10% ethanol solution of sulfuric acid displaing yellow.
The detection of 8 ultraviolet spectra of compound, infrared spectroscopy detection, HR-ESIMS Mass Spectrometer Method, proton magnetic resonance (PMR) are detected,
Nuclear magnetic resonance of carbon detection.As can be seen from Figure 40, the IR spectrum of compound 8 shows hydroxyl (3323cm-1), amide (1650cm-1)
With phenyl ring (1515,1224 and 829cm-1).As can be seen from Figure 41, HR-ESIMS provides quasi-molecular ion peak m/z
306.1055[M+Na]+(calcd for C17H17NO3Na, 306.1106), determine that the molecular weight of the compound is 283, molecule
Formula is C17H17NO3, calculating its degree of unsaturation is 10.
Compound 81H-NMR(600MHz,Methanol-d4) compose as shown in table 8, δ 7.00 (2H, d, J=8.4Hz, H-
2, H-6), 6.69 (2H, d, J=8.4Hz, H-3, H-5) and δ 7.36 (2H, d, J=8.5Hz, H-2', H-6'), 6.71 (2H,
D, J=8.5Hz, H-3', H-5') prompt for proton signal on two groups of contraposition substituted benzene rings.δ 5.79 (1H, d, J=12.5Hz,
H-7) and 6.60 (1H, d, J=12.5Hz, H-8) prompt for the proton signal on one group of cis-double bonds.δ 2.85 (3H, s) prompt
For the proton signal on one group of methoxyl group.Compound 813C-NMR(150 MHz,Methanol-d4) compose as shown in table 8, δ
There are one group of alpha, beta unsaturated ketone carbon signals for 170.3 (C-9), 138.0 (C-7) and 121.4 (C-8) prompt.δ159.3(C-4),
132.2 (C-2, C-6), 127.9 (C-1), 116.3 (C-3, C-5) and δ 156.9 (C-4'), 132.2 (C-2', C-6'), 131.1
(C- 1'), there are the carbon signals on two groups of contraposition substituted benzene rings for 116.0 (C-3', C-5') prompt.
8 compound 8 of table1H(600MHz)and 13C (150MHz) NMR data
The NMR data of compound 8 and cis-N-coumaroyltyramine reported in the literature are compared, data
Unanimously, therefore authenticating compound 8 is cis-N-coumaroyltyramine.Structure is as follows:
Embodiment 12
1. experimental material
1.1 samples: compound 1-8.
1.2 insects: bollworm (is bought) by Henan Jiyuan Baiyun Industry Co., Ltd., Institute of Zoology, Academia Sinica.
2. experimental method
Antifeedant activity test is using selective leaf dish method.Bollworm is raised in illumination box (when day and night
Between than be 16:8,25 DEG C of temperature).In good health, identical two instar bollworm grub of size is selected to be tested, it will before testing
Bollworm Nature enemy 5-6h.It by pakchoi blade cuts is round leaflet dish, each leaf dish with the punch of 1.0 cm diameters
The back side add 20 μ L to include the acetone soln (100 μM, 50 μM, 25 μM) of various concentration sample, blank control adds 20 μ L acetone, to
After solvent volatilizees naturally, 2 processing group leaf dish and 2 blank control group leaf dish right-angled intersections are placed in and are covered with wet filter paper
In culture dish, 22 instar bollworm grubs by Nature enemy are placed in culture dish center.Nimbin A is positive control
Object is closed, experiment is at least repeated 3 times above every time.
3. measuring method
Feeding area to control group leaf dish reaches 80% or more, stops experiment, statistical disposition group and control group leaf dish
Feeding area, anti-food rate are calculate by the following formula: AI (%)=[(C-T)/(C+T)] × 100%, C and T are respectively represented
The feeding area of control group and processing group leaf dish.
4. statistical method
Whole data are tested analysis using SPSS (13.0) statistical package.Each group of data uses One-Way
ANOVA evaluates globality difference, and carries out Dunnett or Dunnett ' sT3 and examine progress comparison among groups.
5. experimental result
As a result as shown in figure 46, it can be seen that 8 kinds of compounds involved by the present invention are equal to bollworm as above-mentioned experimental result
With different degrees of Antifeedant Effects.Wherein the effect of compound 1 and 4 is the most obvious, and when concentration is 100 μM, anti-food rate is more than
50%.Compound 2,3,5 is obvious to the Antifeedant Effects of bollworm.
Benzene acryloyl aminated compounds involved by the present invention, different degrees of Antifeedant Effects are all had to bollworm, can be with
As guide's active material of the pest-resistant pesticides application prospect of plant source, while the development and utilization of the instruction plant can also be provided
Scientific basis.
Extraction separation method of the present invention is simple, favorable reproducibility, and DNA purity is high.The compound of acquisition is to the important evil of agricultural
Worm-bollworm has preferable antifeedant activity effect.
Claims (9)
1. having the benzene acryloyl aminated compounds of Antifeedant Effects in solanum rostratum to bollworm, which is characterized in that structural formula is such as
(I) or shown in (II),
Wherein, R1For one of methoxyl group, hydroxyl, hydrogen；R2For hydroxyl or hydrogen；
Wherein, R3For one of methoxyl group, hydroxyl, hydrogen.
2. having the extraction of the benzene acryloyl aminated compounds of Antifeedant Effects in solanum rostratum described in claim 1 to bollworm
Separation method, which comprises the steps of:
1) it takes the aerial part of dry solanum rostratum to be extracted 2-5 times with 60~80% ethyl alcohol cold soaking, 5~10 days every time, closes
And extracting solution is concentrated under reduced pressure to extract medicinal extract；
2) it after medicinal extract and distilled water suspension will be extracted, is extracted respectively with petroleum ether and ethyl acetate, extract liquor is concentrated under reduced pressure to obtain extraction
Take medicinal extract；
3) extraction medicinal extract uses silica gel column chromatography, is gradually eluted with methylene chloride, methanol system, collects 20~30 fractions altogether,
Through silica gel thin-layer chromatography, tetra- parts Fr.A~Fr.D are merged into；
4) Fr.B uses silica gel column chromatography, and with methylene chloride: methanol system gradually elutes, and 20~30 fractions is collected altogether, through silicon
Glue thin-layer chromatography merges into six parts Fr.B-1~Fr.B-6；
5) Fr.B-2 uses MCI column chromatography, and with methanol: water system gradually elutes, and there are 15~25 fractions, passes through silica gel thin-layer
Plate layer chromatography merges into five parts Fr.B-2-1~Fr.B-2-5；
6) high performance liquid chromatography, using methanol, water system as mobile phase the isolated target in Fr.B-2-2~Fr.B-2-4
Product.
3. extraction separation method according to claim 2, which is characterized in that in step 1), by solid-to-liquid ratio, solanum rostratum
Aerial part: 60~80% ethyl alcohol=1kg:5-7L.
4. extraction separation method according to claim 2, which is characterized in that in step 2), by solid-to-liquid ratio, extract medicinal extract:
Water: petroleum ether: ethyl acetate=1:2-3:2-5:2-5.
5. extraction separation method according to claim 2, which is characterized in that in step 3), by volume, methylene chloride:
Methanol is 100:1~1:1.
6. extraction separation method according to claim 2, which is characterized in that in step 4), by volume, methylene chloride:
Methanol is 50:1~5:1.
7. extraction separation method according to claim 2, which is characterized in that in step 5), by volume, methanol: water is
20:80~70:30.
8. extraction separation method according to claim 2, which is characterized in that in step 6), by volume, and mobile phase, first
Alcohol: water is 10:90~30:70.
9. there is the benzene acryloyl aminated compounds of Antifeedant Effects to inhibit bollworm in solanum rostratum described in claim 1
Application in bollworm feeding effect.
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Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102872064A (en) * | 2012-09-19 | 2013-01-16 | 宁夏回族自治区药品检验所 | Method for extracting alpha-glucosidase activity inhibitor from lycium barbarum seeds and residues after extraction of lycium barbarum oil from lycium barbarum seeds and application thereof |
| CN103044279A (en) * | 2012-12-21 | 2013-04-17 | 苏州永健生物医药有限公司 | Synthetic method of N-Coumaroyldopamine |
-
2019
- 2019-07-19 CN CN201910653329.0A patent/CN110256276B/en active Active
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102872064A (en) * | 2012-09-19 | 2013-01-16 | 宁夏回族自治区药品检验所 | Method for extracting alpha-glucosidase activity inhibitor from lycium barbarum seeds and residues after extraction of lycium barbarum oil from lycium barbarum seeds and application thereof |
| CN103044279A (en) * | 2012-12-21 | 2013-04-17 | 苏州永健生物医药有限公司 | Synthetic method of N-Coumaroyldopamine |
Non-Patent Citations (5)
| Title |
|---|
| LI-QING WANG等: "Phenolic amides with anti-Parkinson’s disease (PD) effects from Nicandra physaloides", 《JOURNAL OF FUNCTIONAL FOODS》 * |
| VITALIY NESTERENKO等: "Identification from a Combinatorial Library of a Small Molecule that Selectively Induces Apoptosis in Cancer Cells", 《JOURNAL OF THE AMERICAN CHEMICAL SOCIETY》 * |
| YU-CHI TSAI等: "The oestrogenic and anti-platelet activities of dihydrobenzofuroisocoumarins and homoisoflavonoids from Liriope platyphylla roots", 《FOOD CHEMISTRY》 * |
| 唐文伟等: "水茄甲醇提取物对小菜蛾的生物活性与化学成分研究", 《江西农业大学学报》 * |
| 舒伟虎等: "水茄的化学成分研究", 《中草药》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN112538016A (en) * | 2021-01-21 | 2021-03-23 | 黄河科技学院 | Method for extracting chlorogenic acid n-butyl ester from peach blossom |
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